diff --git a/core/artwork/artwork.go b/core/artwork/artwork.go
index eeabfa5b9..4b417cfb3 100644
--- a/core/artwork/artwork.go
+++ b/core/artwork/artwork.go
@@ -69,6 +69,8 @@ func (a *artwork) getArtworkReader(ctx context.Context, artID model.ArtworkID, s
 			artReader, err = newAlbumArtworkReader(ctx, a, artID)
 		case model.KindMediaFileArtwork:
 			artReader, err = newMediafileArtworkReader(ctx, a, artID)
+		case model.KindPlaylistArtwork:
+			artReader, err = newPlaylistArtworkReader(ctx, a, artID)
 		default:
 			artReader, err = newPlaceholderReader(ctx, artID)
 		}
diff --git a/core/artwork/reader_mediafile.go b/core/artwork/reader_mediafile.go
index 13b35fcc0..a7c134fc5 100644
--- a/core/artwork/reader_mediafile.go
+++ b/core/artwork/reader_mediafile.go
@@ -30,15 +30,16 @@ func newMediafileArtworkReader(ctx context.Context, artwork *artwork, artID mode
 		album:     *al,
 	}
 	a.cacheKey.artID = artID
-	a.cacheKey.lastUpdate = a.LastUpdated()
+	if al.UpdatedAt.After(mf.UpdatedAt) {
+		a.cacheKey.lastUpdate = al.UpdatedAt
+	} else {
+		a.cacheKey.lastUpdate = mf.UpdatedAt
+	}
 	return a, nil
 }
 
 func (a *mediafileArtworkReader) LastUpdated() time.Time {
-	if a.album.UpdatedAt.After(a.mediafile.UpdatedAt) {
-		return a.album.UpdatedAt
-	}
-	return a.mediafile.UpdatedAt
+	return a.lastUpdate
 }
 
 func (a *mediafileArtworkReader) Reader(ctx context.Context) (io.ReadCloser, string, error) {
diff --git a/core/artwork/reader_playlist.go b/core/artwork/reader_playlist.go
new file mode 100644
index 000000000..844bcf9b4
--- /dev/null
+++ b/core/artwork/reader_playlist.go
@@ -0,0 +1,149 @@
+package artwork
+
+import (
+	"bytes"
+	"context"
+	"errors"
+	"image"
+	"image/draw"
+	"image/png"
+	"io"
+	"math/rand"
+	"time"
+
+	"github.com/disintegration/imaging"
+	"github.com/navidrome/navidrome/model"
+	"golang.org/x/exp/slices"
+)
+
+type playlistArtworkReader struct {
+	cacheKey
+	a  *artwork
+	pl model.Playlist
+}
+
+const tileSize = 600
+
+func newPlaylistArtworkReader(ctx context.Context, artwork *artwork, artID model.ArtworkID) (*playlistArtworkReader, error) {
+	pl, err := artwork.ds.Playlist(ctx).Get(artID.ID)
+	if err != nil {
+		return nil, err
+	}
+	a := &playlistArtworkReader{
+		a:  artwork,
+		pl: *pl,
+	}
+	a.cacheKey.artID = artID
+	a.cacheKey.lastUpdate = pl.UpdatedAt
+	return a, nil
+}
+
+func (a *playlistArtworkReader) LastUpdated() time.Time {
+	return a.lastUpdate
+}
+
+func (a *playlistArtworkReader) Reader(ctx context.Context) (io.ReadCloser, string, error) {
+	var ff []sourceFunc
+	pl, err := a.a.ds.Playlist(ctx).GetWithTracks(a.pl.ID)
+	if err == nil {
+		ff = append(ff, a.fromGeneratedTile(ctx, pl.Tracks))
+	}
+	ff = append(ff, fromPlaceholder())
+	r, source := extractImage(ctx, a.artID, ff...)
+	return r, source, nil
+}
+
+func (a *playlistArtworkReader) fromGeneratedTile(ctx context.Context, tracks model.PlaylistTracks) sourceFunc {
+	return func() (io.ReadCloser, string, error) {
+		tiles, err := a.loadTiles(ctx, tracks)
+		if err != nil {
+			return nil, "", err
+		}
+		r, err := a.createTiledImage(ctx, tiles)
+		return r, "", err
+	}
+}
+
+func compactIDs(tracks model.PlaylistTracks) []model.ArtworkID {
+	slices.SortFunc(tracks, func(a, b model.PlaylistTrack) bool { return a.AlbumID < b.AlbumID })
+	tracks = slices.CompactFunc(tracks, func(a, b model.PlaylistTrack) bool { return a.AlbumID == b.AlbumID })
+	ids := make([]model.ArtworkID, len(tracks))
+	for i, t := range tracks {
+		ids[i] = t.AlbumCoverArtID()
+	}
+	rand.Seed(time.Now().UnixNano())
+	rand.Shuffle(len(ids), func(i, j int) { ids[i], ids[j] = ids[j], ids[i] })
+	return ids
+}
+
+func (a *playlistArtworkReader) loadTiles(ctx context.Context, t model.PlaylistTracks) ([]image.Image, error) {
+	ids := compactIDs(t)
+
+	var tiles []image.Image
+	for len(tiles) < 4 {
+		if len(ids) == 0 {
+			break
+		}
+		id := ids[len(ids)-1]
+		ids = ids[0 : len(ids)-1]
+		r, _, err := fromAlbum(ctx, a.a, id)()
+		if err != nil {
+			continue
+		}
+		tile, err := a.createTile(ctx, r)
+		if err == nil {
+			tiles = append(tiles, tile)
+		}
+		_ = r.Close()
+	}
+	switch len(tiles) {
+	case 0:
+		return nil, errors.New("could not find any eligible cover")
+	case 2:
+		tiles = append(tiles, tiles[1], tiles[0])
+	case 3:
+		tiles = append(tiles, tiles[0])
+	}
+	return tiles, nil
+}
+
+func (a *playlistArtworkReader) createTile(_ context.Context, r io.ReadCloser) (image.Image, error) {
+	img, _, err := image.Decode(r)
+	if err != nil {
+		return nil, err
+	}
+	return imaging.Fill(img, tileSize/2, tileSize/2, imaging.Center, imaging.Lanczos), nil
+}
+
+func (a *playlistArtworkReader) createTiledImage(_ context.Context, tiles []image.Image) (io.ReadCloser, error) {
+	buf := new(bytes.Buffer)
+	var rgba draw.Image
+	var err error
+	if len(tiles) == 4 {
+		rgba = image.NewRGBA(image.Rectangle{Max: image.Point{X: tileSize - 1, Y: tileSize - 1}})
+		draw.Draw(rgba, rect(0), tiles[0], image.Point{}, draw.Src)
+		draw.Draw(rgba, rect(1), tiles[1], image.Point{}, draw.Src)
+		draw.Draw(rgba, rect(2), tiles[2], image.Point{}, draw.Src)
+		draw.Draw(rgba, rect(3), tiles[3], image.Point{}, draw.Src)
+		err = png.Encode(buf, rgba)
+	} else {
+		err = png.Encode(buf, tiles[0])
+	}
+	return io.NopCloser(buf), err
+}
+
+func rect(pos int) image.Rectangle {
+	r := image.Rectangle{}
+	switch pos {
+	case 1:
+		r.Min.X = tileSize / 2
+	case 2:
+		r.Min.Y = tileSize / 2
+	case 3:
+		r.Min.X = tileSize / 2
+		r.Min.Y = tileSize / 2
+	}
+	r.Max.X = r.Min.X + tileSize/2
+	r.Max.Y = r.Min.Y + tileSize/2
+	return r
+}
diff --git a/core/artwork/reader_resized.go b/core/artwork/reader_resized.go
index d7594b12c..09e263018 100644
--- a/core/artwork/reader_resized.go
+++ b/core/artwork/reader_resized.go
@@ -54,7 +54,7 @@ func (a *resizedArtworkReader) Reader(ctx context.Context) (io.ReadCloser, strin
 	r := io.TeeReader(orig, buf)
 	defer orig.Close()
 
