diff --git a/client/src/pages/JourneyDetailPage.tsx b/client/src/pages/JourneyDetailPage.tsx
index f7002877..398f74cd 100644
--- a/client/src/pages/JourneyDetailPage.tsx
+++ b/client/src/pages/JourneyDetailPage.tsx
@@ -1042,7 +1042,7 @@ function GalleryView({ entries, journeyId, userId, trips, onPhotoClick, onRefres
           trips={trips}
           existingAssetIds={new Set(entries.flatMap(e => (e.photos || []).filter(p => p.asset_id).map(p => p.asset_id!)))}
           onClose={() => setShowPicker(false)}
-          onAdd={async (assetIds, entryId, passphrase) => {
+          onAdd={async (groups, entryId) => {
             let targetId = entryId
             if (!targetId) {
               try {
@@ -1055,10 +1055,12 @@ function GalleryView({ entries, journeyId, userId, trips, onPhotoClick, onRefres
               } catch { return }
             }
             let added = 0
-            try {
-              const result = await journeyApi.addProviderPhotos(targetId, pickerProvider!, assetIds, undefined, passphrase)
-              added = result.added || 0
-            } catch {}
+            for (const group of groups) {
+              try {
+                const result = await journeyApi.addProviderPhotos(targetId, pickerProvider!, group.assetIds, undefined, group.passphrase)
+                added += result.added || 0
+              } catch {}
+            }
             if (added > 0) {
               toast.success(t('journey.photosAdded', { count: added }))
               onRefresh()
@@ -1532,7 +1534,7 @@ function ProviderPicker({ provider, userId, entries, trips, existingAssetIds, on
   trips: JourneyTrip[]
   existingAssetIds: Set<string>
   onClose: () => void
-  onAdd: (assetIds: string[], entryId: number | null, passphrase?: string) => Promise<void>
+  onAdd: (groups: Array<{ assetIds: string[]; passphrase?: string }>, entryId: number | null) => Promise<void>
 }) {
   const { t } = useTranslation()
   const [filter, setFilter] = useState<'trip' | 'custom' | 'all' | 'album'>('trip')
@@ -1546,7 +1548,7 @@ function ProviderPicker({ provider, userId, entries, trips, existingAssetIds, on
   const [searchPage, setSearchPage] = useState(1)
   const [searchFrom, setSearchFrom] = useState('')
   const [searchTo, setSearchTo] = useState('')
-  const [selected, setSelected] = useState<Set<string>>(new Set())
+  const [selected, setSelected] = useState<Map<string, { albumId?: string; passphrase?: string }>>(new Map())
   const [customFrom, setCustomFrom] = useState('')
   const [customTo, setCustomTo] = useState('')
   const [targetEntryId, setTargetEntryId] = useState<number | null>(null)
@@ -1638,8 +1640,12 @@ function ProviderPicker({ provider, userId, entries, trips, existingAssetIds, on
 
   const toggleAsset = (id: string) => {
     setSelected(prev => {
-      const next = new Set(prev)
-      if (next.has(id)) next.delete(id); else next.add(id)
+      const next = new Map(prev)
+      if (next.has(id)) {
+        next.delete(id)
+      } else {
+        next.set(id, { albumId: selectedAlbum ?? undefined, passphrase: selectedAlbumPassphrase })
+      }
       return next
     })
   }
@@ -1801,9 +1807,9 @@ function ProviderPicker({ provider, userId, entries, trips, existingAssetIds, on
               <button
                 onClick={() => {
                   if (allSelected) {
-                    setSelected(new Set())
+                    setSelected(new Map())
                   } else {
-                    setSelected(new Set(selectable.map((a: any) => a.id)))
+                    setSelected(new Map(selectable.map((a: any) => [a.id, { albumId: selectedAlbum ?? undefined, passphrase: selectedAlbumPassphrase }])))
                   }
                 }}
                 className="inline-flex items-center gap-1.5 px-2.5 py-1 rounded-lg text-[11px] font-medium border border-zinc-200 dark:border-zinc-700 text-zinc-500 dark:text-zinc-400 hover:bg-zinc-50 dark:hover:bg-zinc-800"
@@ -1905,7 +1911,16 @@ function ProviderPicker({ provider, userId, entries, trips, existingAssetIds, on
               {t('common.cancel')}
             </button>
             <button
-              onClick={() => onAdd([...selected], targetEntryId, selectedAlbumPassphrase)}
+              onClick={() => {
+                const groupMap = new Map<string | undefined, string[]>()
+                for (const [assetId, { passphrase }] of selected.entries()) {
+                  const list = groupMap.get(passphrase) || []
+                  list.push(assetId)
+                  groupMap.set(passphrase, list)
+                }
+                const groups = [...groupMap.entries()].map(([passphrase, assetIds]) => ({ assetIds, passphrase }))
+                onAdd(groups, targetEntryId)
+              }}
               disabled={selected.size === 0}
               className="px-3.5 py-2 rounded-lg bg-zinc-900 dark:bg-white text-white dark:text-zinc-900 text-[13px] font-medium hover:bg-zinc-800 dark:hover:bg-zinc-100 disabled:opacity-40 disabled:cursor-not-allowed"
             >
diff --git a/server/src/services/journeyService.ts b/server/src/services/journeyService.ts
index f0292399..5a759eed 100644
--- a/server/src/services/journeyService.ts
+++ b/server/src/services/journeyService.ts
@@ -1,7 +1,7 @@
 import { db } from '../db/database';
 import { broadcastToUser } from '../websocket';
 import type { Journey, JourneyEntry, JourneyPhoto, JourneyContributor } from '../types';
-import { getOrCreateTrekPhoto, getOrCreateLocalTrekPhoto, setTrekPhotoProvider } from './memories/photoResolverService';
+import { getOrCreateTrekPhoto, getOrCreateLocalTrekPhoto, setTrekPhotoProvider, deleteTrekPhotoIfOrphan } from './memories/photoResolverService';
 
