diff --git a/backend/player/player.go b/backend/player/player.go
index 23d120b..0f9936d 100644
--- a/backend/player/player.go
+++ b/backend/player/player.go
@@ -106,7 +106,7 @@ func (p *Player) registerEventHandlers() {
 		p.logger.Info("Received RequestPlayEvent")
 
 		if err := p.Play(); err != nil {
-			p.logger.Error("failed to play", "err", err)
+			p.logger.Warn("Play requested but not ready", "err", err)
 		}
 	})
 	runtime.EventsOn(p.ctx, events.RequestPause, func(_ ...any) {
diff --git a/backend/queue/queue.go b/backend/queue/queue.go
index 28edfe7..eb28d27 100644
--- a/backend/queue/queue.go
+++ b/backend/queue/queue.go
@@ -133,6 +133,11 @@ func (q *Queue) registerEventHandlers() {
 		return
 	}
 
+	runtime.EventsOn(q.ctx, events.RequestPlay, func(_ ...any) {
+		q.logger.Info("Received RequestPlay")
+		q.PlayFromStart()
+	})
+
 	runtime.EventsOn(q.ctx, events.RequestNext, func(_ ...any) {
 		q.logger.Info("Received RequestNext")
 		q.Next()
@@ -703,6 +708,33 @@ func (q *Queue) Previous() {
 	q.emitQueueChanged()
 }
 
+// PlayFromStart restarts playback from the beginning of the queue.
+// If shuffle is enabled, a new shuffle order is generated and playback
+// starts from a random track. This is a no-op when a track is already
+// active (currentIndex != -1) or the queue is empty.
+func (q *Queue) PlayFromStart() {
+	q.mu.Lock()
+	defer q.mu.Unlock()
+
+	if q.currentIndex != -1 {
+		return
+	}
+
+	if len(q.tracks) == 0 {
+		return
+	}
+
+	if q.shuffleMode {
+		q.generateShuffleOrder()
+		q.currentIndex = q.shuffleOrder[0]
+	} else {
+		q.currentIndex = 0
+	}
+
+	q.playCurrentTrack()
+	q.emitQueueChanged()
+}
+
 // PlayIndex jumps to and plays the track at the given index.
 func (q *Queue) PlayIndex(index int) {
 	q.mu.Lock()
diff --git a/frontend/index.css b/frontend/index.css
index 55e11e1..479f2ef 100644
--- a/frontend/index.css
+++ b/frontend/index.css
@@ -53,7 +53,7 @@ body div.sidebar {
     padding: 0.25em;
     background-color: #343a40;
     display: grid;
-    grid-template-columns: 1fr auto 1fr;
+    grid-template-columns: auto 1fr auto;
     align-items: center;
 
     #now-playing-info {
@@ -87,8 +87,12 @@ body div.sidebar {
         }
     }
 
+    now-playing {
+        max-width: 250px;
+        overflow: hidden;
+    }
+
     audio-player {
-        justify-self: center;
         margin: 0.5em 1em;
     }