Merge pull request #251 from DRYTRIX/Feat-InvoiceUpdate

feat: Add recurring invoices and email integration with template mana…

app/__init__.py

@@ -759,6 +759,7 @@ def create_app(config=None):
     from app.routes.analytics import analytics_bp
     from app.routes.tasks import tasks_bp
     from app.routes.invoices import invoices_bp
+    from app.routes.recurring_invoices import recurring_invoices_bp
     from app.routes.payments import payments_bp
     from app.routes.clients import clients_bp
     from app.routes.client_notes import client_notes_bp
@@ -801,6 +802,7 @@ def create_app(config=None):
     app.register_blueprint(analytics_bp)
     app.register_blueprint(tasks_bp)
     app.register_blueprint(invoices_bp)
+    app.register_blueprint(recurring_invoices_bp)
     app.register_blueprint(payments_bp)
     app.register_blueprint(clients_bp)
     app.register_blueprint(client_notes_bp)

app/models/__init__.py

@@ -36,6 +36,8 @@ from .budget_alert import BudgetAlert
 from .import_export import DataImport, DataExport
 from .invoice_pdf_template import InvoicePDFTemplate
 from .audit_log import AuditLog
+from .recurring_invoice import RecurringInvoice
+from .invoice_email import InvoiceEmail
 
 __all__ = [
     "User",
@@ -79,4 +81,6 @@ __all__ = [
     "InvoicePDFTemplate",
     "ClientPrepaidConsumption",
     "AuditLog",
+    "RecurringInvoice",
+    "InvoiceEmail",
 ]

app/models/invoice.py

@@ -28,6 +28,7 @@ class Invoice(db.Model):
     total_amount = db.Column(db.Numeric(10, 2), nullable=False, default=0)
     currency_code = db.Column(db.String(3), nullable=False, default='EUR')
     template_id = db.Column(db.Integer, db.ForeignKey('invoice_templates.id'), nullable=True, index=True)
+    recurring_invoice_id = db.Column(db.Integer, db.ForeignKey('recurring_invoices.id'), nullable=True, index=True)
     
     # Notes and terms
     notes = db.Column(db.Text, nullable=True)

app/models/invoice_email.py

@@ -0,0 +1,94 @@
+from datetime import datetime
+from app import db
+
+
+class InvoiceEmail(db.Model):
+    """Model for tracking invoice emails sent to clients"""
+    
+    __tablename__ = 'invoice_emails'
+    
+    id = db.Column(db.Integer, primary_key=True)
+    invoice_id = db.Column(db.Integer, db.ForeignKey('invoices.id'), nullable=False, index=True)
+    
+    # Email details
+    recipient_email = db.Column(db.String(200), nullable=False)
+    subject = db.Column(db.String(500), nullable=False)
+    sent_at = db.Column(db.DateTime, nullable=False, default=datetime.utcnow)
+    sent_by = db.Column(db.Integer, db.ForeignKey('users.id'), nullable=False)
+    
+    # Tracking
+    opened_at = db.Column(db.DateTime, nullable=True)  # When email was opened (if tracked)
+    opened_count = db.Column(db.Integer, nullable=False, default=0)  # Number of times opened
+    last_opened_at = db.Column(db.DateTime, nullable=True)  # Last time email was opened
+    
+    # Payment tracking
+    paid_at = db.Column(db.DateTime, nullable=True)  # When invoice was marked as paid (if after email)
+    
+    # Status
+    status = db.Column(db.String(20), nullable=False, default='sent')  # 'sent', 'opened', 'paid', 'bounced', 'failed'
+    
+    # Error tracking
+    error_message = db.Column(db.Text, nullable=True)  # Error message if send failed
+    
+    # Metadata
+    created_at = db.Column(db.DateTime, default=datetime.utcnow, nullable=False)
+    updated_at = db.Column(db.DateTime, default=datetime.utcnow, onupdate=datetime.utcnow, nullable=False)
+    
+    # Relationships
+    invoice = db.relationship('Invoice', backref='email_records')
+    sender = db.relationship('User', backref='sent_invoice_emails')
+    
+    def __init__(self, invoice_id, recipient_email, subject, sent_by, **kwargs):
+        self.invoice_id = invoice_id
+        self.recipient_email = recipient_email
+        self.subject = subject
+        self.sent_by = sent_by
+        self.status = kwargs.get('status', 'sent')
+        self.error_message = kwargs.get('error_message')
+    
+    def __repr__(self):
+        return f'<InvoiceEmail {self.invoice_id} -> {self.recipient_email} ({self.status})>'
+    
+    def mark_opened(self):
+        """Mark email as opened"""
+        if not self.opened_at:
+            self.opened_at = datetime.utcnow()
+        self.last_opened_at = datetime.utcnow()
+        self.opened_count += 1
+        if self.status == 'sent':
+            self.status = 'opened'
+    
+    def mark_paid(self):
+        """Mark invoice as paid (after email was sent)"""
+        if not self.paid_at:
+            self.paid_at = datetime.utcnow()
+        self.status = 'paid'
+    
+    def mark_failed(self, error_message):
+        """Mark email send as failed"""
+        self.status = 'failed'
+        self.error_message = error_message
+    
+    def mark_bounced(self):
+        """Mark email as bounced"""
+        self.status = 'bounced'
+    
+    def to_dict(self):
+        """Convert invoice email to dictionary"""
+        return {
+            'id': self.id,
+            'invoice_id': self.invoice_id,
+            'recipient_email': self.recipient_email,
+            'subject': self.subject,
+            'sent_at': self.sent_at.isoformat() if self.sent_at else None,
+            'sent_by': self.sent_by,
+            'opened_at': self.opened_at.isoformat() if self.opened_at else None,
+            'opened_count': self.opened_count,
+            'last_opened_at': self.last_opened_at.isoformat() if self.last_opened_at else None,
+            'paid_at': self.paid_at.isoformat() if self.paid_at else None,
+            'status': self.status,
+            'error_message': self.error_message,
+            'created_at': self.created_at.isoformat() if self.created_at else None,
+            'updated_at': self.updated_at.isoformat() if self.updated_at else None
+        }
+

app/models/recurring_invoice.py

@@ -0,0 +1,245 @@
+from datetime import datetime, timedelta
+from decimal import Decimal
+from dateutil.relativedelta import relativedelta
+from app import db
+
+
+class RecurringInvoice(db.Model):
+    """Recurring invoice template model for automated billing"""
+    
+    __tablename__ = 'recurring_invoices'
+    
+    id = db.Column(db.Integer, primary_key=True)
+    name = db.Column(db.String(200), nullable=False)  # Template name/description
+    project_id = db.Column(db.Integer, db.ForeignKey('projects.id'), nullable=False, index=True)
+    client_id = db.Column(db.Integer, db.ForeignKey('clients.id'), nullable=False, index=True)
+    
+    # Recurrence settings
+    frequency = db.Column(db.String(20), nullable=False)  # 'daily', 'weekly', 'monthly', 'yearly'
+    interval = db.Column(db.Integer, nullable=False, default=1)  # Every N periods (e.g., every 2 weeks)
+    next_run_date = db.Column(db.Date, nullable=False)  # Next date to generate invoice
+    end_date = db.Column(db.Date, nullable=True)  # Optional end date for recurrence
+    
+    # Invoice template settings (copied to generated invoices)
+    client_name = db.Column(db.String(200), nullable=False)
+    client_email = db.Column(db.String(200), nullable=True)
+    client_address = db.Column(db.Text, nullable=True)
+    due_date_days = db.Column(db.Integer, nullable=False, default=30)  # Days from issue date to due date
+    tax_rate = db.Column(db.Numeric(5, 2), nullable=False, default=0)
+    currency_code = db.Column(db.String(3), nullable=False, default='EUR')
+    notes = db.Column(db.Text, nullable=True)
+    terms = db.Column(db.Text, nullable=True)
+    template_id = db.Column(db.Integer, db.ForeignKey('invoice_templates.id'), nullable=True, index=True)
+    
+    # Auto-send settings
+    auto_send = db.Column(db.Boolean, nullable=False, default=False)  # Automatically send via email when generated
+    auto_include_time_entries = db.Column(db.Boolean, nullable=False, default=True)  # Include unbilled time entries
+    
+    # Status
+    is_active = db.Column(db.Boolean, nullable=False, default=True)
+    
+    # Metadata
+    created_by = db.Column(db.Integer, db.ForeignKey('users.id'), nullable=False)
+    created_at = db.Column(db.DateTime, default=datetime.utcnow, nullable=False)
+    updated_at = db.Column(db.DateTime, default=datetime.utcnow, onupdate=datetime.utcnow, nullable=False)
+    last_generated_at = db.Column(db.DateTime, nullable=True)  # Last time an invoice was generated
+    
+    # Relationships
+    project = db.relationship('Project', backref='recurring_invoices')
+    client = db.relationship('Client', backref='recurring_invoices')
+    creator = db.relationship('User', backref='created_recurring_invoices')
+    template = db.relationship('InvoiceTemplate', backref='recurring_invoices')
+    generated_invoices = db.relationship('Invoice', backref='recurring_invoice_template', lazy='dynamic', foreign_keys='[Invoice.recurring_invoice_id]')
+    
+    def __init__(self, name, project_id, client_id, frequency, next_run_date, created_by, **kwargs):
+        self.name = name
+        self.project_id = project_id
+        self.client_id = client_id
+        self.frequency = frequency
+        self.next_run_date = next_run_date
+        self.created_by = created_by
+        
+        # Set optional fields
+        self.interval = kwargs.get('interval', 1)
+        self.end_date = kwargs.get('end_date')
+        self.client_name = kwargs.get('client_name', '')
+        self.client_email = kwargs.get('client_email')
+        self.client_address = kwargs.get('client_address')
+        self.due_date_days = kwargs.get('due_date_days', 30)
+        self.tax_rate = Decimal(str(kwargs.get('tax_rate', 0)))
+        self.currency_code = kwargs.get('currency_code', 'EUR')
+        self.notes = kwargs.get('notes')
+        self.terms = kwargs.get('terms')
+        self.template_id = kwargs.get('template_id')
+        self.auto_send = kwargs.get('auto_send', False)
+        self.auto_include_time_entries = kwargs.get('auto_include_time_entries', True)
+        self.is_active = kwargs.get('is_active', True)
+    
+    def __repr__(self):
+        return f'<RecurringInvoice {self.name} ({self.frequency})>'
+    
+    def calculate_next_run_date(self, from_date=None):
+        """Calculate the next run date based on frequency and interval"""
+        if from_date is None:
+            from_date = datetime.utcnow().date()
+        
+        if self.frequency == 'daily':
+            return from_date + timedelta(days=self.interval)
+        elif self.frequency == 'weekly':
+            return from_date + timedelta(weeks=self.interval)
+        elif self.frequency == 'monthly':
+            return from_date + relativedelta(months=self.interval)
+        elif self.frequency == 'yearly':
+            return from_date + relativedelta(years=self.interval)
+        else:
+            raise ValueError(f"Invalid frequency: {self.frequency}")
+    
+    def should_generate_today(self):
+        """Check if invoice should be generated today"""
+        if not self.is_active:
+            return False
+        
+        today = datetime.utcnow().date()
+        
+        # Check if we've reached the end date
+        if self.end_date and today > self.end_date:
+            return False
+        
+        # Check if it's time to generate
+        return today >= self.next_run_date
+    
+    def generate_invoice(self):
+        """Generate an invoice from this recurring template"""
+        from app.models import Invoice, InvoiceItem, TimeEntry, Settings
+        
+        if not self.should_generate_today():
+            return None
+        
+        # Get settings for currency
+        settings = Settings.get_settings()
+        currency_code = self.currency_code or (settings.currency if settings else 'EUR')
+        
+        # Calculate dates
+        issue_date = datetime.utcnow().date()
+        due_date = issue_date + timedelta(days=self.due_date_days)
+        
+        # Generate invoice number
+        invoice_number = Invoice.generate_invoice_number()
+        
+        # Create invoice
+        invoice = Invoice(
+            invoice_number=invoice_number,
+            project_id=self.project_id,
+            client_name=self.client_name,
+            due_date=due_date,
+            created_by=self.created_by,
+            client_id=self.client_id,
+            client_email=self.client_email,
+            client_address=self.client_address,
+            tax_rate=self.tax_rate,
+            notes=self.notes,
+            terms=self.terms,
+            currency_code=currency_code,
+            template_id=self.template_id,
+            issue_date=issue_date
+        )
+        
+        # Link to recurring invoice template
+        invoice.recurring_invoice_id = self.id
+        
+        db.session.add(invoice)
+        
+        # Auto-include time entries if enabled
+        if self.auto_include_time_entries:
+            # Get unbilled time entries for this project
+            time_entries = TimeEntry.query.filter(
+                TimeEntry.project_id == self.project_id,
+                TimeEntry.end_time.isnot(None),
+                TimeEntry.billable == True
+            ).order_by(TimeEntry.start_time.desc()).all()
+            
+            # Filter out entries already billed
+            unbilled_entries = []
+            for entry in time_entries:
+                already_billed = False
+                for other_invoice in self.project.invoices:
+                    if other_invoice.id != invoice.id:
+                        for item in other_invoice.items:
+                            if item.time_entry_ids and str(entry.id) in item.time_entry_ids.split(','):
+                                already_billed = True
+                                break
+                    if already_billed:
+                        break
+                
+                if not already_billed:
+                    unbilled_entries.append(entry)
+            
+            # Group and create invoice items
+            if unbilled_entries:
+                from app.models.rate_override import RateOverride
+                grouped_entries = {}
+                for entry in unbilled_entries:
+                    if entry.task_id:
+                        key = f"task_{entry.task_id}"
+                        description = f"Task: {entry.task.name if entry.task else 'Unknown Task'}"
+                    else:
+                        key = f"project_{entry.project_id}"
+                        description = f"Project: {entry.project.name}"
+                    
+                    if key not in grouped_entries:
+                        grouped_entries[key] = {
+                            'description': description,
+                            'entries': [],
+                            'total_hours': Decimal('0'),
+                        }
+                    
+                    grouped_entries[key]['entries'].append(entry)
+                    grouped_entries[key]['total_hours'] += entry.duration_hours
+                
+                # Create invoice items
+                hourly_rate = RateOverride.resolve_rate(self.project)
+                for group in grouped_entries.values():
+                    if group['total_hours'] > 0:
+                        item = InvoiceItem(
+                            invoice_id=invoice.id,
+                            description=group['description'],
+                            quantity=group['total_hours'],
+                            unit_price=hourly_rate,
+                            time_entry_ids=','.join(str(e.id) for e in group['entries'])
+                        )
+                        db.session.add(item)
+        
+        # Calculate totals
+        invoice.calculate_totals()
+        
+        # Update recurring invoice
+        self.last_generated_at = datetime.utcnow()
+        self.next_run_date = self.calculate_next_run_date(issue_date)
+        
+        return invoice
+    
+    def to_dict(self):
+        """Convert recurring invoice to dictionary"""
+        return {
+            'id': self.id,
+            'name': self.name,
+            'project_id': self.project_id,
+            'client_id': self.client_id,
+            'frequency': self.frequency,
+            'interval': self.interval,
+            'next_run_date': self.next_run_date.isoformat() if self.next_run_date else None,
+            'end_date': self.end_date.isoformat() if self.end_date else None,
+            'client_name': self.client_name,
+            'client_email': self.client_email,
+            'due_date_days': self.due_date_days,
+            'tax_rate': float(self.tax_rate),
+            'currency_code': self.currency_code,
+            'auto_send': self.auto_send,
+            'auto_include_time_entries': self.auto_include_time_entries,
+            'is_active': self.is_active,
+            'created_by': self.created_by,
+            'created_at': self.created_at.isoformat() if self.created_at else None,
+            'updated_at': self.updated_at.isoformat() if self.updated_at else None,
+            'last_generated_at': self.last_generated_at.isoformat() if self.last_generated_at else None
+        }
+

