diff --git a/resources/assets/js/components/playlist/PlaylistContextMenu.spec.ts b/resources/assets/js/components/playlist/PlaylistContextMenu.spec.ts
index b41827f8..45e99494 100644
--- a/resources/assets/js/components/playlist/PlaylistContextMenu.spec.ts
+++ b/resources/assets/js/components/playlist/PlaylistContextMenu.spec.ts
@@ -2,7 +2,10 @@ import { expect, it } from 'vitest'
 import UnitTestCase from '@/__tests__/UnitTestCase'
 import { eventBus } from '@/utils'
 import factory from '@/__tests__/factory'
-import { screen } from '@testing-library/vue'
+import { screen, waitFor } from '@testing-library/vue'
+import { songStore } from '@/stores'
+import { playbackService } from '@/services'
+import { MessageToasterStub } from '@/__tests__/stubs'
 import PlaylistContextMenu from './PlaylistContextMenu.vue'
 
 new class extends UnitTestCase {
@@ -42,5 +45,77 @@ new class extends UnitTestCase {
 
       expect(emitMock).toHaveBeenCalledWith('PLAYLIST_DELETE', playlist)
     })
+
+    it('plays', async () => {
+      const playlist = factory<Playlist>('playlist')
+      const songs = factory<Song>('song', 3)
+      const fetchMock = this.mock(songStore, 'fetchForPlaylist').mockResolvedValue(songs)
+      const queueMock = this.mock(playbackService, 'queueAndPlay')
+      const goMock = this.mock(this.router, 'go')
+      await this.renderComponent(playlist)
+
+      await this.user.click(screen.getByText('Play'))
+
+      await waitFor(() => {
+        expect(fetchMock).toHaveBeenCalledWith(playlist)
+        expect(queueMock).toHaveBeenCalledWith(songs)
+        expect(goMock).toHaveBeenCalledWith('queue')
+      })
+    })
+
+    it('warns if attempting to play an empty playlist', async () => {
+      const playlist = factory<Playlist>('playlist')
+      const fetchMock = this.mock(songStore, 'fetchForPlaylist').mockResolvedValue([])
+      const queueMock = this.mock(playbackService, 'queueAndPlay')
+      const goMock = this.mock(this.router, 'go')
+      const warnMock = this.mock(MessageToasterStub.value, 'warning')
+
+      await this.renderComponent(playlist)
+
+      await this.user.click(screen.getByText('Play'))
+
+      await waitFor(() => {
+        expect(fetchMock).toHaveBeenCalledWith(playlist)
+        expect(queueMock).not.toHaveBeenCalled()
+        expect(goMock).not.toHaveBeenCalled()
+        expect(warnMock).toHaveBeenCalledWith('The playlist is empty.')
+      })
+    })
+
+    it('shuffles', async () => {
+      const playlist = factory<Playlist>('playlist')
+      const songs = factory<Song>('song', 3)
+      const fetchMock = this.mock(songStore, 'fetchForPlaylist').mockResolvedValue(songs)
+      const queueMock = this.mock(playbackService, 'queueAndPlay')
+      const goMock = this.mock(this.router, 'go')
+      await this.renderComponent(playlist)
+
+      await this.user.click(screen.getByText('Shuffle'))
+
+      await waitFor(() => {
+        expect(fetchMock).toHaveBeenCalledWith(playlist)
+        expect(queueMock).toHaveBeenCalledWith(songs, true)
+        expect(goMock).toHaveBeenCalledWith('queue')
+      })
+    })
+
+    it('warns if attempting to shuffle an empty playlist', async () => {
+      const playlist = factory<Playlist>('playlist')
+      const fetchMock = this.mock(songStore, 'fetchForPlaylist').mockResolvedValue([])
+      const queueMock = this.mock(playbackService, 'queueAndPlay')
+      const goMock = this.mock(this.router, 'go')
+      const warnMock = this.mock(MessageToasterStub.value, 'warning')
+
+      await this.renderComponent(playlist)
+
+      await this.user.click(screen.getByText('Shuffle'))
+
+      await waitFor(() => {
+        expect(fetchMock).toHaveBeenCalledWith(playlist)
+        expect(queueMock).not.toHaveBeenCalled()
+        expect(goMock).not.toHaveBeenCalled()
+        expect(warnMock).toHaveBeenCalledWith('The playlist is empty.')
+      })
+    })
   }
 }
diff --git a/resources/assets/js/components/playlist/PlaylistContextMenu.vue b/resources/assets/js/components/playlist/PlaylistContextMenu.vue
index ce579e60..f2265b32 100644
--- a/resources/assets/js/components/playlist/PlaylistContextMenu.vue
+++ b/resources/assets/js/components/playlist/PlaylistContextMenu.vue
@@ -1,20 +1,50 @@
 <template>
   <ContextMenuBase ref="base">
-    <li @click="editPlaylist">Edit…</li>
-    <li @click="deletePlaylist">Delete</li>
+    <li @click="play">Play</li>
+    <li @click="shuffle">Shuffle</li>
+    <li class="separator" />
+    <li @click="edit">Edit…</li>
+    <li @click="destroy">Delete</li>
   </ContextMenuBase>
 </template>
 
