diff --git a/src/music/spotify/controller.test.ts b/src/music/spotify/controller.test.ts
index 1bf4efc..797ff7a 100644
--- a/src/music/spotify/controller.test.ts
+++ b/src/music/spotify/controller.test.ts
@@ -97,10 +97,14 @@ class FakeBackend extends EventEmitter implements SpotifyAudioBackend {
   ready = false;
   startShouldReject = false;
   playShouldReject = false;
+  /** When set, start() awaits this before resolving — lets a test interleave
+   *  stop()/error DURING a mid-flight start (Bug I1). */
+  startGate?: Promise<void>;
   readonly pcm = Readable.from([Buffer.alloc(0)]);
 
   async start(): Promise<void> {
     this.startCalls++;
+    if (this.startGate) await this.startGate;
     if (this.startShouldReject) throw new Error("start boom");
     this.ready = true;
   }
@@ -464,6 +468,40 @@ describe("SpotifyController.stop", () => {
     expect(() => ctrl.stop()).not.toThrow();
     expect(be.stopCalls).toBe(0);
   });
+
+  it("Bug I1: stop() DURING a mid-flight start tears the sidecar down instead of resurrecting it", async () => {
+    // A Deferred the test resolves to complete backend.start() on demand.
+    let resolveStart!: () => void;
+    const startGate = new Promise<void>((res) => {
+      resolveStart = res;
+    });
+    const be = new FakeBackend();
+    be.startGate = startGate;
+    const { ctrl } = makeCtrl({ backendFactory: () => be });
+
+    // Kick off ensureStarted but DO NOT await — start() is parked on the gate.
+    const startedP = ctrl.ensureStarted();
+    // Let the ensureStarted IIFE run up to `await backend.start()`.
+    await Promise.resolve();
+    await Promise.resolve();
+    expect(be.startCalls).toBe(1); // start() was entered and is now pending
+
+    // Caller tears the controller down while start() is still in flight
+    // (a user `!stop`/disconnect). Pre-fix this.backend is still null so this
+    // is a no-op and the spawned sidecar is orphaned.
+    ctrl.stop();
+
+    // Now let start() finally resolve. Pre-fix the IIFE would set this.backend
+    // and started=true, RESURRECTING the sidecar the caller already stopped.
+    resolveStart();
+    const result = await startedP;
+
+    // Post-fix: the mid-flight backend is torn down, not promoted.
+    expect(result).toBe(false);
+    expect(be.stopCalls).toBeGreaterThanOrEqual(1); // the fake WAS stopped
+    expect(be.listenerCount("trackEnded")).toBe(0); // listeners detached
+    expect(() => ctrl.getPcmStream()).toThrow(); // not resurrected
+  });
 });
 
 describe("SpotifyController per-bot ports (Fix 3)", () => {
diff --git a/src/music/spotify/controller.ts b/src/music/spotify/controller.ts
index 3b2f937..2fa2e0d 100644
--- a/src/music/spotify/controller.ts
+++ b/src/music/spotify/controller.ts
@@ -105,6 +105,12 @@ export class SpotifyController extends EventEmitter {
   private readonly connect: SpotifyConnectApi;
 
   private backend: SpotifyAudioBackend | null = null;
+  // The in-flight backend during a start() that has not yet completed. A
+  // stop()/handleBackendError() DURING start() clears (or replaces) this so the
+  // mid-start sidecar is torn down and a completing start is discarded by the
+  // ensureStarted post-await guard instead of resurrecting a backend the caller
+  // already tore down (Bug I1).
+  private pendingBackend: SpotifyAudioBackend | null = null;
   private started = false;
   private startPromise: Promise<boolean> | null = null;
 
@@ -218,30 +224,75 @@ export class SpotifyController extends EventEmitter {
     if (this.startPromise) return this.startPromise;
 
