diff --git a/_data/serverState.ts b/_data/serverState.ts
index 5913e3ec9..47ce06b22 100644
--- a/_data/serverState.ts
+++ b/_data/serverState.ts
@@ -29,7 +29,7 @@ const blacklistedGuid = '154B-00EE-0700-9B50CF819816';
 // EBLACKLISTED1
 // EBLACKLISTED2
 // ENOCONN
-const state: string = 'PLUS';
+const state: string = 'ENOKEYFILE';
 
 const uptime = Date.now() - 60 * 60 * 1000; // 1 hour ago
 let expireTime = 0;
@@ -44,7 +44,8 @@ const serverState = {
   expireTime,
   "flashProduct": "SanDisk_3.2Gen1",
   "flashVendor": "USB",
-  "guid": "0781-5583-8355-81071A2B0211",
+  "guid": randomGuid,
+  // "guid": "0781-5583-8355-81071A2B0211",
   "keyfile": "DUMMY_KEYFILE",
   "lanIp": "192.168.254.36",
   "license": "",
@@ -54,7 +55,7 @@ const serverState = {
   "pluginInstalled": false,
   "registered": true,
   "regGen": 0,
-  "regGuid": "0781-5583-8355-81071A2B0211",
+  // "regGuid": "0781-5583-8355-81071A2B0211",
   "site": "http://localhost:4321",
   "state": state,
   "theme": {
diff --git a/components/Modal.vue b/components/Modal.vue
index 3d07fc027..17a542ab1 100644
--- a/components/Modal.vue
+++ b/components/Modal.vue
@@ -98,7 +98,7 @@ const ariaLablledById = computed((): string|undefined => props.title ? `ModalTit
             </header>
             <slot name="main"></slot>
 
-            <footer class="text-14px relative -mx-16px -mb-16px sm:-mx-24px sm:-mb-24px p-4 sm:p-6">
+            <footer v-if="$slots['footer']" class="text-14px relative -mx-16px -mb-16px sm:-mx-24px sm:-mb-24px p-4 sm:p-6">
               <div class="absolute z-0 inset-0 opacity-10 bg-beta"></div>
               <div class="relative z-10">
                 <slot name="footer"></slot>
diff --git a/components/Modals.ce.vue b/components/Modals.ce.vue
index 89c3b6a96..94f06a90d 100644
--- a/components/Modals.ce.vue
+++ b/components/Modals.ce.vue
@@ -5,15 +5,18 @@ import '~/assets/main.css';
 
 import { useCallbackActionsStore } from '~/store/callbackActions';
 import { usePromoStore } from '~/store/promo';
+import { useTrialStore } from '~/store/trial';
 
 const { callbackStatus } = storeToRefs(useCallbackActionsStore());
 const { promoVisible } = storeToRefs(usePromoStore());
+const { trialStatus } = storeToRefs(useTrialStore());
 </script>
 
 <template>
   <div class="relative z-[99999]">
     <UpcCallbackFeedback :open="callbackStatus !== 'ready'" />
     <UpcPromo :open="promoVisible" />
+    <UpcTrial :open="trialStatus === 'requestNew' || trialStatus === 'failed'" />
   </div>
 </template>
 
diff --git a/components/UserProfile/CallbackFeedback.vue b/components/UserProfile/CallbackFeedback.vue
index a7b48e759..f57eec0ff 100644
--- a/components/UserProfile/CallbackFeedback.vue
+++ b/components/UserProfile/CallbackFeedback.vue
@@ -83,6 +83,9 @@ const subheading = computed(() => {
   if (callbackStatus.value === 'success') {
     if (accountActionType.value === 'signIn') return `You're one step closer to enhancing your Unraid experience`;
     if (keyActionType.value === 'purchase') return `Thank you for purchasing an Unraid ${keyType.value} Key!`;
+    if (keyActionType.value === 'replace') return `Your ${keyType.value} Key has been replaced!`;
+    if (keyActionType.value === 'trialExtend') return `Your Trial key has been extended!`;
+    if (keyActionType.value === 'trialStart') return `Your free Trial key provides all the functionality of a Pro Registration key`;
     if (keyActionType.value === 'upgrade') return `Thank you for upgrading to an Unraid ${keyType.value} Key!`;
     return '';
   }
@@ -148,7 +151,7 @@ const { text, copy, copied, isSupported } = useClipboard({ source: keyUrl.value
         <UpcCallbackFeedbackStatus
           v-if="showPromoCta"
           :icon="InformationCircleIcon"
-          :text="'Enhance your Unraid experience with Unraid Connect'" />
+          :text="'Enhance your experience with Unraid Connect'" />
 