 <script lang="ts" setup>
 import { ref } from 'vue'
 import { eventBus } from '@/utils'
-import { useContextMenu } from '@/composables'
+import { useContextMenu, useMessageToaster, useRouter } from '@/composables'
+import { playbackService } from '@/services'
+import { songStore } from '@/stores'
 
 const { base, ContextMenuBase, open, trigger } = useContextMenu()
+const { go } = useRouter()
+const { toastWarning } = useMessageToaster()
+
 const playlist = ref<Playlist>()
 
-const editPlaylist = () => trigger(() => eventBus.emit('MODAL_SHOW_EDIT_PLAYLIST_FORM', playlist.value!))
-const deletePlaylist = () => trigger(() => eventBus.emit('PLAYLIST_DELETE', playlist.value!))
+const edit = () => trigger(() => eventBus.emit('MODAL_SHOW_EDIT_PLAYLIST_FORM', playlist.value!))
+const destroy = () => trigger(() => eventBus.emit('PLAYLIST_DELETE', playlist.value!))
+
+const play = () => trigger(async () => {
+  const songs = await songStore.fetchForPlaylist(playlist.value!)
+
+  if (songs.length) {
+    playbackService.queueAndPlay(songs)
+    go('queue')
+  } else {
+    toastWarning('The playlist is empty.')
+  }
+})
+
+const shuffle = () => trigger(async () => {
+  const songs = await songStore.fetchForPlaylist(playlist.value!)
+
+  if (songs.length) {
+    playbackService.queueAndPlay(songs, true)
+    go('queue')
+  } else {
+    toastWarning('The playlist is empty.')
+  }
+})
 
 eventBus.on('PLAYLIST_CONTEXT_MENU_REQUESTED', async (event, _playlist) => {
   playlist.value = _playlist
diff --git a/resources/assets/js/components/playlist/PlaylistFolderContextMenu.spec.ts b/resources/assets/js/components/playlist/PlaylistFolderContextMenu.spec.ts
index 786152cc..2d159746 100644
--- a/resources/assets/js/components/playlist/PlaylistFolderContextMenu.spec.ts
+++ b/resources/assets/js/components/playlist/PlaylistFolderContextMenu.spec.ts
@@ -5,6 +5,7 @@ import factory from '@/__tests__/factory'
 import { screen, waitFor } from '@testing-library/vue'
 import { playlistStore, songStore } from '@/stores'
 import { playbackService } from '@/services'
+import { MessageToasterStub } from '@/__tests__/stubs'
 import PlaylistFolderContextMenu from './PlaylistFolderContextMenu.vue'
 
 new class extends UnitTestCase {
@@ -52,6 +53,26 @@ new class extends UnitTestCase {
       })
     })
 
