diff --git a/web/components/Registration/ReplaceCheck.vue b/web/components/Registration/ReplaceCheck.vue
index 4b37b8e22..920a44602 100644
--- a/web/components/Registration/ReplaceCheck.vue
+++ b/web/components/Registration/ReplaceCheck.vue
@@ -24,7 +24,7 @@ defineProps<{
       @click="replaceRenewStore.check"
     />
 
-    <Badge v-else :variant="replaceStatusOutput.variant" :icon="replaceStatusOutput.icon" size="md">
+    <Badge v-else :variant="replaceStatusOutput.variant" :icon="replaceStatusOutput.icon" size="md" class="self-center">
       {{ t(replaceStatusOutput.text ?? 'Unknown') }}
     </Badge>
 
diff --git a/web/components/Registration/UpdateExpirationAction.vue b/web/components/Registration/UpdateExpirationAction.vue
index 89910e255..e06796d47 100644
--- a/web/components/Registration/UpdateExpirationAction.vue
+++ b/web/components/Registration/UpdateExpirationAction.vue
@@ -1,15 +1,17 @@
 <script setup lang="ts">
-import { storeToRefs } from 'pinia';
+import { storeToRefs } from "pinia";
+import { computed, h } from "vue";
 
-import { ArrowPathIcon, ArrowTopRightOnSquareIcon } from '@heroicons/vue/24/solid';
-import { BrandButton } from '@unraid/ui';
-import { DOCS_REGISTRATION_LICENSING } from '~/helpers/urls';
+import { ArrowPathIcon, ArrowTopRightOnSquareIcon } from "@heroicons/vue/24/solid";
+import { BrandButton, BrandLoading } from "@unraid/ui";
 
-import type { ComposerTranslation } from 'vue-i18n';
+import { DOCS_REGISTRATION_LICENSING } from "~/helpers/urls";
 
-import useDateTimeHelper from '~/composables/dateTime';
-import { useReplaceRenewStore } from '~/store/replaceRenew';
-import { useServerStore } from '~/store/server';
+import type { ComposerTranslation } from "vue-i18n";
+
+import useDateTimeHelper from "~/composables/dateTime";
+import { useReplaceRenewStore } from "~/store/replaceRenew";
+import { useServerStore } from "~/store/server";
 
 export interface Props {
   t: ComposerTranslation;
@@ -20,15 +22,29 @@ const props = defineProps<Props>();
 const replaceRenewStore = useReplaceRenewStore();
 const serverStore = useServerStore();
 
-const { renewStatus } = storeToRefs(replaceRenewStore);
-const { dateTimeFormat, regExp, regUpdatesExpired, renewAction } = storeToRefs(serverStore);
+const { renewStatus, validationResponseTimestamp } = storeToRefs(replaceRenewStore);
+const { dateTimeFormat, regExp, regUpdatesExpired, renewAction } = storeToRefs(
+  serverStore
+);
 
 const reload = () => {
   window.location.reload();
 };
 
-const { outputDateTimeReadableDiff: readableDiffRegExp, outputDateTimeFormatted: formattedRegExp } =
-  useDateTimeHelper(dateTimeFormat.value, props.t, true, regExp.value);
+const {
+  outputDateTimeReadableDiff: readableDiffRegExp,
+  outputDateTimeFormatted: formattedRegExp,
+} = useDateTimeHelper(dateTimeFormat.value, props.t, true, regExp.value);
+
+const {
+  outputDateTimeReadableDiff: readableDiffValidationResponseTimestamp,
+  outputDateTimeFormatted: formattedValidationResponseTimestamp,
+} = useDateTimeHelper(
+  dateTimeFormat.value,
+  props.t,
+  false,
+  validationResponseTimestamp.value ?? undefined
+);
 
 const output = computed(() => {
   if (!regExp.value) {
@@ -36,29 +52,68 @@ const output = computed(() => {
   }
   return {
     text: regUpdatesExpired.value
-      ? props.t('Ineligible for feature updates released after {0}', [formattedRegExp.value])
-      : props.t('Eligible for free feature updates until {0}', [formattedRegExp.value]),
+      ? props.t("Ineligible for feature updates released after {0}", [
+          formattedRegExp.value,
+        ])
+      : props.t("Eligible for free feature updates until {0}", [formattedRegExp.value]),
     title: regUpdatesExpired.value
-      ? props.t('Ineligible as of {0}', [readableDiffRegExp.value])
-      : props.t('Eligible for free feature updates for {0}', [readableDiffRegExp.value]),
+      ? props.t("Ineligible as of {0}", [readableDiffRegExp.value])
+      : props.t("Eligible for free feature updates for {0}", [readableDiffRegExp.value]),
   };
 });
+
+const showCheckTimestamp = computed(() => {
+  return (
+    validationResponseTimestamp.value && validationResponseTimestamp.value > regExp.value
+  );
+});
+
+const reloadPage = () => {
+  window.location.reload();
+};
+
+const BrandLoadingIcon = () => h(BrandLoading, { size: 'sm' });
+
+const statusContent = computed(() => {
+  switch (renewStatus.value) {
+    case "installed":
+      return {
+        text: props.t(
+          "Your license key was automatically renewed and installed. Reload the page to see updated details."
+        ),
+        action: {
+          icon: ArrowPathIcon,
+          title: "Reload Page",
+          onClick: reloadPage,
+        },
+      };
+    case "checking":
+      return {
+        component: BrandLoadingIcon,
+        text: props.t("Checking for extended license..."),
+      };
+    case "error":
+      return { text: props.t("Error checking for extended license.") };
+    case "ready":
+      return {
+        text: showCheckTimestamp.value ? `Last checked: ${formattedValidationResponseTimestamp.value}` : null,
+        action: {
+          icon: ArrowPathIcon,
+          title: "Check Again for Extended License",
+          onClick: () => replaceRenewStore.check(true), // consider debouncing this
+        },
+      };
+    default:
+      return null;
+  }
+});
 </script>
 
