diff --git a/web/src/lib/api/types.ts b/web/src/lib/api/types.ts
index bb1645c3..34f5d364 100644
--- a/web/src/lib/api/types.ts
+++ b/web/src/lib/api/types.ts
@@ -87,6 +87,12 @@ export type PlaylistTrack = {
   duration_sec: number;
   stream_url: string | null;
   added_at: string;
+  // True when the track still exists but its file is missing from disk
+  // (#2527). Distinct from track_id === null: that one is gone for good,
+  // this one keeps its play history and likes and may come back — the
+  // scanner un-marks it, or adopts it if it returns renamed. Both are
+  // unplayable; only this one is worth telling the user about.
+  unavailable: boolean;
 };
 
 export type PlaylistDetail = Playlist & {
diff --git a/web/src/lib/components/PlaylistCard.test.ts b/web/src/lib/components/PlaylistCard.test.ts
index c5d3bf3c..ef859b29 100644
--- a/web/src/lib/components/PlaylistCard.test.ts
+++ b/web/src/lib/components/PlaylistCard.test.ts
@@ -35,7 +35,8 @@ vi.mock('$lib/api/playlists', () => ({
         album_title: 'Test Album',
         duration_sec: 60,
         stream_url: '/s/t-1',
-        added_at: '2026-01-01T00:00:00Z'
+        added_at: '2026-01-01T00:00:00Z',
+        unavailable: false
       }
     ]
   } as PlaylistDetail),
@@ -66,7 +67,8 @@ vi.mock('$lib/api/playlists', () => ({
         album_title: 'Test Album',
         duration_sec: 60,
         stream_url: '/s/t-9',
-        added_at: '2026-01-01T00:00:00Z'
+        added_at: '2026-01-01T00:00:00Z',
+        unavailable: false
       }
     ]
   } as PlaylistDetail),
diff --git a/web/src/lib/components/PlaylistTrackRow.svelte b/web/src/lib/components/PlaylistTrackRow.svelte
index d3fb6d0c..9238da84 100644
--- a/web/src/lib/components/PlaylistTrackRow.svelte
+++ b/web/src/lib/components/PlaylistTrackRow.svelte
@@ -22,7 +22,15 @@
     onMove?: (fromPos: number, toPos: number) => void;
   } = $props();
 
-  const isUnavailable = $derived(row.track_id === null);
+  // Two different ways a row can be dead, with the same behaviour and
+  // deliberately different copy. A removed track is gone for good; a
+  // missing file is a track we still have — history, likes and all —
+  // whose bytes aren't on disk right now (#2527). Telling the user
+  // "file missing" invites them to fix it; a strikethrough would say
+  // "deleted", which is a lie about a file that may well come back.
+  const isMissingFile = $derived(row.unavailable);
+  const isRemoved = $derived(row.track_id === null);
+  const isUnavailable = $derived(isRemoved || isMissingFile);
 
   // Reconstruct a minimal TrackRef for the kebab menu when the
   // upstream track still exists. When unavailable, the menu is hidden.
@@ -108,10 +116,16 @@
     class="min-w-0 flex-1 text-left"
     onclick={() => !isUnavailable && onPlay(row.position)}
     disabled={isUnavailable}
+    title={isMissingFile
+      ? 'This track’s file is missing from the library, so it can’t be played. It stays in the playlist, and returns automatically if the file comes back.'
+      : undefined}
   >
-    <div class="truncate {isUnavailable ? 'line-through' : ''}">{row.title}</div>
+    <div class="truncate {isRemoved ? 'line-through' : ''}">{row.title}</div>
     <div class="truncate text-xs text-text-muted">
       {row.artist_name} · {row.album_title}
+      {#if isMissingFile}
+        <span class="text-action-destructive"> · File missing</span>
+      {/if}
     </div>
   </button>
 
