diff --git a/src/utils/orbit/cleanup.test.ts b/src/utils/orbit/cleanup.test.ts
new file mode 100644
index 00000000..4a6e7803
--- /dev/null
+++ b/src/utils/orbit/cleanup.test.ts
@@ -0,0 +1,76 @@
+import { beforeEach, describe, expect, it, vi } from 'vitest';
+import { makeInitialOrbitState } from '../../api/orbit';
+
+const playlists = vi.hoisted(() => ({ getPlaylists: vi.fn(), deletePlaylist: vi.fn() }));
+const lastSession = vi.hoisted(() => ({ readOrbitLastSessionSid: vi.fn() }));
+const orbitStoreState = vi.hoisted(() => ({ sessionId: null as string | null }));
+
+vi.mock('../../api/subsonicPlaylists', () => playlists);
+vi.mock('../../store/authStore', () => ({
+  useAuthStore: { getState: () => ({ getActiveServer: () => ({ username: 'bob' }) }) },
+}));
+vi.mock('../../store/orbitStore', () => ({
+  useOrbitStore: { getState: () => orbitStoreState },
+}));
+vi.mock('./lastSession', () => lastSession);
+
+import { cleanupOrphanedOrbitPlaylists } from './cleanup';
+
+function sessionComment(sid: string, ageMs = 0): string {
+  const s = makeInitialOrbitState({ sid, host: 'bob', name: 'X' });
+  return JSON.stringify({ ...s, positionAt: Date.now() - ageMs });
+}
+const pl = (name: string, comment: string | undefined, id = name) => ({
+  id, name, owner: 'bob', comment, changed: undefined as string | undefined,
+});
+
+beforeEach(() => {
+  vi.clearAllMocks();
+  orbitStoreState.sessionId = null;
+  lastSession.readOrbitLastSessionSid.mockReturnValue(null);
+  playlists.deletePlaylist.mockResolvedValue(undefined);
+});
+
+describe('cleanupOrphanedOrbitPlaylists', () => {
+  it('does not prune a live session protected by the reconnect breadcrumb', async () => {
+    // Regression: the bare session name (`__psyorbit_<sid>__`) must match the
+    // regex so the sid-skip is reached. A mis-anchored regex treated it as
+    // corrupt and deleted it before the breadcrumb guard — killing reconnect.
+    lastSession.readOrbitLastSessionSid.mockReturnValue('aaaa1111');
+    playlists.getPlaylists.mockResolvedValue([
+      pl('__psyorbit_aaaa1111__', sessionComment('aaaa1111', 60 * 60_000)),
+      pl('__psyorbit_aaaa1111_from_bob__', JSON.stringify({ ts: Date.now() - 60 * 60_000 })),
+    ]);
+
+    const deleted = await cleanupOrphanedOrbitPlaylists();
+
+    expect(deleted).toBe(0);
+    expect(playlists.deletePlaylist).not.toHaveBeenCalled();
+  });
+
+  it('recognises a fresh session playlist instead of pruning the bare name', async () => {
+    playlists.getPlaylists.mockResolvedValue([
+      pl('__psyorbit_bbbb2222__', sessionComment('bbbb2222', 0)),
+    ]);
+    const deleted = await cleanupOrphanedOrbitPlaylists();
+    expect(deleted).toBe(0);
+    expect(playlists.deletePlaylist).not.toHaveBeenCalled();
+  });
+
+  it('prunes a stale, unprotected session', async () => {
+    playlists.getPlaylists.mockResolvedValue([
+      pl('__psyorbit_cccc3333__', sessionComment('cccc3333', 60 * 60_000)),
+    ]);
+    const deleted = await cleanupOrphanedOrbitPlaylists();
+    expect(deleted).toBe(1);
+    expect(playlists.deletePlaylist).toHaveBeenCalledWith('__psyorbit_cccc3333__');
+  });
+
+  it('prunes a corrupt / unrecognised orbit name', async () => {
+    playlists.getPlaylists.mockResolvedValue([
+      pl('__psyorbit_not-hex-no-suffix', undefined),
+    ]);
+    const deleted = await cleanupOrphanedOrbitPlaylists();
+    expect(deleted).toBe(1);
+  });
+});
diff --git a/src/utils/orbit/cleanup.ts b/src/utils/orbit/cleanup.ts
index 9e8d0b32..d868ec20 100644
--- a/src/utils/orbit/cleanup.ts
+++ b/src/utils/orbit/cleanup.ts
@@ -31,7 +31,12 @@ export async function cleanupOrphanedOrbitPlaylists(): Promise<number> {
   // the next sweep prunes it.
   const reconnectSid = readOrbitLastSessionSid();
 
-  const nameRe = new RegExp(`^${ORBIT_PLAYLIST_PREFIX}([a-f0-9]+)(_from_.+__)?$`);
+  // Matches both a session playlist (`__psyorbit_<sid>__`) and an outbox
+  // (`__psyorbit_<sid>_from_<user>__`). The trailing `__` must live outside the
+  // optional `_from_…` group, otherwise a bare session name fails to match and
+  // gets pruned as "corrupt" — which would delete a live session a restart is
+  // about to reconnect to.
+  const nameRe = new RegExp(`^${ORBIT_PLAYLIST_PREFIX}([a-f0-9]+)(_from_.+)?__$`);
   let deleted = 0;
 
   for (const p of all) {