         <UpcCallbackFeedbackStatus
           v-if="showSignInCta"
diff --git a/components/UserProfile/DropdownLaunchpad.vue b/components/UserProfile/DropdownLaunchpad.vue
index a61f8abcf..b5f62c0e7 100644
--- a/components/UserProfile/DropdownLaunchpad.vue
+++ b/components/UserProfile/DropdownLaunchpad.vue
@@ -4,15 +4,17 @@ import { useServerStore } from '~/store/server';
 import 'tailwindcss/tailwind.css';
 import '~/assets/main.css';
 
-const { expireTime, pluginInstalled, state, stateData } = storeToRefs(useServerStore());
+const { expireTime, pluginInstalled, registered, state, stateData } = storeToRefs(useServerStore());
+
+const showConnectCopy = computed(() => (pluginInstalled.value && !registered.value));
 
 const heading = computed(() => {
-  if (pluginInstalled.value) return 'Thank you for installing Connect!';
+  if (showConnectCopy.value) return 'Thank you for installing Connect!';
   return stateData.value.heading;
 });
 
 const subheading = computed(() => {
-  if (pluginInstalled.value) return 'Sign In to your Unraid.net account to get started';
+  if (showConnectCopy.value) return 'Sign In to your Unraid.net account to get started';
   return stateData.value.message;
 });
 
@@ -23,7 +25,7 @@ const showExpireTime = computed(() => {
 
 <template>
   <div class="flex flex-col gap-y-24px w-full min-w-300px md:min-w-[500px] max-w-4xl p-16px">
-    <header :class="{ 'text-center': pluginInstalled }">
+    <header :class="{ 'text-center': showConnectCopy }">
       <h2 class="text-24px text-center font-semibold" v-html="heading" />
       <div v-html="subheading" class="flex flex-col gap-y-8px" />
       <UpcUptimeExpire v-if="showExpireTime" class="opacity-75 mt-12px" />
diff --git a/components/UserProfile/Trial.vue b/components/UserProfile/Trial.vue
new file mode 100644
index 000000000..9e795b535
--- /dev/null
+++ b/components/UserProfile/Trial.vue
@@ -0,0 +1,66 @@
+<script lang="ts" setup>
+import { storeToRefs } from "pinia";
+import { useTrialStore } from "~/store/trial";
+
+export interface Props {
+  open?: boolean;
+}
+
+withDefaults(defineProps<Props>(), {
+  open: false,
+});
+
+const trialStore = useTrialStore();
+const { trialStatus } = storeToRefs(trialStore);
+
+const heading = computed(() => {
+  if (trialStatus.value === 'failed') return 'Failed to start your free 30 day trial';
+  if (trialStatus.value === 'requestNew') return 'Starting your free 30 day trial…';
+  if (trialStatus.value === 'success') return 'Free 30 Day Trial Created';
+  return '';
+});
+const subheading = computed(() => {
+  /** @todo show response error */
+  if (trialStatus.value === 'failed') return 'Key server did not return a trial key. Please try again later.';
+  if (trialStatus.value === 'requestNew') return 'Please wait while and keep this window open';
+  if (trialStatus.value === 'success') return 'Please wait while the page reloads to install your trial key';
+  return '';
+});
+
+const close = () => {
+  if (trialStatus.value === 'requestNew') return console.debug("[close] not allowed");
+  trialStore.setTrialStatus('ready');
+};
+</script>
+
+<template>
+  <Modal
+    @close="close"
+    :open="open"
+    :title="heading"
+    :description="subheading"
+    :show-close-x="trialStatus !== 'requestNew'"
+    max-width="max-w-640px"
+  >
+    <template #main>
+      <BrandLoading v-if="trialStatus === 'requestNew'" class="w-[150px] mx-auto my-24px" />
+      <div v-if="trialStatus === 'failed'" class="my-24px">
+        <p class="text-red"></p>
+      </div>
+    </template>
+
+    <template v-if="trialStatus !== 'requestNew'" #footer>
+      <div class="w-full max-w-xs flex flex-col items-center gap-y-16px mx-auto">
+        <div>
+          <button
+            @click="close"
+            class="text-12px tracking-wide inline-block mx-8px opacity-60 hover:opacity-100 focus:opacity-100 underline transition"
+            :title="'Close Modal'"
+          >
+            {{ "Close" }}
+          </button>
+        </div>
+      </div>
+    </template>
+  </Modal>
+</template>
diff --git a/composables/preventClose.ts b/composables/preventClose.ts
new file mode 100644
index 000000000..37e61e773
--- /dev/null
+++ b/composables/preventClose.ts
@@ -0,0 +1,15 @@
+export const preventClose = (e: { preventDefault: () => void; returnValue: string; }) => {
+  e.preventDefault();
+  // eslint-disable-next-line no-param-reassign
+  e.returnValue = '';
+  // eslint-disable-next-line no-alert
+  alert('Closing this pop-up window while actions are being preformed may lead to unintended errors.');
+};
+
+export const addPreventClose = () => {
+  window.addEventListener('beforeunload', preventClose);
+};
+
+export const removePreventClose = () => {
+  window.removeEventListener('beforeunload', preventClose);
+};
\ No newline at end of file
diff --git a/composables/services/keyServer.ts b/composables/services/keyServer.ts
new file mode 100644
index 000000000..161942e83
--- /dev/null
+++ b/composables/services/keyServer.ts
@@ -0,0 +1,33 @@
+import { request } from '~/composables/services/request';
+
+const KeyServer = request.url('https://keys.lime-technology.com');
+
+export interface StartTrialPayload {
+  guid: string;
+  timestamp: number; // timestamp in seconds
+}
+export interface StartTrialResponse {
+  license?: string; 
+  trial?: string
+};
+export const startTrial = (payload: StartTrialPayload) => KeyServer
+  .url('/account/trial')
+  .formUrl(payload)
+  .post();
+
+export interface KeyServerTroubleshootPayload {
+  email: string;
+  subject: string;
+  message: string;
+  guid?: string; // if passed it'll be appended to the email subject instead of date/time
+  comments?: string; // HONEYPOT FIELD. Passing a non-empty value for 'comments' will trigger the honeypot, thus not send an email but won't return any errors.
+}
+export const troubleshoot = (payload: KeyServerTroubleshootPayload) => KeyServer
+  .url('/ips/troubleshoot')
+  .formUrl(payload)
+  .post();
+
+export const validateGuid = (payload: { guid: string }) => KeyServer
+  .url('/validate/guid')
+  .formUrl(payload)
+  .post();
diff --git a/store/callback.ts b/store/callback.ts
index 718053084..cecfd7af4 100644
--- a/store/callback.ts
+++ b/store/callback.ts
@@ -104,16 +104,16 @@ export const useCallbackStoreGeneric = (
   defineStore('callback', () => {
     const callbackActions = useCallbackActions();
     const encryptionKey = 'Uyv2o8e*FiQe8VeLekTqyX6Z*8XonB';
-    const sendType = 'fromUpc';
+    const defaultSendType = 'fromUpc';
 