app/routes/admin.py

@@ -1560,3 +1560,155 @@ def get_email_config():
         'password_set': bool(settings.mail_password),
         'default_sender': settings.mail_default_sender or ''
     }), 200
+
+
+# ==================== Email Template Management ====================
+
+@admin_bp.route('/admin/email-templates')
+@login_required
+@admin_or_permission_required('manage_settings')
+def list_email_templates():
+    """List all email templates"""
+    from app.models import InvoiceTemplate
+    
+    templates = InvoiceTemplate.query.order_by(InvoiceTemplate.name).all()
+    
+    return render_template('admin/email_templates/list.html', templates=templates)
+
+
+@admin_bp.route('/admin/email-templates/create', methods=['GET', 'POST'])
+@login_required
+@admin_or_permission_required('manage_settings')
+def create_email_template():
+    """Create a new email template"""
+    from app.models import InvoiceTemplate
+    
+    if request.method == 'POST':
+        name = request.form.get('name', '').strip()
+        description = request.form.get('description', '').strip()
+        html = request.form.get('html', '').strip()
+        css = request.form.get('css', '').strip()
+        is_default = request.form.get('is_default') == 'on'
+        
+        # Validate
+        if not name:
+            flash(_('Template name is required'), 'error')
+            return render_template('admin/email_templates/create.html')
+        
+        # Check for duplicate name
+        existing = InvoiceTemplate.query.filter_by(name=name).first()
+        if existing:
+            flash(_('A template with this name already exists'), 'error')
+            return render_template('admin/email_templates/create.html', 
+                                 name=name, description=description, html=html, css=css)
+        
+        # If setting as default, unset other defaults
+        if is_default:
+            InvoiceTemplate.query.update({InvoiceTemplate.is_default: False})
+        
+        # Create template
+        template = InvoiceTemplate(
+            name=name,
+            description=description if description else None,
+            html=html if html else None,
+            css=css if css else None,
+            is_default=is_default
+        )
+        
+        db.session.add(template)
+        if not safe_commit('create_email_template', {'name': name}):
+            flash(_('Could not create email template due to a database error.'), 'error')
+            return render_template('admin/email_templates/create.html')
+        
+        flash(_('Email template created successfully'), 'success')
+        return redirect(url_for('admin.list_email_templates'))
+    
+    return render_template('admin/email_templates/create.html')
+
+
+@admin_bp.route('/admin/email-templates/<int:template_id>')
+@login_required
+@admin_or_permission_required('manage_settings')
+def view_email_template(template_id):
+    """View email template details"""
+    from app.models import InvoiceTemplate
+    
+    template = InvoiceTemplate.query.get_or_404(template_id)
+    
+    return render_template('admin/email_templates/view.html', template=template)
+
+
+@admin_bp.route('/admin/email-templates/<int:template_id>/edit', methods=['GET', 'POST'])
+@login_required
+@admin_or_permission_required('manage_settings')
+def edit_email_template(template_id):
+    """Edit email template"""
+    from app.models import InvoiceTemplate
+    
+    template = InvoiceTemplate.query.get_or_404(template_id)
+    
+    if request.method == 'POST':
+        name = request.form.get('name', '').strip()
+        description = request.form.get('description', '').strip()
+        html = request.form.get('html', '').strip()
+        css = request.form.get('css', '').strip()
+        is_default = request.form.get('is_default') == 'on'
+        
+        # Validate
+        if not name:
+            flash(_('Template name is required'), 'error')
+            return render_template('admin/email_templates/edit.html', template=template)
+        
+        # Check for duplicate name (excluding current template)
+        existing = InvoiceTemplate.query.filter(
+            InvoiceTemplate.name == name,
+            InvoiceTemplate.id != template_id
+        ).first()
+        if existing:
+            flash(_('A template with this name already exists'), 'error')
+            return render_template('admin/email_templates/edit.html', template=template)
+        
+        # If setting as default, unset other defaults
+        if is_default:
+            InvoiceTemplate.query.filter(InvoiceTemplate.id != template_id).update({InvoiceTemplate.is_default: False})
+        
+        # Update template
+        template.name = name
+        template.description = description if description else None
+        template.html = html if html else None
+        template.css = css if css else None
+        template.is_default = is_default
+        template.updated_at = datetime.utcnow()
+        
+        if not safe_commit('edit_email_template', {'template_id': template_id}):
+            flash(_('Could not update email template due to a database error.'), 'error')
+            return render_template('admin/email_templates/edit.html', template=template)
+        
+        flash(_('Email template updated successfully'), 'success')
+        return redirect(url_for('admin.view_email_template', template_id=template_id))
+    
+    return render_template('admin/email_templates/edit.html', template=template)
+
+
+@admin_bp.route('/admin/email-templates/<int:template_id>/delete', methods=['POST'])
+@login_required
+@admin_or_permission_required('manage_settings')
+def delete_email_template(template_id):
+    """Delete email template"""
+    from app.models import InvoiceTemplate
+    
+    template = InvoiceTemplate.query.get_or_404(template_id)
+    template_name = template.name
+    
+    # Check if template is in use
+    if template.invoices.count() > 0 or template.recurring_invoices.count() > 0:
+        flash(_('Cannot delete template that is in use by invoices or recurring invoices'), 'error')
+        return redirect(url_for('admin.list_email_templates'))
+    
+    db.session.delete(template)
+    if not safe_commit('delete_email_template', {'template_id': template_id}):
+        flash(_('Could not delete email template due to a database error.'), 'error')
+    else:
+        flash(_('Email template "%(name)s" deleted successfully', name=template_name), 'success')
+    
+    return redirect(url_for('admin.list_email_templates'))

app/routes/invoices.py

@@ -197,6 +197,7 @@ def create_invoice():
 @login_required
 def view_invoice(invoice_id):
     """View invoice details"""
+    from app.models import InvoiceTemplate
     invoice = Invoice.query.get_or_404(invoice_id)
     
     # Check access permissions
@@ -210,7 +211,10 @@ def view_invoice(invoice_id):
         "invoice_number": invoice.invoice_number
     })
     
-    return render_template('invoices/view.html', invoice=invoice)
+    # Get email templates for selection
+    email_templates = InvoiceTemplate.query.order_by(InvoiceTemplate.name).all()
+    
+    return render_template('invoices/view.html', invoice=invoice, email_templates=email_templates)
 
 @invoices_bp.route('/invoices/<int:invoice_id>/edit', methods=['GET', 'POST'])
 @login_required
@@ -323,8 +327,10 @@ def edit_invoice(invoice_id):
         return redirect(url_for('invoices.view_invoice', invoice_id=invoice.id))
     
     # GET request - show edit form
+    from app.models import InvoiceTemplate
     projects = Project.query.filter_by(status='active').order_by(Project.name).all()
-    return render_template('invoices/edit.html', invoice=invoice, projects=projects)
+    email_templates = InvoiceTemplate.query.order_by(InvoiceTemplate.name).all()
+    return render_template('invoices/edit.html', invoice=invoice, projects=projects, email_templates=email_templates)
 
 @invoices_bp.route('/invoices/<int:invoice_id>/status', methods=['POST'])
 @login_required
@@ -931,3 +937,55 @@ def export_invoices_excel():
         as_attachment=True,
         download_name=filename
     )
+
+@invoices_bp.route('/invoices/<int:invoice_id>/send-email', methods=['POST'])
+@login_required
+def send_invoice_email_route(invoice_id):
+    """Send invoice via email"""
+    invoice = Invoice.query.get_or_404(invoice_id)
+    
+    # Check access permissions
+    if not current_user.is_admin and invoice.created_by != current_user.id:
+        return jsonify({'error': 'Permission denied'}), 403
+    
+    # Get recipient email from request
+    recipient_email = request.form.get('recipient_email', '').strip() or request.json.get('recipient_email', '').strip() if request.is_json else ''
+    
+    if not recipient_email:
+        # Try to use invoice client email
+        recipient_email = invoice.client_email
+    
+    if not recipient_email:
+        return jsonify({'error': 'Recipient email address is required'}), 400
+    
+    # Get custom message if provided
+    custom_message = request.form.get('custom_message', '').strip() or (request.json.get('custom_message', '').strip() if request.is_json else '')
+    
+    # Get email template ID if provided
+    email_template_id = request.form.get('email_template_id', type=int) or (request.json.get('email_template_id') if request.is_json else None)
+    
+    try:
+        from app.utils.email import send_invoice_email
+        
+        success, invoice_email, message = send_invoice_email(
+            invoice=invoice,
+            recipient_email=recipient_email,
+            sender_user=current_user,
+            custom_message=custom_message if custom_message else None,
+            email_template_id=email_template_id
+        )
+        
+        if success:
+            flash(f'Invoice email sent successfully to {recipient_email}', 'success')
+            return jsonify({
+                'success': True,
+                'message': message,
+                'invoice_email_id': invoice_email.id if invoice_email else None
+            })
+        else:
+            return jsonify({'error': message}), 500
+    
+    except Exception as e:
+        logger.error(f"Error sending invoice email: {type(e).__name__}: {str(e)}")
+        logger.exception("Full error traceback:")
+        return jsonify({'error': f'Failed to send email: {str(e)}'}), 500

