diff --git a/CHANGELOG.md b/CHANGELOG.md
index 986a03ac..320b73d1 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -26,6 +26,13 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 * New cover-source picker under Discord Rich Presence settings: **None** (app icon only), **Server**, or **Apple Music**. Mutually exclusive.
 * Fresh installs default to **Server** for opt-in-friendly cover art with no third-party data leak. Existing users keep their previous Apple-covers preference via migration.
 
+### Queue — preserve "Play Next" insertion order (toggle)
+
+**By [@Psychotoxical](https://github.com/Psychotoxical), suggested by [@Sayykii](https://github.com/Sayykii), PR [#464](https://github.com/Psychotoxical/psysonic/pull/464)**
+
+* New optional toggle in Settings → Audio → Playback ("Preserve Play Next order"). When on, multiple "Play Next" insertions **queue up behind each other** instead of the latest one bumping earlier picks down. Default off — existing behaviour unchanged.
+* Side-benefit: single-song "Play Next" now goes through the unified `enqueueAt` path and gets undo + server-sync support that the album path already had.
+
 ## Changed
 
 ### Dependencies — npm / Cargo refresh and rodio 0.22
diff --git a/src/components/ContextMenu.tsx b/src/components/ContextMenu.tsx
index 32bb6d3d..a5729575 100644
--- a/src/components/ContextMenu.tsx
+++ b/src/components/ContextMenu.tsx
@@ -1019,12 +1019,13 @@ function MultiPlaylistToPlaylistSubmenu({ playlists, onDone, triggerId }: { play
 export default function ContextMenu() {
   const { t } = useTranslation();
   const orbitRole = useOrbitStore(s => s.role);
-  const { contextMenu, closeContextMenu, playTrack, enqueue, queue, currentTrack, removeTrack, lastfmLovedCache, setLastfmLovedForSong, starredOverrides, setStarredOverride, openSongInfo, userRatingOverrides, setUserRatingOverride } = usePlayerStore(
+  const { contextMenu, closeContextMenu, playTrack, enqueue, playNext, queue, currentTrack, removeTrack, lastfmLovedCache, setLastfmLovedForSong, starredOverrides, setStarredOverride, openSongInfo, userRatingOverrides, setUserRatingOverride } = usePlayerStore(
     useShallow(s => ({
       contextMenu: s.contextMenu,
       closeContextMenu: s.closeContextMenu,
       playTrack: s.playTrack,
       enqueue: s.enqueue,
+      playNext: s.playNext,
       queue: s.queue,
       currentTrack: s.currentTrack,
       removeTrack: s.removeTrack,
@@ -1528,16 +1529,7 @@ export default function ContextMenu() {
               <div className="context-menu-item" onClick={() => handleAction(() => playTrack(song, [song]))}>
                 <Play size={14} /> {t('contextMenu.playNow')}
               </div>
-              <div className="context-menu-item" onClick={() => handleAction(() => {
-                if (!currentTrack) {
-                  playTrack(song, [song]);
-                  return;
-                }
-                const currentIdx = usePlayerStore.getState().queueIndex;
-                const newQueue = [...queue];
-                newQueue.splice(currentIdx + 1, 0, song);
-                usePlayerStore.setState({ queue: newQueue });
-              })}>
+              <div className="context-menu-item" onClick={() => handleAction(() => playNext([song]))}>
                 <ChevronsRight size={14} /> {t('contextMenu.playNext')}
               </div>
               <div className="context-menu-item" onClick={() => handleAction(() => enqueue([song]))}>
@@ -1691,16 +1683,7 @@ export default function ContextMenu() {
               <div className="context-menu-item" onClick={() => handleAction(() => playTrack(song, [song]))}>
                 <Play size={14} /> {t('contextMenu.playNow')}
               </div>
-              <div className="context-menu-item" onClick={() => handleAction(() => {
-                if (!currentTrack) {
-                  playTrack(song, [song]);
-                  return;
-                }
-                const currentIdx = usePlayerStore.getState().queueIndex;
-                const newQueue = [...queue];
-                newQueue.splice(currentIdx + 1, 0, song);
-                usePlayerStore.setState({ queue: newQueue });
-              })}>
