diff --git a/src/admin/AdminPhotosTable.tsx b/src/admin/AdminPhotosTable.tsx
index a8db1804..36a969a5 100644
--- a/src/admin/AdminPhotosTable.tsx
+++ b/src/admin/AdminPhotosTable.tsx
@@ -14,7 +14,7 @@ import EditButton from './EditButton';
 import DeleteButton from './DeleteButton';
 import {
   deletePhotoFormAction,
-  syncPhotoExifDataAction,
+  syncPhotoAction,
 } from '@/photo/actions';
 import { useAppState } from '@/state/AppState';
 import { RevalidatePhoto } from '@/photo/InfinitePhotoScroll';
@@ -24,10 +24,12 @@ export default function AdminPhotosTable({
   photos,
   onLastPhotoVisible,
   revalidatePhoto,
+  hasAiTextGeneration,
 }: {
   photos: Photo[],
   onLastPhotoVisible?: () => void
   revalidatePhoto?: RevalidatePhoto
+  hasAiTextGeneration?: boolean
 }) {
   const { invalidateSwr } = useAppState();
 
@@ -82,11 +84,11 @@ export default function AdminPhotosTable({
           )}>
             <EditButton path={pathForAdminPhotoEdit(photo)} />
             <PhotoSyncButton
-              action={syncPhotoExifDataAction}
+              action={syncPhotoAction}
               photoTitle={titleForPhoto(photo)}
               formData={{ photoId: photo.id }}
               onFormSubmit={invalidateSwr}
-              includeLabel={false}
+              hasAiTextGeneration={hasAiTextGeneration}
               shouldConfirm
               shouldToast
             />
diff --git a/src/admin/AdminPhotosTableInfinite.tsx b/src/admin/AdminPhotosTableInfinite.tsx
index ad7f61fc..33b8b793 100644
--- a/src/admin/AdminPhotosTableInfinite.tsx
+++ b/src/admin/AdminPhotosTableInfinite.tsx
@@ -7,9 +7,11 @@ import AdminPhotosTable from './AdminPhotosTable';
 export default function AdminPhotosTableInfinite({
   initialOffset,
   itemsPerPage,
+  hasAiTextGeneration,
 }: {
   initialOffset: number
   itemsPerPage: number
+  hasAiTextGeneration?: boolean
 }) {
   return (
     <InfinitePhotoScroll
@@ -24,6 +26,7 @@ export default function AdminPhotosTableInfinite({
           photos={photos}
           onLastPhotoVisible={onLastPhotoVisible}
           revalidatePhoto={revalidatePhoto}
+          hasAiTextGeneration={hasAiTextGeneration}
         />}
     </InfinitePhotoScroll>
   );
diff --git a/src/admin/ClearCacheButton.tsx b/src/admin/ClearCacheButton.tsx
index e00b9a6b..32d07050 100644
--- a/src/admin/ClearCacheButton.tsx
+++ b/src/admin/ClearCacheButton.tsx
@@ -1,7 +1,7 @@
 'use client';
 
 import SubmitButtonWithStatus from '@/components/SubmitButtonWithStatus';
-import { syncCacheAction } from '@/photo/actions';
+import { clearCacheAction } from '@/photo/actions';
 import { useAppState } from '@/state/AppState';
 import { BiTrash } from 'react-icons/bi';
 
@@ -9,7 +9,7 @@ export default function ClearCacheButton() {
   const { invalidateSwr } = useAppState();
 
   return (
-    <form action={syncCacheAction}>
+    <form action={clearCacheAction}>
       <SubmitButtonWithStatus
         icon={<BiTrash size={16} />}
         onFormSubmit={invalidateSwr}
diff --git a/src/admin/PhotoSyncButton.tsx b/src/admin/PhotoSyncButton.tsx
index ccfbcdaf..61a1eb31 100644
--- a/src/admin/PhotoSyncButton.tsx
+++ b/src/admin/PhotoSyncButton.tsx
@@ -6,35 +6,38 @@ import { ComponentProps } from 'react';
 
