diff --git a/src/haunt_fm/api/feedback.py b/src/haunt_fm/api/feedback.py
index 4c6f563..13cf9ad 100644
--- a/src/haunt_fm/api/feedback.py
+++ b/src/haunt_fm/api/feedback.py
@@ -6,7 +6,7 @@ from sqlalchemy.orm import joinedload
 
 from haunt_fm.db import get_session
 from haunt_fm.models.track import FeedbackEvent, Track
-from haunt_fm.services.feedback import compute_contextual_score, record_feedback
+from haunt_fm.services.feedback import compute_contextual_score, delete_feedback, record_feedback
 
 router = APIRouter(prefix="/api/feedback")
 
@@ -41,6 +41,24 @@ async def submit_feedback(req: FeedbackRequest, session: AsyncSession = Depends(
     }
 
 
+@router.delete("/{event_id}")
+async def retract_feedback(event_id: int, session: AsyncSession = Depends(get_session)):
+    """Delete a feedback event entirely, removing its influence on scoring."""
+    event = await delete_feedback(session, event_id)
+    if event is None:
+        raise HTTPException(status_code=404, detail=f"Feedback event {event_id} not found")
+
+    return {
+        "id": event.id,
+        "playlist_id": event.playlist_id,
+        "track_id": event.track_id,
+        "signal": event.signal,
+        "signal_weight": event.signal_weight,
+        "vibe_text": event.vibe_text,
+        "created_at": event.created_at.isoformat(),
+    }
+
+
 @router.post("/score")
 async def get_score(req: ScoreRequest, session: AsyncSession = Depends(get_session)):
     """Compute the contextual feedback score for a track given a vibe description."""
diff --git a/src/haunt_fm/api/playlists.py b/src/haunt_fm/api/playlists.py
index a2d1589..e6a52dc 100644
--- a/src/haunt_fm/api/playlists.py
+++ b/src/haunt_fm/api/playlists.py
@@ -62,6 +62,7 @@ async def generate(req: GenerateRequest, session: AsyncSession = Depends(get_ses
             "artist": t.artist,
             "title": t.title,
             "album": t.album,
+            "duration_ms": t.duration_ms,
             "is_known": pt.is_known,
             "similarity_score": pt.similarity_score,
         }
@@ -72,6 +73,11 @@ async def generate(req: GenerateRequest, session: AsyncSession = Depends(get_ses
     if req.auto_play and req.speaker_entity:
         await play_playlist_on_speaker(track_list, req.speaker_entity)
 
+        # Register with skip detector for automatic skip feedback
+        from haunt_fm.services.skip_detector import register_session
+
+        register_session(req.speaker_entity, playlist.id, track_list)
+
     return {
         "playlist_id": playlist.id,
         "name": playlist.name,
diff --git a/src/haunt_fm/api/status.py b/src/haunt_fm/api/status.py
index 0d623f5..6d94539 100644
--- a/src/haunt_fm/api/status.py
+++ b/src/haunt_fm/api/status.py
@@ -16,6 +16,8 @@ from haunt_fm.config import settings
 from haunt_fm.services.embedding import is_model_loaded
 from haunt_fm.services.embedding_worker import is_running as is_worker_running
 from haunt_fm.services.embedding_worker import last_processed as worker_last_processed
+from haunt_fm.services.skip_detector import get_sessions as get_skip_sessions
+from haunt_fm.services.skip_detector import is_running as is_skip_detector_running
 
 router = APIRouter(prefix="/api")
 
@@ -103,6 +105,25 @@ async def status(session: AsyncSession = Depends(get_session)):
                 "total_generated": total_playlists,
                 "last_generated": last_playlist.isoformat() if last_playlist else None,
             },
+            "skip_detector": {
+                "running": is_skip_detector_running(),
+                "active_sessions": len(get_skip_sessions()),
+                "sessions": [
+                    {
+                        "speaker_entity": entity,
+                        "playlist_id": s.playlist_id,
+                        "current_position": s.current_position,
+                        "total_tracks": len(s.tracks),
+                        "current_track": (
+                            f"{s.tracks[s.current_position]['artist']} - {s.tracks[s.current_position]['title']}"
+                            if s.current_position < len(s.tracks)
+                            else None
+                        ),
+                        "last_activity": s.last_activity_at.isoformat(),
+                    }
+                    for entity, s in get_skip_sessions().items()
+                ],
+            },
         },
         "dependencies": {
             "lastfm_api": "configured" if settings.lastfm_api_key else "not_configured",
diff --git a/src/haunt_fm/config.py b/src/haunt_fm/config.py
index 2e35c38..5b46da5 100644
--- a/src/haunt_fm/config.py
+++ b/src/haunt_fm/config.py
@@ -25,7 +25,14 @@ class Settings(BaseSettings):
 
