diff --git a/src/audio/AudioEngine.ts b/src/audio/AudioEngine.ts
index baaf726..92676b2 100644
--- a/src/audio/AudioEngine.ts
+++ b/src/audio/AudioEngine.ts
@@ -65,6 +65,9 @@ export class AudioEngine extends EventEmitter<AudioEngineEvents> {
       () => this.playlistManager.getTotalDuration(),
       (state) => this.emit('stateChange', { state }),
       (time) => {
+        // emit seeked first so listeners can update their tracking refs
+        // before the subsequent songChange fires
+        this.emit('seeked', { time });
         const entry = this.playlist.getEntryAtTime(time);
         if (entry)
           this.emit('songChange', {
diff --git a/src/audio/TransportController.ts b/src/audio/TransportController.ts
index deed3e0..86a82c0 100644
--- a/src/audio/TransportController.ts
+++ b/src/audio/TransportController.ts
@@ -70,14 +70,14 @@ export class TransportController {
     const totalDuration = this.getDuration();
     this.pausedAt = Math.max(0, Math.min(time, totalDuration));
 
+    // Notify before restarting the scheduler to ensure seeked fires before songChange
+    this.onSeek(this.pausedAt);
+
     if (this.state === 'playing') {
       this.scheduler.stopAll();
       this.contextTimeAtPlay = this.ctx.currentTime;
       this.transportTimeAtPlay = this.pausedAt;
       this.scheduler.start(this.pausedAt, this.contextTimeAtPlay);
-    } else {
-      // paused/stopped: playhead moves but no audio, notify so song title updates
-      this.onSeek(this.pausedAt);
     }
   }
 
diff --git a/src/audio/types.ts b/src/audio/types.ts
index 29fc3d7..56591c7 100644
--- a/src/audio/types.ts
+++ b/src/audio/types.ts
@@ -66,6 +66,7 @@ export type AudioEngineEvents = {
   timelineChange: { entries: ScheduledEntry[] };
   playlistChange: { entries: PlaylistEntry[] };
   error: { message: string; error?: unknown };
+  seeked: { time: Seconds };
 };
 
 export type { ID, Seconds, Gain, Fade, FadeType };
diff --git a/src/components/NowPlaying.tsx b/src/components/NowPlaying.tsx
index 85ca7ac..203ef94 100644
--- a/src/components/NowPlaying.tsx
+++ b/src/components/NowPlaying.tsx
@@ -116,10 +116,15 @@ export default function NowPlaying({ libraryItems }: NowPlayingProps) {
   };
 
   const handlePlayPause = () => {
-    if (isPlaying) {
+    // Read state directly from the engine, not React state.
+    // play() is async (awaits ctx.resume), so transportState can lag or miss errors,
+    // leaving isPlaying stale and causing no-op play() calls. getState() stays accurate.
+    if (engine.transport.getState() === 'playing') {
       engine.transport.pause();
     } else {
-      void engine.transport.play();
+      engine.transport.play().catch((err: unknown) => {
+        console.error('Playback failed to start:', err);
+      });
     }
   };
 
diff --git a/src/components/SetList.tsx b/src/components/SetList.tsx
index 90481b2..5cb44e4 100644
--- a/src/components/SetList.tsx
+++ b/src/components/SetList.tsx
@@ -54,8 +54,14 @@ export default function SetList({
     currentEntryIdRef.current = engine.getCurrentEntry()?.entryId ?? null;
 
     const unsubSong = engine.on('songChange', ({ entryId }) => {
-      if (repeatModeRef.current === 'one' && currentEntryIdRef.current !== null) {
-        // Song changed - seek back to the start of the previous song.
+      // Only handle real track changes. songChange also fires on seek within the same track,
+      // so without this guard, Repeat One would override seeks by jumping back to absoluteStart.
+      if (
+        repeatModeRef.current === 'one' &&
+        currentEntryIdRef.current !== null &&
+        entryId !== currentEntryIdRef.current
+      ) {
+        // A genuine automatic song transition occurred - seek back to the start of the previous song.
         const prev = engine.getTimeline().find((e) => e.entryId === currentEntryIdRef.current);
         if (prev) {
           engine.transport.seek(prev.absoluteStart);
@@ -65,6 +71,17 @@ export default function SetList({
       currentEntryIdRef.current = entryId;
     });
 
+    // When the user seeks on the timeline, update currentEntryIdRef to the song at the new position
+    // to prevent Repeat One from interfering with intentional navigation
+    const unsubSeeked = engine.on('seeked', ({ time }) => {
+      const entry = engine
+        .getTimeline()
+        .find((e) => time >= e.absoluteStart && time < e.absoluteEnd);
+      if (entry) {
+        currentEntryIdRef.current = entry.entryId;
+      }
+    });
+
     const unsubState = engine.on('stateChange', ({ state }) => {
       if (state === 'playing') {
         wasPlayingRef.current = true;
@@ -74,6 +91,17 @@ export default function SetList({
           wasPlayingRef.current = false;
           engine.transport.seek(0);
           void engine.transport.play();
+        } else if (repeatModeRef.current === 'one' && wasPlayingRef.current) {
+          // When the last song finishes, songChange doesn't fire, so Repeat One would silently fall through
+          // This seeks back to the start of the current song and replays it, similar to how songChange handles mid-playlist transitions
+          wasPlayingRef.current = false;
+          const entry = engine.getTimeline().find((e) => e.entryId === currentEntryIdRef.current);
+          if (entry) {
+            engine.transport.seek(entry.absoluteStart);
+            engine.transport.play().catch((err: unknown) => {
+              console.error('Repeat One: playback failed to restart:', err);
+            });
+          }
         } else {
           wasPlayingRef.current = false;
         }
@@ -82,6 +110,7 @@ export default function SetList({
 
     return () => {
       unsubSong();
+      unsubSeeked();
       unsubState();
     };
     // engine is a stable singleton - this runs exactly once on mount.