 export default function PhotoSyncButton({
   action,
-  includeLabel = true,
+  label,
   onFormSubmit,
   formData: { photoId, photoUrl } = {},
   photoTitle,
+  hasAiTextGeneration,
   shouldConfirm,
   shouldToast,
 }: {
   action: (formData: FormData) => void
-  includeLabel?: boolean
+  label?: string
   formData?: {
     photoId?: string
     photoUrl?: string
   }
   photoTitle?: string
+  hasAiTextGeneration?: boolean
   shouldConfirm?: boolean
   shouldToast?: boolean
 } & ComponentProps<typeof SubmitButtonWithStatus>) {
-  const confirmText =
-    'Are you sure you want to overwrite EXIF data ' + (photoTitle
-      ? `for "${photoTitle}" from source file? `
-      : 'from source file? '
-    ) + 'This action cannot be undone.';
+  const confirmText = ['Overwrite'];
+  if (photoTitle) { confirmText.push(`"${photoTitle}"`); }
+  confirmText.push('data from original file?');
+  if (hasAiTextGeneration) { confirmText.push(
+    'This will also auto-generate AI text for undefined fields.'); }
+  confirmText.push('This action cannot be undone.');
   return (
     <FormWithConfirm
       action={action}
-      confirmText={shouldConfirm ? confirmText : undefined}
+      confirmText={shouldConfirm ? confirmText.join(' ') : undefined}
     >
       {photoId && 
-        <input name="id" value={photoId} hidden readOnly />}
+        <input name="photoId" value={photoId} hidden readOnly />}
       {photoUrl && 
         <input name="photoUrl" value={photoUrl} hidden readOnly />}
       <SubmitButtonWithStatus
@@ -42,16 +45,16 @@ export default function PhotoSyncButton({
         icon={<IconGrSync
           className={clsx(
             'translate-y-[0.5px] translate-x-[0.5px]',
-            includeLabel && 'sm:translate-x-[-0.5px]',
+            label && 'sm:translate-x-[-0.5px]',
           )} />}
         onFormSubmitToastMessage={shouldToast
           ? photoTitle
-            ? `"${photoTitle}" EXIF data synced`
-            : 'EXIF data synced'
+            ? `"${photoTitle}" data synced`
+            : 'Data synced'
           : undefined}
         onFormSubmit={onFormSubmit}
       >
-        {includeLabel ? 'EXIF' : null}
+        {label}
       </SubmitButtonWithStatus>
     </FormWithConfirm>
   );
diff --git a/src/app/admin/photos/page.tsx b/src/app/admin/photos/page.tsx
index 66609ca0..542c0d65 100644
--- a/src/app/admin/photos/page.tsx
+++ b/src/app/admin/photos/page.tsx
@@ -2,7 +2,7 @@ import PhotoUpload from '@/photo/PhotoUpload';
 import { clsx } from 'clsx/lite';
 import SiteGrid from '@/components/SiteGrid';
 import AdminUploadsTable from '@/admin/AdminUploadsTable';
-import { PRO_MODE_ENABLED } from '@/site/config';
+import { AI_TEXT_GENERATION_ENABLED, PRO_MODE_ENABLED } from '@/site/config';
 import { getStoragePhotoUrlsNoStore } from '@/services/storage/cache';
 import { getPhotos } from '@/photo/db/query';
 import { revalidatePath } from 'next/cache';
@@ -58,11 +58,15 @@ export default async function AdminPhotosPage() {
               />
             </div>}
           <div className="space-y-4">
-            <AdminPhotosTable photos={photos} />
+            <AdminPhotosTable
+              photos={photos}
+              hasAiTextGeneration={AI_TEXT_GENERATION_ENABLED}
+            />
             {photosCount > photos.length &&
               <AdminPhotosTableInfinite
                 initialOffset={INFINITE_SCROLL_INITIAL_ADMIN_PHOTOS}
                 itemsPerPage={INFINITE_SCROLL_MULTIPLE_ADMIN_PHOTOS}
+                hasAiTextGeneration={AI_TEXT_GENERATION_ENABLED}
               />}
           </div>
         </div>}
diff --git a/src/middleware.ts b/src/middleware.ts
index 43386d1e..ac78095a 100644
--- a/src/middleware.ts
+++ b/src/middleware.ts
@@ -40,14 +40,13 @@ export default function middleware(req: NextRequest, res:NextResponse) {
 }
 
