diff --git a/web/__test__/store/replaceRenew.test.ts b/web/__test__/store/replaceRenew.test.ts
index 1dd096a7b2..d551180d52 100644
--- a/web/__test__/store/replaceRenew.test.ts
+++ b/web/__test__/store/replaceRenew.test.ts
@@ -14,6 +14,10 @@ import { useServerStore } from '~/store/server';
 
 vi.mock('@unraid/shared-callbacks', () => ({}));
 
+vi.mock('@unraid/ui', () => ({
+  BrandLoading: {},
+}));
+
 vi.mock('~/composables/services/keyServer', () => ({
   validateGuid: vi.fn(),
 }));
@@ -62,7 +66,7 @@ describe('ReplaceRenew Store', () => {
       expect(store.replaceStatus).toBe('ready');
     });
 
-    it('should initialize with error state when guid is missing', () => {
+    it('should initialize with ready state even when guid is missing', () => {
       vi.mocked(useServerStore).mockReturnValueOnce({
         guid: undefined,
         keyfile: mockKeyfile,
@@ -72,7 +76,8 @@ describe('ReplaceRenew Store', () => {
 
       const newStore = useReplaceRenewStore();
 
-      expect(newStore.replaceStatus).toBe('error');
+      // Store now always initializes as 'ready' - errors are set when check() is called
+      expect(newStore.replaceStatus).toBe('ready');
     });
   });
 
@@ -138,6 +143,18 @@ describe('ReplaceRenew Store', () => {
       expect(store.renewStatus).toBe('installing');
     });
 
+    it('should reset all states with reset action', () => {
+      store.setReplaceStatus('error');
+      store.keyLinkedStatus = 'error';
+      store.error = { name: 'Error', message: 'Test error' };
+
+      store.reset();
+
+      expect(store.replaceStatus).toBe('ready');
+      expect(store.keyLinkedStatus).toBe('ready');
+      expect(store.error).toBeNull();
+    });
+
     describe('check action', () => {
       const mockResponse = {
         hasNewerKeyfile: false,
@@ -326,8 +343,59 @@ describe('ReplaceRenew Store', () => {
         await store.check();
 
         expect(store.replaceStatus).toBe('error');
+        expect(store.keyLinkedStatus).toBe('error');
         expect(console.error).toHaveBeenCalledWith('[ReplaceCheck.check]', testError);
-        expect(store.error).toEqual(testError);
+        expect(store.error).toEqual({ name: 'Error', message: 'Test error' });
+      });
+
+      it('should set error when guid is missing during check', async () => {
+        vi.mocked(useServerStore).mockReturnValue({
+          guid: '',
+          keyfile: mockKeyfile,
+        } as unknown as ReturnType<typeof useServerStore>);
+
+        setActivePinia(createPinia());
+        const testStore = useReplaceRenewStore();
+
+        await testStore.check();
+
+        expect(testStore.replaceStatus).toBe('error');
+        expect(testStore.keyLinkedStatus).toBe('error');
+        expect(testStore.error?.message).toBe('Flash GUID required to check replacement status');
+      });
+
+      it('should set error when keyfile is missing during check', async () => {
+        vi.mocked(useServerStore).mockReturnValue({
+          guid: mockGuid,
+          keyfile: '',
+        } as unknown as ReturnType<typeof useServerStore>);
+
+        setActivePinia(createPinia());
+        const testStore = useReplaceRenewStore();
+
+        await testStore.check();
+
+        expect(testStore.replaceStatus).toBe('error');
+        expect(testStore.keyLinkedStatus).toBe('error');
+        expect(testStore.error?.message).toBe('Keyfile required to check replacement status');
+      });
+
+      it('should provide descriptive error for 403 status', async () => {
+        const error403 = { response: { status: 403 }, message: 'Forbidden' };
+        vi.mocked(validateGuid).mockRejectedValueOnce(error403);
+
+        await store.check();
+
+        expect(store.error?.message).toBe('Access denied - license may be linked to another account');
+      });
+
+      it('should provide descriptive error for 500+ status', async () => {
+        const error500 = { response: { status: 500 }, message: 'Server Error' };
+        vi.mocked(validateGuid).mockRejectedValueOnce(error500);
+
+        await store.check();
+
+        expect(store.error?.message).toBe('Key server temporarily unavailable - please try again later');
       });
     });
   });
diff --git a/web/src/components/Registration/ReplaceCheck.vue b/web/src/components/Registration/ReplaceCheck.vue
index c67b4e843b..2061ee0922 100644
--- a/web/src/components/Registration/ReplaceCheck.vue
+++ b/web/src/components/Registration/ReplaceCheck.vue
@@ -1,8 +1,9 @@
 <script setup lang="ts">
+import { computed } from 'vue';
 import { useI18n } from 'vue-i18n';
 import { storeToRefs } from 'pinia';
 
-import { ArrowTopRightOnSquareIcon, KeyIcon } from '@heroicons/vue/24/solid';
+import { ArrowPathIcon, ArrowTopRightOnSquareIcon, KeyIcon } from '@heroicons/vue/24/solid';
 import { Badge, BrandButton } from '@unraid/ui';
 import { DOCS_REGISTRATION_REPLACE_KEY } from '~/helpers/urls';
 