 <template>
   <div v-if="output" class="flex flex-col gap-8px">
     <RegistrationUpdateExpiration :t="t" />
 
-    <p class="text-14px opacity-90">
-      <template v-if="renewStatus === 'installed'">
-        {{
-          t(
-            'Your license key was automatically renewed and installed. Reload the page to see updated details.'
-          )
-        }}
-      </template>
-    </p>
-    <div class="flex flex-wrap items-start justify-between gap-8px">
+    <div class="flex flex-wrap items-center justify-between gap-8px">
       <BrandButton
         v-if="renewStatus === 'installed'"
         :icon="ArrowPathIcon"
@@ -87,6 +142,21 @@ const output = computed(() => {
         :text="t('Learn More')"
         class="text-14px"
       />
+
+      <p class="text-14px opacity-90 w-full flex flex-wrap gap-8px items-center">
+        <template v-if="statusContent">
+          <BrandButton
+            v-if="statusContent.action"
+            variant="underline"
+            :icon="statusContent.action.icon"
+            :title="statusContent.action.title"
+            size="12px"
+            @click="statusContent.action.onClick"
+          />
+          <component :is="statusContent.component" v-if="statusContent.component" />
+          <span v-if="statusContent.text">{{ statusContent.text }}</span>
+        </template>
+      </p>
     </div>
   </div>
 </template>
diff --git a/web/components/UserProfile/Dropdown.vue b/web/components/UserProfile/Dropdown.vue
index a50756b3a..7ca06972c 100644
--- a/web/components/UserProfile/Dropdown.vue
+++ b/web/components/UserProfile/Dropdown.vue
@@ -1,12 +1,12 @@
 <script setup lang="ts">
-import { storeToRefs } from 'pinia';
+import { storeToRefs } from "pinia";
 
-import { TransitionRoot } from '@headlessui/vue';
+import { TransitionRoot } from "@headlessui/vue";
 
-import type { ComposerTranslation } from 'vue-i18n';
+import type { ComposerTranslation } from "vue-i18n";
 
-import { useDropdownStore } from '~/store/dropdown';
-import { useServerStore } from '~/store/server';
+import { useDropdownStore } from "~/store/dropdown";
+import { useServerStore } from "~/store/server";
 
 defineProps<{ t: ComposerTranslation }>();
 
@@ -15,7 +15,7 @@ const dropdownStore = useDropdownStore();
 const { dropdownVisible } = storeToRefs(dropdownStore);
 const { state } = storeToRefs(useServerStore());
 
-const showLaunchpad = computed(() => state.value === 'ENOKEYFILE');
+const showLaunchpad = computed(() => state.value === "ENOKEYFILE");
 </script>
 
 <template>
@@ -28,9 +28,7 @@ const showLaunchpad = computed(() => state.value === 'ENOKEYFILE');
     leave-from="opacity-100"
     leave-to="opacity-0 translate-y-[16px]"
   >
-    <UpcDropdownWrapper
-      class="DropdownWrapper_blip text-foreground absolute z-30 top-full right-0 transition-all"
-    >
+    <UpcDropdownWrapper>
       <UpcDropdownLaunchpad v-if="showLaunchpad" :t="t" />
       <UpcDropdownContent v-else :t="t" />
     </UpcDropdownWrapper>
diff --git a/web/components/UserProfile/DropdownWrapper.vue b/web/components/UserProfile/DropdownWrapper.vue
index f2267ecdb..fd160dd0e 100644
--- a/web/components/UserProfile/DropdownWrapper.vue
+++ b/web/components/UserProfile/DropdownWrapper.vue
@@ -2,7 +2,7 @@
 </script>
 