+              <div className="context-menu-item" onClick={() => handleAction(() => playNext([song]))}>
                 <ChevronsRight size={14} /> {t('contextMenu.playNext')}
               </div>
               <div className="context-menu-item" onClick={() => handleAction(() => enqueue([song]))}>
@@ -1830,12 +1813,7 @@ export default function ContextMenu() {
                 const albumData = await getAlbum(album.id);
                 const tracks = albumData.songs.map(songToTrack);
                 if (tracks.length === 0) return;
-                if (!currentTrack) {
-                  playTrack(tracks[0], tracks);
-                  return;
-                }
-                const currentIdx = usePlayerStore.getState().queueIndex;
-                usePlayerStore.getState().enqueueAt(tracks, currentIdx + 1);
+                playNext(tracks);
               })}>
                 <ChevronsRight size={14} /> {t('contextMenu.playNext')}
               </div>
diff --git a/src/locales/de.ts b/src/locales/de.ts
index 918100db..899f2253 100644
--- a/src/locales/de.ts
+++ b/src/locales/de.ts
@@ -891,6 +891,8 @@ export const deTranslation = {
     notWithCrossfade: 'Nicht verfügbar wenn Crossfade aktiv ist',
     gapless: 'Nahtlose Wiedergabe',
     gaplessDesc: 'Nächsten Track vorpuffern um Lücken zwischen Songs zu vermeiden',
+    preservePlayNextOrder: '„Als Nächstes"-Reihenfolge bewahren',
+    preservePlayNextOrderDesc: 'Neu hinzugefügte „Als Nächstes"-Titel reihen sich hinten an statt sich vorn einzuschieben.',
     trackPreviewsTitle: 'Track-Vorschau',
     trackPreviewsToggle: 'Track-Vorschau aktivieren',
     trackPreviewsDesc: 'Inline Play- und Vorschau-Buttons in den Tracklisten anzeigen für eine kurze Hörprobe mitten im Song.',
diff --git a/src/locales/en.ts b/src/locales/en.ts
index 5815d342..e470a649 100644
--- a/src/locales/en.ts
+++ b/src/locales/en.ts
@@ -897,6 +897,8 @@ export const enTranslation = {
     notWithCrossfade: 'Not available while Crossfade is active',
     gapless: 'Gapless Playback',
     gaplessDesc: 'Pre-buffer next track to eliminate gaps between songs',
+    preservePlayNextOrder: 'Preserve "Play Next" order',
+    preservePlayNextOrderDesc: 'Newly added Play Next items queue up behind earlier ones instead of jumping in front.',
     trackPreviewsTitle: 'Track Previews',
     trackPreviewsToggle: 'Enable track previews',
     trackPreviewsDesc: 'Show inline Play and Preview buttons in tracklists for a quick mid-song sample.',
diff --git a/src/locales/es.ts b/src/locales/es.ts
index d72c11a8..d0c201e0 100644
--- a/src/locales/es.ts
+++ b/src/locales/es.ts
@@ -884,6 +884,8 @@ export const esTranslation = {
     notWithCrossfade: 'No disponible mientras Crossfade está activo',
     gapless: 'Reproducción Gapless',
     gaplessDesc: 'Precarga siguiente pista para eliminar silencios entre canciones',
+    preservePlayNextOrder: 'Mantener el orden de "Reproducir Siguiente"',
+    preservePlayNextOrderDesc: 'Los elementos añadidos a "Reproducir Siguiente" se encolan detrás de los anteriores en vez de saltar al principio.',
     trackPreviewsTitle: 'Previsualizaciones de pistas',
     trackPreviewsToggle: 'Activar previsualizaciones',
     trackPreviewsDesc: 'Mostrar botones de Reproducir y Previsualización en las listas de pistas para una muestra rápida a mitad de canción.',
diff --git a/src/locales/fr.ts b/src/locales/fr.ts
index 9b8b1a31..f74da8c9 100644
--- a/src/locales/fr.ts
+++ b/src/locales/fr.ts
@@ -879,6 +879,8 @@ export const frTranslation = {
     notWithCrossfade: 'Non disponible quand le fondu enchaîné est actif',
     gapless: 'Lecture sans blanc',
     gaplessDesc: 'Préparer la piste suivante pour éliminer les silences entre les morceaux',
+    preservePlayNextOrder: "Préserver l'ordre « Lire ensuite »",
+    preservePlayNextOrderDesc: 'Les nouveaux éléments « Lire ensuite » s\'ajoutent à la fin de la file existante au lieu de la doubler.',
     trackPreviewsTitle: 'Aperçus de pistes',
     trackPreviewsToggle: 'Activer les aperçus de pistes',
     trackPreviewsDesc: 'Affiche les boutons Lecture et Aperçu dans les listes pour un court extrait au milieu du morceau.',
diff --git a/src/locales/nb.ts b/src/locales/nb.ts
index f140cbcc..a5844b42 100644
--- a/src/locales/nb.ts
