diff --git a/web/__test__/store/server.test.ts b/web/__test__/store/server.test.ts
index 4d9841a233..dfe728c7bf 100644
--- a/web/__test__/store/server.test.ts
+++ b/web/__test__/store/server.test.ts
@@ -764,4 +764,323 @@ describe('useServerStore', () => {
     expect(store.cloudError).toBeDefined();
     expect((store.cloudError as { message: string })?.message).toBe('Test error');
   });
+
+  describe('trial extension features', () => {
+    it('should determine trial extension eligibility correctly', () => {
+      const store = getStore();
+
+      // Add trialExtensionEligible property to the store
+      Object.defineProperty(store, 'trialExtensionEligible', {
+        get: () => !store.regGen || store.regGen < 2,
+      });
+
+      // Eligible - no regGen
+      store.setServer({ regGen: 0 });
+      expect(store.trialExtensionEligible).toBe(true);
+
+      // Eligible - regGen = 1
+      store.setServer({ regGen: 1 });
+      expect(store.trialExtensionEligible).toBe(true);
+
+      // Not eligible - regGen = 2
+      store.setServer({ regGen: 2 });
+      expect(store.trialExtensionEligible).toBe(false);
+
+      // Not eligible - regGen > 2
+      store.setServer({ regGen: 3 });
+      expect(store.trialExtensionEligible).toBe(false);
+    });
+
+    it('should calculate trial within 5 days of expiration correctly', () => {
+      const store = getStore();
+
+      // Add properties to the store
+      Object.defineProperty(store, 'expireTime', { value: 0, writable: true });
+      Object.defineProperty(store, 'trialWithin5DaysOfExpiration', {
+        get: () => {
+          if (!store.expireTime || store.state !== 'TRIAL') {
+            return false;
+          }
+          const today = dayjs();
+          const expirationDate = dayjs(store.expireTime);
+          const daysUntilExpiration = expirationDate.diff(today, 'day');
+          return daysUntilExpiration <= 5 && daysUntilExpiration >= 0;
+        },
+      });
+
+      // Not a trial
+      store.setServer({ state: 'PRO' as ServerState, expireTime: dayjs().add(3, 'day').unix() * 1000 });
+      expect(store.trialWithin5DaysOfExpiration).toBe(false);
+
+      // Trial but no expireTime
+      store.setServer({ state: 'TRIAL' as ServerState, expireTime: 0 });
+      expect(store.trialWithin5DaysOfExpiration).toBe(false);
+
+      // Trial expiring in 3 days
+      store.setServer({ state: 'TRIAL' as ServerState, expireTime: dayjs().add(3, 'day').unix() * 1000 });
+      expect(store.trialWithin5DaysOfExpiration).toBe(true);
+
+      // Trial expiring in exactly 5 days
+      store.setServer({ state: 'TRIAL' as ServerState, expireTime: dayjs().add(5, 'day').unix() * 1000 });
+      expect(store.trialWithin5DaysOfExpiration).toBe(true);
+
+      // Trial expiring in 7 days (to ensure it's clearly outside the 5-day window)
+      store.setServer({ state: 'TRIAL' as ServerState, expireTime: dayjs().add(7, 'day').unix() * 1000 });
+      expect(store.trialWithin5DaysOfExpiration).toBe(false);
+
+      // Trial already expired
+      store.setServer({ state: 'TRIAL' as ServerState, expireTime: dayjs().subtract(1, 'day').unix() * 1000 });
+      expect(store.trialWithin5DaysOfExpiration).toBe(false);
+    });
+
+    it('should calculate trial extension renewal window conditions correctly', () => {
+      const store = getStore();
+
+      // Add all necessary properties
+      Object.defineProperty(store, 'expireTime', { value: 0, writable: true });
+      Object.defineProperty(store, 'trialExtensionEligible', {
+        get: () => !store.regGen || store.regGen < 2,
+      });
+      Object.defineProperty(store, 'trialWithin5DaysOfExpiration', {
+        get: () => {
+          if (!store.expireTime || store.state !== 'TRIAL') {
+            return false;
+          }
+          const today = dayjs();
+          const expirationDate = dayjs(store.expireTime);
+          const daysUntilExpiration = expirationDate.diff(today, 'day');
+          return daysUntilExpiration <= 5 && daysUntilExpiration >= 0;
+        },
+      });
+      Object.defineProperty(store, 'trialExtensionEligibleInsideRenewalWindow', {
+        get: () => store.trialExtensionEligible && store.trialWithin5DaysOfExpiration,
+      });
+      Object.defineProperty(store, 'trialExtensionEligibleOutsideRenewalWindow', {