app/routes/recurring_invoices.py

@@ -0,0 +1,264 @@
+from flask import Blueprint, render_template, request, redirect, url_for, flash, jsonify
+from flask_babel import gettext as _
+from flask_login import login_required, current_user
+from app import db, log_event
+from app.models import RecurringInvoice, Project, Client, Settings, Invoice
+from datetime import datetime, timedelta
+from decimal import Decimal
+import logging
+from app.utils.db import safe_commit
+
+recurring_invoices_bp = Blueprint('recurring_invoices', __name__)
+logger = logging.getLogger(__name__)
+
+
+@recurring_invoices_bp.route('/recurring-invoices')
+@login_required
+def list_recurring_invoices():
+    """List all recurring invoices"""
+    # Get filter parameters
+    is_active = request.args.get('is_active', '').strip()
+    
+    # Build query
+    if current_user.is_admin:
+        query = RecurringInvoice.query
+    else:
+        query = RecurringInvoice.query.filter_by(created_by=current_user.id)
+    
+    # Apply active filter
+    if is_active == 'true':
+        query = query.filter_by(is_active=True)
+    elif is_active == 'false':
+        query = query.filter_by(is_active=False)
+    
+    # Get recurring invoices
+    recurring_invoices = query.order_by(RecurringInvoice.next_run_date.asc()).all()
+    
+    return render_template('recurring_invoices/list.html', recurring_invoices=recurring_invoices)
+
+
+@recurring_invoices_bp.route('/recurring-invoices/create', methods=['GET', 'POST'])
+@login_required
+def create_recurring_invoice():
+    """Create a new recurring invoice"""
+    if request.method == 'POST':
+        # Get form data
+        name = request.form.get('name', '').strip()
+        project_id = request.form.get('project_id', type=int)
+        client_id = request.form.get('client_id', type=int)
+        frequency = request.form.get('frequency', '').strip()
+        interval = request.form.get('interval', type=int, default=1)
+        next_run_date_str = request.form.get('next_run_date', '').strip()
+        end_date_str = request.form.get('end_date', '').strip()
+        client_name = request.form.get('client_name', '').strip()
+        client_email = request.form.get('client_email', '').strip()
+        client_address = request.form.get('client_address', '').strip()
+        due_date_days = request.form.get('due_date_days', type=int, default=30)
+        tax_rate = request.form.get('tax_rate', '0').strip()
+        notes = request.form.get('notes', '').strip()
+        terms = request.form.get('terms', '').strip()
+        auto_send = request.form.get('auto_send') == 'on'
+        auto_include_time_entries = request.form.get('auto_include_time_entries') != 'off'
+        
+        # Validate required fields
+        if not name or not project_id or not client_id or not frequency or not next_run_date_str:
+            flash('Name, project, client, frequency, and next run date are required', 'error')
+            return render_template('recurring_invoices/create.html')
+        
+        try:
+            next_run_date = datetime.strptime(next_run_date_str, '%Y-%m-%d').date()
+        except ValueError:
+            flash('Invalid next run date format', 'error')
+            return render_template('recurring_invoices/create.html')
+        
+        end_date = None
+        if end_date_str:
+            try:
+                end_date = datetime.strptime(end_date_str, '%Y-%m-%d').date()
+            except ValueError:
+                flash('Invalid end date format', 'error')
+                return render_template('recurring_invoices/create.html')
+        
+        try:
+            tax_rate = Decimal(tax_rate)
+        except ValueError:
+            flash('Invalid tax rate format', 'error')
+            return render_template('recurring_invoices/create.html')
+        
+        # Get project and client
+        project = Project.query.get(project_id)
+        client = Client.query.get(client_id)
+        if not project or not client:
+            flash('Selected project or client not found', 'error')
+            return render_template('recurring_invoices/create.html')
+        
+        # Get currency from settings
+        settings = Settings.get_settings()
+        currency_code = settings.currency if settings else 'EUR'
+        
+        # Use client info if not provided
+        if not client_name:
+            client_name = client.name
+        if not client_email:
+            client_email = client.email
+        
+        # Create recurring invoice
+        recurring = RecurringInvoice(
+            name=name,
+            project_id=project_id,
+            client_id=client_id,
+            frequency=frequency,
+            next_run_date=next_run_date,
+            created_by=current_user.id,
+            interval=interval,
+            end_date=end_date,
+            client_name=client_name,
+            client_email=client_email,
+            client_address=client_address,
+            due_date_days=due_date_days,
+            tax_rate=tax_rate,
+            notes=notes,
+            terms=terms,
+            currency_code=currency_code,
+            auto_send=auto_send,
+            auto_include_time_entries=auto_include_time_entries
+        )
+        
+        db.session.add(recurring)
+        if not safe_commit('create_recurring_invoice', {'name': name, 'project_id': project_id}):
+            flash('Could not create recurring invoice due to a database error. Please check server logs.', 'error')
+            return render_template('recurring_invoices/create.html')
+        
+        flash(f'Recurring invoice "{name}" created successfully', 'success')
+        return redirect(url_for('recurring_invoices.list_recurring_invoices'))
+    
+    # GET request - show form
+    projects = Project.query.filter_by(status='active', billable=True).order_by(Project.name).all()
+    clients = Client.query.filter_by(status='active').order_by(Client.name).all()
+    settings = Settings.get_settings()
+    
+    # Set default next run date to tomorrow
+    default_next_run_date = (datetime.utcnow() + timedelta(days=1)).strftime('%Y-%m-%d')
+    
+    return render_template('recurring_invoices/create.html', 
+                         projects=projects, 
+                         clients=clients,
+                         settings=settings,
+                         default_next_run_date=default_next_run_date)
+
+
+@recurring_invoices_bp.route('/recurring-invoices/<int:recurring_id>')
+@login_required
+def view_recurring_invoice(recurring_id):
+    """View recurring invoice details"""
+    recurring = RecurringInvoice.query.get_or_404(recurring_id)
+    
+    # Check access permissions
+    if not current_user.is_admin and recurring.created_by != current_user.id:
+        flash('You do not have permission to view this recurring invoice', 'error')
+        return redirect(url_for('recurring_invoices.list_recurring_invoices'))
+    
+    # Get generated invoices
+    generated_invoices = recurring.generated_invoices.order_by(Invoice.created_at.desc()).limit(10).all()
+    
+    return render_template('recurring_invoices/view.html', recurring=recurring, generated_invoices=generated_invoices)
+
+
+@recurring_invoices_bp.route('/recurring-invoices/<int:recurring_id>/edit', methods=['GET', 'POST'])
+@login_required
+def edit_recurring_invoice(recurring_id):
+    """Edit recurring invoice"""
+    recurring = RecurringInvoice.query.get_or_404(recurring_id)
+    
+    # Check access permissions
+    if not current_user.is_admin and recurring.created_by != current_user.id:
+        flash('You do not have permission to edit this recurring invoice', 'error')
+        return redirect(url_for('recurring_invoices.list_recurring_invoices'))
+    
+    if request.method == 'POST':
+        # Update recurring invoice
+        recurring.name = request.form.get('name', '').strip()
+        recurring.frequency = request.form.get('frequency', '').strip()
+        recurring.interval = request.form.get('interval', type=int, default=1)
+        recurring.next_run_date = datetime.strptime(request.form.get('next_run_date'), '%Y-%m-%d').date()
+        
+        end_date_str = request.form.get('end_date', '').strip()
+        recurring.end_date = datetime.strptime(end_date_str, '%Y-%m-%d').date() if end_date_str else None
+        
+        recurring.client_name = request.form.get('client_name', '').strip()
+        recurring.client_email = request.form.get('client_email', '').strip()
+        recurring.client_address = request.form.get('client_address', '').strip()
+        recurring.due_date_days = request.form.get('due_date_days', type=int, default=30)
+        recurring.tax_rate = Decimal(request.form.get('tax_rate', '0'))
+        recurring.notes = request.form.get('notes', '').strip()
+        recurring.terms = request.form.get('terms', '').strip()
+        recurring.auto_send = request.form.get('auto_send') == 'on'
+        recurring.auto_include_time_entries = request.form.get('auto_include_time_entries') != 'off'
+        recurring.is_active = request.form.get('is_active') == 'on'
+        
+        if not safe_commit('edit_recurring_invoice', {'recurring_id': recurring.id}):
+            flash('Could not update recurring invoice due to a database error. Please check server logs.', 'error')
+            return render_template('recurring_invoices/edit.html', recurring=recurring, projects=Project.query.filter_by(status='active').order_by(Project.name).all(), clients=Client.query.filter_by(status='active').order_by(Client.name).all())
+        
+        flash('Recurring invoice updated successfully', 'success')
+        return redirect(url_for('recurring_invoices.view_recurring_invoice', recurring_id=recurring.id))
+    
+    # GET request - show edit form
+    projects = Project.query.filter_by(status='active').order_by(Project.name).all()
+    clients = Client.query.filter_by(status='active').order_by(Client.name).all()
+    return render_template('recurring_invoices/edit.html', recurring=recurring, projects=projects, clients=clients)
+
+
+@recurring_invoices_bp.route('/recurring-invoices/<int:recurring_id>/delete', methods=['POST'])
+@login_required
+def delete_recurring_invoice(recurring_id):
+    """Delete recurring invoice"""
+    recurring = RecurringInvoice.query.get_or_404(recurring_id)
+    
+    # Check access permissions
+    if not current_user.is_admin and recurring.created_by != current_user.id:
+        flash('You do not have permission to delete this recurring invoice', 'error')
+        return redirect(url_for('recurring_invoices.list_recurring_invoices'))
+    
+    name = recurring.name
+    db.session.delete(recurring)
+    if not safe_commit('delete_recurring_invoice', {'recurring_id': recurring.id}):
+        flash('Could not delete recurring invoice due to a database error. Please check server logs.', 'error')
+        return redirect(url_for('recurring_invoices.list_recurring_invoices'))
+    
+    flash(f'Recurring invoice "{name}" deleted successfully', 'success')
+    return redirect(url_for('recurring_invoices.list_recurring_invoices'))
+
+
+@recurring_invoices_bp.route('/recurring-invoices/<int:recurring_id>/generate', methods=['POST'])
+@login_required
+def generate_invoice_now(recurring_id):
+    """Manually generate an invoice from a recurring template"""
+    recurring = RecurringInvoice.query.get_or_404(recurring_id)
+    
+    # Check access permissions
+    if not current_user.is_admin and recurring.created_by != current_user.id:
+        return jsonify({'error': 'Permission denied'}), 403
+    
+    try:
+        # Temporarily set next_run_date to today to allow generation
+        original_next_run_date = recurring.next_run_date
+        recurring.next_run_date = datetime.utcnow().date()
+        
+        invoice = recurring.generate_invoice()
+        if invoice:
+            db.session.commit()
+            flash(f'Invoice {invoice.invoice_number} generated successfully', 'success')
+            return jsonify({
+                'success': True,
+                'invoice_id': invoice.id,
+                'invoice_number': invoice.invoice_number
+            })
+        else:
+            recurring.next_run_date = original_next_run_date
+            return jsonify({'error': 'Failed to generate invoice'}), 400
+    
+    except Exception as e:
+        logger.error(f"Error generating invoice from recurring template: {e}")
+        return jsonify({'error': str(e)}), 500
+

app/static/error-handling-enhanced.js

@@ -367,12 +367,12 @@ class EnhancedErrorHandler {
         if (window.toastManager) {
             const toastId = window.toastManager.error(message, 'Error', 0);
             
-            // Find toast element by ID or by checking the container
+            // Find toast element by ID
             const toastElement = window.toastManager.container.querySelector(
                 `[data-toast-id="${toastId}"]`
             ) || Array.from(window.toastManager.container.children).find(
                 el => el.getAttribute('data-toast-id') === String(toastId)
-            ) || document.querySelector(`#toast-${toastId}`);
+            );
             
             if (toastElement) {
                 const retryContainer = document.createElement('div');

app/static/toast-notifications.js

@@ -48,8 +48,8 @@ class ToastNotificationManager {
             dismissible: options.dismissible !== false
         };
 
-        const toast = this.createToast(config);
         const toastId = Date.now() + Math.random();
+        const toast = this.createToast(config, toastId);
         
         this.toasts.set(toastId, {
             element: toast,
@@ -80,12 +80,15 @@ class ToastNotificationManager {
         return toastId;
     }
 
-    createToast(config) {
+    createToast(config, toastId) {
         const toast = document.createElement('div');
         toast.className = `toast-notification toast-${config.type}`;
         toast.setAttribute('role', 'alert');
         toast.setAttribute('aria-live', config.type === 'error' ? 'assertive' : 'polite');
         toast.setAttribute('aria-atomic', 'true');
+        if (toastId) {
+            toast.setAttribute('data-toast-id', String(toastId));
+        }
 
         // Icon
         const icon = this.getIcon(config.type);

app/templates/admin/dashboard.html

@@ -43,6 +43,11 @@
             <div>Email Configuration</div>
             <div class="text-xs mt-1 opacity-90">Test & Configure</div>
         </a>
+        <a href="{{ url_for('admin.list_email_templates') }}" class="bg-purple-600 text-white p-4 rounded-lg text-center hover:bg-purple-700">
+            <i class="fas fa-file-alt mb-2"></i>
+            <div>Email Templates</div>
+            <div class="text-xs mt-1 opacity-90">Invoice Email Templates</div>
+        </a>
         <a href="{{ url_for('admin.settings') }}" class="bg-primary text-white p-4 rounded-lg text-center hover:bg-blue-600">
             <i class="fas fa-cog mb-2"></i>
             <div>Settings</div>

app/templates/admin/email_templates/create.html

@@ -0,0 +1,64 @@
+{% extends "base.html" %}
+{% from "components/ui.html" import page_header %}
+
+{% block content %}
+{% set breadcrumbs = [
+    {'text': 'Admin', 'url': url_for('admin.admin_dashboard')},
+    {'text': 'Email Templates', 'url': url_for('admin.list_email_templates')},
+    {'text': 'Create Template'}
+] %}
+
+{{ page_header(
+    icon_class='fas fa-envelope',
+    title_text='Create Email Template',
+    subtitle_text='Create a new email template for invoice emails',
+    breadcrumbs=breadcrumbs
+) }}
+
+<div class="bg-card-light dark:bg-card-dark p-6 rounded-lg shadow">
+    <form method="POST" class="space-y-6">
+        <input type="hidden" name="csrf_token" value="{{ csrf_token() }}">
+        
+        <div class="grid grid-cols-1 md:grid-cols-2 gap-6">
+            <div class="md:col-span-2">
+                <label for="name" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Template Name *</label>
+                <input type="text" id="name" name="name" required value="{{ name or '' }}" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+                <p class="text-xs text-gray-500 dark:text-gray-400 mt-1">A unique name to identify this template</p>
+            </div>
+            
+            <div class="md:col-span-2">
+                <label for="description" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Description</label>
+                <input type="text" id="description" name="description" value="{{ description or '' }}" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+                <p class="text-xs text-gray-500 dark:text-gray-400 mt-1">Optional description of this template</p>
+            </div>
+            
+            <div class="md:col-span-2">
+                <label class="flex items-center">
+                    <input type="checkbox" name="is_default" class="rounded border-gray-300 text-primary focus:ring-primary">
+                    <span class="ml-2 text-sm text-gray-700 dark:text-gray-300">Set as default template</span>
+                </label>
+            </div>
+            
+            <div class="md:col-span-2">
+                <label for="html" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">HTML Template *</label>
+                <textarea id="html" name="html" rows="15" required class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100 font-mono text-sm">{{ html or '' }}</textarea>
+                <p class="text-xs text-gray-500 dark:text-gray-400 mt-1">
+                    HTML content for the email. Use Jinja2 syntax: <code>{{ '{{ invoice.invoice_number }}' }}</code>, <code>{{ '{{ company_name }}' }}</code>, <code>{{ '{{ custom_message }}' }}</code>
+                </p>
+            </div>
+            
+            <div class="md:col-span-2">
+                <label for="css" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">CSS Styles (Optional)</label>
+                <textarea id="css" name="css" rows="10" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100 font-mono text-sm">{{ css or '' }}</textarea>
+                <p class="text-xs text-gray-500 dark:text-gray-400 mt-1">CSS styles for the email template. Will be automatically wrapped in &lt;style&gt; tags.</p>
+            </div>
+        </div>
+        
+        <div class="flex justify-end gap-3">
+            <a href="{{ url_for('admin.list_email_templates') }}" class="px-4 py-2 bg-gray-300 dark:bg-gray-600 text-gray-700 dark:text-gray-200 rounded-lg hover:bg-gray-400 dark:hover:bg-gray-500">{{ _('Cancel') }}</a>
+            <button type="submit" class="px-4 py-2 bg-primary text-white rounded-lg hover:bg-primary/90">{{ _('Create Template') }}</button>
+        </div>
+    </form>
+</div>
+{% endblock %}
+

app/templates/admin/email_templates/edit.html

@@ -0,0 +1,62 @@
+{% extends "base.html" %}
+{% from "components/ui.html" import page_header %}
+
+{% block content %}
+{% set breadcrumbs = [
+    {'text': 'Admin', 'url': url_for('admin.admin_dashboard')},
+    {'text': 'Email Templates', 'url': url_for('admin.list_email_templates')},
+    {'text': template.name}
+] %}
+
+{{ page_header(
+    icon_class='fas fa-envelope',
+    title_text='Edit Email Template',
+    subtitle_text=template.name,
+    breadcrumbs=breadcrumbs
+) }}
+
+<div class="bg-card-light dark:bg-card-dark p-6 rounded-lg shadow">
+    <form method="POST" class="space-y-6">
+        <input type="hidden" name="csrf_token" value="{{ csrf_token() }}">
+        
+        <div class="grid grid-cols-1 md:grid-cols-2 gap-6">
+            <div class="md:col-span-2">
+                <label for="name" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Template Name *</label>
+                <input type="text" id="name" name="name" required value="{{ template.name }}" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+            </div>
+            
+            <div class="md:col-span-2">
+                <label for="description" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Description</label>
+                <input type="text" id="description" name="description" value="{{ template.description or '' }}" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+            </div>
+            
+            <div class="md:col-span-2">
+                <label class="flex items-center">
+                    <input type="checkbox" name="is_default" {% if template.is_default %}checked{% endif %} class="rounded border-gray-300 text-primary focus:ring-primary">
+                    <span class="ml-2 text-sm text-gray-700 dark:text-gray-300">Set as default template</span>
+                </label>
+            </div>
+            
+            <div class="md:col-span-2">
+                <label for="html" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">HTML Template *</label>
+                <textarea id="html" name="html" rows="15" required class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100 font-mono text-sm">{{ template.html or '' }}</textarea>
+                <p class="text-xs text-gray-500 dark:text-gray-400 mt-1">
+                    HTML content for the email. Use Jinja2 syntax: <code>{{ '{{ invoice.invoice_number }}' }}</code>, <code>{{ '{{ company_name }}' }}</code>, <code>{{ '{{ custom_message }}' }}</code>
+                </p>
+            </div>
+            
+            <div class="md:col-span-2">
+                <label for="css" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">CSS Styles (Optional)</label>
+                <textarea id="css" name="css" rows="10" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100 font-mono text-sm">{{ template.css or '' }}</textarea>
+                <p class="text-xs text-gray-500 dark:text-gray-400 mt-1">CSS styles for the email template. Will be automatically wrapped in &lt;style&gt; tags.</p>
+            </div>
+        </div>
+        
+        <div class="flex justify-end gap-3">
+            <a href="{{ url_for('admin.list_email_templates') }}" class="px-4 py-2 bg-gray-300 dark:bg-gray-600 text-gray-700 dark:text-gray-200 rounded-lg hover:bg-gray-400 dark:hover:bg-gray-500">{{ _('Cancel') }}</a>
+            <button type="submit" class="px-4 py-2 bg-primary text-white rounded-lg hover:bg-primary/90">{{ _('Update Template') }}</button>
+        </div>
+    </form>
+</div>
+{% endblock %}
+