     # Feedback
     feedback_overlap_threshold: float = 0.85
-    feedback_signal_weights: dict = {"up": 1.0, "down": -1.0, "skip": -0.3}
+    feedback_signal_weights: dict = {"up": 1.0, "down": -1.0, "skip": -0.3, "neutral": 0.0}
+
+    # Skip detection
+    skip_detector_enabled: bool = True
+    skip_detector_poll_interval_seconds: float = 3.0
+    skip_detector_skip_threshold: float = 0.4  # < 40% played = skip
+    skip_detector_session_timeout_minutes: int = 30
+    skip_detector_min_track_duration_ms: int = 30000  # ignore tracks < 30s
 
 
 settings = Settings()
diff --git a/src/haunt_fm/main.py b/src/haunt_fm/main.py
index f153fae..69d7639 100644
--- a/src/haunt_fm/main.py
+++ b/src/haunt_fm/main.py
@@ -27,15 +27,24 @@ async def lifespan(app: FastAPI):
         worker_task = asyncio.create_task(run_worker())
         logger.info("Embedding worker task created")
 
+    # Start skip detector in background
+    skip_detector_task = None
+    if settings.skip_detector_enabled:
+        from haunt_fm.services.skip_detector import run_skip_detector
+
+        skip_detector_task = asyncio.create_task(run_skip_detector())
+        logger.info("Skip detector task created")
+
     yield
 
     # Shutdown
-    if worker_task:
-        worker_task.cancel()
-        try:
-            await worker_task
-        except asyncio.CancelledError:
-            pass
+    for task in [worker_task, skip_detector_task]:
+        if task:
+            task.cancel()
+            try:
+                await task
+            except asyncio.CancelledError:
+                pass
     logger.info("haunt-fm shut down")
 
 
diff --git a/src/haunt_fm/services/feedback.py b/src/haunt_fm/services/feedback.py
index 2beb264..6f34c85 100644
--- a/src/haunt_fm/services/feedback.py
+++ b/src/haunt_fm/services/feedback.py
@@ -122,6 +122,19 @@ def compute_contextual_score(
     return score
 
 
+async def delete_feedback(session: AsyncSession, event_id: int) -> FeedbackEvent | None:
+    """Delete a feedback event by ID. Returns the event if found, None otherwise."""
+    event = await session.get(FeedbackEvent, event_id)
+    if event is None:
+        return None
+
+    await session.delete(event)
+    await session.commit()
+
+    logger.info("Deleted feedback event %d (signal=%s, track=%d)", event.id, event.signal, event.track_id)
+    return event
+
+
 async def apply_feedback_adjustments(
     session: AsyncSession,
     recommendations: list[dict],
diff --git a/src/haunt_fm/services/music_assistant.py b/src/haunt_fm/services/music_assistant.py
index d396768..c16dd08 100644
--- a/src/haunt_fm/services/music_assistant.py
+++ b/src/haunt_fm/services/music_assistant.py
@@ -33,6 +33,27 @@ async def is_ha_reachable() -> bool:
         return False
 