 function ts(): number {
   return Date.now();
@@ -718,6 +718,7 @@ export function deletePhoto(photoId: number, userId: number): (JourneyPhoto & {
   if (!canEdit(photo.journey_id, userId)) return null;
 
   db.prepare('DELETE FROM journey_photos WHERE id = ?').run(photoId);
+  deleteTrekPhotoIfOrphan(photo.photo_id);
 
   // clean up empty Gallery entries left behind
   const remaining = db.prepare('SELECT 1 FROM journey_photos WHERE entry_id = ?').get(photo.entry_id);
diff --git a/server/src/services/memories/photoResolverService.ts b/server/src/services/memories/photoResolverService.ts
index f0e7c816..3af080e5 100644
--- a/server/src/services/memories/photoResolverService.ts
+++ b/server/src/services/memories/photoResolverService.ts
@@ -22,7 +22,7 @@ export function getOrCreateTrekPhoto(
   ).get(provider, assetId, ownerId) as { id: number } | undefined;
   if (existing) {
     if (passphrase) {
-      db.prepare('UPDATE trek_photos SET passphrase = ? WHERE id = ? AND passphrase IS NULL')
+      db.prepare('UPDATE trek_photos SET passphrase = ? WHERE id = ?')
         .run(encrypt_api_key(passphrase), existing.id);
     }
     return existing.id;
@@ -145,6 +145,19 @@ export function setTrekPhotoProvider(
   ).run(provider, assetId, ownerId, trekPhotoId);
 }
 
+// ── Orphan cleanup ───────────────────────────────────────────────────────
+
+export function deleteTrekPhotoIfOrphan(photoId: number): void {
+  const stillUsed = db.prepare(`
+    SELECT 1 FROM trip_photos WHERE photo_id = ?
+    UNION ALL
+    SELECT 1 FROM journey_photos WHERE photo_id = ?
+    LIMIT 1
+  `).get(photoId, photoId);
+  if (stillUsed) return;
+  db.prepare("DELETE FROM trek_photos WHERE id = ? AND provider != 'local'").run(photoId);
+}
+
 // ── Delete local file for a trek_photo ──────────────────────────────────
 
 export function getTrekPhotoFilePath(photoId: number): string | null {
diff --git a/server/src/services/memories/unifiedService.ts b/server/src/services/memories/unifiedService.ts
index 888f2710..c884ee6b 100644
--- a/server/src/services/memories/unifiedService.ts
+++ b/server/src/services/memories/unifiedService.ts
@@ -8,7 +8,7 @@ import {
   mapDbError,
   Selection,
 } from './helpersService';
-import { getOrCreateTrekPhoto } from './photoResolverService';
+import { getOrCreateTrekPhoto, deleteTrekPhotoIfOrphan } from './photoResolverService';
 import { encrypt_api_key } from '../apiKeyCrypto';
 
 
@@ -212,6 +212,7 @@ export function removeTripPhoto(
         AND photo_id = ?
     `).run(tripId, userId, photoId);
 
+    deleteTrekPhotoIfOrphan(photoId);
     broadcast(tripId, 'memories:updated', { userId }, sid);
 
     return success(true);
@@ -269,13 +270,20 @@ export function removeAlbumLink(tripId: string, linkId: string, userId: number):
   }
 
