diff --git a/.github/workflows/macos-installer-arm.yml b/.github/workflows/macos-installer-arm.yml
index bb22f47a..9b544ff9 100644
--- a/.github/workflows/macos-installer-arm.yml
+++ b/.github/workflows/macos-installer-arm.yml
@@ -342,6 +342,26 @@ jobs:
                   'qrcode.image.pil',
                   'routes',
                   'main',
+                  # Apprise notification support
+                  'apprise',
+                  'apprise.common', 
+                  'apprise.conversion',
+                  'apprise.decorators',
+                  'apprise.locale',
+                  'apprise.logger',
+                  'apprise.manager',
+                  'apprise.utils',
+                  'apprise.URLBase',
+                  'apprise.AppriseAsset',
+                  'apprise.AppriseAttachment',
+                  'apprise.AppriseConfig',
+                  'apprise.cli',
+                  'apprise.config',
+                  'apprise.attachment',
+                  'apprise.plugins',
+                  'markdown',
+                  'yaml',
+                  'cryptography',
               ],
               hookspath=['hooks'],
               hooksconfig={},
@@ -406,7 +426,7 @@ jobs:
           EOF
 
       - name: Build macOS app bundle
-        run: python -m PyInstaller Huntarr.spec --clean
+        run: python -m PyInstaller Huntarr.spec --clean --collect-all apprise
 
       - name: Create PKG installer
         run: |
diff --git a/.github/workflows/macos-installer-intel.yml b/.github/workflows/macos-installer-intel.yml
index 6130095d..8f4c73b0 100644
--- a/.github/workflows/macos-installer-intel.yml
+++ b/.github/workflows/macos-installer-intel.yml
@@ -338,6 +338,26 @@ jobs:
                   'qrcode.image.pil',
                   'routes',
                   'main',
+                  # Apprise notification support
+                  'apprise',
+                  'apprise.common', 
+                  'apprise.conversion',
+                  'apprise.decorators',
+                  'apprise.locale',
+                  'apprise.logger',
+                  'apprise.manager',
+                  'apprise.utils',
+                  'apprise.URLBase',
+                  'apprise.AppriseAsset',
+                  'apprise.AppriseAttachment',
+                  'apprise.AppriseConfig',
+                  'apprise.cli',
+                  'apprise.config',
+                  'apprise.attachment',
+                  'apprise.plugins',
+                  'markdown',
+                  'yaml',
+                  'cryptography',
               ],
               hookspath=['hooks'],
               hooksconfig={},
@@ -402,7 +422,7 @@ jobs:
           EOF
 
       - name: Build macOS app bundle
-        run: python -m PyInstaller Huntarr.spec --clean
+        run: python -m PyInstaller Huntarr.spec --clean --collect-all apprise
 
       - name: Create PKG installer
         run: |
diff --git a/.github/workflows/windows-build-nsis.yml b/.github/workflows/windows-build-nsis.yml
index 792ada05..1b62ace5 100644
--- a/.github/workflows/windows-build-nsis.yml
+++ b/.github/workflows/windows-build-nsis.yml
@@ -45,6 +45,10 @@ jobs:
         pip install -r requirements.txt
         pip install pyinstaller==5.13.0
         pip install pywin32
+        # Explicitly install apprise and its dependencies for Windows build
+        pip install apprise==1.6.0
+        pip install markdown==3.4.3
+        pip install pyyaml==6.0
 
     - name: Create directories
       run: |
@@ -60,7 +64,9 @@ jobs:
         # Use the dedicated build script from the distribution directory
         python -m pip install -r requirements.txt
         python -m pip install pywin32
-        pyinstaller -y distribution/windows/huntarr.spec
+        
+        # Build with apprise support - use --collect-all apprise to fix attachment directory error
+        pyinstaller -y --collect-all apprise distribution/windows/huntarr.spec
         
         # Display contents of dist/Huntarr
         dir dist/Huntarr
diff --git a/distribution/windows/build.py b/distribution/windows/build.py
index 473885fc..fadc1085 100644
--- a/distribution/windows/build.py
+++ b/distribution/windows/build.py
@@ -64,7 +64,8 @@ def build_exe():
     # Make sure we're in the project root directory when running PyInstaller
     # This helps with finding relative paths
     # Add the -y option to force overwrite of the output directory
-    result = run_command([sys.executable, "-m", "PyInstaller", "-y", str(spec_file)], cwd=str(ROOT_DIR))
+    # Add --collect-all apprise to bundle all apprise data files and dependencies
+    result = run_command([sys.executable, "-m", "PyInstaller", "-y", "--collect-all", "apprise", str(spec_file)], cwd=str(ROOT_DIR))
     
     if not result:
         print("ERROR: PyInstaller failed to build the executable")
diff --git a/distribution/windows/huntarr.spec b/distribution/windows/huntarr.spec
index 781594a4..4e4874dd 100644
--- a/distribution/windows/huntarr.spec
+++ b/distribution/windows/huntarr.spec
@@ -41,6 +41,27 @@ datas = [
     (str(project_dir / 'src'), 'src'),
 ]
 
+# Add apprise data files to fix attachment directory error
+try:
+    import apprise
+    import os
+    apprise_path = os.path.dirname(apprise.__file__)
+    # Add apprise's attachment, plugins, and config directories
+    apprise_attachment_path = os.path.join(apprise_path, 'attachment')
+    apprise_plugins_path = os.path.join(apprise_path, 'plugins')
+    apprise_config_path = os.path.join(apprise_path, 'config')
+    
+    if os.path.exists(apprise_attachment_path):
+        datas.append((apprise_attachment_path, 'apprise/attachment'))
+    if os.path.exists(apprise_plugins_path):
+        datas.append((apprise_plugins_path, 'apprise/plugins'))
+    if os.path.exists(apprise_config_path):
+        datas.append((apprise_config_path, 'apprise/config'))
+        
+    print(f"Added apprise data directories from: {apprise_path}")
+except ImportError:
+    print("Warning: apprise not found, skipping apprise data files")
+
 # Add tools directory if it exists
 if os.path.exists(str(project_dir / 'tools')):
     datas.append((str(project_dir / 'tools'), 'tools'))