app/templates/admin/email_templates/list.html

@@ -0,0 +1,102 @@
+{% extends "base.html" %}
+{% from "components/ui.html" import page_header %}
+
+{% block content %}
+{% set breadcrumbs = [
+    {'text': 'Admin', 'url': url_for('admin.admin_dashboard')},
+    {'text': 'Email Templates'}
+] %}
+
+{{ page_header(
+    icon_class='fas fa-envelope',
+    title_text='Email Templates',
+    subtitle_text='Manage email templates for invoice emails',
+    breadcrumbs=breadcrumbs,
+    actions_html='<a href="' + url_for("admin.create_email_template") + '" class="bg-primary text-white px-4 py-2 rounded-lg hover:bg-primary/90 transition-colors"><i class="fas fa-plus mr-2"></i>Create Template</a>'
+) }}
+
+{% if templates %}
+<div class="bg-card-light dark:bg-card-dark p-6 rounded-lg shadow">
+    <div class="overflow-x-auto">
+        <table class="min-w-full divide-y divide-border-light dark:divide-border-dark">
+            <thead>
+                <tr>
+                    <th class="px-6 py-3 text-left text-xs font-medium text-text-muted-light dark:text-text-muted-dark uppercase tracking-wider">Name</th>
+                    <th class="px-6 py-3 text-left text-xs font-medium text-text-muted-light dark:text-text-muted-dark uppercase tracking-wider">Description</th>
+                    <th class="px-6 py-3 text-left text-xs font-medium text-text-muted-light dark:text-text-muted-dark uppercase tracking-wider">Status</th>
+                    <th class="px-6 py-3 text-left text-xs font-medium text-text-muted-light dark:text-text-muted-dark uppercase tracking-wider">Created</th>
+                    <th class="px-6 py-3 text-right text-xs font-medium text-text-muted-light dark:text-text-muted-dark uppercase tracking-wider">Actions</th>
+                </tr>
+            </thead>
+            <tbody class="bg-card-light dark:bg-card-dark divide-y divide-border-light dark:divide-border-dark">
+                {% for template in templates %}
+                <tr>
+                    <td class="px-6 py-4 whitespace-nowrap text-sm font-medium text-text-light dark:text-text-dark">
+                        <a href="{{ url_for('admin.view_email_template', template_id=template.id) }}" class="text-primary hover:underline">{{ template.name }}</a>
+                    </td>
+                    <td class="px-6 py-4 text-sm text-text-muted-light dark:text-text-muted-dark">
+                        {{ template.description or '-' }}
+                    </td>
+                    <td class="px-6 py-4 whitespace-nowrap text-sm">
+                        {% if template.is_default %}
+                            <span class="px-2 inline-flex text-xs leading-5 font-semibold rounded-full bg-green-100 text-green-800 dark:bg-green-900/30 dark:text-green-300">Default</span>
+                        {% else %}
+                            <span class="px-2 inline-flex text-xs leading-5 font-semibold rounded-full bg-gray-100 text-gray-800 dark:bg-gray-700 dark:text-gray-300">Active</span>
+                        {% endif %}
+                    </td>
+                    <td class="px-6 py-4 whitespace-nowrap text-sm text-text-muted-light dark:text-text-muted-dark">
+                        {{ template.created_at.strftime('%Y-%m-%d') if template.created_at else '-' }}
+                    </td>
+                    <td class="px-6 py-4 whitespace-nowrap text-right text-sm font-medium">
+                        <a href="{{ url_for('admin.view_email_template', template_id=template.id) }}" class="text-indigo-600 hover:text-indigo-900 dark:text-indigo-400 dark:hover:text-indigo-300 mr-3">View</a>
+                        <a href="{{ url_for('admin.edit_email_template', template_id=template.id) }}" class="text-blue-600 hover:text-blue-900 dark:text-blue-400 dark:hover:text-blue-300 mr-3">Edit</a>
+                        <button type="button" onclick="showDeleteModal('{{ template.id }}', '{{ template.name }}')" class="text-red-600 hover:text-red-900 dark:text-red-400 dark:hover:text-red-300">Delete</button>
+                    </td>
+                </tr>
+                {% endfor %}
+            </tbody>
+        </table>
+    </div>
+</div>
+{% else %}
+<div class="bg-card-light dark:bg-card-dark p-6 rounded-lg shadow text-center text-text-muted-light dark:text-text-muted-dark">
+    <p class="text-lg">{{ _('No email templates found.') }}</p>
+    <p class="mt-2">{{ _('Create your first email template to customize invoice emails.') }}</p>
+    <a href="{{ url_for('admin.create_email_template') }}" class="mt-4 inline-flex items-center px-4 py-2 border border-transparent text-sm font-medium rounded-md shadow-sm text-white bg-primary hover:bg-primary/90">
+        <i class="fas fa-plus mr-2"></i>{{ _('Create Email Template') }}
+    </a>
+</div>
+{% endif %}
+
+<!-- Delete Modal -->
+<div id="deleteTemplateModal" class="hidden fixed inset-0 bg-gray-600 bg-opacity-50 overflow-y-auto h-full w-full z-50">
+    <div class="relative top-20 mx-auto p-5 border w-96 shadow-lg rounded-md bg-white dark:bg-gray-800">
+        <div class="mt-3 text-center">
+            <h3 class="text-lg leading-6 font-medium text-gray-900 dark:text-gray-100">{{ _('Delete Email Template') }}</h3>
+            <div class="mt-2 px-7 py-3">
+                <p class="text-sm text-gray-500 dark:text-gray-400">{{ _('Are you sure you want to delete') }} "<strong id="deleteTemplateName"></strong>"? {{ _('This action cannot be undone.') }}</p>
+            </div>
+            <div class="items-center px-4 py-3">
+                <button id="cancelDelete" onclick="hideDeleteModal()" class="px-4 py-2 bg-gray-300 dark:bg-gray-600 text-gray-700 dark:text-gray-200 rounded-lg hover:bg-gray-400 dark:hover:bg-gray-500 mr-2">{{ _('Cancel') }}</button>
+                <form id="deleteTemplateForm" method="POST" class="inline-block">
+                    <input type="hidden" name="csrf_token" value="{{ csrf_token() }}">
+                    <button type="submit" class="px-4 py-2 bg-red-600 text-white rounded-lg hover:bg-red-700">{{ _('Delete') }}</button>
+                </form>
+            </div>
+        </div>
+    </div>
+</div>
+
+<script>
+function showDeleteModal(templateId, name) {
+    document.getElementById('deleteTemplateName').textContent = name;
+    document.getElementById('deleteTemplateForm').action = "{{ url_for('admin.delete_email_template', template_id=0) }}".replace('0', templateId);
+    document.getElementById('deleteTemplateModal').classList.remove('hidden');
+}
+
+function hideDeleteModal() {
+    document.getElementById('deleteTemplateModal').classList.add('hidden');
+}
+</script>
+{% endblock %}
+

app/templates/admin/email_templates/view.html

@@ -0,0 +1,68 @@
+{% extends "base.html" %}
+{% from "components/ui.html" import page_header %}
+
+{% block content %}
+{% set breadcrumbs = [
+    {'text': 'Admin', 'url': url_for('admin.admin_dashboard')},
+    {'text': 'Email Templates', 'url': url_for('admin.list_email_templates')},
+    {'text': template.name}
+] %}
+
+{{ page_header(
+    icon_class='fas fa-envelope',
+    title_text=template.name,
+    subtitle_text='Email template details',
+    breadcrumbs=breadcrumbs,
+    actions_html='' +
+        '<a href="' + url_for("admin.edit_email_template", template_id=template.id) + '" class="bg-primary text-white px-4 py-2 rounded-lg hover:bg-primary/90 transition-colors"><i class="fas fa-edit mr-2"></i>Edit</a>'
+) }}
+
+<div class="bg-card-light dark:bg-card-dark p-6 rounded-lg shadow mb-6">
+    <h2 class="text-lg font-semibold mb-4">Template Information</h2>
+    <dl class="grid grid-cols-1 md:grid-cols-2 gap-4">
+        <div>
+            <dt class="text-sm font-medium text-gray-500 dark:text-gray-400">Name</dt>
+            <dd class="text-sm text-gray-900 dark:text-gray-100">{{ template.name }}</dd>
+        </div>
+        {% if template.description %}
+        <div>
+            <dt class="text-sm font-medium text-gray-500 dark:text-gray-400">Description</dt>
+            <dd class="text-sm text-gray-900 dark:text-gray-100">{{ template.description }}</dd>
+        </div>
+        {% endif %}
+        <div>
+            <dt class="text-sm font-medium text-gray-500 dark:text-gray-400">Status</dt>
+            <dd class="text-sm text-gray-900 dark:text-gray-100">
+                {% if template.is_default %}
+                    <span class="px-2 inline-flex text-xs leading-5 font-semibold rounded-full bg-green-100 text-green-800 dark:bg-green-900/30 dark:text-green-300">Default</span>
+                {% else %}
+                    <span class="px-2 inline-flex text-xs leading-5 font-semibold rounded-full bg-gray-100 text-gray-800 dark:bg-gray-700 dark:text-gray-300">Active</span>
+                {% endif %}
+            </dd>
+        </div>
+        <div>
+            <dt class="text-sm font-medium text-gray-500 dark:text-gray-400">Created</dt>
+            <dd class="text-sm text-gray-900 dark:text-gray-100">{{ template.created_at.strftime('%Y-%m-%d %H:%M') if template.created_at else '-' }}</dd>
+        </div>
+        <div>
+            <dt class="text-sm font-medium text-gray-500 dark:text-gray-400">Last Updated</dt>
+            <dd class="text-sm text-gray-900 dark:text-gray-100">{{ template.updated_at.strftime('%Y-%m-%d %H:%M') if template.updated_at else '-' }}</dd>
+        </div>
+    </dl>
+</div>
+
+{% if template.html %}
+<div class="bg-card-light dark:bg-card-dark p-6 rounded-lg shadow mb-6">
+    <h2 class="text-lg font-semibold mb-4">HTML Template</h2>
+    <pre class="bg-gray-100 dark:bg-gray-800 p-4 rounded-lg overflow-x-auto text-sm"><code>{{ template.html }}</code></pre>
+</div>
+{% endif %}
+
+{% if template.css %}
+<div class="bg-card-light dark:bg-card-dark p-6 rounded-lg shadow">
+    <h2 class="text-lg font-semibold mb-4">CSS Styles</h2>
+    <pre class="bg-gray-100 dark:bg-gray-800 p-4 rounded-lg overflow-x-auto text-sm"><code>{{ template.css }}</code></pre>
+</div>
+{% endif %}
+{% endblock %}
+

app/templates/base.html

@@ -162,7 +162,7 @@
             <nav class="flex-1">
                 {% set ep = request.endpoint or '' %}
                 {% set work_open = ep.startswith('projects.') or ep.startswith('clients.') or ep.startswith('tasks.') or ep.startswith('timer.') or ep.startswith('kanban.') or ep.startswith('weekly_goals.') %}
-                {% set finance_open = ep.startswith('reports.') or ep.startswith('invoices.') or ep.startswith('payments.') or ep.startswith('expenses.') or ep.startswith('budget_alerts.') or ep.startswith('mileage.') or (ep.startswith('per_diem.') and not ep.startswith('per_diem.list_rates')) %}
+                {% set finance_open = ep.startswith('reports.') or ep.startswith('invoices.') or ep.startswith('recurring_invoices.') or ep.startswith('payments.') or ep.startswith('expenses.') or ep.startswith('budget_alerts.') or ep.startswith('mileage.') or (ep.startswith('per_diem.') and not ep.startswith('per_diem.list_rates')) %}
                 {% set analytics_open = ep.startswith('analytics.') %}
                 {% set tools_open = ep.startswith('import_export.') or ep.startswith('saved_filters.') %}
                 {% set admin_open = ep.startswith('admin.') or ep.startswith('permissions.') or (ep.startswith('expense_categories.') and current_user.is_admin) or (ep.startswith('per_diem.list_rates') and current_user.is_admin) or ep.startswith('time_entry_templates.') or ep.startswith('audit_logs.') %}
@@ -240,6 +240,7 @@
                         <ul id="financeDropdown" class="{% if not finance_open %}hidden {% endif %}mt-2 space-y-2 ml-6">
                             {% set nav_active_reports = ep.startswith('reports.') %}
                             {% set nav_active_invoices = ep.startswith('invoices.') %}
+                            {% set nav_active_recurring_invoices = ep.startswith('recurring_invoices.') %}
                             {% set nav_active_payments = ep.startswith('payments.') %}
                             {% set nav_active_expenses = ep.startswith('expenses.') %}
                             {% set nav_active_mileage = ep.startswith('mileage.') %}
@@ -255,6 +256,11 @@
                                     <i class="fas fa-file-invoice w-4 mr-2"></i>{{ _('Invoices') }}
                                 </a>
                             </li>
+                            <li>
+                                <a class="block px-2 py-1 rounded {% if nav_active_recurring_invoices %}text-primary font-semibold bg-background-light dark:bg-background-dark{% else %}text-text-light dark:text-text-dark hover:bg-background-light dark:hover:bg-background-dark{% endif %}" href="{{ url_for('recurring_invoices.list_recurring_invoices') }}">
+                                    <i class="fas fa-sync-alt w-4 mr-2"></i>{{ _('Recurring Invoices') }}
+                                </a>
+                            </li>
                             <li>
                                 <a class="block px-2 py-1 rounded {% if nav_active_payments %}text-primary font-semibold bg-background-light dark:bg-background-dark{% else %}text-text-light dark:text-text-dark hover:bg-background-light dark:hover:bg-background-dark{% endif %}" href="{{ url_for('payments.list_payments') }}">
                                     <i class="fas fa-credit-card w-4 mr-2"></i>{{ _('Payments') }}

app/templates/email/invoice.html

@@ -0,0 +1,111 @@
+<!DOCTYPE html>
+<html>
+<head>
+    <meta charset="UTF-8">
+    <style>
+        body {
+            font-family: Arial, sans-serif;
+            line-height: 1.6;
+            color: #333;
+            max-width: 600px;
+            margin: 0 auto;
+            padding: 20px;
+        }
+        .header {
+            background-color: #3b82f6;
+            color: white;
+            padding: 20px;
+            text-align: center;
+            border-radius: 5px;
+        }
+        .content {
+            background-color: #f9fafb;
+            padding: 20px;
+            margin-top: 20px;
+            border-radius: 5px;
+        }
+        .invoice-details {
+            background-color: white;
+            padding: 15px;
+            margin: 15px 0;
+            border-left: 4px solid #3b82f6;
+        }
+        .invoice-details table {
+            width: 100%;
+            border-collapse: collapse;
+        }
+        .invoice-details td {
+            padding: 8px 0;
+        }
+        .invoice-details td:first-child {
+            font-weight: bold;
+            width: 40%;
+        }
+        .custom-message {
+            background-color: #fef3c7;
+            padding: 15px;
+            margin: 15px 0;
+            border-left: 4px solid #f59e0b;
+            border-radius: 5px;
+        }
+        .footer {
+            text-align: center;
+            color: #6b7280;
+            font-size: 12px;
+            margin-top: 30px;
+            padding-top: 20px;
+            border-top: 1px solid #e5e7eb;
+        }
+    </style>
+</head>
+<body>
+    <div class="header">
+        <h1>Invoice {{ invoice.invoice_number }}</h1>
+    </div>
+    
+    <div class="content">
+        <p>Hello,</p>
+        
+        <p>Please find attached invoice <strong>{{ invoice.invoice_number }}</strong> for your records.</p>
+        
+        <div class="invoice-details">
+            <table>
+                <tr>
+                    <td>Invoice Number:</td>
+                    <td>{{ invoice.invoice_number }}</td>
+                </tr>
+                <tr>
+                    <td>Issue Date:</td>
+                    <td>{{ invoice.issue_date.strftime('%Y-%m-%d') if invoice.issue_date else 'N/A' }}</td>
+                </tr>
+                <tr>
+                    <td>Due Date:</td>
+                    <td>{{ invoice.due_date.strftime('%Y-%m-%d') if invoice.due_date else 'N/A' }}</td>
+                </tr>
+                <tr>
+                    <td>Amount:</td>
+                    <td><strong>{{ invoice.currency_code }} {{ invoice.total_amount }}</strong></td>
+                </tr>
+            </table>
+        </div>
+        
+        {% if custom_message %}
+        <div class="custom-message">
+            <p><strong>Message:</strong></p>
+            <p>{{ custom_message }}</p>
+        </div>
+        {% endif %}
+        
+        <p>Please remit payment by the due date.</p>
+        
+        <p>Thank you for your business!</p>
+    </div>
+    
+    <div class="footer">
+        <p><strong>{{ company_name }}</strong></p>
+        <p>TimeTracker - Time Tracking & Project Management</p>
+        <p>This invoice was sent automatically. Please contact us if you have any questions.</p>
+    </div>
+</body>
+</html>
+

app/templates/invoices/edit.html

@@ -10,6 +10,9 @@
         <a href="{{ url_for('invoices.view_invoice', invoice_id=invoice.id) }}" class="bg-gray-200 dark:bg-gray-700 px-4 py-2 rounded-lg hover:bg-gray-300 dark:hover:bg-gray-600 transition">
             <i class="fas fa-arrow-left mr-2"></i>{{ _('Back') }}
         </a>
+        <button type="button" onclick="showSendEmailModal()" class="bg-blue-500 text-white px-4 py-2 rounded-lg hover:bg-blue-600">
+            <i class="fas fa-envelope mr-1"></i>{{ _('Send Email') }}
+        </button>
     </div>
 </div>
 