 
+async def get_speaker_state(speaker_entity: str) -> dict | None:
+    """Get current playback state from a HA media_player entity.
+
+    Returns dict with state, media_title, media_artist, media_duration, media_position
+    or None if unreachable.
+    """
+    try:
+        data = await _ha_request("GET", f"/api/states/{speaker_entity}")
+        attrs = data.get("attributes", {})
+        return {
+            "state": data.get("state"),
+            "media_title": attrs.get("media_title"),
+            "media_artist": attrs.get("media_artist"),
+            "media_duration": attrs.get("media_duration"),
+            "media_position": attrs.get("media_position"),
+        }
+    except Exception:
+        logger.debug("Failed to get state for %s", speaker_entity)
+        return None
+
+
 async def play_media_on_speaker(
     media_content_id: str,
     speaker_entity: str,
diff --git a/src/haunt_fm/services/skip_detector.py b/src/haunt_fm/services/skip_detector.py
new file mode 100644
index 0000000..f29ee2d
--- /dev/null
+++ b/src/haunt_fm/services/skip_detector.py
@@ -0,0 +1,297 @@
+"""Background skip detection for haunt-fm playlists.
+
+Polls Home Assistant media_player state to detect when tracks are skipped
+(played < threshold % of duration) and automatically records skip feedback.
+"""
+
+import asyncio
+import difflib
+import logging
+import re
+from dataclasses import dataclass, field
+from datetime import datetime, timezone
+
+from haunt_fm.config import settings
+from haunt_fm.db import async_session
+from haunt_fm.services.feedback import record_feedback
+from haunt_fm.services.music_assistant import get_speaker_state
+
+logger = logging.getLogger(__name__)
+
+_running = False
+_sessions: dict[str, "PlaylistSession"] = {}
+
+
+@dataclass
+class PlaylistSession:
+    playlist_id: int
+    speaker_entity: str
+    tracks: list[dict]  # each: {track_id, artist, title, duration_ms, position}
+    current_position: int = 0
+    current_track_started_at: datetime = field(default_factory=lambda: datetime.now(timezone.utc))
+    last_activity_at: datetime = field(default_factory=lambda: datetime.now(timezone.utc))
+    last_ha_media_title: str | None = None
+    last_ha_media_artist: str | None = None
+
+
+def is_running() -> bool:
+    return _running
+
+
+def get_sessions() -> dict[str, "PlaylistSession"]:
+    return dict(_sessions)
+
+
+def register_session(speaker_entity: str, playlist_id: int, tracks: list[dict]) -> None:
+    """Register a new playlist session for skip detection.
+
+    Called from playlists.py after auto_play succeeds.
+    """
+    session = PlaylistSession(
+        playlist_id=playlist_id,
+        speaker_entity=speaker_entity,
+        tracks=tracks,
+    )
+    _sessions[speaker_entity] = session
+    logger.info(
+        "Skip detector: registered session for %s (playlist %d, %d tracks)",
+        speaker_entity,
+        playlist_id,
+        len(tracks),
+    )
+
+
+# --- String normalization and fuzzy matching ---
+
+_PAREN_SUFFIX = re.compile(r"\s*\(.*\)\s*$")
+_EXTRA_WHITESPACE = re.compile(r"\s+")
+
+
+def _normalize(s: str) -> str:
+    """Normalize a string for fuzzy comparison."""
+    s = s.lower().strip()
+    s = _PAREN_SUFFIX.sub("", s)  # strip "(Remastered)", "(Live)", etc.
+    s = _EXTRA_WHITESPACE.sub(" ", s)
+    return s
+
+
+def _fuzzy_score(a: str, b: str) -> float:
+    """Fuzzy similarity score between two strings (0-1)."""
+    return difflib.SequenceMatcher(None, _normalize(a), _normalize(b)).ratio()
+
+
+def _match_track(
+    ha_title: str, ha_artist: str, tracks: list[dict], hint_position: int
+) -> int | None:
+    """Find the best matching track in the playlist for the current HA playback.
+
+    Returns the track's position index, or None if no match found.
+    Checks hint_position+1 first (sequential playback is the common case).
+    """
+    best_idx = None
+    best_score = 0.0
+    threshold = 0.5
+
+    # Check the next sequential position first (most common case)
+    candidates = []
+    next_pos = hint_position + 1
+    if next_pos < len(tracks):
+        candidates.append(next_pos)
+    # Then check all other positions
+    candidates.extend(i for i in range(len(tracks)) if i != next_pos)
+
+    for idx in candidates:
+        t = tracks[idx]
+        title_score = _fuzzy_score(ha_title, t["title"])
+        artist_score = _fuzzy_score(ha_artist, t["artist"])
+        combined = title_score * 0.7 + artist_score * 0.3
+
+        if combined > best_score:
+            best_score = combined
+            best_idx = idx
+
+        # If sequential position matches well, use it immediately
+        if idx == next_pos and combined >= threshold:
+            return idx
+
+    if best_score >= threshold:
+        return best_idx
+    return None
+
+
+# --- Core polling loop ---
+
+
+async def _evaluate_skip(
+    session: PlaylistSession, track: dict, elapsed_ms: float
+) -> None:
+    """Check if a track was skipped and record feedback if so."""
+    duration_ms = track.get("duration_ms")
+    if duration_ms is None or duration_ms <= 0:
+        logger.debug("Skip eval: no duration for track %d, skipping evaluation", track["track_id"])
+        return
+
+    if duration_ms < settings.skip_detector_min_track_duration_ms:
+        logger.debug(
+            "Skip eval: track %d too short (%dms), ignoring",