+++ b/src/locales/nb.ts
@@ -878,6 +878,8 @@ export const nbTranslation = {
     notWithCrossfade: 'Ikke tilgjengelig mens Crossfade er aktiv',
     gapless: 'Gapless avspilling',
     gaplessDesc: 'Forhåndsbuffer neste spor for å eliminere mellomrom mellom sanger',
+    preservePlayNextOrder: 'Behold "Spill neste"-rekkefølge',
+    preservePlayNextOrderDesc: 'Nye "Spill neste"-elementer havner bak de eksisterende i stedet for å snike seg foran.',
     trackPreviewsTitle: 'Sporforhåndsvisning',
     trackPreviewsToggle: 'Aktiver sporforhåndsvisning',
     trackPreviewsDesc: 'Vis innebygde Spill- og Forhåndsvisning-knapper i sporlister for en kort smakebit fra midten av sangen.',
diff --git a/src/locales/nl.ts b/src/locales/nl.ts
index 873d5875..5169a723 100644
--- a/src/locales/nl.ts
+++ b/src/locales/nl.ts
@@ -878,6 +878,8 @@ export const nlTranslation = {
     notWithCrossfade: 'Niet beschikbaar als overgang actief is',
     gapless: 'Naadloos afspelen',
     gaplessDesc: 'Volgend nummer vooraf bufferen om stiltes tussen nummers te elimineren',
+    preservePlayNextOrder: '"Volgende afspelen"-volgorde behouden',
+    preservePlayNextOrderDesc: 'Nieuwe "Volgende afspelen"-items komen achter bestaande te staan in plaats van ervoor.',
     trackPreviewsTitle: 'Track-voorvertoning',
     trackPreviewsToggle: 'Track-voorvertoning inschakelen',
     trackPreviewsDesc: 'Inline Play- en Voorvertoning-knoppen in trackslijsten tonen voor een korte sample midden in het nummer.',
diff --git a/src/locales/ru.ts b/src/locales/ru.ts
index 2fda4c18..fc0f9a7f 100644
--- a/src/locales/ru.ts
+++ b/src/locales/ru.ts
@@ -930,6 +930,8 @@ export const ruTranslation = {
     notWithCrossfade: 'Недоступно при включённом кроссфейде',
     gapless: 'Без пауз между треками',
     gaplessDesc: 'Заранее подгружать следующий трек, чтобы не было тишины',
+    preservePlayNextOrder: 'Сохранять порядок «Играть следующим»',
+    preservePlayNextOrderDesc: 'Новые элементы «Играть следующим» становятся в конец очереди, а не лезут вперёд.',
     trackPreviewsTitle: 'Превью треков',
     trackPreviewsToggle: 'Включить превью треков',
     trackPreviewsDesc: 'Показывать встроенные кнопки воспроизведения и превью в списках треков для быстрого прослушивания фрагмента.',
diff --git a/src/locales/zh.ts b/src/locales/zh.ts
index 10f0083d..7cd915fd 100644
--- a/src/locales/zh.ts
+++ b/src/locales/zh.ts
@@ -873,6 +873,8 @@ export const zhTranslation = {
     notWithCrossfade: '交叉淡入淡出开启时不可用',
     gapless: '无缝播放',
     gaplessDesc: '预缓冲下一首曲目以消除歌曲间的间隙',
+    preservePlayNextOrder: '保留"下一首播放"顺序',
+    preservePlayNextOrderDesc: '新添加的"下一首播放"项目排在现有项目之后，而不是插到前面。',
     trackPreviewsTitle: '曲目预览',
     trackPreviewsToggle: '启用曲目预览',
     trackPreviewsDesc: '在曲目列表中显示内联播放与预览按钮，可快速试听歌曲中段。',
diff --git a/src/pages/Settings.tsx b/src/pages/Settings.tsx
index 5ac28c26..4c505987 100644
--- a/src/pages/Settings.tsx
+++ b/src/pages/Settings.tsx
@@ -360,6 +360,7 @@ const CONTRIBUTORS = [
       'Settings: 3-state animation mode (Full / Reduced / Static) — replaces boolean reduce-animations toggle (PR #441)',
       'Tracks: Highly Rated rail and per-card star display, with cache layer for ndListSongs (PR #443)',
       'Random Mix: playlist-size picker (50/75/100/125/150) and filter-panel layout cleanup (PR #445)',
+      'Queue: optional "Preserve Play Next order" toggle — multiple Play Next inserts queue up behind each other instead of latest-on-top (PR #464)',
     ],
   },
 ] as const;
@@ -2552,6 +2553,22 @@ export default function Settings() {
                   <span className="toggle-track" />
                 </label>
               </div>
+
+              <div className="settings-toggle-row" style={{ marginTop: '0.75rem' }}>
+                <div>
+                  <div style={{ fontWeight: 500 }}>
+                    {t('settings.preservePlayNextOrder')}
+                  </div>
+                  <div style={{ fontSize: 12, color: 'var(--text-muted)' }}>
+                    {t('settings.preservePlayNextOrderDesc')}
+                  </div>
+                </div>
+                <label className="toggle-switch" aria-label={t('settings.preservePlayNextOrder')}>
+                  <input type="checkbox" checked={auth.preservePlayNextOrder}