   try {
+    const linkedPhotos = db.prepare('SELECT photo_id FROM trip_photos WHERE trip_id = ? AND album_link_id = ?')
+      .all(tripId, linkId) as Array<{ photo_id: number }>;
+
     db.transaction(() => {
       db.prepare('DELETE FROM trip_photos WHERE trip_id = ? AND album_link_id = ?')
         .run(tripId, linkId);
       db.prepare('DELETE FROM trip_album_links WHERE id = ? AND trip_id = ? AND user_id = ?')
         .run(linkId, tripId, userId);
     })();
-    
+
+    for (const { photo_id } of linkedPhotos) {
+      deleteTrekPhotoIfOrphan(photo_id);
+    }
+
     return success(true);
   } catch (error) {
     return mapDbError(error, 'Failed to remove album link');
diff --git a/server/tests/integration/memories-synology.test.ts b/server/tests/integration/memories-synology.test.ts
index d5880310..8f0acddf 100644
--- a/server/tests/integration/memories-synology.test.ts
+++ b/server/tests/integration/memories-synology.test.ts
@@ -1169,3 +1169,74 @@ describe('Synology SSRF blocked error handling', () => {
     expect(res.body.albums.length).toBeGreaterThan(0);
   });
 });
+
+// ── Passphrase persistence fixes ─────────────────────────────────────────────
+
+import { getOrCreateTrekPhoto, deleteTrekPhotoIfOrphan } from '../../src/services/memories/photoResolverService';
+import { decrypt_api_key } from '../../src/services/apiKeyCrypto';
+
+describe('trek_photos passphrase healing (SYNO-090)', () => {
+  it('SYNO-090 — getOrCreateTrekPhoto overwrites an existing bad passphrase when a new one is supplied', () => {
+    const { user } = createUser(testDb);
+
+    const wrongPass = 'wrong-passphrase';
+    const correctPass = 'correct-passphrase';
+
+    const id1 = getOrCreateTrekPhoto('synologyphotos', 'asset-heal-test', user.id, wrongPass);
+    const row1 = testDb.prepare('SELECT passphrase FROM trek_photos WHERE id = ?').get(id1) as { passphrase: string };
+    expect(decrypt_api_key(row1.passphrase)).toBe(wrongPass);
+
+    const id2 = getOrCreateTrekPhoto('synologyphotos', 'asset-heal-test', user.id, correctPass);
+    expect(id2).toBe(id1);
+    const row2 = testDb.prepare('SELECT passphrase FROM trek_photos WHERE id = ?').get(id2) as { passphrase: string };
+    expect(decrypt_api_key(row2.passphrase)).toBe(correctPass);
+  });
+});
+
+describe('trek_photos orphan cleanup (SYNO-091)', () => {
+  it('SYNO-091 — deleteTrekPhotoIfOrphan removes the trek_photos row when no trip_photos or journey_photos reference it', () => {
+    const { user } = createUser(testDb);
+    const trip = createTrip(testDb, user.id);
+    testDb.prepare("UPDATE photo_providers SET enabled = 1 WHERE id = 'synologyphotos'").run();
+
+    const trekPhotoId = getOrCreateTrekPhoto('synologyphotos', 'asset-orphan-test', user.id, 'pass-A');
+
+    testDb.prepare(
+      'INSERT OR IGNORE INTO trip_photos (trip_id, user_id, photo_id, shared) VALUES (?, ?, ?, 1)'
+    ).run(trip.id, user.id, trekPhotoId);
+
+    // Still referenced — must not be deleted.
+    deleteTrekPhotoIfOrphan(trekPhotoId);
+    expect(testDb.prepare('SELECT id FROM trek_photos WHERE id = ?').get(trekPhotoId)).toBeDefined();
+
+    // Remove the reference, then orphan-cleanup should delete the trek_photos row.
+    testDb.prepare('DELETE FROM trip_photos WHERE photo_id = ?').run(trekPhotoId);
+    deleteTrekPhotoIfOrphan(trekPhotoId);
+    expect(testDb.prepare('SELECT id FROM trek_photos WHERE id = ?').get(trekPhotoId)).toBeUndefined();
+  });
+
+  it('SYNO-092 — re-adding a previously removed Synology photo stores the new passphrase correctly', () => {
+    const { user } = createUser(testDb);
+    const trip = createTrip(testDb, user.id);
+    testDb.prepare("UPDATE photo_providers SET enabled = 1 WHERE id = 'synologyphotos'").run();
+
+    const firstPass = 'first-passphrase';
+    const secondPass = 'second-passphrase';
+
+    // Add with wrong passphrase, then remove (simulating the bug scenario).
+    const id1 = getOrCreateTrekPhoto('synologyphotos', 'asset-readd-test', user.id, firstPass);
+    testDb.prepare(
+      'INSERT OR IGNORE INTO trip_photos (trip_id, user_id, photo_id, shared) VALUES (?, ?, ?, 1)'
+    ).run(trip.id, user.id, id1);
+    testDb.prepare('DELETE FROM trip_photos WHERE photo_id = ?').run(id1);
+    deleteTrekPhotoIfOrphan(id1);
+
+    // trek_photos row should be gone.
+    expect(testDb.prepare('SELECT id FROM trek_photos WHERE id = ?').get(id1)).toBeUndefined();
+
+    // Re-add with the correct passphrase.
+    const id2 = getOrCreateTrekPhoto('synologyphotos', 'asset-readd-test', user.id, secondPass);
+    const row = testDb.prepare('SELECT passphrase FROM trek_photos WHERE id = ?').get(id2) as { passphrase: string };
+    expect(decrypt_api_key(row.passphrase)).toBe(secondPass);
+  });
+});