-	resized, origSize, err := resizeImage(r, a.size)
+	resized, origSize, err := resizeImageIntoReader(r, a.size)
 	log.Trace(ctx, "Resizing artwork", "artID", a.artID, "original", origSize, "resized", a.size)
 	if err != nil {
 		log.Warn(ctx, "Could not resize image. Will return image as is", "artID", a.artID, "size", a.size, err)
@@ -74,12 +74,7 @@ func asImageReader(r io.Reader) (io.Reader, string, error) {
 	return br, http.DetectContentType(buf), nil
 }
 
-func resizeImage(reader io.Reader, size int) (io.Reader, int, error) {
-	r, format, err := asImageReader(reader)
-	if err != nil {
-		return nil, 0, err
-	}
-
+func resizeImage(r io.Reader, size int) (image.Image, int, error) {
 	img, _, err := image.Decode(r)
 	if err != nil {
 		return nil, 0, err
@@ -94,6 +89,20 @@ func resizeImage(reader io.Reader, size int) (io.Reader, int, error) {
 		m = imaging.Resize(img, 0, size, imaging.Lanczos)
 	}
 
+	return m, number.Max(bounds.Max.X, bounds.Max.Y), err
+}
+
+func resizeImageIntoReader(reader io.Reader, size int) (io.Reader, int, error) {
+	r, format, err := asImageReader(reader)
+	if err != nil {
+		return nil, 0, err
+	}
+
+	m, origSize, err := resizeImage(r, size)
+	if err != nil {
+		return nil, 0, err
+	}
+
 	buf := new(bytes.Buffer)
 	buf.Reset()
 	if format == "image/png" {
@@ -101,5 +110,5 @@ func resizeImage(reader io.Reader, size int) (io.Reader, int, error) {
 	} else {
 		err = jpeg.Encode(buf, m, &jpeg.Options{Quality: conf.Server.CoverJpegQuality})
 	}
-	return buf, number.Max(bounds.Max.X, bounds.Max.Y), err
+	return buf, origSize, err
 }
diff --git a/core/artwork/sources.go b/core/artwork/sources.go
index 328f0b994..0afa6b373 100644
--- a/core/artwork/sources.go
+++ b/core/artwork/sources.go
@@ -40,7 +40,9 @@ type sourceFunc func() (r io.ReadCloser, path string, err error)
 func (f sourceFunc) String() string {
 	name := runtime.FuncForPC(reflect.ValueOf(f).Pointer()).Name()
 	name = strings.TrimPrefix(name, "github.com/navidrome/navidrome/core/artwork.")
-	name = strings.TrimPrefix(name, "(*artwork).")
+	if _, after, found := strings.Cut(name, ")."); found {
+		name = after
+	}
 	name = strings.TrimSuffix(name, ".func1")
 	return name
 }