diff --git a/CHANGELOG.md b/CHANGELOG.md
index e03b3220..ff1817b3 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -127,6 +127,13 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ## Fixed
 
+### Context menu "Play Now" and resize behaviour
+
+**By [@Psychotoxical](https://github.com/Psychotoxical), PR [#1174](https://github.com/Psychotoxical/psysonic/pull/1174)**, reported by [@peri4ko](https://github.com/peri4ko)
+
+* On the Playlists page, right-clicking a playlist and choosing "Play Now" only opened the playlist instead of playing it. It now starts playback.
+* Resizing the window while a context menu was open could leave the menu stranded and drifting off-screen. The context menu now closes when the window is resized.
+
 ### Artist header showing the plain image instead of the external background
 
 **By [@Psychotoxical](https://github.com/Psychotoxical), PR [#1172](https://github.com/Psychotoxical/psysonic/pull/1172)**
diff --git a/src/components/ContextMenu.tsx b/src/components/ContextMenu.tsx
index d4de40bd..d0ca337c 100644
--- a/src/components/ContextMenu.tsx
+++ b/src/components/ContextMenu.tsx
@@ -132,6 +132,18 @@ export default function ContextMenu() {
     }
   }, [contextMenu.isOpen, contextMenu.x, contextMenu.y]);
 
+  // Close on any window resize. The menu is absolutely positioned at fixed
+  // coordinates, so a resize would otherwise leave it stranded and drifting
+  // off-screen. Whether a resize closed the menu was inconsistent across
+  // setups (it stayed open on some Windows and Linux environments); always
+  // closing it here makes the behaviour the same everywhere.
+  useEffect(() => {
+    if (!contextMenu.isOpen) return;
+    const onResize = () => closeContextMenu();
+    window.addEventListener('resize', onResize);
+    return () => window.removeEventListener('resize', onResize);
+  }, [contextMenu.isOpen, closeContextMenu]);
+
   useEffect(() => {
     if (contextMenu.isOpen) {
       previousFocusRef.current = document.activeElement as HTMLElement | null;
diff --git a/src/components/contextMenu/PlaylistContextItems.tsx b/src/components/contextMenu/PlaylistContextItems.tsx
index 190ec290..fa233200 100644
--- a/src/components/contextMenu/PlaylistContextItems.tsx
+++ b/src/components/contextMenu/PlaylistContextItems.tsx
@@ -1,6 +1,5 @@
 import { useTranslation } from 'react-i18next';
 import { Play, ChevronRight, FolderTree, ListMusic, Trash2 } from 'lucide-react';
-import { useNavigate } from 'react-router-dom';
 import type { SubsonicPlaylist } from '../../api/subsonicTypes';
 import { usePlaylistStore } from '../../store/playlistStore';
 import { MultiPlaylistToPlaylistSubmenu, SinglePlaylistToPlaylistSubmenu } from './PlaylistToPlaylistSubmenus';
@@ -16,7 +15,6 @@ export default function PlaylistContextItems(props: ContextMenuItemsProps) {
     offlinePolicy,
   } = props;
   const { t } = useTranslation();
-  const navigate = useNavigate();
 
   return (
     <>
@@ -24,7 +22,14 @@ export default function PlaylistContextItems(props: ContextMenuItemsProps) {
           const playlist = item as SubsonicPlaylist;
           return (
             <>
-              <div className="context-menu-item" onClick={() => handleAction(() => navigate(`/playlists/${playlist.id}`))}>
+              <div className="context-menu-item" onClick={() => handleAction(async () => {
+                const { playPlaylistById } = await import('../../utils/playlist/playPlaylistById');
+                try {
+                  await playPlaylistById(playlist.id);
+                } catch {
+                  // Network/load failure — leave playback untouched rather than crash.
+                }
+              })}>
                 <Play size={14} /> {t('contextMenu.playNow')}
               </div>
               <div className="context-menu-divider" />
diff --git a/src/utils/playlist/playPlaylistById.ts b/src/utils/playlist/playPlaylistById.ts
new file mode 100644
index 00000000..f013e873
--- /dev/null
+++ b/src/utils/playlist/playPlaylistById.ts
@@ -0,0 +1,21 @@
+import { getPlaylist } from '../../api/subsonicPlaylists';
+import { songToTrack } from '../playback/songToTrack';
+import { usePlayerStore } from '../../store/playerStore';
+import { usePlaylistStore } from '../../store/playlistStore';
+import { playPlaylistAll } from './playlistBulkPlayActions';
+
+/**
+ * Load a playlist's songs and start playback immediately ("Play Now").
+ *
+ * Used where only the playlist metadata is on hand — the playlist context menu
+ * on the Playlists overview — so the tracks have to be fetched first. Once
+ * loaded it defers to {@link playPlaylistAll}, the same action the playlist
+ * detail "Play All" button uses, so playback behaviour stays in one place.
+ */
+export async function playPlaylistById(id: string): Promise<void> {
+  const { songs } = await getPlaylist(id);
+  const tracks = songs.map(songToTrack);
+  const { playTrack, enqueue } = usePlayerStore.getState();
+  const { touchPlaylist } = usePlaylistStore.getState();
+  playPlaylistAll({ songsLength: tracks.length, id, tracks, touchPlaylist, playTrack, enqueue });
+}