+                    onChange={e => auth.setPreservePlayNextOrder(e.target.checked)} />
+                  <span className="toggle-track" />
+                </label>
+              </div>
             </div>
           </SettingsSubSection>
 
diff --git a/src/store/authStore.ts b/src/store/authStore.ts
index 1df00177..679e29ac 100644
--- a/src/store/authStore.ts
+++ b/src/store/authStore.ts
@@ -130,6 +130,7 @@ interface AuthState {
   preloadMode: 'off' | 'balanced' | 'early' | 'custom';
   preloadCustomSeconds: number;
   infiniteQueueEnabled: boolean;
+  preservePlayNextOrder: boolean;
   showArtistImages: boolean;
   showTrayIcon: boolean;
   minimizeToTray: boolean;
@@ -307,6 +308,7 @@ interface AuthState {
   setPreloadMode: (v: 'off' | 'balanced' | 'early' | 'custom') => void;
   setPreloadCustomSeconds: (v: number) => void;
   setInfiniteQueueEnabled: (v: boolean) => void;
+  setPreservePlayNextOrder: (v: boolean) => void;
   setShowArtistImages: (v: boolean) => void;
   setShowTrayIcon: (v: boolean) => void;
   setMinimizeToTray: (v: boolean) => void;
@@ -444,6 +446,7 @@ export const useAuthStore = create<AuthState>()(
       preloadMode: 'balanced',
       preloadCustomSeconds: 30,
       infiniteQueueEnabled: false,
+      preservePlayNextOrder: false,
       showArtistImages: false,
       showTrayIcon: true,
       minimizeToTray: false,
@@ -607,6 +610,7 @@ export const useAuthStore = create<AuthState>()(
       setPreloadMode: (v: 'off' | 'balanced' | 'early' | 'custom') => set({ preloadMode: v }),
       setPreloadCustomSeconds: (v: number) => set({ preloadCustomSeconds: v }),
       setInfiniteQueueEnabled: (v) => set({ infiniteQueueEnabled: v }),
+      setPreservePlayNextOrder: (v) => set({ preservePlayNextOrder: v }),
       setShowArtistImages: (v) => set({ showArtistImages: v }),
       setShowTrayIcon: (v) => set({ showTrayIcon: v }),
       setMinimizeToTray: (v) => set({ minimizeToTray: v }),
diff --git a/src/store/playerStore.ts b/src/store/playerStore.ts
index ac554be9..f011646f 100644
--- a/src/store/playerStore.ts
+++ b/src/store/playerStore.ts
@@ -73,6 +73,10 @@ export interface Track {
   size?: number;
   autoAdded?: boolean;
   radioAdded?: boolean;
+  /** Inserted via "Play Next". Used by the preserve-order toggle to find the
+   *  end of the current Play-Next streak. Stale flags behind queueIndex are
+   *  harmless — the streak scan only looks forward from queueIndex+1. */
+  playNextAdded?: boolean;
 }
 
 export function songToTrack(song: SubsonicSong): Track {
@@ -260,6 +264,12 @@ interface PlayerState {
    setProgress: (t: number, duration: number) => void;
   enqueue: (tracks: Track[], _orbitConfirmed?: boolean) => void;
   enqueueAt: (tracks: Track[], insertIndex: number, _orbitConfirmed?: boolean) => void;
+  /** "Play Next" — inserts after the current track. When
+   *  `preservePlayNextOrder` is on, appends to the existing Play-Next streak
+   *  (Spotify-style); otherwise inserts directly after the current track and
+   *  pushes any earlier Play-Next items down (default). Falls back to
+   *  `playTrack` when nothing is currently playing. */
+  playNext: (tracks: Track[]) => void;
   enqueueRadio: (tracks: Track[], artistId?: string) => void;
   setRadioArtistId: (artistId: string) => void;
   /** For Lucky Mix: drop upcoming tail; keep the currently playing item only. */
@@ -3247,6 +3257,23 @@ export const usePlayerStore = create<PlayerState>()(
         });
       },
 
+      playNext: (tracks) => {
+        if (tracks.length === 0) return;
+        const state = get();
+        const tagged = tracks.map(t => ({ ...t, playNextAdded: true as const }));
+        if (!state.currentTrack) {
+          state.playTrack(tagged[0], tagged);
+          return;
+        }
+        const baseIdx = state.queueIndex + 1;
+        let insertIdx = baseIdx;
+        if (useAuthStore.getState().preservePlayNextOrder) {
+          const q = state.queue;
+          while (insertIdx < q.length && q[insertIdx].playNextAdded) insertIdx++;
+        }
+        get().enqueueAt(tagged, insertIdx);
+      },
+
       clearQueue: () => {
         invoke('audio_stop').catch(console.error);
         isAudioPaused = false;