-    const send = (url: string, payload: SendPayloads) => {
+    const send = (url: string, payload: SendPayloads, sendType?: 'fromUpc' | 'forUpc') => {
       console.debug('[callback.send]');
       const stringifiedData = JSON.stringify({
         actions: [
           ...payload,
         ],
         sender: window.location.href,
-        type: sendType,
+        type: sendType ?? defaultSendType,
       });
       const encryptedMessage = AES.encrypt(stringifiedData, encryptionKey).toString();
       // build and go to url
diff --git a/store/callbackActions.ts b/store/callbackActions.ts
index b90632515..dabc76b6c 100644
--- a/store/callbackActions.ts
+++ b/store/callbackActions.ts
@@ -1,8 +1,10 @@
 import { defineStore } from 'pinia';
 
-import { useAccountStore } from './account';
-import { useInstallKeyStore } from './installKey';
-import { useCallbackStoreGeneric, type ExternalPayload, type ExternalKeyActions, type QueryPayloads } from './callback';
+import { addPreventClose, removePreventClose } from '~/composables/preventClose';
+import { useAccountStore } from '~/store/account';
+import { useInstallKeyStore } from '~/store/installKey';
+import { useCallbackStoreGeneric, type ExternalPayload, type ExternalKeyActions, type QueryPayloads } from '~/store/callback';
+import { remove } from '@vue/shared';
 // import { useServerStore } from './server';
 
 export const useCallbackActionsStore = defineStore(
@@ -59,21 +61,13 @@ export const useCallbackActionsStore = defineStore(
 
   const setCallbackStatus = (status: CallbackStatus) => callbackStatus.value = status;
 