 <template>
-  <nav class="flex flex-col gap-y-8px p-8px bg-popover rounded-lg shadow-xl shadow-orange/10">
+  <nav class="text-foreground absolute z-30 top-full right-0 flex flex-col gap-y-8px p-8px bg-popover rounded-lg shadow-xl shadow-orange/10">
     <slot />
   </nav>
 </template>
diff --git a/web/store/replaceRenew.ts b/web/store/replaceRenew.ts
index 06b3a3ba5..f9084b79e 100644
--- a/web/store/replaceRenew.ts
+++ b/web/store/replaceRenew.ts
@@ -17,16 +17,16 @@ import { BrandLoading } from '@unraid/ui';
 
 import type { BadgeProps } from '@unraid/ui';
 import type {
-  // type KeyLatestResponse,
+  KeyLatestResponse,
   ValidateGuidResponse,
 } from '~/composables/services/keyServer';
 import type { WretchError } from 'wretch';
 
 import {
-  // keyLatest,
+  keyLatest,
   validateGuid,
 } from '~/composables/services/keyServer';
-// import { useCallbackStore } from '~/store/callbackActions';
+import { useCallbackStore } from '~/store/callbackActions';
 import { useServerStore } from '~/store/server';
 
 /**
@@ -44,12 +44,12 @@ interface CachedValidationResponse extends ValidateGuidResponse {
   timestamp: number;
 }
 
-const BrandLoadingIcon = () => h(BrandLoading, { variant: 'white' });
+const BrandLoadingIcon = () => h(BrandLoading, { size: 'sm' });
 
 export const REPLACE_CHECK_LOCAL_STORAGE_KEY = 'unraidReplaceCheck';
 
 export const useReplaceRenewStore = defineStore('replaceRenewCheck', () => {
-  // const callbackStore = useCallbackStore();
+  const callbackStore = useCallbackStore();
   const serverStore = useServerStore();
 
   const guid = computed(() => serverStore.guid);
@@ -156,6 +156,8 @@ export const useReplaceRenewStore = defineStore('replaceRenewCheck', () => {
       : undefined
   );
 
+  const validationResponseTimestamp = computed<number | null>(() => validationResponse.value?.timestamp ?? null);
+
   const purgeValidationResponse = async () => {
     validationResponse.value = undefined;
     await sessionStorage.removeItem(REPLACE_CHECK_LOCAL_STORAGE_KEY);
@@ -190,6 +192,8 @@ export const useReplaceRenewStore = defineStore('replaceRenewCheck', () => {
       error.value = { name: 'Error', message: 'Keyfile required to check replacement status' };
     }
 
+    console.log('[ReplaceCheck.check]');
+
     try {
       if (skipCache) {
         await purgeValidationResponse();
@@ -200,6 +204,7 @@ export const useReplaceRenewStore = defineStore('replaceRenewCheck', () => {
 
       setKeyLinked('checking');
       setReplaceStatus('checking');
+      setRenewStatus('checking');
       error.value = null;
       /**
        * If the session already has a validation response, use that instead of making a new request
@@ -222,35 +227,38 @@ export const useReplaceRenewStore = defineStore('replaceRenewCheck', () => {
         (replaceStatus.value === 'eligible' || replaceStatus.value === 'ineligible') &&
         !validationResponse.value
       ) {
+        validationResponse.value = {
+          key: keyfileShort.value,
+          timestamp: Date.now(),
+          ...response,
+        };
         sessionStorage.setItem(
           REPLACE_CHECK_LOCAL_STORAGE_KEY,
-          JSON.stringify({
-            key: keyfileShort.value,
-            timestamp: Date.now(),
-            ...response,
-          })
+          JSON.stringify(validationResponse.value)
         );
       }
 
-      // if (response?.hasNewerKeyfile) {
-      //   setRenewStatus('checking');
+      if (!response?.hasNewerKeyfile) {
+        setRenewStatus('ready');
+      } else if (response?.hasNewerKeyfile) {
+        setRenewStatus('checking');
 
-      //   const keyLatestResponse: KeyLatestResponse = await keyLatest({
-      //     keyfile: keyfile.value,
-      //   });
+        const keyLatestResponse: KeyLatestResponse = await keyLatest({
+          keyfile: keyfile.value,
+        });
 
-      //   if (keyLatestResponse?.license) {
-      //     callbackStore.send(
-      //       window.location.href,
-      //       [{
-      //         keyUrl: keyLatestResponse.license,
-      //         type: 'renew',
-      //       }],
-      //       undefined,
-      //       'forUpc',
-      //     );
-      //   }
-      // }
+        if (keyLatestResponse?.license) {
+          callbackStore.send(
+            window.location.href,
+            [{
+              keyUrl: keyLatestResponse.license,
+              type: 'renew',
+            }],
+            undefined,
+            'forUpc',
+          );
+        }
+      }
     } catch (err) {
       const catchError = err as WretchError;
       setReplaceStatus('error');
@@ -266,6 +274,7 @@ export const useReplaceRenewStore = defineStore('replaceRenewCheck', () => {
     renewStatus,
     replaceStatus,
     replaceStatusOutput,
+    validationResponseTimestamp,
     // actions
     check,
     purgeValidationResponse,