@@ -522,4 +525,122 @@ document.addEventListener('DOMContentLoaded', function() {
     });
 });
 </script>
+
+<!-- Send Email Modal -->
+<div id="sendEmailModal" class="hidden fixed inset-0 bg-gray-600 bg-opacity-50 overflow-y-auto h-full w-full z-50">
+  <div class="relative top-20 mx-auto p-5 border w-96 shadow-lg rounded-md bg-white dark:bg-gray-800">
+    <div class="mt-3">
+      <h3 class="text-lg font-medium text-gray-900 dark:text-gray-100 mb-4">Send Invoice via Email</h3>
+      <form id="sendEmailForm" onsubmit="sendInvoiceEmail(event)">
+        <input type="hidden" name="csrf_token" value="{{ csrf_token() }}">
+        <div class="mb-4">
+          <label for="recipient_email" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Recipient Email *</label>
+          <input type="email" id="recipient_email" name="recipient_email" value="{{ invoice.client_email }}" required class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-700 text-gray-900 dark:text-gray-100">
+        </div>
+        <div class="mb-4">
+          <label for="email_template_id" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Email Template (Optional)</label>
+          <select id="email_template_id" name="email_template_id" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-700 text-gray-900 dark:text-gray-100">
+            <option value="">Default Template</option>
+            {% for template in email_templates %}
+            <option value="{{ template.id }}">{{ template.name }}</option>
+            {% endfor %}
+          </select>
+        </div>
+        <div class="mb-4">
+          <label for="custom_message" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Custom Message (Optional)</label>
+          <textarea id="custom_message" name="custom_message" rows="4" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-700 text-gray-900 dark:text-gray-100"></textarea>
+        </div>
+        <div class="flex justify-end space-x-3">
+          <button type="button" onclick="hideSendEmailModal()" class="px-4 py-2 bg-gray-300 dark:bg-gray-600 text-gray-700 dark:text-gray-200 rounded-lg hover:bg-gray-400 dark:hover:bg-gray-500">Cancel</button>
+          <button type="submit" class="px-4 py-2 bg-blue-500 text-white rounded-lg hover:bg-blue-600">Send Email</button>
+        </div>
+      </form>
+    </div>
+  </div>
+</div>
+
+<script>
+function showSendEmailModal() {
+  const modal = document.getElementById('sendEmailModal');
+  if (modal) modal.classList.remove('hidden');
+}
+
+function hideSendEmailModal() {
+  const modal = document.getElementById('sendEmailModal');
+  if (modal) modal.classList.add('hidden');
+}
+
+function sendInvoiceEmail(event) {
+  event.preventDefault();
+  const form = event.target;
+  const formData = new FormData(form);
+  
+  // Show loading state
+  const submitBtn = form.querySelector('button[type="submit"]');
+  const originalText = submitBtn.textContent;
+  submitBtn.disabled = true;
+  submitBtn.textContent = 'Sending...';
+  
+  fetch("{{ url_for('invoices.send_invoice_email_route', invoice_id=invoice.id) }}", {
+    method: 'POST',
+    body: formData
+  })
+  .then(async response => {
+    // Check content type to determine how to parse
+    const contentType = response.headers.get('content-type') || '';
+    const isJson = contentType.includes('application/json');
+    
+    // Always try JSON first if content-type suggests it, otherwise read as text
+    if (isJson) {
+      const data = await response.json();
+      // Handle both success and error responses
+      if (!response.ok) {
+        return { success: false, error: data.error || data.message || `HTTP ${response.status}: ${response.statusText}` };
+      }
+      return data;
+    } else {
+      // Not JSON, read as text (only once)
+      const text = await response.text();
+      if (!response.ok) {
+        throw new Error(text || `HTTP ${response.status}: ${response.statusText}`);
+      }
+      // If successful but not JSON, return error format
+      return { success: false, error: text || 'Unexpected response format' };
+    }
+  })
+  .then(data => {
+    if (data.success) {
+      if (window.toastManager) {
+        window.toastManager.success('Invoice email sent successfully!');
+      } else {
+        alert('Invoice email sent successfully!');
+      }
+      hideSendEmailModal();
+      // Optionally reload the page to show updated status
+      setTimeout(() => window.location.reload(), 1000);
+    } else {
+      const errorMsg = data.error || 'Failed to send email';
+      console.error('Email send error:', errorMsg);
+      if (window.toastManager) {
+        window.toastManager.error('Error: ' + errorMsg);
+      } else {
+        alert('Error: ' + errorMsg);
+      }
+      submitBtn.disabled = false;
+      submitBtn.textContent = originalText;
+    }
+  })
+  .catch(error => {
+    console.error('Email send error:', error);
+    const errorMsg = error.message || 'Failed to send email. Please check server logs for details.';
+    if (window.toastManager) {
+      window.toastManager.error(errorMsg);
+    } else {
+      alert(errorMsg);
+    }
+    submitBtn.disabled = false;
+    submitBtn.textContent = originalText;
+  });
+}
+</script>
 {% endblock %}

app/templates/invoices/list.html

@@ -14,6 +14,7 @@
     breadcrumbs=breadcrumbs,
     actions_html=''
         + '<div class="flex gap-2">'
+        +   '<a href="' + url_for("recurring_invoices.list_recurring_invoices") + '" class="bg-purple-600 text-white px-4 py-2 rounded-lg hover:bg-purple-700 inline-flex items-center"><i class="fas fa-sync-alt mr-2"></i>Recurring Invoices</a>'
         +   '<a href="' + url_for("invoices.export_invoices_excel") + '" class="bg-green-600 text-white px-4 py-2 rounded-lg hover:bg-green-700 inline-flex items-center"><i class="fas fa-file-excel mr-2"></i>Export to Excel</a>'
         +   '<a href="' + url_for("invoices.create_invoice") + '" class="bg-primary text-white px-4 py-2 rounded-lg hover:bg-primary/90 transition-colors"><i class="fas fa-plus mr-2"></i>Create Invoice</a>'
         + '</div>'

app/templates/invoices/view.html

@@ -16,6 +16,9 @@
             </select>
             <a id="export-pdf-link" href="{{ url_for('invoices.export_invoice_pdf', invoice_id=invoice.id) }}" class="bg-secondary text-white px-4 py-2 rounded-lg hover:bg-secondary-dark">Export PDF</a>
         </div>
+        <button type="button" onclick="showSendEmailModal()" class="bg-blue-500 text-white px-4 py-2 rounded-lg hover:bg-blue-600">
+            <i class="fas fa-envelope mr-1"></i>Send Email
+        </button>
         <a href="{{ url_for('payments.create_payment', invoice_id=invoice.id) }}" class="bg-green-500 text-white px-4 py-2 rounded-lg hover:bg-green-600">Record Payment</a>
         <button type="button" onclick="showDeleteModal('{{ invoice.id }}', '{{ invoice.invoice_number }}')" class="bg-red-500 text-white px-4 py-2 rounded-lg hover:bg-red-600">
             <i class="fas fa-trash mr-1"></i>Delete
@@ -276,7 +279,123 @@
   </div>
 </div>
 
+<!-- Send Email Modal -->
+<div id="sendEmailModal" class="hidden fixed inset-0 bg-gray-600 bg-opacity-50 overflow-y-auto h-full w-full z-50">
+  <div class="relative top-20 mx-auto p-5 border w-96 shadow-lg rounded-md bg-white dark:bg-gray-800">
+    <div class="mt-3">
+      <h3 class="text-lg font-medium text-gray-900 dark:text-gray-100 mb-4">Send Invoice via Email</h3>
+      <form id="sendEmailForm" onsubmit="sendInvoiceEmail(event)">
+        <input type="hidden" name="csrf_token" value="{{ csrf_token() }}">
+        <div class="mb-4">
+          <label for="recipient_email" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Recipient Email *</label>
+          <input type="email" id="recipient_email" name="recipient_email" value="{{ invoice.client_email }}" required class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-700 text-gray-900 dark:text-gray-100">
+        </div>
+        <div class="mb-4">
+          <label for="email_template_id" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Email Template (Optional)</label>
+          <select id="email_template_id" name="email_template_id" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-700 text-gray-900 dark:text-gray-100">
+            <option value="">Default Template</option>
+            {% for template in email_templates %}
+            <option value="{{ template.id }}">{{ template.name }}</option>
+            {% endfor %}
+          </select>
+        </div>
+        <div class="mb-4">
+          <label for="custom_message" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Custom Message (Optional)</label>
+          <textarea id="custom_message" name="custom_message" rows="4" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-700 text-gray-900 dark:text-gray-100"></textarea>
+        </div>
+        <div class="flex justify-end space-x-3">
+          <button type="button" onclick="hideSendEmailModal()" class="px-4 py-2 bg-gray-300 dark:bg-gray-600 text-gray-700 dark:text-gray-200 rounded-lg hover:bg-gray-400 dark:hover:bg-gray-500">Cancel</button>
+          <button type="submit" class="px-4 py-2 bg-blue-500 text-white rounded-lg hover:bg-blue-600">Send Email</button>
+        </div>
+      </form>
+    </div>
+  </div>
+</div>
+
 <script>
+function showSendEmailModal() {
+  const modal = document.getElementById('sendEmailModal');
+  if (modal) modal.classList.remove('hidden');
+}
+
+function hideSendEmailModal() {
+  const modal = document.getElementById('sendEmailModal');
+  if (modal) modal.classList.add('hidden');
+}
+
+function sendInvoiceEmail(event) {
+  event.preventDefault();
+  const form = event.target;
+  const formData = new FormData(form);
+  
+  // Show loading state
+  const submitBtn = form.querySelector('button[type="submit"]');
+  const originalText = submitBtn.textContent;
+  submitBtn.disabled = true;
+  submitBtn.textContent = 'Sending...';
+  
+  fetch("{{ url_for('invoices.send_invoice_email_route', invoice_id=invoice.id) }}", {
+    method: 'POST',
+    body: formData
+  })
+  .then(async response => {
+    // Check content type to determine how to parse
+    const contentType = response.headers.get('content-type') || '';
+    const isJson = contentType.includes('application/json');
+    
+    // Always try JSON first if content-type suggests it, otherwise read as text
+    if (isJson) {
+      const data = await response.json();
+      // Handle both success and error responses
+      if (!response.ok) {
+        return { success: false, error: data.error || data.message || `HTTP ${response.status}: ${response.statusText}` };
+      }
+      return data;
+    } else {
+      // Not JSON, read as text (only once)
+      const text = await response.text();
+      if (!response.ok) {
+        throw new Error(text || `HTTP ${response.status}: ${response.statusText}`);
+      }
+      // If successful but not JSON, return error format
+      return { success: false, error: text || 'Unexpected response format' };
+    }
+  })
+  .then(data => {
+    if (data.success) {
+      if (window.toastManager) {
+        window.toastManager.success('Invoice email sent successfully!');
+      } else {
+        alert('Invoice email sent successfully!');
+      }
+      hideSendEmailModal();
+      // Optionally reload the page to show updated status
+      setTimeout(() => window.location.reload(), 1000);
+    } else {
+      const errorMsg = data.error || 'Failed to send email';
+      console.error('Email send error:', errorMsg);
+      if (window.toastManager) {
+        window.toastManager.error('Error: ' + errorMsg);
+      } else {
+        alert('Error: ' + errorMsg);
+      }
+      submitBtn.disabled = false;
+      submitBtn.textContent = originalText;
+    }
+  })
+  .catch(error => {
+    console.error('Email send error:', error);
+    const errorMsg = error.message || 'Failed to send email. Please check server logs for details.';
+    if (window.toastManager) {
+      window.toastManager.error(errorMsg);
+    } else {
+      alert(errorMsg);
+    }
+    submitBtn.disabled = false;
+    submitBtn.textContent = originalText;
+  });
+}
+
 function showDeleteModal(invoiceId, invoiceNumber) {
   const numberEl = document.getElementById('deleteInvoiceNumber');
   const formEl = document.getElementById('deleteInvoiceForm');