 export const config = {
-  /* Excludes:
-     - /api + /api/auth*
-     - /_next/static*
-     - /_next/image*
-     - /favicon.ico + /favicons/*
-     - /grid
-     - / (root)
-  */
+  // Excludes:
+  // - /api + /api/auth*
+  // - /_next/static*
+  // - /_next/image*
+  // - /favicon.ico + /favicons/*
+  // - /grid
+  // - / (root)
   // eslint-disable-next-line max-len
   matcher: ['/((?!api$|api/auth|_next/static|_next/image|favicon.ico$|favicons/|grid$|$).*)'],
 };
diff --git a/src/photo/PhotoEditPageClient.tsx b/src/photo/PhotoEditPageClient.tsx
index 34303e8a..8b7fc05f 100644
--- a/src/photo/PhotoEditPageClient.tsx
+++ b/src/photo/PhotoEditPageClient.tsx
@@ -70,6 +70,7 @@ export default function PhotoEditPageClient({
             <AiButton {...{ aiContent, shouldConfirm: hasTextContent }} />}
           <PhotoSyncButton
             action={action}
+            label="EXIF"
             formData={{ photoUrl: photo.url }}
           />
         </div>}
diff --git a/src/photo/actions.ts b/src/photo/actions.ts
index 82236f2d..b9ba4144 100644
--- a/src/photo/actions.ts
+++ b/src/photo/actions.ts
@@ -279,31 +279,62 @@ export const getExifDataAction = async (
     return {};
   });
 
-// Accessed from admin photo table
-// will update blur data
-export const syncPhotoExifDataAction = async (formData: FormData) =>
+// Accessed from admin photo table, will:
+// - update EXIF data
+// - anonymize storage url if necessary
+// - update blur data (or destroy if blur is disabled)
+// - generate AI text data, if enabled, and auto-generated fields are empty
+export const syncPhotoAction = async (formData: FormData) =>
   runAuthenticatedAdminServerAction(async () => {
-    const photoId = formData.get('id') as string;
-    if (photoId) {
-      const photo = await getPhoto(photoId);
-      if (photo) {
-        const { photoFormExif } = await extractImageDataFromBlobPath(
-          photo.url, {
-            generateBlurData: BLUR_ENABLED,
-          });
-        if (photoFormExif) {
-          const photoFormDbInsert = convertFormDataToPhotoDbInsert({
-            ...convertPhotoToFormData(photo),
-            ...photoFormExif,
-          });
-          await updatePhoto(photoFormDbInsert);
-          revalidatePhotosKey();
+    const photoId = formData.get('photoId') as string | undefined;
+    const photo = await getPhoto(photoId ?? '', true);
+
+    if (photo) {
+      const {
+        photoFormExif,
+        imageResizedBase64,
+      } = await extractImageDataFromBlobPath(photo.url, {
+        includeInitialPhotoFields: false,
+        generateBlurData: BLUR_ENABLED,
+        generateResizedImage: AI_TEXT_GENERATION_ENABLED,
+      });
+
+      if (photoFormExif) {
+        if (photo.url.includes(photo.id)) {
+          // Anonymize storage url on update if necessary by
+          // re-running image upload transfer logic
+          const url = await convertUploadToPhoto(photo.url);
+          if (url) { photo.url = url; }
         }
+
+        const {
+          title: atTitle,
+          caption: aiCaption,
+          tags: aiTags,
+          semanticDescription: aiSemanticDescription,
+        } = await generateAiImageQueries(
+          imageResizedBase64,
+          AI_TEXT_AUTO_GENERATED_FIELDS
+        );
+
+        const photoFormDbInsert = convertFormDataToPhotoDbInsert({
+          ...convertPhotoToFormData(photo),
+          ...photoFormExif,
+          ...!BLUR_ENABLED && { blurData: undefined },
+          ...!photo.title && { title: atTitle },
+          ...!photo.caption && { caption: aiCaption },
+          ...photo.tags.length === 0 && { tags: aiTags },
+          ...!photo.semanticDescription &&
+          { semanticDescription: aiSemanticDescription },
+        });
+
+        await updatePhoto(photoFormDbInsert);
+        revalidateAllKeysAndPaths();
       }
     }
   });
 
-export const syncCacheAction = async () =>
+export const clearCacheAction = async () =>
   runAuthenticatedAdminServerAction(revalidateAllKeysAndPaths);
 
 export const streamAiImageQueryAction = async (