+    it('warns if attempting to play with no songs in folder', async () => {
+      const folder = this.createPlayableFolder()
+
+      const fetchMock = this.mock(songStore, 'fetchForPlaylistFolder').mockResolvedValue([])
+      const queueMock = this.mock(playbackService, 'queueAndPlay')
+      const goMock = this.mock(this.router, 'go')
+      const warnMock = this.mock(MessageToasterStub.value, 'warning')
+
+      await this.renderComponent(folder)
+
+      await this.user.click(screen.getByText('Play All'))
+
+      await waitFor(() => {
+        expect(fetchMock).toHaveBeenCalledWith(folder)
+        expect(queueMock).not.toHaveBeenCalled()
+        expect(goMock).not.toHaveBeenCalled()
+        expect(warnMock).toHaveBeenCalledWith('No songs available.')
+      })
+    })
+
     it('shuffles', async () => {
       const folder = this.createPlayableFolder()
       const songs = factory<Song>('song', 3)
@@ -76,6 +97,26 @@ new class extends UnitTestCase {
       expect(screen.queryByText('Shuffle All')).toBeNull()
       expect(screen.queryByText('Play All')).toBeNull()
     })
+
+    it('warns if attempting to shuffle with no songs in folder', async () => {
+      const folder = this.createPlayableFolder()
+
+      const fetchMock = this.mock(songStore, 'fetchForPlaylistFolder').mockResolvedValue([])
+      const queueMock = this.mock(playbackService, 'queueAndPlay')
+      const goMock = this.mock(this.router, 'go')
+      const warnMock = this.mock(MessageToasterStub.value, 'warning')
+
+      await this.renderComponent(folder)
+
+      await this.user.click(screen.getByText('Shuffle All'))
+
+      await waitFor(() => {
+        expect(fetchMock).toHaveBeenCalledWith(folder)
+        expect(queueMock).not.toHaveBeenCalled()
+        expect(goMock).not.toHaveBeenCalled()
+        expect(warnMock).toHaveBeenCalledWith('No songs available.')
+      })
+    })
   }
 
   private createPlayableFolder () {
diff --git a/resources/assets/js/components/playlist/PlaylistFolderContextMenu.vue b/resources/assets/js/components/playlist/PlaylistFolderContextMenu.vue
index 2ebfda46..08e467d3 100644
--- a/resources/assets/js/components/playlist/PlaylistFolderContextMenu.vue
+++ b/resources/assets/js/components/playlist/PlaylistFolderContextMenu.vue
@@ -20,10 +20,11 @@ import { computed, ref } from 'vue'
 import { eventBus } from '@/utils'
 import { playlistStore, songStore } from '@/stores'
 import { playbackService } from '@/services'
-import { useContextMenu, useRouter } from '@/composables'
+import { useContextMenu, useMessageToaster, useRouter } from '@/composables'
 
-const { go } = useRouter()
 const { base, ContextMenuBase, open, trigger } = useContextMenu()
+const { go } = useRouter()
+const { toastWarning } = useMessageToaster()
 
 const folder = ref<PlaylistFolder>()
 
@@ -31,13 +32,25 @@ const playlistsInFolder = computed(() => folder.value ? playlistStore.byFolder(f
 const playable = computed(() => playlistsInFolder.value.length > 0)
 
 const play = () => trigger(async () => {
-  playbackService.queueAndPlay(await songStore.fetchForPlaylistFolder(folder.value!))
-  go('queue')
+  const songs = await songStore.fetchForPlaylistFolder(folder.value!)
+
+  if (songs.length) {
+    playbackService.queueAndPlay(songs)
+    go('queue')
+  } else {
+    toastWarning('No songs available.')
+  }
 })
 
 const shuffle = () => trigger(async () => {
-  playbackService.queueAndPlay(await songStore.fetchForPlaylistFolder(folder.value!), true)
-  go('queue')
+  const songs = await songStore.fetchForPlaylistFolder(folder.value!)
+
+  if (songs.length) {
+    playbackService.queueAndPlay(songs, true)
+    go('queue')
+  } else {
+    toastWarning('No songs available.')
+  }
 })
 
 const createPlaylist = () => trigger(() => eventBus.emit('MODAL_SHOW_CREATE_PLAYLIST_FORM', folder.value!))