     this.startPromise = (async () => {
+      const backend = this.buildBackend(kind);
+      // Publish the in-flight backend BEFORE the (potentially ~20s) start()
+      // await so a concurrent stop()/handleBackendError() can reach and tear
+      // down this mid-start sidecar (Bug I1).
+      this.pendingBackend = backend;
+      backend.on("trackEnded", (e: SpotifyTrackEndedEvent) =>
+        this.emit("trackEnded", e),
+      );
+      backend.on("metadata", (m: SpotifyNowPlaying) =>
+        this.emit("metadata", m),
+      );
+      // C3: do NOT re-emit "error". Log and mark not-ready so the next
+      // ensureStarted() relaunches a fresh backend.
+      backend.on("error", (err?: unknown) => this.handleBackendError(err));
       try {
-        const backend = this.buildBackend(kind);
-        backend.on("trackEnded", (e: SpotifyTrackEndedEvent) =>
-          this.emit("trackEnded", e),
-        );
-        backend.on("metadata", (m: SpotifyNowPlaying) =>
-          this.emit("metadata", m),
-        );
-        // C3: do NOT re-emit "error". Log and mark not-ready so the next
-        // ensureStarted() relaunches a fresh backend.
-        backend.on("error", (err?: unknown) => this.handleBackendError(err));
         await backend.start();
-        this.backend = backend;
-        this.started = true;
-        return true;
       } catch (err) {
         this.logger.error({ err }, "Spotify backend failed to start");
+        if (this.pendingBackend === backend) this.pendingBackend = null;
         this.startPromise = null;
         return false;
       }
+      // Post-await guard (Bug I1): if teardown ran DURING start() — stop() or
+      // handleBackendError() cleared/replaced pendingBackend — do NOT promote
+      // this backend. Tear the just-started sidecar down so it is neither
+      // leaked nor resurrected, and report failure to the caller.
+      if (this.pendingBackend !== backend) {
+        this.teardownBackend(
+          backend,
+          "Spotify backend stop() threw tearing down a superseded start",
+        );
+        return false;
+      }
+      this.pendingBackend = null;
+      this.backend = backend;
+      this.started = true;
+      return true;
     })();
     return this.startPromise;
   }
 
+  /**
+   * Stop a backend and detach ALL its listeners, swallowing+logging any throw
+   * from stop() so teardown never propagates. Shared by the error/stop paths
+   * and the ensureStarted post-await guard.
+   */
+  private teardownBackend(be: SpotifyAudioBackend, stopMsg: string): void {
+    try {
+      be.stop();
+    } catch (stopErr) {
+      this.logger.error({ err: stopErr }, stopMsg);
+    }
+    (be as unknown as EventEmitter).removeAllListeners();
+  }
+
+  /**
+   * Tear down an in-flight (mid-start) backend so a start() still awaiting is
+   * discarded by ensureStarted's post-await guard rather than promoted, and its
+   * spawned sidecar is killed rather than orphaned (Bug I1).
+   */
+  private teardownPendingBackend(): void {
+    if (!this.pendingBackend) return;
+    this.teardownBackend(
+      this.pendingBackend,
+      "Spotify backend stop() threw tearing down in-flight start",
+    );
+    this.pendingBackend = null;
+  }
+
   /**
    * C3 backend-error handler. Never re-emits "error" (an unhandled "error" on
    * an EventEmitter throws). Logs, tears the errored backend down, and marks
@@ -249,16 +300,15 @@ export class SpotifyController extends EventEmitter {
    */
   private handleBackendError(err: unknown): void {
     this.logger.error({ err }, "Spotify backend error; marking not-ready");
-    try {
-      this.backend?.stop();
-    } catch (stopErr) {
-      this.logger.error(
-        { err: stopErr },
+    if (this.backend) {
+      this.teardownBackend(
+        this.backend,
         "Spotify backend stop() threw during error teardown",
       );
     }
-    (this.backend as unknown as EventEmitter | null)?.removeAllListeners();
     this.backend = null;
+    // Also kill an in-flight start so its post-await guard discards it.
+    this.teardownPendingBackend();
     this.started = false;
     this.startPromise = null;
   }
@@ -301,16 +351,16 @@ export class SpotifyController extends EventEmitter {
    * a fresh backend.
    */
   stop(): void {
-    try {
-      this.backend?.stop();
-    } catch (stopErr) {
-      this.logger.error(
-        { err: stopErr },
+    if (this.backend) {
+      this.teardownBackend(
+        this.backend,
         "Spotify backend stop() threw during teardown",
       );
     }
-    (this.backend as unknown as EventEmitter | null)?.removeAllListeners();
     this.backend = null;
+    // Also kill an in-flight start so its post-await guard discards it rather
+    // than resurrecting the sidecar this stop() just tore down (Bug I1).
+    this.teardownPendingBackend();
     this.started = false;
     this.startPromise = null;
   }
diff --git a/src/music/spotify/rust-librespot.test.ts b/src/music/spotify/rust-librespot.test.ts
index 2e539c7..64a8b7f 100644
--- a/src/music/spotify/rust-librespot.test.ts
+++ b/src/music/spotify/rust-librespot.test.ts
@@ -2,7 +2,7 @@ import { describe, it, expect, vi } from "vitest";
 import { EventEmitter } from "node:events";
 import { PassThrough } from "node:stream";
 import pino from "pino";
-import { RustLibrespotBackend } from "./rust-librespot.js";
+import { RustLibrespotBackend, type RustLibrespotBackendDeps } from "./rust-librespot.js";
 