diff --git a/web/src/lib/components/PlaylistTrackRow.test.ts b/web/src/lib/components/PlaylistTrackRow.test.ts
index 5ea34d6b..f743db15 100644
--- a/web/src/lib/components/PlaylistTrackRow.test.ts
+++ b/web/src/lib/components/PlaylistTrackRow.test.ts
@@ -41,7 +41,8 @@ const live: PlaylistTrack = {
   album_title: 'MHTRTC',
   duration_sec: 137,
   stream_url: '/api/tracks/t-1/stream',
-  added_at: ''
+  added_at: '',
+  unavailable: false
 };
 
 const removed: PlaylistTrack = {
@@ -52,6 +53,15 @@ const removed: PlaylistTrack = {
   stream_url: null
 };
 
+// Missing file (#2527): the track row still exists — ids intact, history
+// intact — but the server withholds the stream URL because the bytes are
+// not on disk. Deliberately distinct from `removed` above.
+const missingFile: PlaylistTrack = {
+  ...live,
+  stream_url: null,
+  unavailable: true
+};
+
 afterEach(() => vi.clearAllMocks());
 
 describe('PlaylistTrackRow', () => {
@@ -119,4 +129,31 @@ describe('PlaylistTrackRow', () => {
     await fireEvent.click(screen.getByText('Roygbiv'));
     expect(onPlay).toHaveBeenCalledWith(2);
   });
+
+  // A missing file is NOT a removed track: the row says so, and says it
+  // without the strikethrough that would imply the track is gone for good.
+  test('missing file is labelled and not struck through', () => {
+    render(PlaylistTrackRow, {
+      props: { row: missingFile, isOwner: true, onRemove: vi.fn(), onPlay: vi.fn() }
+    });
+    expect(screen.getByText(/file missing/i)).toBeTruthy();
+    expect(screen.getByText('Roygbiv').className).not.toContain('line-through');
+  });
+
+  test('clicking a missing-file row does not play it', async () => {
+    const onPlay = vi.fn();
+    render(PlaylistTrackRow, {
+      props: { row: missingFile, isOwner: true, onRemove: vi.fn(), onPlay }
+    });
+    await fireEvent.click(screen.getByText('Roygbiv'));
+    expect(onPlay).not.toHaveBeenCalled();
+  });
+
+  // The owner must still be able to take the dead entry out of their list.
+  test('remove stays available on a missing-file row', () => {
+    render(PlaylistTrackRow, {
+      props: { row: missingFile, isOwner: true, onRemove: vi.fn(), onPlay: vi.fn() }
+    });
+    expect(screen.getByLabelText(/remove roygbiv from playlist/i)).toBeTruthy();
+  });
 });
diff --git a/web/src/lib/playlists/playlistTrackToRef.test.ts b/web/src/lib/playlists/playlistTrackToRef.test.ts
new file mode 100644
index 00000000..3bee4760
--- /dev/null
+++ b/web/src/lib/playlists/playlistTrackToRef.test.ts
@@ -0,0 +1,51 @@
+import { describe, expect, test } from 'vitest';
+import type { PlaylistTrack } from '$lib/api/types';
+import { playlistTrackToRef } from './playlistTrackToRef';
+
+const row: PlaylistTrack = {
+  position: 0,
+  track_id: 't-1',
+  album_id: 'a-1',
+  artist_id: 'ar-1',
+  title: 'Roygbiv',
+  artist_name: 'Boards of Canada',
+  album_title: 'MHTRTC',
+  duration_sec: 137,
+  stream_url: '/api/tracks/t-1/stream',
+  added_at: '',
+  unavailable: false
+};
+
+describe('playlistTrackToRef', () => {
+  test('maps a playable row onto a TrackRef', () => {
+    expect(playlistTrackToRef(row)).toEqual({
+      id: 't-1',
+      title: 'Roygbiv',
+      album_id: 'a-1',
+      album_title: 'MHTRTC',
+      artist_id: 'ar-1',
+      artist_name: 'Boards of Canada',
+      duration_sec: 137,
+      stream_url: '/api/tracks/t-1/stream'
+    });
+  });
+
+  test('returns null when the upstream track was removed', () => {
+    expect(playlistTrackToRef({ ...row, track_id: null, stream_url: null })).toBeNull();
+  });
+
+  // This is what makes a missing file "get skipped": every queue builder
+  // filters the nulls out of this mapper, so nothing downstream has to know
+  // about missing_since. If this stops returning null, the player will try
+  // to stream a file that is not there.
+  test('returns null when the file is missing, even with ids intact', () => {
+    expect(playlistTrackToRef({ ...row, unavailable: true, stream_url: null })).toBeNull();
+  });
+
+  // Belt and braces: the server withholds stream_url for a missing file, but
+  // the flag alone must be enough — a client that trusted only the URL would
+  // happily queue a stale one from cache.
+  test('the flag alone disqualifies a row', () => {
+    expect(playlistTrackToRef({ ...row, unavailable: true })).toBeNull();
+  });
+});
diff --git a/web/src/lib/playlists/playlistTrackToRef.ts b/web/src/lib/playlists/playlistTrackToRef.ts
index 929c1d4e..2ff34dd6 100644
--- a/web/src/lib/playlists/playlistTrackToRef.ts
+++ b/web/src/lib/playlists/playlistTrackToRef.ts
@@ -2,13 +2,19 @@
 // by play queues + track menus. Centralizes the mapping so server
 // additions (new TrackRef fields) only update one site.
 //
-// Returns null when the upstream track has been removed (track_id
-// is null on the playlist row); callers should filter nulls.
+// Returns null when the row cannot be played, for either of the two
+// reasons a playlist entry can outlive its track:
+//   - track_id is null — the track was removed from the library and only
+//     the playlist's text snapshot remains.
+//   - unavailable — the track is still there, with its history intact,
+//     but its file is missing from disk (#2527).
+// Callers filter nulls, which is what makes a missing file "get skipped"
+// everywhere a queue is built rather than at each call site.
 