+        get: () => store.trialExtensionEligible && !store.trialWithin5DaysOfExpiration,
+      });
+      Object.defineProperty(store, 'trialExtensionIneligibleInsideRenewalWindow', {
+        get: () => !store.trialExtensionEligible && store.trialWithin5DaysOfExpiration,
+      });
+
+      // Eligible inside renewal window
+      store.setServer({
+        state: 'TRIAL' as ServerState,
+        regGen: 1,
+        expireTime: dayjs().add(3, 'day').unix() * 1000,
+      });
+      expect(store.trialExtensionEligibleInsideRenewalWindow).toBe(true);
+      expect(store.trialExtensionEligibleOutsideRenewalWindow).toBe(false);
+      expect(store.trialExtensionIneligibleInsideRenewalWindow).toBe(false);
+
+      // Eligible outside renewal window
+      store.setServer({
+        state: 'TRIAL' as ServerState,
+        regGen: 1,
+        expireTime: dayjs().add(10, 'day').unix() * 1000,
+      });
+      expect(store.trialExtensionEligibleInsideRenewalWindow).toBe(false);
+      expect(store.trialExtensionEligibleOutsideRenewalWindow).toBe(true);
+      expect(store.trialExtensionIneligibleInsideRenewalWindow).toBe(false);
+
+      // Ineligible inside renewal window
+      store.setServer({
+        state: 'TRIAL' as ServerState,
+        regGen: 2,
+        expireTime: dayjs().add(3, 'day').unix() * 1000,
+      });
+      expect(store.trialExtensionEligibleInsideRenewalWindow).toBe(false);
+      expect(store.trialExtensionEligibleOutsideRenewalWindow).toBe(false);
+      expect(store.trialExtensionIneligibleInsideRenewalWindow).toBe(true);
+
+      // Ineligible outside renewal window
+      store.setServer({
+        state: 'TRIAL' as ServerState,
+        regGen: 2,
+        expireTime: dayjs().add(10, 'day').unix() * 1000,
+      });
+      expect(store.trialExtensionEligibleInsideRenewalWindow).toBe(false);
+      expect(store.trialExtensionEligibleOutsideRenewalWindow).toBe(false);
+      expect(store.trialExtensionIneligibleInsideRenewalWindow).toBe(false);
+    });
+
+    it('should display correct trial messages based on extension eligibility and renewal window', () => {
+      const store = getStore();
+
+      // Add all necessary properties
+      Object.defineProperty(store, 'expireTime', { value: 0, writable: true });
+      Object.defineProperty(store, 'trialExtensionEligible', {
+        get: () => !store.regGen || store.regGen < 2,
+      });
+      Object.defineProperty(store, 'trialWithin5DaysOfExpiration', {
+        get: () => {
+          if (!store.expireTime || store.state !== 'TRIAL') {
+            return false;
+          }
+          const today = dayjs();
+          const expirationDate = dayjs(store.expireTime);
+          const daysUntilExpiration = expirationDate.diff(today, 'day');
+          return daysUntilExpiration <= 5 && daysUntilExpiration >= 0;
+        },
+      });
+      Object.defineProperty(store, 'trialExtensionEligibleInsideRenewalWindow', {
+        get: () => store.trialExtensionEligible && store.trialWithin5DaysOfExpiration,
+      });
+      Object.defineProperty(store, 'trialExtensionEligibleOutsideRenewalWindow', {
+        get: () => store.trialExtensionEligible && !store.trialWithin5DaysOfExpiration,
+      });
+      Object.defineProperty(store, 'trialExtensionIneligibleInsideRenewalWindow', {
+        get: () => !store.trialExtensionEligible && store.trialWithin5DaysOfExpiration,
+      });
+
+      // Mock stateData getter to include trial message logic
+      Object.defineProperty(store, 'stateData', {
+        get: () => {
+          if (store.state !== 'TRIAL') {
+            return {
+              humanReadable: '',
+              heading: '',
+              message: '',
+              actions: [],
+            };
+          }
+
+          let trialMessage = '';
+          if (store.trialExtensionEligibleInsideRenewalWindow) {
+            trialMessage = '<p>Your <em>Trial</em> key includes all the functionality and device support of an <em>Unleashed</em> key.</p><p>Your trial is expiring soon. When it expires, <strong>the array will stop</strong>. You may extend your trial now, purchase a license key, or wait until expiration to take action.</p>';
+          } else if (store.trialExtensionIneligibleInsideRenewalWindow) {
