diff --git a/src/admin/AdminPhotoMenu.tsx b/src/admin/AdminPhotoMenu.tsx
index 7ce6a06b..c8c69221 100644
--- a/src/admin/AdminPhotoMenu.tsx
+++ b/src/admin/AdminPhotoMenu.tsx
@@ -21,7 +21,6 @@ import { RevalidatePhoto } from '@/photo/InfinitePhotoScroll';
 import { MdOutlineFileDownload } from 'react-icons/md';
 import MoreMenuItem from '@/components/more/MoreMenuItem';
 import IconGrSync from '@/components/icons/IconGrSync';
-import { isPhotoOutdated } from '@/photo/outdated';
 import InsightsIndicatorDot from './insights/InsightsIndicatorDot';
 import IconFavs from '@/components/icons/IconFavs';
 import IconEdit from '@/components/icons/IconEdit';
@@ -79,7 +78,7 @@ export default function AdminPhotoMenu({
       label: 'Sync',
       labelComplex: <span className="inline-flex items-center gap-2">
         <span>Sync</span>
-        {isPhotoOutdated(photo) &&
+        {photo.needsSync &&
           <InsightsIndicatorDot
             colorOverride="blue"
             className="translate-y-[1.5px]"
diff --git a/src/photo/db/query.ts b/src/photo/db/query.ts
index 376a58d7..267c143a 100644
--- a/src/photo/db/query.ts
+++ b/src/photo/db/query.ts
@@ -24,7 +24,7 @@ import { getWheresFromOptions } from '.';
 import { FocalLengths } from '@/focal';
 import { Lenses, createLensKey } from '@/lens';
 import { migrationForError } from './migration';
-import { UPDATED_BEFORE_01, UPDATED_BEFORE_02 } from '../outdated';
+import { UPDATED_BEFORE_01, UPDATED_BEFORE_02 } from '../sync';
 import { MAKE_FUJIFILM } from '@/platforms/fujifilm';
 import { Recipes } from '@/recipe';
 
diff --git a/src/photo/index.ts b/src/photo/index.ts
index 94bb6162..e03c97cd 100644
--- a/src/photo/index.ts
+++ b/src/photo/index.ts
@@ -23,6 +23,7 @@ import { isBefore } from 'date-fns';
 import type { Metadata } from 'next';
 import { FujifilmRecipe } from '@/platforms/fujifilm/recipe';
 import { FujifilmSimulation } from '@/platforms/fujifilm/simulation';
+import { doesPhotoNeedSync } from './sync';
 
 // INFINITE SCROLL: FEED
 export const INFINITE_SCROLL_FEED_INITIAL =
@@ -109,13 +110,14 @@ export interface Photo extends Omit<PhotoDb, 'recipeData'> {
   exposureCompensationFormatted?: string
   takenAtNaiveFormatted: string
   recipeData?: FujifilmRecipe
+  needsSync?: boolean
 }
 
 export const parsePhotoFromDb = (photoDbRaw: PhotoDb): Photo => {
   const photoDb = camelcaseKeys(
     photoDbRaw as unknown as Record<string, unknown>,
   ) as unknown as PhotoDb;
-  return {
+  const photo: Photo ={
     ...photoDb,
     tags: photoDb.tags ?? [],
     focalLengthFormatted:
@@ -130,15 +132,17 @@ export const parsePhotoFromDb = (photoDbRaw: PhotoDb): Photo => {
       formatExposureTime(photoDb.exposureTime),
     exposureCompensationFormatted:
       formatExposureCompensation(photoDb.exposureCompensation),
+    takenAtNaiveFormatted:
+      formatDateFromPostgresString(photoDb.takenAtNaive),
     recipeData: photoDb.recipeData
       // Legacy check on escaped, string-based JSON
       ? typeof photoDb.recipeData === 'string'
         ? JSON.parse(photoDb.recipeData)
         : photoDb.recipeData
       : undefined,
-    takenAtNaiveFormatted:
-      formatDateFromPostgresString(photoDb.takenAtNaive),
   };
+  photo.needsSync = doesPhotoNeedSync(photo);
+  return photo;
 };
 
 export const parseCachedPhotoDates = (photo: Photo) => ({
diff --git a/src/photo/outdated.ts b/src/photo/outdated.ts
deleted file mode 100644
index 31d1fdfe..00000000
--- a/src/photo/outdated.ts
+++ /dev/null
@@ -1,13 +0,0 @@
-import { MAKE_FUJIFILM } from '@/platforms/fujifilm';
-import { Photo } from '.';
-
-export const UPDATED_BEFORE_01 = new Date('2024-06-16');
-// UTC 2025-02-24 05:30:00
-export const UPDATED_BEFORE_02 = new Date(Date.UTC(2025, 1, 24, 5, 30, 0));
-
-export const isPhotoOutdated = (photo: Photo) => {
-  return photo.updatedAt < UPDATED_BEFORE_01 || (
-    photo.updatedAt < UPDATED_BEFORE_02 &&
-    photo.make === MAKE_FUJIFILM
-  );
-};
diff --git a/src/photo/sync.ts b/src/photo/sync.ts
new file mode 100644
index 00000000..f4a9d311
--- /dev/null
+++ b/src/photo/sync.ts
@@ -0,0 +1,28 @@
+import { MAKE_FUJIFILM } from '@/platforms/fujifilm';
+import { Photo } from '.';
+import { AI_TEXT_AUTO_GENERATED_FIELDS } from '@/app/config';
+
+export const UPDATED_BEFORE_01 = new Date('2024-06-16');
+// UTC 2025-02-24 05:30:00
+export const UPDATED_BEFORE_02 = new Date(Date.UTC(2025, 1, 24, 5, 30, 0));
+
+const isPhotoOutdated = (photo: Photo) =>
+  photo.updatedAt < UPDATED_BEFORE_01 || (
+    photo.updatedAt < UPDATED_BEFORE_02 &&
+    photo.make === MAKE_FUJIFILM
+  );
+
+const doesPhotoNeedAiText = ({
+  title,
+  caption,
+  tags = [],
+  semanticDescription,
+}: Photo) =>
+  (AI_TEXT_AUTO_GENERATED_FIELDS.includes('title') && !title) ||
+  (AI_TEXT_AUTO_GENERATED_FIELDS.includes('caption') && !caption) ||
+  (AI_TEXT_AUTO_GENERATED_FIELDS.includes('tags') && tags.length === 0) ||
+  (AI_TEXT_AUTO_GENERATED_FIELDS.includes('semantic') && !semanticDescription);
+
+export const doesPhotoNeedSync = (photo: Photo) =>
+  isPhotoOutdated(photo) ||
+  doesPhotoNeedAiText(photo);