 import type { PlaylistTrack, TrackRef } from '$lib/api/types';
 
 export function playlistTrackToRef(row: PlaylistTrack): TrackRef | null {
-  if (!row.track_id) return null;
+  if (!row.track_id || row.unavailable) return null;
   return {
     id: row.track_id,
     title: row.title,
diff --git a/web/src/routes/playlists/[id]/playlist.test.ts b/web/src/routes/playlists/[id]/playlist.test.ts
index fd1fbfd6..21b638d5 100644
--- a/web/src/routes/playlists/[id]/playlist.test.ts
+++ b/web/src/routes/playlists/[id]/playlist.test.ts
@@ -52,8 +52,8 @@ const ownDetail: PlaylistDetail = {
   description: '', is_public: false, kind: 'user', system_variant: null, refreshable: false, seed_artist_id: null, cover_url: '', track_count: 2, duration_sec: 274,
   created_at: '', updated_at: '',
   tracks: [
-    { position: 0, track_id: 't1', album_id: 'a1', artist_id: 'ar1', title: 'A', artist_name: 'X', album_title: 'Y', duration_sec: 137, stream_url: '/api/tracks/t1/stream', added_at: '' },
-    { position: 1, track_id: 't2', album_id: 'a1', artist_id: 'ar1', title: 'B', artist_name: 'X', album_title: 'Y', duration_sec: 137, stream_url: '/api/tracks/t2/stream', added_at: '' }
+    { position: 0, track_id: 't1', album_id: 'a1', artist_id: 'ar1', title: 'A', artist_name: 'X', album_title: 'Y', duration_sec: 137, stream_url: '/api/tracks/t1/stream', added_at: '', unavailable: false },
+    { position: 1, track_id: 't2', album_id: 'a1', artist_id: 'ar1', title: 'B', artist_name: 'X', album_title: 'Y', duration_sec: 137, stream_url: '/api/tracks/t2/stream', added_at: '', unavailable: false }
   ]
 };