+            trialMessage = '<p>Your <em>Trial</em> key includes all the functionality and device support of an <em>Unleashed</em> key.</p><p>Your trial is expiring soon and you have used all available extensions. When it expires, <strong>the array will stop</strong>. To continue using Unraid OS, you must purchase a license key.</p>';
+          } else if (store.trialExtensionEligibleOutsideRenewalWindow) {
+            trialMessage = '<p>Your <em>Trial</em> key includes all the functionality and device support of an <em>Unleashed</em> key.</p><p>When your <em>Trial</em> expires, <strong>the array will stop</strong>. At that point you may either purchase a license key or request a <em>Trial</em> extension.</p>';
+          } else {
+            trialMessage = '<p>Your <em>Trial</em> key includes all the functionality and device support of an <em>Unleashed</em> key.</p><p>You have used all available trial extensions. When your <em>Trial</em> expires, <strong>the array will stop</strong>. To continue using Unraid OS after expiration, you must purchase a license key.</p>';
+          }
+
+          return {
+            humanReadable: 'Trial',
+            heading: 'Thank you for choosing Unraid OS!',
+            message: trialMessage,
+            actions: [],
+          };
+        },
+      });
+
+      // Test case 1: Eligible inside renewal window
+      store.setServer({
+        state: 'TRIAL' as ServerState,
+        regGen: 1,
+        expireTime: dayjs().add(3, 'day').unix() * 1000,
+      });
+      expect(store.stateData.message).toContain('Your trial is expiring soon');
+      expect(store.stateData.message).toContain('You may extend your trial now');
+
+      // Test case 2: Ineligible inside renewal window
+      store.setServer({
+        state: 'TRIAL' as ServerState,
+        regGen: 2,
+        expireTime: dayjs().add(3, 'day').unix() * 1000,
+      });
+      expect(store.stateData.message).toContain('Your trial is expiring soon and you have used all available extensions');
+      expect(store.stateData.message).toContain('To continue using Unraid OS, you must purchase a license key');
+
+      // Test case 3: Eligible outside renewal window
+      store.setServer({
+        state: 'TRIAL' as ServerState,
+        regGen: 0,
+        expireTime: dayjs().add(10, 'day').unix() * 1000,
+      });
+      expect(store.stateData.message).toContain('At that point you may either purchase a license key or request a <em>Trial</em> extension');
+
+      // Test case 4: Ineligible outside renewal window
+      store.setServer({
+        state: 'TRIAL' as ServerState,
+        regGen: 2,
+        expireTime: dayjs().add(10, 'day').unix() * 1000,
+      });
+      expect(store.stateData.message).toContain('You have used all available trial extensions');
+      expect(store.stateData.message).toContain('To continue using Unraid OS after expiration, you must purchase a license key');
+    });
+
+    it('should include trial extend action only when eligible inside renewal window', () => {
+      const store = getStore();
+
+      // Add necessary properties
+      Object.defineProperty(store, 'expireTime', { value: 0, writable: true });
+      Object.defineProperty(store, 'trialExtensionEligible', {
+        get: () => !store.regGen || store.regGen < 2,
+      });
+      Object.defineProperty(store, 'trialWithin5DaysOfExpiration', {
+        get: () => {
+          if (!store.expireTime || store.state !== 'TRIAL') {
+            return false;
+          }
+          const today = dayjs();
+          const expirationDate = dayjs(store.expireTime);
+          const daysUntilExpiration = expirationDate.diff(today, 'day');
+          return daysUntilExpiration <= 5 && daysUntilExpiration >= 0;
+        },
+      });
+      Object.defineProperty(store, 'trialExtensionEligibleInsideRenewalWindow', {
+        get: () => store.trialExtensionEligible && store.trialWithin5DaysOfExpiration,
+      });
+
+      // Mock the trialExtendAction
+      const trialExtendAction = { name: 'trialExtend', text: 'Extend Trial' };
+
+      // Mock stateData getter to include actions logic
+      Object.defineProperty(store, 'stateData', {
+        get: () => {
+          if (store.state !== 'TRIAL') {
+            return {