app/templates/recurring_invoices/create.html

@@ -0,0 +1,167 @@
+{% extends "base.html" %}
+{% from "components/ui.html" import page_header %}
+
+{% block content %}
+{% set breadcrumbs = [
+    {'text': 'Recurring Invoices', 'url': url_for('recurring_invoices.list_recurring_invoices')},
+    {'text': 'Create'}
+] %}
+
+{{ page_header(
+    icon_class='fas fa-sync-alt',
+    title_text='Create Recurring Invoice',
+    subtitle_text='Set up automated invoice generation',
+    breadcrumbs=breadcrumbs
+) }}
+
+<div class="bg-card-light dark:bg-card-dark p-6 rounded-lg shadow">
+    <form method="POST" class="space-y-6">
+        <input type="hidden" name="csrf_token" value="{{ csrf_token() }}">
+        <div class="grid grid-cols-1 md:grid-cols-2 gap-6">
+            <div>
+                <label for="name" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Template Name *</label>
+                <input type="text" id="name" name="name" required class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+            </div>
+            
+            <div>
+                <label for="project_id" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Project *</label>
+                <select id="project_id" name="project_id" required class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+                    <option value="">Select Project</option>
+                    {% for project in projects %}
+                    <option value="{{ project.id }}" data-client-id="{{ project.client_id if project.client_id else '' }}" data-client-name="{{ project.client_obj.name if project.client_obj else '' }}" data-client-email="{{ project.client_obj.email if project.client_obj else '' }}" data-client-address="{{ project.client_obj.address if project.client_obj else '' }}">{{ project.name }}</option>
+                    {% endfor %}
+                </select>
+            </div>
+            
+            <div>
+                <label for="client_id" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Client *</label>
+                <select id="client_id" name="client_id" required class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+                    <option value="">Select Client</option>
+                    {% for client in clients %}
+                    <option value="{{ client.id }}">{{ client.name }}</option>
+                    {% endfor %}
+                </select>
+            </div>
+            
+            <div>
+                <label for="frequency" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Frequency *</label>
+                <select id="frequency" name="frequency" required class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+                    <option value="daily">Daily</option>
+                    <option value="weekly">Weekly</option>
+                    <option value="monthly" selected>Monthly</option>
+                    <option value="yearly">Yearly</option>
+                </select>
+            </div>
+            
+            <div>
+                <label for="interval" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Interval</label>
+                <input type="number" id="interval" name="interval" value="1" min="1" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+                <p class="text-xs text-gray-500 mt-1">Every N periods (e.g., every 2 weeks)</p>
+            </div>
+            
+            <div>
+                <label for="next_run_date" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Next Run Date *</label>
+                <input type="date" id="next_run_date" name="next_run_date" value="{{ default_next_run_date }}" required class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+            </div>
+            
+            <div>
+                <label for="end_date" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">End Date (Optional)</label>
+                <input type="date" id="end_date" name="end_date" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+            </div>
+            
+            <div>
+                <label for="due_date_days" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Due Date (Days from Issue)</label>
+                <input type="number" id="due_date_days" name="due_date_days" value="30" min="1" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+            </div>
+            
+            <div>
+                <label for="tax_rate" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Tax Rate (%)</label>
+                <input type="number" id="tax_rate" name="tax_rate" value="0" step="0.01" min="0" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+            </div>
+        </div>
+        
+        <div>
+            <label for="client_name" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Client Name</label>
+            <input type="text" id="client_name" name="client_name" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+        </div>
+        
+        <div>
+            <label for="client_email" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Client Email</label>
+            <input type="email" id="client_email" name="client_email" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+        </div>
+        
+        <div>
+            <label for="client_address" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Client Address</label>
+            <textarea id="client_address" name="client_address" rows="3" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100"></textarea>
+        </div>
+        
+        <div>
+            <label for="notes" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Notes</label>
+            <textarea id="notes" name="notes" rows="3" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100"></textarea>
+        </div>
+        
+        <div>
+            <label for="terms" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Terms</label>
+            <textarea id="terms" name="terms" rows="3" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100"></textarea>
+        </div>
+        
+        <div class="flex items-center space-x-4">
+            <label class="flex items-center">
+                <input type="checkbox" name="auto_send" class="mr-2">
+                <span class="text-sm text-gray-700 dark:text-gray-300">Automatically send invoices via email when generated</span>
+            </label>
+        </div>
+        
+        <div class="flex items-center space-x-4">
+            <label class="flex items-center">
+                <input type="checkbox" name="auto_include_time_entries" checked class="mr-2">
+                <span class="text-sm text-gray-700 dark:text-gray-300">Automatically include unbilled time entries</span>
+            </label>
+        </div>
+        
+        <div class="flex justify-end space-x-4">
+            <a href="{{ url_for('recurring_invoices.list_recurring_invoices') }}" class="px-4 py-2 border border-gray-300 dark:border-gray-600 rounded-lg hover:bg-gray-50 dark:hover:bg-gray-800">Cancel</a>
+            <button type="submit" class="px-4 py-2 bg-primary text-white rounded-lg hover:bg-primary/90">Create Recurring Invoice</button>
+        </div>
+    </form>
+</div>
+
+<script>
+document.addEventListener('DOMContentLoaded', function() {
+    var projectSelect = document.getElementById('project_id');
+    var clientSelect = document.getElementById('client_id');
+    var clientName = document.getElementById('client_name');
+    var clientEmail = document.getElementById('client_email');
+    var clientAddress = document.getElementById('client_address');
+
+    if (projectSelect && clientSelect) {
+        projectSelect.addEventListener('change', function() {
+            var opt = projectSelect.options[projectSelect.selectedIndex];
+            if (!opt || !opt.value) return;
+            
+            var clientId = opt.getAttribute('data-client-id');
+            var name = opt.getAttribute('data-client-name') || '';
+            var email = opt.getAttribute('data-client-email') || '';
+            var address = opt.getAttribute('data-client-address') || '';
+            
+            // Set client dropdown
+            if (clientId) {
+                clientSelect.value = clientId;
+            }
+            
+            // Set client details fields
+            if (name && clientName) {
+                clientName.value = name;
+            }
+            if (email && clientEmail) {
+                clientEmail.value = email;
+            }
+            if (address && clientAddress) {
+                clientAddress.value = address;
+            }
+        });
+    }
+});
+</script>
+{% endblock %}
+

app/templates/recurring_invoices/edit.html

@@ -0,0 +1,116 @@
+{% extends "base.html" %}
+{% from "components/ui.html" import page_header %}
+
+{% block content %}
+{% set breadcrumbs = [
+    {'text': 'Recurring Invoices', 'url': url_for('recurring_invoices.list_recurring_invoices')},
+    {'text': recurring.name, 'url': url_for('recurring_invoices.view_recurring_invoice', recurring_id=recurring.id)},
+    {'text': 'Edit'}
+] %}
+
+{{ page_header(
+    icon_class='fas fa-sync-alt',
+    title_text='Edit Recurring Invoice',
+    subtitle_text=recurring.name,
+    breadcrumbs=breadcrumbs
+) }}
+
+<div class="bg-card-light dark:bg-card-dark p-6 rounded-lg shadow">
+    <form method="POST" class="space-y-6">
+        <input type="hidden" name="csrf_token" value="{{ csrf_token() }}">
+        <div class="grid grid-cols-1 md:grid-cols-2 gap-6">
+            <div>
+                <label for="name" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Template Name *</label>
+                <input type="text" id="name" name="name" value="{{ recurring.name }}" required class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+            </div>
+            
+            <div>
+                <label for="frequency" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Frequency *</label>
+                <select id="frequency" name="frequency" required class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+                    <option value="daily" {% if recurring.frequency == 'daily' %}selected{% endif %}>Daily</option>
+                    <option value="weekly" {% if recurring.frequency == 'weekly' %}selected{% endif %}>Weekly</option>
+                    <option value="monthly" {% if recurring.frequency == 'monthly' %}selected{% endif %}>Monthly</option>
+                    <option value="yearly" {% if recurring.frequency == 'yearly' %}selected{% endif %}>Yearly</option>
+                </select>
+            </div>
+            
+            <div>
+                <label for="interval" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Interval</label>
+                <input type="number" id="interval" name="interval" value="{{ recurring.interval }}" min="1" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+            </div>
+            
+            <div>
+                <label for="next_run_date" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Next Run Date *</label>
+                <input type="date" id="next_run_date" name="next_run_date" value="{{ recurring.next_run_date.strftime('%Y-%m-%d') if recurring.next_run_date else '' }}" required class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+            </div>
+            
+            <div>
+                <label for="end_date" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">End Date (Optional)</label>
+                <input type="date" id="end_date" name="end_date" value="{{ recurring.end_date.strftime('%Y-%m-%d') if recurring.end_date else '' }}" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+            </div>
+            
+            <div>
+                <label for="due_date_days" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Due Date (Days from Issue)</label>
+                <input type="number" id="due_date_days" name="due_date_days" value="{{ recurring.due_date_days }}" min="1" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+            </div>
+            
+            <div>
+                <label for="tax_rate" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Tax Rate (%)</label>
+                <input type="number" id="tax_rate" name="tax_rate" value="{{ recurring.tax_rate }}" step="0.01" min="0" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+            </div>
+        </div>
+        
+        <div>
+            <label for="client_name" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Client Name</label>
+            <input type="text" id="client_name" name="client_name" value="{{ recurring.client_name }}" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+        </div>
+        
+        <div>
+            <label for="client_email" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Client Email</label>
+            <input type="email" id="client_email" name="client_email" value="{{ recurring.client_email or '' }}" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">
+        </div>
+        
+        <div>
+            <label for="client_address" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Client Address</label>
+            <textarea id="client_address" name="client_address" rows="3" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">{{ recurring.client_address or '' }}</textarea>
+        </div>
+        
+        <div>
+            <label for="notes" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Notes</label>
+            <textarea id="notes" name="notes" rows="3" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">{{ recurring.notes or '' }}</textarea>
+        </div>
+        
+        <div>
+            <label for="terms" class="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Terms</label>
+            <textarea id="terms" name="terms" rows="3" class="w-full px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-800 text-gray-900 dark:text-gray-100">{{ recurring.terms or '' }}</textarea>
+        </div>
+        
+        <div class="flex items-center space-x-4">
+            <label class="flex items-center">
+                <input type="checkbox" name="auto_send" {% if recurring.auto_send %}checked{% endif %} class="mr-2">
+                <span class="text-sm text-gray-700 dark:text-gray-300">Automatically send invoices via email when generated</span>
+            </label>
+        </div>
+        
+        <div class="flex items-center space-x-4">
+            <label class="flex items-center">
+                <input type="checkbox" name="auto_include_time_entries" {% if recurring.auto_include_time_entries %}checked{% endif %} class="mr-2">
+                <span class="text-sm text-gray-700 dark:text-gray-300">Automatically include unbilled time entries</span>
+            </label>
+        </div>
+        
+        <div class="flex items-center space-x-4">
+            <label class="flex items-center">
+                <input type="checkbox" name="is_active" {% if recurring.is_active %}checked{% endif %} class="mr-2">
+                <span class="text-sm text-gray-700 dark:text-gray-300">Active</span>
+            </label>
+        </div>
+        
+        <div class="flex justify-end space-x-4">
+            <a href="{{ url_for('recurring_invoices.view_recurring_invoice', recurring_id=recurring.id) }}" class="px-4 py-2 border border-gray-300 dark:border-gray-600 rounded-lg hover:bg-gray-50 dark:hover:bg-gray-800">Cancel</a>
+            <button type="submit" class="px-4 py-2 bg-primary text-white rounded-lg hover:bg-primary/90">Update Recurring Invoice</button>
+        </div>
+    </form>
+</div>
+{% endblock %}
+

app/templates/recurring_invoices/list.html

@@ -0,0 +1,114 @@
+{% extends "base.html" %}
+{% from "components/ui.html" import page_header, button %}
+
+{% block content %}
+{% set breadcrumbs = [
+    {'text': 'Recurring Invoices'}
+] %}
+
+{{ page_header(
+    icon_class='fas fa-sync-alt',
+    title_text='Recurring Invoices',
+    subtitle_text='Automate invoice generation for subscription-based billing',
+    breadcrumbs=breadcrumbs,
+    actions_html=''
+        + '<a href="' + url_for("recurring_invoices.create_recurring_invoice") + '" class="bg-primary text-white px-4 py-2 rounded-lg hover:bg-primary/90 transition-colors"><i class="fas fa-plus mr-2"></i>Create Recurring Invoice</a>'
+) }}
+
+<div class="bg-card-light dark:bg-card-dark p-6 rounded-lg shadow">
+    <div class="overflow-x-auto">
+        <table class="min-w-full divide-y divide-gray-200 dark:divide-gray-700">
+            <thead class="bg-gray-50 dark:bg-gray-800">
+                <tr>
+                    <th class="px-6 py-3 text-left text-xs font-medium text-gray-500 dark:text-gray-400 uppercase tracking-wider">Name</th>
+                    <th class="px-6 py-3 text-left text-xs font-medium text-gray-500 dark:text-gray-400 uppercase tracking-wider">Project</th>
+                    <th class="px-6 py-3 text-left text-xs font-medium text-gray-500 dark:text-gray-400 uppercase tracking-wider">Client</th>
+                    <th class="px-6 py-3 text-left text-xs font-medium text-gray-500 dark:text-gray-400 uppercase tracking-wider">Frequency</th>
+                    <th class="px-6 py-3 text-left text-xs font-medium text-gray-500 dark:text-gray-400 uppercase tracking-wider">Next Run</th>
+                    <th class="px-6 py-3 text-left text-xs font-medium text-gray-500 dark:text-gray-400 uppercase tracking-wider">Status</th>
+                    <th class="px-6 py-3 text-left text-xs font-medium text-gray-500 dark:text-gray-400 uppercase tracking-wider">Actions</th>
+                </tr>
+            </thead>
+            <tbody class="bg-white dark:bg-gray-900 divide-y divide-gray-200 dark:divide-gray-700">
+                {% for recurring in recurring_invoices %}
+                <tr>
+                    <td class="px-6 py-4 whitespace-nowrap">
+                        <div class="text-sm font-medium text-gray-900 dark:text-gray-100">{{ recurring.name }}</div>
+                    </td>
+                    <td class="px-6 py-4 whitespace-nowrap">
+                        <div class="text-sm text-gray-500 dark:text-gray-400">{{ recurring.project.name if recurring.project else 'N/A' }}</div>
+                    </td>
+                    <td class="px-6 py-4 whitespace-nowrap">
+                        <div class="text-sm text-gray-500 dark:text-gray-400">{{ recurring.client_name }}</div>
+                    </td>
+                    <td class="px-6 py-4 whitespace-nowrap">
+                        <div class="text-sm text-gray-500 dark:text-gray-400">
+                            Every {{ recurring.interval }} {{ recurring.frequency }}{{ 's' if recurring.interval > 1 else '' }}
+                        </div>
+                    </td>
+                    <td class="px-6 py-4 whitespace-nowrap">
+                        <div class="text-sm text-gray-500 dark:text-gray-400">{{ recurring.next_run_date.strftime('%Y-%m-%d') if recurring.next_run_date else 'N/A' }}</div>
+                    </td>
+                    <td class="px-6 py-4 whitespace-nowrap">
+                        {% if recurring.is_active %}
+                        <span class="px-2 inline-flex text-xs leading-5 font-semibold rounded-full bg-green-100 text-green-800 dark:bg-green-900 dark:text-green-200">Active</span>
+                        {% else %}
+                        <span class="px-2 inline-flex text-xs leading-5 font-semibold rounded-full bg-gray-100 text-gray-800 dark:bg-gray-900 dark:text-gray-200">Inactive</span>
+                        {% endif %}
+                    </td>
+                    <td class="px-6 py-4 whitespace-nowrap text-sm font-medium">
+                        <a href="{{ url_for('recurring_invoices.view_recurring_invoice', recurring_id=recurring.id) }}" class="text-primary hover:text-primary/80 mr-3">View</a>
+                        <a href="{{ url_for('recurring_invoices.edit_recurring_invoice', recurring_id=recurring.id) }}" class="text-blue-600 hover:text-blue-900 mr-3">Edit</a>
+                        <button onclick="generateInvoice({{ recurring.id }})" class="text-green-600 hover:text-green-900 mr-3">Generate Now</button>
+                        <form method="POST" action="{{ url_for('recurring_invoices.delete_recurring_invoice', recurring_id=recurring.id) }}" class="inline" onsubmit="return confirm('Are you sure you want to delete this recurring invoice?');">
+                            <input type="hidden" name="csrf_token" value="{{ csrf_token() }}">
+                            <button type="submit" class="text-red-600 hover:text-red-900">Delete</button>
+                        </form>
+                    </td>
+                </tr>
+                {% else %}
+                <tr>
+                    <td colspan="7" class="px-6 py-4 text-center text-gray-500 dark:text-gray-400">No recurring invoices found. <a href="{{ url_for('recurring_invoices.create_recurring_invoice') }}" class="text-primary">Create one</a> to get started.</td>
+                </tr>
+                {% endfor %}
+            </tbody>
+        </table>
+    </div>
+</div>
+
+<script>
+function generateInvoice(recurringId) {
+    if (!confirm('Generate an invoice from this recurring template now?')) {
+        return;
+    }
+    
+    // Get CSRF token from meta tag
+    const csrfToken = document.querySelector('meta[name="csrf-token"]')?.content || '';
+    
+    fetch(`/recurring-invoices/${recurringId}/generate`, {
+        method: 'POST',
+        headers: {
+            'Content-Type': 'application/json',
+            'X-CSRFToken': csrfToken
+        },
+        body: JSON.stringify({
+            csrf_token: csrfToken
+        })
+    })
+    .then(response => response.json())
+    .then(data => {
+        if (data.success) {
+            alert(`Invoice ${data.invoice_number} generated successfully!`);
+            window.location.href = `/invoices/${data.invoice_id}/edit`;
+        } else {
+            alert('Error: ' + (data.error || 'Failed to generate invoice'));
+        }
+    })
+    .catch(error => {
+        console.error('Error:', error);
+        alert('Failed to generate invoice');
+    });
+}
+</script>
+{% endblock %}
+

