diff --git a/Model/Player/PlayerQueue.swift b/Model/Player/PlayerQueue.swift
index 4f064173..4dd29825 100644
--- a/Model/Player/PlayerQueue.swift
+++ b/Model/Player/PlayerQueue.swift
@@ -8,7 +8,9 @@ extension PlayerModel {
         currentItem?.video
     }
 
-    func play(_ videos: [Video]) {
+    func play(_ videos: [Video], shuffling: Bool = false) {
+        playbackMode = shuffling ? .shuffle : .queue
+
         videos.forEach { enqueueVideo($0, loadDetails: false) }
 
         #if os(iOS)
diff --git a/Shared/Navigation/AppSidebarPlaylists.swift b/Shared/Navigation/AppSidebarPlaylists.swift
index 20f5c16b..cb79f555 100644
--- a/Shared/Navigation/AppSidebarPlaylists.swift
+++ b/Shared/Navigation/AppSidebarPlaylists.swift
@@ -18,6 +18,9 @@ struct AppSidebarPlaylists: View {
                     Button("Play All") {
                         player.play(playlists.find(id: playlist.id)?.videos ?? [])
                     }
+                    Button("Shuffle All") {
+                        player.play(playlists.find(id: playlist.id)?.videos ?? [], shuffling: true)
+                    }
                     Button("Edit") {
                         navigation.presentEditPlaylistForm(playlists.find(id: playlist.id))
                     }
diff --git a/Shared/Playlists/PlaylistsView.swift b/Shared/Playlists/PlaylistsView.swift
index 0fe825eb..6177cf6b 100644
--- a/Shared/Playlists/PlaylistsView.swift
+++ b/Shared/Playlists/PlaylistsView.swift
@@ -299,13 +299,21 @@ struct PlaylistsView: View {
 
     private var playButton: some View {
         Button {
-            player.playbackMode = .queue
             player.play(items.compactMap(\.video))
         } label: {
             Image(systemName: "play")
                 .padding(8)
                 .contentShape(Rectangle())
         }
+        .contextMenu {
+            Button {
+                player.play(items.compactMap(\.video), shuffling: true)
+            } label: {
+                Label("Shuffle", systemImage: "shuffle")
+                    .padding(8)
+                    .contentShape(Rectangle())
+            }
+        }
     }
 
     private var currentPlaylist: Playlist? {
diff --git a/Shared/Views/ChannelPlaylistView.swift b/Shared/Views/ChannelPlaylistView.swift
index dc7c30e9..187f64c7 100644
--- a/Shared/Views/ChannelPlaylistView.swift
+++ b/Shared/Views/ChannelPlaylistView.swift
@@ -121,11 +121,17 @@ struct ChannelPlaylistView: View {
 
     private var playButton: some View {
         Button {
-            player.playbackMode = .queue
             player.play(videos)
         } label: {
             Label("Play All", systemImage: "play")
         }
+        .contextMenu {
+            Button {
+                player.play(videos, shuffling: true)
+            } label: {
+                Label("Shuffle All", systemImage: "shuffle")
+            }
+        }
     }
 
     private var videos: [Video] {
diff --git a/Shared/Views/PlaylistVideosView.swift b/Shared/Views/PlaylistVideosView.swift
index b7d139f3..202f2bb0 100644
--- a/Shared/Views/PlaylistVideosView.swift
+++ b/Shared/Views/PlaylistVideosView.swift
@@ -70,11 +70,17 @@ struct PlaylistVideosView: View {
                     FavoriteButton(item: FavoriteItem(section: .channelPlaylist(playlist.id, playlist.title)))
 
                     Button {
-                        player.playbackMode = .queue
                         player.play(videos)
                     } label: {
                         Label("Play All", systemImage: "play")
                     }
+                    .contextMenu {
+                        Button {
+                            player.play(videos, shuffling: true)
+                        } label: {
+                            Label("Shuffle All", systemImage: "shuffle")
+                        }
+                    }
                 }
             }
         }