 const log = pino({ level: "silent" });
 
@@ -36,7 +36,9 @@ function makeOAuth() {
   };
 }
 
-function makeHarness(over: { connect?: any; oauth?: any } = {}) {
+function makeHarness(
+  over: { connect?: any; oauth?: any; deps?: Partial<RustLibrespotBackendDeps> } = {},
+) {
   const calls: string[] = [];
   const librespotChild = makeFakeChild();
   const ffmpegChild = makeFakeChild();
@@ -68,6 +70,7 @@ function makeHarness(over: { connect?: any; oauth?: any } = {}) {
       readyTimeoutMs: 100,
       // huge so the background setInterval never fires; tests drive pollState() directly.
       statePollIntervalMs: 10_000_000,
+      ...over.deps,
     },
   });
 
@@ -280,6 +283,117 @@ describe("RustLibrespotBackend track-end poll loop", () => {
   });
 });
 
+describe("RustLibrespotBackend playback-start watchdog (I4 degrade-to-skip)", () => {
+  /** A controllable timer seam matching the file's injected-deps style. */
+  function makeFakeTimer() {
+    const pending: Array<{ cb: () => void; ms: number; handle: object }> = [];
+    const setTimer = vi.fn((cb: () => void, ms: number) => {
+      const handle = {};
+      pending.push({ cb, ms, handle });
+      return handle;
+    });
+    const clearTimer = vi.fn((h: unknown) => {
+      const i = pending.findIndex((p) => p.handle === h);
+      if (i >= 0) pending.splice(i, 1);
+    });
+    // "advance fake timers": run (and drain) every armed callback.
+    const advance = () => pending.splice(0).forEach((p) => p.cb());
+    return { setTimer, clearTimer, advance, pending };
+  }
+
+  it("emits exactly ONE trackEnded{reason:'error'} when playback never starts", async () => {
+    const timer = makeFakeTimer();
+    const h = makeHarness({
+      deps: {
+        playbackStartTimeoutMs: 8000,
+        setTimeout: timer.setTimer as any,
+        clearTimeout: timer.clearTimer as any,
+      },
+    });
+    const ended = vi.fn();
+    h.backend.on("trackEnded", ended);
+
+    // The connect layer NEVER reports our track playing (204 / idle).
+    h.connect.getPlaybackState.mockResolvedValue(null);
+    await h.backend.playTrack("spotify:track:stuck");
+    // Polls that never observe playback must NOT emit anything on their own.
+    await (h.backend as any).pollState();
+    await (h.backend as any).pollState();
+    expect(ended).not.toHaveBeenCalled();
+
+    // The watchdog is armed exactly once; advance past playbackStartTimeoutMs.
+    expect(timer.pending).toHaveLength(1);
+    expect(timer.pending[0].ms).toBe(8000);
+    timer.advance();
+
+    // Degraded-to-skip: one trackEnded with reason "error" for our uri.
+    expect(ended).toHaveBeenCalledTimes(1);
+    expect(ended).toHaveBeenCalledWith({ uri: "spotify:track:stuck", reason: "error" });
+
+    // A late idle poll after the watchdog fired does not double-emit.
+    await (h.backend as any).pollState();
+    expect(ended).toHaveBeenCalledTimes(1);
+    h.backend.stop();
+  });
+
+  it("does NOT fire the watchdog when the device actually starts playing", async () => {
+    const timer = makeFakeTimer();
+    const h = makeHarness({
+      deps: {
+        playbackStartTimeoutMs: 8000,
+        setTimeout: timer.setTimer as any,
+        clearTimeout: timer.clearTimer as any,
+      },
+    });
+    const ended = vi.fn();
+    h.backend.on("trackEnded", ended);
+
+    await h.backend.playTrack("spotify:track:ok");
+    // Our device reports the track actually playing -> watchdog is disarmed.
+    h.connect.getPlaybackState.mockResolvedValue({
+      isPlaying: true,
+      progressMs: 1000,