app/templates/recurring_invoices/view.html

@@ -0,0 +1,159 @@
+{% extends "base.html" %}
+{% from "components/ui.html" import page_header %}
+
+{% block content %}
+{% set breadcrumbs = [
+    {'text': 'Recurring Invoices', 'url': url_for('recurring_invoices.list_recurring_invoices')},
+    {'text': recurring.name}
+] %}
+
+{{ page_header(
+    icon_class='fas fa-sync-alt',
+    title_text=recurring.name,
+    subtitle_text='Recurring Invoice Template',
+    breadcrumbs=breadcrumbs,
+    actions_html=''
+        + '<a href="' + url_for("recurring_invoices.edit_recurring_invoice", recurring_id=recurring.id) + '" class="bg-blue-600 text-white px-4 py-2 rounded-lg hover:bg-blue-700 mr-2">Edit</a>'
+        + '<button onclick="generateInvoice(' + recurring.id|string + ')" class="bg-green-600 text-white px-4 py-2 rounded-lg hover:bg-green-700">Generate Now</button>'
+) }}
+
+<div class="grid grid-cols-1 md:grid-cols-2 gap-6 mb-6">
+    <div class="bg-card-light dark:bg-card-dark p-6 rounded-lg shadow">
+        <h3 class="text-lg font-semibold mb-4">Template Details</h3>
+        <dl class="space-y-2">
+            <dt class="text-sm font-medium text-gray-500 dark:text-gray-400">Project</dt>
+            <dd class="text-sm text-gray-900 dark:text-gray-100">{{ recurring.project.name if recurring.project else 'N/A' }}</dd>
+            
+            <dt class="text-sm font-medium text-gray-500 dark:text-gray-400">Client</dt>
+            <dd class="text-sm text-gray-900 dark:text-gray-100">{{ recurring.client_name }}</dd>
+            
+            <dt class="text-sm font-medium text-gray-500 dark:text-gray-400">Frequency</dt>
+            <dd class="text-sm text-gray-900 dark:text-gray-100">Every {{ recurring.interval }} {{ recurring.frequency }}{{ 's' if recurring.interval > 1 else '' }}</dd>
+            
+            <dt class="text-sm font-medium text-gray-500 dark:text-gray-400">Next Run Date</dt>
+            <dd class="text-sm text-gray-900 dark:text-gray-100">{{ recurring.next_run_date.strftime('%Y-%m-%d') if recurring.next_run_date else 'N/A' }}</dd>
+            
+            {% if recurring.end_date %}
+            <dt class="text-sm font-medium text-gray-500 dark:text-gray-400">End Date</dt>
+            <dd class="text-sm text-gray-900 dark:text-gray-100">{{ recurring.end_date.strftime('%Y-%m-%d') }}</dd>
+            {% endif %}
+            
+            <dt class="text-sm font-medium text-gray-500 dark:text-gray-400">Status</dt>
+            <dd class="text-sm">
+                {% if recurring.is_active %}
+                <span class="px-2 inline-flex text-xs leading-5 font-semibold rounded-full bg-green-100 text-green-800 dark:bg-green-900 dark:text-green-200">Active</span>
+                {% else %}
+                <span class="px-2 inline-flex text-xs leading-5 font-semibold rounded-full bg-gray-100 text-gray-800 dark:bg-gray-900 dark:text-gray-200">Inactive</span>
+                {% endif %}
+            </dd>
+        </dl>
+    </div>
+    
+    <div class="bg-card-light dark:bg-card-dark p-6 rounded-lg shadow">
+        <h3 class="text-lg font-semibold mb-4">Invoice Settings</h3>
+        <dl class="space-y-2">
+            <dt class="text-sm font-medium text-gray-500 dark:text-gray-400">Due Date (Days)</dt>
+            <dd class="text-sm text-gray-900 dark:text-gray-100">{{ recurring.due_date_days }} days from issue date</dd>
+            
+            <dt class="text-sm font-medium text-gray-500 dark:text-gray-400">Tax Rate</dt>
+            <dd class="text-sm text-gray-900 dark:text-gray-100">{{ recurring.tax_rate }}%</dd>
+            
+            <dt class="text-sm font-medium text-gray-500 dark:text-gray-400">Currency</dt>
+            <dd class="text-sm text-gray-900 dark:text-gray-100">{{ recurring.currency_code }}</dd>
+            
+            <dt class="text-sm font-medium text-gray-500 dark:text-gray-400">Auto Send</dt>
+            <dd class="text-sm text-gray-900 dark:text-gray-100">
+                {% if recurring.auto_send %}
+                <span class="text-green-600">Yes</span>
+                {% else %}
+                <span class="text-gray-500">No</span>
+                {% endif %}
+            </dd>
+            
+            <dt class="text-sm font-medium text-gray-500 dark:text-gray-400">Auto Include Time Entries</dt>
+            <dd class="text-sm text-gray-900 dark:text-gray-100">
+                {% if recurring.auto_include_time_entries %}
+                <span class="text-green-600">Yes</span>
+                {% else %}
+                <span class="text-gray-500">No</span>
+                {% endif %}
+            </dd>
+            
+            {% if recurring.last_generated_at %}
+            <dt class="text-sm font-medium text-gray-500 dark:text-gray-400">Last Generated</dt>
+            <dd class="text-sm text-gray-900 dark:text-gray-100">{{ recurring.last_generated_at.strftime('%Y-%m-%d %H:%M') }}</dd>
+            {% endif %}
+        </dl>
+    </div>
+</div>
+
+{% if generated_invoices %}
+<div class="bg-card-light dark:bg-card-dark p-6 rounded-lg shadow">
+    <h3 class="text-lg font-semibold mb-4">Recently Generated Invoices</h3>
+    <div class="overflow-x-auto">
+        <table class="min-w-full divide-y divide-gray-200 dark:divide-gray-700">
+            <thead class="bg-gray-50 dark:bg-gray-800">
+                <tr>
+                    <th class="px-6 py-3 text-left text-xs font-medium text-gray-500 dark:text-gray-400 uppercase">Invoice Number</th>
+                    <th class="px-6 py-3 text-left text-xs font-medium text-gray-500 dark:text-gray-400 uppercase">Issue Date</th>
+                    <th class="px-6 py-3 text-left text-xs font-medium text-gray-500 dark:text-gray-400 uppercase">Amount</th>
+                    <th class="px-6 py-3 text-left text-xs font-medium text-gray-500 dark:text-gray-400 uppercase">Status</th>
+                    <th class="px-6 py-3 text-left text-xs font-medium text-gray-500 dark:text-gray-400 uppercase">Actions</th>
+                </tr>
+            </thead>
+            <tbody class="bg-white dark:bg-gray-900 divide-y divide-gray-200 dark:divide-gray-700">
+                {% for invoice in generated_invoices %}
+                <tr>
+                    <td class="px-6 py-4 whitespace-nowrap text-sm text-gray-900 dark:text-gray-100">{{ invoice.invoice_number }}</td>
+                    <td class="px-6 py-4 whitespace-nowrap text-sm text-gray-500 dark:text-gray-400">{{ invoice.issue_date.strftime('%Y-%m-%d') if invoice.issue_date else 'N/A' }}</td>
+                    <td class="px-6 py-4 whitespace-nowrap text-sm text-gray-500 dark:text-gray-400">{{ invoice.currency_code }} {{ invoice.total_amount }}</td>
+                    <td class="px-6 py-4 whitespace-nowrap text-sm">
+                        <span class="px-2 inline-flex text-xs leading-5 font-semibold rounded-full bg-blue-100 text-blue-800 dark:bg-blue-900 dark:text-blue-200">{{ invoice.status }}</span>
+                    </td>
+                    <td class="px-6 py-4 whitespace-nowrap text-sm font-medium">
+                        <a href="{{ url_for('invoices.view_invoice', invoice_id=invoice.id) }}" class="text-primary hover:text-primary/80">View</a>
+                    </td>
+                </tr>
+                {% endfor %}
+            </tbody>
+        </table>
+    </div>
+</div>
+{% endif %}
+
+<script>
+function generateInvoice(recurringId) {
+    if (!confirm('Generate an invoice from this recurring template now?')) {
+        return;
+    }
+    
+    // Get CSRF token from meta tag
+    const csrfToken = document.querySelector('meta[name="csrf-token"]')?.content || '';
+    
+    fetch(`/recurring-invoices/${recurringId}/generate`, {
+        method: 'POST',
+        headers: {
+            'Content-Type': 'application/json',
+            'X-CSRFToken': csrfToken
+        },
+        body: JSON.stringify({
+            csrf_token: csrfToken
+        })
+    })
+    .then(response => response.json())
+    .then(data => {
+        if (data.success) {
+            alert(`Invoice ${data.invoice_number} generated successfully!`);
+            window.location.href = `/invoices/${data.invoice_id}/edit`;
+        } else {
+            alert('Error: ' + (data.error || 'Failed to generate invoice'));
+        }
+    })
+    .catch(error => {
+        console.error('Error:', error);
+        alert('Failed to generate invoice');
+    });
+}
+</script>
+{% endblock %}
+

app/utils/email.py

@@ -2,9 +2,11 @@
 
 import os
 from flask import current_app, render_template, url_for
+from jinja2 import Template as JinjaTemplate
 from flask_mail import Mail, Message
 from threading import Thread
 from datetime import datetime, timedelta
+from app import db
 
 
 mail = Mail()
@@ -463,3 +465,228 @@ TimeTracker - Time Tracking & Project Management
         current_app.logger.exception("[EMAIL TEST] Full exception trace:")
         return False, f'Failed to send test email: {str(e)}'
 