-  const preventClose = (e: { preventDefault: () => void; returnValue: string; }) => {
-    e.preventDefault();
-    // eslint-disable-next-line no-param-reassign
-    e.returnValue = '';
-    // eslint-disable-next-line no-alert
-    alert('Closing this pop-up window while actions are being preformed may lead to unintended errors.');
-  };
-
-  watch(callbackStatus, (newVal, _oldVal) => {
+  watch(callbackStatus, (newVal, oldVal) => {
     console.debug('[callbackStatus]', newVal);
-    if (newVal === 'ready') {
-      window.addEventListener('beforeunload', preventClose);
+    if (newVal === 'loading') {
+      addPreventClose();
     }
-    if (newVal !== 'ready') {
-      window.removeEventListener('beforeunload', preventClose);
+    if (oldVal === 'loading') {
+      removePreventClose();
       // removing query string once actions are done so users can't refresh the page and go through the same actions
       window.history.replaceState(null, '', window.location.pathname);
     }
diff --git a/store/server.ts b/store/server.ts
index 093874b38..5bb8b6f0e 100644
--- a/store/server.ts
+++ b/store/server.ts
@@ -185,6 +185,9 @@ export const useServerStore = defineStore('server', () => {
     name: 'signIn',
     text: 'Sign In with Unraid.net Account',
   };
+  /**
+   * @todo implment conditional sign out to show that a keyfile is required
+   */
   const signOutAction: ServerStateDataAction = {
     click: () => { accountStore.signOut() },
     external: true,
@@ -200,7 +203,7 @@ export const useServerStore = defineStore('server', () => {
     text: 'Extend Trial',
   };
   const trialStartAction: ServerStateDataAction = {
-    click: () => { trialStore.start() },
+    click: () => { trialStore.setTrialStatus('requestNew') },
     external: true,
     icon: KeyIcon,
     name: 'trialStart',
diff --git a/store/trial.ts b/store/trial.ts
index efaf14a8a..f7cd7ffdf 100644
--- a/store/trial.ts
+++ b/store/trial.ts
@@ -1,17 +1,28 @@
 import { defineStore, createPinia, setActivePinia } from 'pinia';
-import { useCallbackStore } from './callbackActions';
-import { useServerStore } from './server';
+
+import { addPreventClose, removePreventClose } from '~/composables/preventClose';
+import { startTrial, type StartTrialResponse } from '~/composables/services/keyServer';
+
+import { useCallbackStore, useCallbackActionsStore } from '~/store/callbackActions';
+import { useDropdownStore } from '~/store/dropdown';
+import { useServerStore } from '~/store/server';
+import type { ExternalPayload } from '~/store/callback';
 
 /**
  * @see https://stackoverflow.com/questions/73476371/using-pinia-with-vue-js-web-components
  * @see https://github.com/vuejs/pinia/discussions/1085
- */
+*/
 setActivePinia(createPinia());
 
 export const useTrialStore = defineStore('trial', () => {
   const callbackStore = useCallbackStore();
+  const callbackActionsStore = useCallbackActionsStore();
+  const dropdownStore = useDropdownStore();
   const serverStore = useServerStore();
 
+  type TrialStatus = 'failed' | 'ready' | 'requestNew' | 'success';
+  const trialStatus = ref<TrialStatus>('ready');
+
   const extend = () => {
     console.debug('[extend]');
     callbackStore.send('https://localhost:8008/connect', [{
@@ -21,20 +32,65 @@ export const useTrialStore = defineStore('trial', () => {
       type: 'trialExtend',
     }]);
   };
-  const start = () => {
-    console.debug('[start]');
-    callbackStore.send('https://localhost:8008/connect', [{
-      server: {
-        ...serverStore.serverAccountPayload,
-      },
-      type: 'trialStart',
-    }]);
+
+  // @todo post to key server
+  const requestTrialNew = async () => {
+    console.debug('[requestTrialNew]');
+    try {
+      const payload = {
+        guid: serverStore.guid,
+        timestamp: Math.floor(Date.now() / 1000),
+      };
+      const response: StartTrialResponse = await startTrial(payload).json();
+      console.debug('[requestTrialNew]', response);
+      if (!response.license) {
+        trialStatus.value = 'failed';
+        return console.error('[requestTrialNew]', 'No license returned', response);
+      }
+      // manually create a payload to mimic a callback for key installs
+      const trialStartData: ExternalPayload = {
+        actions: [
+          {
+            keyUrl: response.license,
+            type: 'trialStart',
+          },
+        ],
+        sender: window.location.href,
+        type: 'forUpc',
+      };
+      console.debug('[requestTrialNew]', trialStartData);
+      trialStatus.value = 'success';
+      return callbackActionsStore.redirectToCallbackType(trialStartData);
+    } catch (error) {
+      trialStatus.value = 'failed';
+      console.error('[requestTrialNew]', error);
+    }
   };
 
+  const setTrialStatus = (status: TrialStatus) => trialStatus.value = status;
+
+  watch(trialStatus, (newVal, oldVal) => {
+    console.debug('[trialStatus]', newVal, oldVal);
+    // opening
+    if (newVal === 'requestNew') {
+      addPreventClose();
+      dropdownStore.dropdownHide(); // close the dropdown when the trial modal is opened
+      setTimeout(() => {
+        requestTrialNew();
+      }, 1500);
+    }
+    // allow closure
+    if (newVal === 'failed' || newVal === 'success') {
+      removePreventClose();
+    }
+  });
+
   return {
     // State
+    trialStatus,
     // Actions
     extend,
-    start,
+    requestTrialNew,
+    setTrialStatus,
   };
 });