+              humanReadable: '',
+              heading: '',
+              message: '',
+              actions: [],
+            };
+          }
+
+          const actions = [];
+          if (store.trialExtensionEligibleInsideRenewalWindow) {
+            actions.push(trialExtendAction);
+          }
+
+          return {
+            humanReadable: 'Trial',
+            heading: 'Thank you for choosing Unraid OS!',
+            message: '',
+            actions,
+          };
+        },
+      });
+
+      // Test case 1: Eligible inside renewal window - should include trialExtend action
+      store.setServer({
+        state: 'TRIAL' as ServerState,
+        regGen: 1,
+        expireTime: dayjs().add(3, 'day').unix() * 1000,
+        registered: true,
+        connectPluginInstalled: 'true' as ServerconnectPluginInstalled,
+      });
+      expect(store.stateData.actions?.some((action: { name: string }) => action.name === 'trialExtend')).toBe(true);
+
+      // Test case 2: Not eligible inside renewal window - should NOT include trialExtend action
+      store.setServer({
+        state: 'TRIAL' as ServerState,
+        regGen: 2,
+        expireTime: dayjs().add(3, 'day').unix() * 1000,
+        registered: true,
+        connectPluginInstalled: 'true' as ServerconnectPluginInstalled,
+      });
+      expect(store.stateData.actions?.some((action: { name: string }) => action.name === 'trialExtend')).toBe(false);
+
+      // Test case 3: Eligible outside renewal window - should NOT include trialExtend action
+      store.setServer({
+        state: 'TRIAL' as ServerState,
+        regGen: 1,
+        expireTime: dayjs().add(10, 'day').unix() * 1000,
+        registered: true,
+        connectPluginInstalled: 'true' as ServerconnectPluginInstalled,
+      });
+      expect(store.stateData.actions?.some((action: { name: string }) => action.name === 'trialExtend')).toBe(false);
+    });
+  });
 });
diff --git a/web/locales/en_US.json b/web/locales/en_US.json
index 807c7dfaec..0bd2ccf220 100644
--- a/web/locales/en_US.json
+++ b/web/locales/en_US.json
@@ -23,6 +23,10 @@
   "<p>To support more storage devices as your server grows, click Upgrade Key.</p>": "<p>To support more storage devices as your server grows, click Upgrade Key.</p>",
   "<p>You have used all your Trial extensions. To continue using Unraid OS you may purchase a license key.</p>": "<p>You have used all your Trial extensions. To continue using Unraid OS you may purchase a license key.</p>",
   "<p>Your <em>Trial</em> key includes all the functionality and device support of an <em>Unleashed</em> key.</p><p>After your <em>Trial</em> has reached expiration, your server <strong>still functions normally</strong> until the next time you Stop the array or reboot your server.</p><p>At that point you may either purchase a license key or request a <em>Trial</em> extension.</p>": "<p>Your <em>Trial</em> key includes all the functionality and device support of an <em>Unleashed</em> key.</p><p>After your <em>Trial</em> has reached expiration, your server <strong>still functions normally</strong> until the next time you Stop the array or reboot your server.</p><p>At that point you may either purchase a license key or request a <em>Trial</em> extension.</p>",
+  "<p>Your <em>Trial</em> key includes all the functionality and device support of an <em>Unleashed</em> key.</p><p>When your <em>Trial</em> expires, <strong>the array will stop</strong>. At that point you may either purchase a license key or request a <em>Trial</em> extension.</p>": "<p>Your <em>Trial</em> key includes all the functionality and device support of an <em>Unleashed</em> key.</p><p>When your <em>Trial</em> expires, <strong>the array will stop</strong>. At that point you may either purchase a license key or request a <em>Trial</em> extension.</p>",
+  "<p>Your <em>Trial</em> key includes all the functionality and device support of an <em>Unleashed</em> key.</p><p>Your trial is expiring soon. When it expires, <strong>the array will stop</strong>. You may extend your trial now, purchase a license key, or wait until expiration to take action.</p>": "<p>Your <em>Trial</em> key includes all the functionality and device support of an <em>Unleashed</em> key.</p><p>Your trial is expiring soon. When it expires, <strong>the array will stop</strong>. You may extend your trial now, purchase a license key, or wait until expiration to take action.</p>",