+
+def send_invoice_email(invoice, recipient_email, sender_user=None, custom_message=None, email_template_id=None):
+    """Send an invoice via email with PDF attachment
+    
+    Args:
+        invoice: Invoice object
+        recipient_email: Email address to send to
+        sender_user: User object who is sending (for tracking)
+        custom_message: Optional custom message to include in email
+        email_template_id: Optional email template ID to use
+        
+    Returns:
+        tuple: (success: bool, invoice_email: InvoiceEmail or None, message: str)
+    """
+    try:
+        from app.models import InvoiceEmail, Settings
+        
+        current_app.logger.info(f"[INVOICE EMAIL] Sending invoice {invoice.invoice_number} to {recipient_email}")
+        
+        # Generate PDF
+        pdf_bytes = None
+        try:
+            from app.utils.pdf_generator import InvoicePDFGenerator
+            settings = Settings.get_settings()
+            pdf_generator = InvoicePDFGenerator(invoice, settings=settings, page_size='A4')
+            pdf_bytes = pdf_generator.generate_pdf()
+            if not pdf_bytes:
+                raise ValueError("PDF generator returned None")
+            current_app.logger.info(f"[INVOICE EMAIL] PDF generated successfully - size: {len(pdf_bytes)} bytes")
+        except Exception as pdf_error:
+            current_app.logger.warning(f"[INVOICE EMAIL] PDF generation failed, trying fallback: {pdf_error}")
+            current_app.logger.exception("[INVOICE EMAIL] PDF generation error details:")
+            try:
+                from app.utils.pdf_generator_fallback import InvoicePDFGeneratorFallback
+                settings = Settings.get_settings()
+                pdf_generator = InvoicePDFGeneratorFallback(invoice, settings=settings)
+                pdf_bytes = pdf_generator.generate_pdf()
+                if not pdf_bytes:
+                    raise ValueError("PDF fallback generator returned None")
+                current_app.logger.info(f"[INVOICE EMAIL] PDF generated via fallback - size: {len(pdf_bytes)} bytes")
+            except Exception as fallback_error:
+                current_app.logger.error(f"[INVOICE EMAIL] Both PDF generators failed: {fallback_error}")
+                current_app.logger.exception("[INVOICE EMAIL] Fallback PDF generation error details:")
+                return False, None, f'PDF generation failed: {str(fallback_error)}'
+        
+        if not pdf_bytes:
+            current_app.logger.error("[INVOICE EMAIL] PDF bytes is None after generation")
+            return False, None, 'PDF generation returned empty result'
+        
+        # Get settings for email subject/body
+        settings = Settings.get_settings()
+        company_name = settings.company_name if settings else 'Your Company'
+        
+        # Create email subject
+        subject = f"Invoice {invoice.invoice_number} from {company_name}"
+        
+        # Get email template if specified
+        html_body = None
+        text_body = None
+        
+        if email_template_id:
+            try:
+                from app.models import InvoiceTemplate
+                email_template = InvoiceTemplate.query.get(email_template_id)
+                if email_template and email_template.html:
+                    # Use custom template
+                    # Ensure the HTML is properly formatted for email
+                    template_html = email_template.html.strip()
+                    
+                    # If CSS is provided separately, wrap it in <style> tags
+                    if email_template.css and email_template.css.strip():
+                        css_content = email_template.css.strip()
+                        # Check if CSS is already wrapped in <style> tags
+                        if not css_content.startswith('<style'):
+                            css_content = f'<style>\n{css_content}\n</style>'
+                        # Insert CSS into HTML if not already present
+                        if '<style>' not in template_html and '</style>' not in template_html:
+                            # Try to insert before </head> or at the beginning if no head tag
+                            if '</head>' in template_html:
+                                template_html = template_html.replace('</head>', f'{css_content}\n</head>')
+                            elif '<body>' in template_html:
+                                template_html = template_html.replace('<body>', f'{css_content}\n<body>')
+                            else:
+                                template_html = f'{css_content}\n{template_html}'
+                    
+                    # Ensure HTML has proper structure
+                    if not template_html.strip().startswith('<!DOCTYPE') and not template_html.strip().startswith('<html'):
+                        # Wrap in minimal HTML structure if needed
+                        if '<html' not in template_html:
+                            template_html = f'''<!DOCTYPE html>
+<html>
+<head>
+    <meta charset="UTF-8">
+</head>
+<body>
+{template_html}
+</body>
+</html>'''
+                    
+                    template = JinjaTemplate(template_html)
+                    html_body = template.render(
+                        invoice=invoice,
+                        company_name=company_name,
+                        custom_message=custom_message
+                    )
+                    # Generate text version from HTML if needed
+                    text_body = f"Invoice {invoice.invoice_number} - Please see attached PDF for details."
+            except Exception as template_error:
+                current_app.logger.warning(f"[INVOICE EMAIL] Custom template failed: {template_error}")
+                current_app.logger.exception("[INVOICE EMAIL] Template error details:")
+        
+        # Fallback to default template
+        if not html_body:
+            # Create email body
+            text_body = f"""
+Hello,
+
+Please find attached invoice {invoice.invoice_number} for your records.
+
+Invoice Details:
+- Invoice Number: {invoice.invoice_number}
+- Issue Date: {invoice.issue_date.strftime('%Y-%m-%d') if invoice.issue_date else 'N/A'}
+- Due Date: {invoice.due_date.strftime('%Y-%m-%d') if invoice.due_date else 'N/A'}
+- Amount: {invoice.currency_code} {invoice.total_amount}
+
+"""
+            
+            if custom_message:
+                text_body += f"\n{custom_message}\n\n"
+            
+            text_body += f"""
+Please remit payment by the due date.
+
+Thank you for your business!
+
+---
+{company_name}
+"""
+            
+            # Render HTML template
+            try:
+                html_body = render_template(
+                    'email/invoice.html',
+                    invoice=invoice,
+                    company_name=company_name,
+                    custom_message=custom_message
+                )
+            except Exception as template_error:
+                current_app.logger.warning(f"[INVOICE EMAIL] HTML template not available: {template_error}")
+                html_body = None
+        
+        # Get sender user ID
+        sender_id = sender_user.id if sender_user else None
+        if not sender_id:
+            # Try to get from invoice creator
+            sender_id = invoice.created_by
+        
+        # Send email synchronously to catch errors
+        attachments = [
+            (f'invoice_{invoice.invoice_number}.pdf', 'application/pdf', pdf_bytes)
+        ]
+        
+        # Create message
+        msg = Message(
+            subject=subject,
+            recipients=[recipient_email],
+            body=text_body,
+            html=html_body,
+            sender=current_app.config['MAIL_DEFAULT_SENDER']
+        )
+        
+        # Add attachments
+        for filename, content_type, data in attachments:
+            msg.attach(filename, content_type, data)
+        
+        # Send synchronously to catch errors
+        try:
+            current_app.logger.info(f"[INVOICE EMAIL] Attempting to send email to {recipient_email}")
+            current_app.logger.debug(f"[INVOICE EMAIL] Email config - Server: {current_app.config.get('MAIL_SERVER')}, Port: {current_app.config.get('MAIL_PORT')}")
+            mail.send(msg)
+            current_app.logger.info(f"[INVOICE EMAIL] ✓ Email sent successfully to {recipient_email}")
+        except Exception as send_error:
+            current_app.logger.error(f"[INVOICE EMAIL] ✗ Failed to send email: {type(send_error).__name__}: {str(send_error)}")
+            current_app.logger.exception("[INVOICE EMAIL] Email send error details:")
+            raise send_error
+        
+        # Create email tracking record
+        invoice_email = InvoiceEmail(
+            invoice_id=invoice.id,
+            recipient_email=recipient_email,
+            subject=subject,
+            sent_by=sender_id
+        )
+        db.session.add(invoice_email)
+        
+        # Update invoice status to 'sent' if it's still 'draft'
+        if invoice.status == 'draft':
+            invoice.status = 'sent'
+        
+        db.session.commit()
+        
+        return True, invoice_email, f'Invoice email sent successfully to {recipient_email}'
+        
+    except Exception as e:
+        current_app.logger.error(f"[INVOICE EMAIL] ✗ Failed to send invoice email: {type(e).__name__}: {str(e)}")
+        current_app.logger.exception("[INVOICE EMAIL] Full exception trace:")
+        
+        # Try to create failed tracking record
+        try:
+            from app.models import InvoiceEmail
+            sender_id = sender_user.id if sender_user else invoice.created_by
+            invoice_email = InvoiceEmail(
+                invoice_id=invoice.id,
+                recipient_email=recipient_email,
+                subject=f"Invoice {invoice.invoice_number}",
+                sent_by=sender_id
+            )
+            invoice_email.mark_failed(str(e))
+            db.session.add(invoice_email)
+            db.session.commit()
+        except Exception:
+            db.session.rollback()
+        
+        return False, None, f'Failed to send invoice email: {str(e)}'
+

app/utils/scheduled_tasks.py

@@ -4,7 +4,7 @@ import logging
 from datetime import datetime, timedelta
 from flask import current_app
 from app import db
-from app.models import Invoice, User, TimeEntry, Project, BudgetAlert
+from app.models import Invoice, User, TimeEntry, Project, BudgetAlert, RecurringInvoice
 from app.utils.email import send_overdue_invoice_notification, send_weekly_summary
 from app.utils.budget_forecasting import check_budget_alerts
 
@@ -189,6 +189,66 @@ def check_project_budget_alerts():
         return 0
 
 
+def generate_recurring_invoices():
+    """Generate invoices from active recurring invoice templates
+    
+    This task should be run daily to check for recurring invoices that need to be generated.
+    """
+    try:
+        logger.info("Generating recurring invoices...")
+        
+        # Get all active recurring invoices that should generate today
+        today = datetime.utcnow().date()
+        recurring_invoices = RecurringInvoice.query.filter(
+            RecurringInvoice.is_active == True,
+            RecurringInvoice.next_run_date <= today
+        ).all()
+        
+        logger.info(f"Found {len(recurring_invoices)} recurring invoices to process")
+        
+        invoices_generated = 0
+        emails_sent = 0
+        
+        for recurring in recurring_invoices:
+            try:
+                # Check if we've reached the end date
+                if recurring.end_date and today > recurring.end_date:
+                    logger.info(f"Recurring invoice {recurring.id} has reached end date, deactivating")
+                    recurring.is_active = False
+                    db.session.commit()
+                    continue
+                
+                # Generate invoice
+                invoice = recurring.generate_invoice()
+                if invoice:
+                    db.session.commit()
+                    invoices_generated += 1
+                    logger.info(f"Generated invoice {invoice.invoice_number} from recurring template {recurring.name}")
+                    
+                    # Auto-send if enabled
+                    if recurring.auto_send and invoice.client_email:
+                        try:
+                            from app.utils.email import send_invoice_email
+                            send_invoice_email(invoice, invoice.client_email, sender_user=recurring.creator)
+                            emails_sent += 1
+                            logger.info(f"Auto-sent invoice {invoice.invoice_number} to {invoice.client_email}")
+                        except Exception as e:
+                            logger.error(f"Failed to auto-send invoice {invoice.invoice_number}: {e}")
+                else:
+                    logger.warning(f"Failed to generate invoice from recurring template {recurring.id}")
+            
+            except Exception as e:
+                logger.error(f"Error processing recurring invoice {recurring.id}: {e}")
+                db.session.rollback()
+        
+        logger.info(f"Generated {invoices_generated} invoices, sent {emails_sent} emails")
+        return invoices_generated
+    
+    except Exception as e:
+        logger.error(f"Error generating recurring invoices: {e}")
+        return 0
+
+
 def register_scheduled_tasks(scheduler):
     """Register all scheduled tasks with APScheduler
     
@@ -233,6 +293,18 @@ def register_scheduled_tasks(scheduler):
         )
         logger.info("Registered budget alerts check task")
         
+        # Generate recurring invoices daily at 8 AM
+        scheduler.add_job(
+            func=generate_recurring_invoices,
+            trigger='cron',
+            hour=8,
+            minute=0,
+            id='generate_recurring_invoices',
+            name='Generate recurring invoices',
+            replace_existing=True
+        )
+        logger.info("Registered recurring invoices generation task")
+        
     except Exception as e:
         logger.error(f"Error registering scheduled tasks: {e}")
 

migrations/versions/045_add_recurring_invoices_and_email_tracking.py

@@ -0,0 +1,116 @@
+"""Add recurring invoices and email tracking
+
+Revision ID: 045
+Revises: 044
+Create Date: 2025-01-22
+
+"""
+from alembic import op
+import sqlalchemy as sa
+from sqlalchemy.dialects import postgresql
+
+
+# revision identifiers, used by Alembic.
+revision = '045'
+down_revision = '044'
+branch_labels = None
+depends_on = None
+
+
+def upgrade():
+    """Create recurring_invoices and invoice_emails tables, add recurring_invoice_id to invoices"""
+    
+    # Create recurring_invoices table
+    op.create_table('recurring_invoices',
+        sa.Column('id', sa.Integer(), nullable=False),
+        sa.Column('name', sa.String(length=200), nullable=False),
+        sa.Column('project_id', sa.Integer(), nullable=False),
+        sa.Column('client_id', sa.Integer(), nullable=False),
+        sa.Column('frequency', sa.String(length=20), nullable=False),
+        sa.Column('interval', sa.Integer(), nullable=False, server_default='1'),
+        sa.Column('next_run_date', sa.Date(), nullable=False),
+        sa.Column('end_date', sa.Date(), nullable=True),
+        sa.Column('client_name', sa.String(length=200), nullable=False),
+        sa.Column('client_email', sa.String(length=200), nullable=True),
+        sa.Column('client_address', sa.Text(), nullable=True),
+        sa.Column('due_date_days', sa.Integer(), nullable=False, server_default='30'),
+        sa.Column('tax_rate', sa.Numeric(precision=5, scale=2), nullable=False, server_default='0'),
+        sa.Column('currency_code', sa.String(length=3), nullable=False, server_default='EUR'),
+        sa.Column('notes', sa.Text(), nullable=True),
+        sa.Column('terms', sa.Text(), nullable=True),
+        sa.Column('template_id', sa.Integer(), nullable=True),
+        sa.Column('auto_send', sa.Boolean(), nullable=False, server_default='false'),
+        sa.Column('auto_include_time_entries', sa.Boolean(), nullable=False, server_default='true'),
+        sa.Column('is_active', sa.Boolean(), nullable=False, server_default='true'),
+        sa.Column('created_by', sa.Integer(), nullable=False),
+        sa.Column('created_at', sa.DateTime(), nullable=False, server_default=sa.text('CURRENT_TIMESTAMP')),
+        sa.Column('updated_at', sa.DateTime(), nullable=False, server_default=sa.text('CURRENT_TIMESTAMP')),
+        sa.Column('last_generated_at', sa.DateTime(), nullable=True),
+        sa.ForeignKeyConstraint(['project_id'], ['projects.id'], ondelete='CASCADE'),
+        sa.ForeignKeyConstraint(['client_id'], ['clients.id'], ondelete='CASCADE'),
+        sa.ForeignKeyConstraint(['created_by'], ['users.id'], ondelete='CASCADE'),
+        sa.ForeignKeyConstraint(['template_id'], ['invoice_templates.id'], ondelete='SET NULL'),
+        sa.PrimaryKeyConstraint('id')
+    )
+    
+    # Create indexes for recurring_invoices
+    op.create_index('ix_recurring_invoices_project_id', 'recurring_invoices', ['project_id'])
+    op.create_index('ix_recurring_invoices_client_id', 'recurring_invoices', ['client_id'])
+    op.create_index('ix_recurring_invoices_next_run_date', 'recurring_invoices', ['next_run_date'])
+    op.create_index('ix_recurring_invoices_is_active', 'recurring_invoices', ['is_active'])
+    
+    # Create invoice_emails table
+    op.create_table('invoice_emails',
+        sa.Column('id', sa.Integer(), nullable=False),
+        sa.Column('invoice_id', sa.Integer(), nullable=False),
+        sa.Column('recipient_email', sa.String(length=200), nullable=False),
+        sa.Column('subject', sa.String(length=500), nullable=False),
+        sa.Column('sent_at', sa.DateTime(), nullable=False, server_default=sa.text('CURRENT_TIMESTAMP')),
+        sa.Column('sent_by', sa.Integer(), nullable=False),
+        sa.Column('opened_at', sa.DateTime(), nullable=True),
+        sa.Column('opened_count', sa.Integer(), nullable=False, server_default='0'),
+        sa.Column('last_opened_at', sa.DateTime(), nullable=True),
+        sa.Column('paid_at', sa.DateTime(), nullable=True),
+        sa.Column('status', sa.String(length=20), nullable=False, server_default='sent'),
+        sa.Column('error_message', sa.Text(), nullable=True),
+        sa.Column('created_at', sa.DateTime(), nullable=False, server_default=sa.text('CURRENT_TIMESTAMP')),
+        sa.Column('updated_at', sa.DateTime(), nullable=False, server_default=sa.text('CURRENT_TIMESTAMP')),
+        sa.ForeignKeyConstraint(['invoice_id'], ['invoices.id'], ondelete='CASCADE'),
+        sa.ForeignKeyConstraint(['sent_by'], ['users.id'], ondelete='CASCADE'),
+        sa.PrimaryKeyConstraint('id')
+    )
+    
+    # Create indexes for invoice_emails
+    op.create_index('ix_invoice_emails_invoice_id', 'invoice_emails', ['invoice_id'])
+    op.create_index('ix_invoice_emails_recipient_email', 'invoice_emails', ['recipient_email'])
+    op.create_index('ix_invoice_emails_status', 'invoice_emails', ['status'])
+    op.create_index('ix_invoice_emails_sent_at', 'invoice_emails', ['sent_at'])
+    
+    # Add recurring_invoice_id to invoices table
+    op.add_column('invoices', sa.Column('recurring_invoice_id', sa.Integer(), nullable=True))
+    op.create_index('ix_invoices_recurring_invoice_id', 'invoices', ['recurring_invoice_id'])
+    op.create_foreign_key('fk_invoices_recurring_invoice_id', 'invoices', 'recurring_invoices', ['recurring_invoice_id'], ['id'], ondelete='SET NULL')
+
+
+def downgrade():
+    """Remove recurring invoices and email tracking tables"""
+    
+    # Remove recurring_invoice_id from invoices
+    op.drop_constraint('fk_invoices_recurring_invoice_id', 'invoices', type_='foreignkey')
+    op.drop_index('ix_invoices_recurring_invoice_id', table_name='invoices')
+    op.drop_column('invoices', 'recurring_invoice_id')
+    
+    # Drop invoice_emails table
+    op.drop_index('ix_invoice_emails_sent_at', table_name='invoice_emails')
+    op.drop_index('ix_invoice_emails_status', table_name='invoice_emails')
+    op.drop_index('ix_invoice_emails_recipient_email', table_name='invoice_emails')
+    op.drop_index('ix_invoice_emails_invoice_id', table_name='invoice_emails')
+    op.drop_table('invoice_emails')
+    
+    # Drop recurring_invoices table
+    op.drop_index('ix_recurring_invoices_is_active', table_name='recurring_invoices')
+    op.drop_index('ix_recurring_invoices_next_run_date', table_name='recurring_invoices')
+    op.drop_index('ix_recurring_invoices_client_id', table_name='recurring_invoices')
+    op.drop_index('ix_recurring_invoices_project_id', table_name='recurring_invoices')
+    op.drop_table('recurring_invoices')
+