+            track["track_id"],
+            duration_ms,
+        )
+        return
+
+    fraction_played = elapsed_ms / duration_ms
+    if fraction_played < settings.skip_detector_skip_threshold:
+        logger.info(
+            "Skip detected: '%s - %s' played %.0f%% (track_id=%d, playlist_id=%d)",
+            track["artist"],
+            track["title"],
+            fraction_played * 100,
+            track["track_id"],
+            session.playlist_id,
+        )
+        try:
+            async with async_session() as db:
+                await record_feedback(
+                    db, session.playlist_id, track["track_id"], "skip"
+                )
+            logger.info(
+                "Skip feedback recorded for track %d in playlist %d",
+                track["track_id"],
+                session.playlist_id,
+            )
+        except ValueError as e:
+            # Playlist without vibe_embedding — can't record contextual feedback
+            logger.warning(
+                "Could not record skip feedback for track %d: %s",
+                track["track_id"],
+                e,
+            )
+        except Exception:
+            logger.exception(
+                "Error recording skip feedback for track %d", track["track_id"]
+            )
+    else:
+        logger.debug(
+            "Track '%s - %s' played %.0f%%, not a skip",
+            track["artist"],
+            track["title"],
+            fraction_played * 100,
+        )
+
+
+async def _poll_all_sessions() -> None:
+    """Single poll cycle across all active sessions."""
+    now = datetime.now(timezone.utc)
+    to_remove = []
+
+    for entity, session in list(_sessions.items()):
+        # Check session timeout
+        idle_minutes = (now - session.last_activity_at).total_seconds() / 60
+        if idle_minutes > settings.skip_detector_session_timeout_minutes:
+            logger.info(
+                "Skip detector: session for %s timed out (idle %.0f min)",
+                entity,
+                idle_minutes,
+            )
+            to_remove.append(entity)
+            continue
+
+        # Poll HA for current state
+        state = await get_speaker_state(entity)
+        if state is None:
+            continue  # HA unreachable, try again next cycle
+
+        ha_title = state.get("media_title")
+        ha_artist = state.get("media_artist")
+
+        # No media info — speaker might be idle
+        if not ha_title or not ha_artist:
+            continue
+
+        session.last_activity_at = now
+
+        # Check if track changed
+        if (
+            ha_title == session.last_ha_media_title
+            and ha_artist == session.last_ha_media_artist
+        ):
+            # Same track still playing — no transition
+            continue
+
+        # Track transition detected
+        logger.debug(
+            "Track transition on %s: '%s - %s' → '%s - %s'",
+            entity,
+            session.last_ha_media_artist,
+            session.last_ha_media_title,
+            ha_artist,
+            ha_title,
+        )
+
+        # Evaluate previous track for skip (if we had one)
+        if session.last_ha_media_title is not None:
+            prev_track = (
+                session.tracks[session.current_position]
+                if session.current_position < len(session.tracks)
+                else None
+            )
+            if prev_track:
+                elapsed_ms = (now - session.current_track_started_at).total_seconds() * 1000
+                await _evaluate_skip(session, prev_track, elapsed_ms)
+
+        # Match new track to playlist
+        matched_pos = _match_track(
+            ha_title, ha_artist, session.tracks, session.current_position
+        )
+
+        if matched_pos is None:
+            logger.info(
+                "Skip detector: '%s - %s' on %s doesn't match playlist — killing session",
+                ha_artist,
+                ha_title,
+                entity,
+            )
+            to_remove.append(entity)
+            continue
+
+        # Update session state
+        session.current_position = matched_pos
+        session.current_track_started_at = now
+        session.last_ha_media_title = ha_title
+        session.last_ha_media_artist = ha_artist
+
+        logger.debug(
+            "Skip detector: %s now at position %d (%s - %s)",
+            entity,
+            matched_pos,
+            session.tracks[matched_pos]["artist"],
+            session.tracks[matched_pos]["title"],
+        )
+
+    for entity in to_remove:
+        _sessions.pop(entity, None)
+
+
+async def run_skip_detector() -> None:
+    """Background loop that polls HA and detects skips."""
+    global _running
+
+    if not settings.skip_detector_enabled:
+        logger.info("Skip detector disabled")
+        return
+
+    _running = True
+    logger.info("Skip detector started (poll interval: %.1fs)", settings.skip_detector_poll_interval_seconds)
+
+    try:
+        while True:
+            try:
+                if _sessions:
+                    await _poll_all_sessions()
+            except Exception:
+                logger.exception("Skip detector poll error")
+
+            await asyncio.sleep(settings.skip_detector_poll_interval_seconds)
+    finally:
+        _running = False
+        logger.info("Skip detector stopped")