@@ -11,20 +12,30 @@ import { useReplaceRenewStore } from '~/store/replaceRenew';
 const { t } = useI18n();
 const replaceRenewStore = useReplaceRenewStore();
 const { replaceStatusOutput } = storeToRefs(replaceRenewStore);
+
+const isError = computed(() => replaceStatusOutput.value?.variant === 'red');
+const showButton = computed(() => !replaceStatusOutput.value || isError.value);
+
+const handleCheck = () => {
+  if (isError.value) {
+    replaceRenewStore.reset();
+  }
+  replaceRenewStore.check(true);
+};
 </script>
 
 <template>
   <div class="flex flex-wrap items-center justify-between gap-2">
     <BrandButton
-      v-if="!replaceStatusOutput"
-      :icon="KeyIcon"
-      :text="t('registration.replaceCheck.checkEligibility')"
+      v-if="showButton"
+      :icon="isError ? ArrowPathIcon : KeyIcon"
+      :text="isError ? t('common.retry') : t('registration.replaceCheck.checkEligibility')"
       class="grow"
-      @click="replaceRenewStore.check"
+      @click="handleCheck"
     />
 
-    <Badge v-else :variant="replaceStatusOutput.variant" :icon="replaceStatusOutput.icon" size="md">
-      {{ t(replaceStatusOutput.text ?? 'Unknown') }}
+    <Badge v-else :variant="replaceStatusOutput?.variant" :icon="replaceStatusOutput?.icon" size="md">
+      {{ t(replaceStatusOutput?.text ?? 'Unknown') }}
     </Badge>
 
     <span class="inline-flex flex-wrap items-center justify-end gap-2">
diff --git a/web/src/locales/en.json b/web/src/locales/en.json
index e44fbea98a..e7cc530f47 100644
--- a/web/src/locales/en.json
+++ b/web/src/locales/en.json
@@ -30,6 +30,7 @@
   "common.installed": "Installed",
   "common.installing": "Installing",
   "common.learnMore": "Learn More",
+  "common.retry": "Retry",
   "common.loading2": "Loading…",
   "common.success": "Success!",
   "common.unknown": "Unknown",
diff --git a/web/src/store/replaceRenew.ts b/web/src/store/replaceRenew.ts
index a7c459c807..7c7191cb59 100644
--- a/web/src/store/replaceRenew.ts
+++ b/web/src/store/replaceRenew.ts
@@ -95,9 +95,7 @@ export const useReplaceRenewStore = defineStore('replaceRenewCheck', () => {
     renewStatus.value = status;
   };
 
-  const replaceStatus = ref<'checking' | 'eligible' | 'error' | 'ineligible' | 'ready'>(
-    guid.value ? 'ready' : 'error'
-  );
+  const replaceStatus = ref<'checking' | 'eligible' | 'error' | 'ineligible' | 'ready'>('ready');
   const setReplaceStatus = (status: typeof replaceStatus.value) => {
     replaceStatus.value = status;
   };
@@ -169,11 +167,15 @@ export const useReplaceRenewStore = defineStore('replaceRenewCheck', () => {
   const check = async (skipCache: boolean = false) => {
     if (!guid.value) {
       setReplaceStatus('error');
+      setKeyLinked('error');
       error.value = { name: 'Error', message: 'Flash GUID required to check replacement status' };
+      return;
     }
     if (!keyfile.value) {
       setReplaceStatus('error');
+      setKeyLinked('error');
       error.value = { name: 'Error', message: 'Keyfile required to check replacement status' };
+      return;
     }
 
     try {
@@ -240,11 +242,32 @@ export const useReplaceRenewStore = defineStore('replaceRenewCheck', () => {
     } catch (err) {
       const catchError = err as WretchError;
       setReplaceStatus('error');
-      error.value = catchError?.message ? catchError : { name: 'Error', message: 'Unknown error' };
+      setKeyLinked('error');
+
+      let errorMessage = 'Unknown error';
+      if (catchError?.response?.status === 401) {
+        errorMessage = 'Authentication failed - please sign in again';
+      } else if (catchError?.response?.status === 403) {
+        errorMessage = 'Access denied - license may be linked to another account';
+      } else if (catchError?.response?.status && catchError.response.status >= 500) {
+        errorMessage = 'Key server temporarily unavailable - please try again later';
+      } else if (catchError?.message) {
+        errorMessage = catchError.message;
+      } else if (typeof navigator !== 'undefined' && !navigator.onLine) {
+        errorMessage = 'No internet connection';
+      }
+
+      error.value = { name: 'Error', message: errorMessage };
       console.error('[ReplaceCheck.check]', catchError);
     }
   };
 
+  const reset = () => {
+    replaceStatus.value = 'ready';
+    keyLinkedStatus.value = 'ready';
+    error.value = null;
+  };
+
   return {
     // state
     keyLinkedStatus,
@@ -255,6 +278,7 @@ export const useReplaceRenewStore = defineStore('replaceRenewCheck', () => {
     // actions
     check,
     purgeValidationResponse,
+    reset,
     setReplaceStatus,
     setRenewStatus,
     error,