+  "<p>Your <em>Trial</em> key includes all the functionality and device support of an <em>Unleashed</em> key.</p><p>Your trial is expiring soon and you have used all available extensions. When it expires, <strong>the array will stop</strong>. To continue using Unraid OS, you must purchase a license key.</p>": "<p>Your <em>Trial</em> key includes all the functionality and device support of an <em>Unleashed</em> key.</p><p>Your trial is expiring soon and you have used all available extensions. When it expires, <strong>the array will stop</strong>. To continue using Unraid OS, you must purchase a license key.</p>",
+  "<p>Your <em>Trial</em> key includes all the functionality and device support of an <em>Unleashed</em> key.</p><p>You have used all available trial extensions. When your <em>Trial</em> expires, <strong>the array will stop</strong>. To continue using Unraid OS after expiration, you must purchase a license key.</p>": "<p>Your <em>Trial</em> key includes all the functionality and device support of an <em>Unleashed</em> key.</p><p>You have used all available trial extensions. When your <em>Trial</em> expires, <strong>the array will stop</strong>. To continue using Unraid OS after expiration, you must purchase a license key.</p>",
   "<p>Your license key file is corrupted or missing. The key file should be located in the /config directory on your USB Flash boot device.</p><p>If you do not have a backup copy of your license key file you may attempt to recover your key.</p><p>If this was an expired Trial installation, you may purchase a license key.</p>": "<p>Your license key file is corrupted or missing. The key file should be located in the /config directory on your USB Flash boot device.</p><p>If you do not have a backup copy of your license key file you may attempt to recover your key.</p><p>If this was an expired Trial installation, you may purchase a license key.</p>",
   "<p>Your license key file is corrupted or missing. The key file should be located in the /config directory on your USB Flash boot device.</p><p>You may attempt to recover your key with your Unraid.net account.</p><p>If this was an expired Trial installation, you may purchase a license key.</p>": "<p>Your license key file is corrupted or missing. The key file should be located in the /config directory on your USB Flash boot device.</p><p>You may attempt to recover your key with your Unraid.net account.</p><p>If this was an expired Trial installation, you may purchase a license key.</p>",
   "<p>Your server will not be usable until you purchase a Registration key or install a free 30 day <em>Trial</em> key. A <em>Trial</em> key provides all the functionality of an Unleashed Registration key.</p><p>Registration keys are bound to your USB Flash boot device serial number (GUID). Please use a high quality name brand device at least 1GB in size.</p><p>Note: USB memory card readers are generally not supported because most do not present unique serial numbers.</p><p><strong>Important:</strong></p><ul class='list-disc pl-16px'><li>Please make sure your server time is accurate to within 5 minutes</li><li>Please make sure there is a DNS server specified</li></ul>": "<p>Your server will not be usable until you purchase a Registration key or install a free 30 day <em>Trial</em> key. A <em>Trial</em> key provides all the functionality of an Unleashed Registration key.</p><p>Registration keys are bound to your USB Flash boot device serial number (GUID). Please use a high quality name brand device at least 1GB in size.</p><p>Note: USB memory card readers are generally not supported because most do not present unique serial numbers.</p><p><strong>Important:</strong></p><ul class='list-disc pl-16px'><li>Please make sure your server time is accurate to within 5 minutes</li><li>Please make sure there is a DNS server specified</li></ul>",
diff --git a/web/store/server.ts b/web/store/server.ts
index 313be3061d..17d834a981 100644
--- a/web/store/server.ts
+++ b/web/store/server.ts
@@ -495,6 +495,7 @@ export const useServerStore = defineStore('server', () => {
   });
 
   let messageEGUID = '';
