diff --git a/src/main.cpp b/src/main.cpp
index 18f6c04..3b8e845 100644
--- a/src/main.cpp
+++ b/src/main.cpp
@@ -78,6 +78,9 @@ DirectoryNode *currentNode = nullptr;
 
 volatile bool newRfidInt = false;
 volatile bool playButtonDown = false;
+// Track if play button hold is active and if volume was adjusted during this hold
+volatile bool playHoldActive = false;
+volatile bool volumeAdjustedDuringHold = false;
 volatile uint8_t sd_lock_flag = 0;
 
 /* Simple spinlock using older GCC sync builtins (no libatomic required).
@@ -1509,7 +1512,7 @@ void loop()
     server.begin();
   }
 
-  if (audio.isRunning() && webreq_cnt == 0)
+  if (audio.isRunning())
   {
     if (asyncStop)
     {
@@ -1583,7 +1586,7 @@ void loop()
     asyncTogglePlayPause = false;
     togglePlayPause();
   }
-  else if (asyncNext && webreq_cnt == 0)
+  else if (asyncNext)
   {
     asyncNext = false;
     // If the play/start button is held, treat NEXT as volume up
@@ -1595,6 +1598,7 @@ void loop()
         vol++;
         audio.setVolume(vol);
         volume = vol; // update stored volume for mute/unmute
+        volumeAdjustedDuringHold = true;
       }
       // do not play the startup sound when changing volume while holding play
     }
@@ -1629,6 +1633,7 @@ void loop()
         vol--;
         audio.setVolume(vol);
         volume = vol; // update stored volume for mute/unmute
+        volumeAdjustedDuringHold = true;
       }
       // do not play the startup sound when changing volume while holding play
     }
@@ -1704,9 +1709,32 @@ void loop2(void *parameter)
 
   for (;;)
   {
-    // Track whether the play/start button is currently held down so the main loop
-    // can interpret NEXT/PREV as volume changes while play is held.
-    playButtonDown = (digitalRead(BTN_START_STOP) == LOW);
+    // Track whether the play/start button is currently held down and detect press/release
+    bool currentDown = (digitalRead(BTN_START_STOP) == LOW);
+    static bool prevDown = false;
+    playButtonDown = currentDown;
+
+    // On press: start hold tracking and reset volume-change marker
+    if (currentDown && !prevDown)
+    {
+      playHoldActive = true;
+      volumeAdjustedDuringHold = false;
+      lastInteraction = millis();
+    }
+    // On release: toggle only if no volume change occurred during hold
+    if (!currentDown && prevDown)
+    {
+      if (playHoldActive)
+      {
+        if (!volumeAdjustedDuringHold)
+        {
+          asyncTogglePlayPause = true;
+        }
+        playHoldActive = false;
+        volumeAdjustedDuringHold = false;
+      }
+    }
+    prevDown = currentDown;
 
     if (buttonPressed(BTN_NEXT))
     {
@@ -1716,10 +1744,6 @@ void loop2(void *parameter)
     {
       asyncPrev = true;
     }
-    if (buttonPressed(BTN_START_STOP))
-    {
-      asyncTogglePlayPause = true;
-    }
     if (!loggingDone)
     {
       Serial.println("loop2 started");