+      trackUri: "spotify:track:ok",
+      durationMs: 200000,
+    });
+    await (h.backend as any).pollState();
+
+    // Real playback observed -> the watchdog was cleared, not left armed.
+    expect(timer.clearTimer).toHaveBeenCalled();
+    expect(timer.pending).toHaveLength(0);
+    // Even if a stale timer somehow fired, no "error" end must be emitted.
+    timer.advance();
+    expect(ended).not.toHaveBeenCalledWith(
+      expect.objectContaining({ reason: "error" }),
+    );
+    h.backend.stop();
+  });
+
+  it("a new playTrack() cancels the previous track's watchdog (at-most-one per track)", async () => {
+    const timer = makeFakeTimer();
+    const h = makeHarness({
+      deps: {
+        playbackStartTimeoutMs: 8000,
+        setTimeout: timer.setTimer as any,
+        clearTimeout: timer.clearTimer as any,
+      },
+    });
+    const ended = vi.fn();
+    h.backend.on("trackEnded", ended);
+    h.connect.getPlaybackState.mockResolvedValue(null);
+
+    await h.backend.playTrack("spotify:track:one");
+    await h.backend.playTrack("spotify:track:two");
+    // The first track's watchdog was cleared; only the second remains armed.
+    expect(timer.clearTimer).toHaveBeenCalled();
+    expect(timer.pending).toHaveLength(1);
+    timer.advance();
+    expect(ended).toHaveBeenCalledTimes(1);
+    expect(ended).toHaveBeenCalledWith({ uri: "spotify:track:two", reason: "error" });
+    h.backend.stop();
+  });
+});
+
 describe("RustLibrespotBackend.stop", () => {
   it("kills librespot + ffmpeg, clears ready, and is idempotent", async () => {
     const h = makeHarness();
diff --git a/src/music/spotify/rust-librespot.ts b/src/music/spotify/rust-librespot.ts
index 7dc9f19..a2081fc 100644
--- a/src/music/spotify/rust-librespot.ts
+++ b/src/music/spotify/rust-librespot.ts
@@ -40,6 +40,15 @@ export interface RustLibrespotBackendDeps {
   readyPollIntervalMs?: number;
   readyTimeoutMs?: number;
   statePollIntervalMs?: number;
+  /**
+   * I4 (§13): bounded window after playTrack() within which our own track must
+   * be observed playing, else we degrade-to-skipped (emit trackEnded
+   * reason:"error"). Injectable timer seams (default real setTimeout, unref'd)
+   * let tests advance it deterministically.
+   */
+  playbackStartTimeoutMs?: number;
+  setTimeout?: (cb: () => void, ms: number) => unknown;
+  clearTimeout?: (handle: unknown) => void;
 }
 
 const DEFAULT_READY_POLL_MS = 500;
@@ -47,6 +56,13 @@ const DEFAULT_READY_TIMEOUT_MS = 20_000;
 const DEFAULT_STATE_POLL_MS = 2_000;
 /** How close to the end (ms) counts as "track finished" when polling player state. */
 const END_OF_TRACK_WINDOW_MS = 1_500;
+/**
+ * I4 (§13): if our own track has not been observed playing within this window
+ * after playTrack(), degrade-to-skipped so the queue advances instead of
+ * stalling on a persistently-failing play (403 non-Premium, 404 outliving
+ * retries). Bounded and injectable for tests.
+ */
+const DEFAULT_PLAYBACK_START_TIMEOUT_MS = 8_000;
 
 const defaultSleep = (ms: number) => new Promise<void>((r) => setTimeout(r, ms));
 
@@ -60,6 +76,9 @@ export class RustLibrespotBackend extends EventEmitter implements SpotifyAudioBa
   private proc: ChildProcess | null = null;
   private ffmpeg: ChildProcess | null = null;
   private pollTimer: ReturnType<typeof setInterval> | null = null;
+  // I4 (§13): "did our track actually start playing?" watchdog handle (opaque —
+  // produced by the injectable setTimeout seam). null when disarmed.
+  private watchdogTimer: unknown = null;
   private ready = false;
   private positionMs = 0;
 
