diff --git a/src/bot/instance.ts b/src/bot/instance.ts
index 0478483..0174207 100755
--- a/src/bot/instance.ts
+++ b/src/bot/instance.ts
@@ -736,21 +736,23 @@ export class BotInstance extends EventEmitter {
 
   /**
    * Advance the queue and play the next song. If the resolved URL fails
-   * (e.g., copyright/region restrictions for QQ), skips up to 3 more
-   * songs looking for a playable one. Public so REST endpoints that
+   * (e.g., copyright/region restrictions for QQ), skips up to `maxRetries`
+   * more songs looking for a playable one. Public so REST endpoints that
    * seed the queue can fall back to this retry-skip behavior.
+   *
+   * Returns true if a song actually started playing, false otherwise.
    */
-  async playNext(): Promise<void> {
-    if (this.isAdvancing || !this.connected) return;
+  async playNext(maxRetries = 3): Promise<boolean> {
+    if (this.isAdvancing || !this.connected) return false;
     this.isAdvancing = true;
     try {
       this.voteSkipUsers.clear();
       const next = this.queue.next();
+      let started = false;
       if (next) {
-        let started = await this.resolveAndPlay(next);
+        started = await this.resolveAndPlay(next);
         if (!started) {
-          // Skip to next if URL resolve fails (up to 3 retries)
-          for (let i = 0; i < 3 && this.connected; i++) {
+          for (let i = 0; i < maxRetries && this.connected; i++) {
             const retry = this.queue.next();
             if (!retry) break;
             if (await this.resolveAndPlay(retry)) {
@@ -772,8 +774,9 @@ export class BotInstance extends EventEmitter {
           await this.refillFm();
           const refillNext = this.queue.next();
           if (refillNext) {
-            await this.resolveAndPlay(refillNext);
-          } else {
+            started = await this.resolveAndPlay(refillNext);
+          }
+          if (!started) {
             this.player.stop();
             this.profileManager.onSongChange(null).catch(() => {});
           }
@@ -783,6 +786,7 @@ export class BotInstance extends EventEmitter {
         }
       }
       this.emit("stateChange");
+      return started;
     } finally {
       this.isAdvancing = false;
     }
diff --git a/src/web/api/player.ts b/src/web/api/player.ts
index 68f7cb6..faf74f9 100644
--- a/src/web/api/player.ts
+++ b/src/web/api/player.ts
@@ -266,13 +266,13 @@ export function createPlayerRouter(
       }
 
       // If the first picked song can't resolve (e.g., QQ song with no
-      // streaming entitlement → result 104003), fall back to the same
-      // retry-skip behavior playNext uses for trackEnd auto-advance.
-      // Otherwise the bot would sit silently on a dead song.
+      // streaming entitlement → result 104003), fall back to playNext's
+      // retry-skip behavior. Use a higher retry budget than the default
+      // trackEnd auto-advance because user-initiated playlist plays
+      // commonly have long contiguous runs of unplayable songs.
       let started = first ? await bot.resolveAndPlay(first) : false;
       if (first && !started) {
-        await bot.playNext();
-        started = !!queue.current();
+        started = await bot.playNext(20);
       }
 
       const playing = queue.current();