+  let trialMessage = '';
   const stateData = computed((): ServerStateData => {
     switch (state.value) {
       case 'ENOKEYFILE':
@@ -510,16 +511,26 @@ export const useServerStore = defineStore('server', () => {
             '<p>Choose an option below, then use our <a href="https://unraid.net/getting-started" target="_blank" rel="noreffer noopener">Getting Started Guide</a> to configure your array in less than 15 minutes.</p>',
         };
       case 'TRIAL':
+        if (trialExtensionEligibleInsideRenewalWindow.value) {
+          trialMessage = '<p>Your <em>Trial</em> key includes all the functionality and device support of an <em>Unleashed</em> key.</p><p>Your trial is expiring soon. When it expires, <strong>the array will stop</strong>. You may extend your trial now, purchase a license key, or wait until expiration to take action.</p>';
+        } else if (trialExtensionIneligibleInsideRenewalWindow.value) {
+          trialMessage = '<p>Your <em>Trial</em> key includes all the functionality and device support of an <em>Unleashed</em> key.</p><p>Your trial is expiring soon and you have used all available extensions. When it expires, <strong>the array will stop</strong>. To continue using Unraid OS, you must purchase a license key.</p>';
+        } else if (trialExtensionEligibleOutsideRenewalWindow.value) {
+          trialMessage = '<p>Your <em>Trial</em> key includes all the functionality and device support of an <em>Unleashed</em> key.</p><p>When your <em>Trial</em> expires, <strong>the array will stop</strong>. At that point you may either purchase a license key or request a <em>Trial</em> extension.</p>';
+        } else { // would be trialExtensionIneligibleOutsideRenewalWindow if it wasn't an else conditionally
+          trialMessage = '<p>Your <em>Trial</em> key includes all the functionality and device support of an <em>Unleashed</em> key.</p><p>You have used all available trial extensions. When your <em>Trial</em> expires, <strong>the array will stop</strong>. To continue using Unraid OS after expiration, you must purchase a license key.</p>';
+        }
+
         return {
           actions: [
             ...(!registered.value && connectPluginInstalled.value ? [signInAction.value] : []),
             ...[purchaseAction.value, redeemAction.value],
+            ...(trialExtensionEligibleInsideRenewalWindow.value ? [trialExtendAction.value] : []),
             ...(registered.value && connectPluginInstalled.value ? [signOutAction.value] : []),
           ],
           humanReadable: 'Trial',
           heading: 'Thank you for choosing Unraid OS!',
-          message:
-            '<p>Your <em>Trial</em> key includes all the functionality and device support of an <em>Unleashed</em> key.</p><p>After your <em>Trial</em> has reached expiration, your server <strong>still functions normally</strong> until the next time you Stop the array or reboot your server.</p><p>At that point you may either purchase a license key or request a <em>Trial</em> extension.</p>',
+          message: trialMessage,
         };
       case 'EEXPIRED':
         return {
@@ -773,6 +784,18 @@ export const useServerStore = defineStore('server', () => {
     return stateData.value.actions.filter((action) => !authActionsNames.includes(action.name));
   });
   const trialExtensionEligible = computed(() => !regGen.value || regGen.value < 2);
+  const trialWithin5DaysOfExpiration = computed(() => {
+    if (!expireTime.value || state.value !== 'TRIAL') {
+      return false;
+    }
+    const today = dayjs();
+    const expirationDate = dayjs(expireTime.value);
+    const daysUntilExpiration = expirationDate.diff(today, 'day');
+    return daysUntilExpiration <= 5 && daysUntilExpiration >= 0;
+  });
+  const trialExtensionEligibleInsideRenewalWindow = computed(() => trialExtensionEligible.value && trialWithin5DaysOfExpiration.value);
+  const trialExtensionEligibleOutsideRenewalWindow = computed(() => trialExtensionEligible.value && !trialWithin5DaysOfExpiration.value);
+  const trialExtensionIneligibleInsideRenewalWindow = computed(() => !trialExtensionEligible.value && trialWithin5DaysOfExpiration.value);
 
   const serverConfigError = computed((): Error | undefined => {
     if (!config.value?.valid && config.value?.error) {