@@ -253,7 +272,11 @@ export class RustLibrespotBackend extends EventEmitter implements SpotifyAudioBa
       this.emit("metadata", np);
     }
 
-    if (state.isPlaying) this.hasPlayed = true;
+    if (state.isPlaying) {
+      this.hasPlayed = true;
+      // Real playback observed -> the I4 degrade-to-skip watchdog is moot.
+      this.clearPlaybackWatchdog();
+    }
     if (!this.currentUri || this.endedForCurrent) return;
 
     // C3.4: EVERY end condition is gated on hasPlayed so no end can fire until
@@ -289,6 +312,9 @@ export class RustLibrespotBackend extends EventEmitter implements SpotifyAudioBa
     // uri playing. currentUri is cleared so the next poll re-detects the track
     // (fresh metadata) rather than treating it as unchanged. Arming here is the
     // primary guarantee that no end/metadata can fire before the bot plays.
+    // Cancel the previous track's degrade-to-skip watchdog first (at-most-one
+    // trackEnded per track, I4).
+    this.clearPlaybackWatchdog();
     this.currentUri = null;
     this.hasPlayed = false;
     this.endedForCurrent = false;
@@ -298,6 +324,58 @@ export class RustLibrespotBackend extends EventEmitter implements SpotifyAudioBa
     // begin playback.
     await this.connect.transfer(deviceId, false);
     await this.connect.play(deviceId, uri);
+    // I4 (§13): arm the "did it actually start playing?" watchdog. If our own
+    // track is never seen playing within the window, degrade-to-skipped so the
+    // queue advances instead of hanging on a silent, persistently-failing play.
+    this.armPlaybackWatchdog(uri);
+  }
+
+  /**
+   * I4 (§13) degrade-to-skip watchdog. Arms a bounded timer; if our own track
+   * has not been observed playing by the time it fires, emit a single
+   * trackEnded{reason:"error"} so the controller re-emits it and BotInstance
+   * advances the queue. Cleared when real playback is observed, on stop(), and
+   * at the start of a new playTrack().
+   */
+  private armPlaybackWatchdog(uri: string): void {
+    this.clearPlaybackWatchdog();
+    const timeoutMs = this.deps.playbackStartTimeoutMs ?? DEFAULT_PLAYBACK_START_TIMEOUT_MS;
+    const setTimer =
+      this.deps.setTimeout ??
+      ((cb: () => void, ms: number) => {
+        const t = setTimeout(cb, ms);
+        (t as { unref?: () => void }).unref?.();
+        return t;
+      });
+    this.watchdogTimer = setTimer(() => {
+      this.watchdogTimer = null;
+      this.onPlaybackStartTimeout(uri);
+    }, timeoutMs);
+  }
+
+  private clearPlaybackWatchdog(): void {
+    if (this.watchdogTimer == null) return;
+    const clearTimer =
+      this.deps.clearTimeout ??
+      ((h: unknown) => clearTimeout(h as ReturnType<typeof setTimeout>));
+    clearTimer(this.watchdogTimer);
+    this.watchdogTimer = null;
+  }
+
+  /**
+   * Fired when the playback-start window elapses with no observed playback.
+   * C3.6: never throws up the queue path. Guarded by the same endedForCurrent
+   * latch as normal end-detection so at most one trackEnded per track (no
+   * double-emit with the poll-loop end detection).
+   */
+  private onPlaybackStartTimeout(uri: string): void {
+    // Real playback was seen (hasPlayed) or the track already ended -> moot.
+    if (this.hasPlayed || this.endedForCurrent) return;
+    this.endedForCurrent = true; // latch
+    this.currentUri = null;
+    this.positionMs = 0;
+    const e: SpotifyTrackEndedEvent = { uri, reason: "error" };
+    this.emit("trackEnded", e);
   }
 
   async pause(): Promise<void> {
@@ -325,6 +403,8 @@ export class RustLibrespotBackend extends EventEmitter implements SpotifyAudioBa
 
   stop(): void {
     this.ready = false;
+    // Disarm the I4 degrade-to-skip watchdog so a stopped backend never emits.
+    this.clearPlaybackWatchdog();
     // Clear the state poll interval FIRST so no poll fires mid-teardown.
     if (this.pollTimer) {
       clearInterval(this.pollTimer);