diff --git a/rotary_phone_web.py b/rotary_phone_web.py
index db225d0..6257f15 100644
--- a/rotary_phone_web.py
+++ b/rotary_phone_web.py
@@ -495,6 +495,15 @@ class RotaryPhone:
                     print("Handset hung up, stopping recording immediately")
                     break
 
+                # Check extra button during recording
+                if EXTRA_BUTTON_ENABLED and GPIO.input(EXTRA_BUTTON_PIN) == EXTRA_BUTTON_PRESSED:
+                    print(f"[BUTTON] Button pressed during recording!")
+                    if not self.extra_button_playing:
+                        print(f"[BUTTON] Triggering button sound...")
+                        button_thread = threading.Thread(target=self.play_extra_button_sound, daemon=True)
+                        button_thread.start()
+                        time.sleep(0.5)  # Debounce to prevent multiple triggers
+
                 try:
                     data = stream.read(CHUNK, exception_on_overflow=False)
                     frames.append(data)
@@ -554,32 +563,45 @@ class RotaryPhone:
     def play_extra_button_sound(self):
         """Play sound when extra button is pressed (only during recording)"""
         if not EXTRA_BUTTON_ENABLED:
+            print("[BUTTON] Extra button disabled in config")
             return
 
         # Only play if currently recording
         if not self.recording:
-            print("Extra button ignored - not recording")
+            print("[BUTTON] Extra button ignored - not recording")
             return
 
         button_sound = self.get_extra_button_sound_path()
+        print(f"[BUTTON] Button sound path: {button_sound}")
+
         if not os.path.exists(button_sound):
-            print(f"Extra button sound not found: {button_sound}")
+            print(f"[BUTTON] ERROR: Sound file not found: {button_sound}")
             return
 
-        print(f"\n=== Extra button pressed ===")
+        print(f"[BUTTON] Playing extra button sound...")
         self.extra_button_playing = True
 
         try:
             # Use a separate PyAudio instance for playback during recording
             # This allows simultaneous input (recording) and output (button sound)
+            print(f"[BUTTON] Opening audio file...")
             audio_playback = pyaudio.PyAudio()
 
             wf = wave.open(button_sound, 'rb')
+            file_rate = wf.getframerate()
+            file_channels = wf.getnchannels()
+            file_width = wf.getsampwidth()
 
+            print(f"[BUTTON] File info - Rate: {file_rate}Hz, Channels: {file_channels}, Width: {file_width}")
+
+            if file_rate != RATE:
+                print(f"[BUTTON] WARNING: File sample rate ({file_rate}Hz) != configured rate ({RATE}Hz)")
+
+            print(f"[BUTTON] Opening audio stream on device {AUDIO_DEVICE_INDEX}...")
             stream = audio_playback.open(
-                format=audio_playback.get_format_from_width(wf.getsampwidth()),
-                channels=wf.getnchannels(),
-                rate=wf.getframerate(),
+                format=audio_playback.get_format_from_width(file_width),
+                channels=file_channels,
+                rate=file_rate,
                 output=True,
                 output_device_index=AUDIO_DEVICE_INDEX,
                 frames_per_buffer=CHUNK
@@ -587,9 +609,12 @@ class RotaryPhone:
 
             # Get volume multiplier
             volume = self.get_volume() / 100.0
+            print(f"[BUTTON] Volume: {int(volume * 100)}%")
 
             # Play the sound
+            print(f"[BUTTON] Starting playback...")
             data = wf.readframes(CHUNK)
+            chunk_count = 0
             while data:
                 # Apply volume
                 if volume < 1.0:
@@ -599,36 +624,48 @@ class RotaryPhone:
 
                 stream.write(data)
                 data = wf.readframes(CHUNK)
+                chunk_count += 1
 
             stream.stop_stream()
             stream.close()
             wf.close()
             audio_playback.terminate()
 
-            print("Extra button sound playback finished")
+            print(f"[BUTTON] Playback finished ({chunk_count} chunks)")
 
         except Exception as e:
-            print(f"Error playing button sound: {e}")
+            print(f"[BUTTON] ERROR playing button sound: {e}")
+            import traceback
+            traceback.print_exc()
         finally:
             self.extra_button_playing = False
+            print(f"[BUTTON] Button playback complete")
 
     def phone_loop(self):
         """Main phone handling loop"""
         print("Rotary Phone System Started")
         print(f"Hook pin: GPIO {HOOK_PIN}")
         if EXTRA_BUTTON_ENABLED:
-            print(f"Extra button: GPIO {EXTRA_BUTTON_PIN}")
+            print(f"Extra button: ENABLED on GPIO {EXTRA_BUTTON_PIN}")
+            print(f"Extra button pressed state: {EXTRA_BUTTON_PRESSED} ({'LOW' if EXTRA_BUTTON_PRESSED == GPIO.LOW else 'HIGH'})")
+            print(f"Extra button sound: {self.get_extra_button_sound_path()}")
+        else:
+            print(f"Extra button: DISABLED")
         print(f"Recordings will be saved to: {OUTPUT_DIR}")
 
         try:
             while True:
                 # Check extra button first (higher priority)
                 if EXTRA_BUTTON_ENABLED and GPIO.input(EXTRA_BUTTON_PIN) == EXTRA_BUTTON_PRESSED:
+                    print(f"[BUTTON] Button pressed detected (recording={self.recording}, playing={self.extra_button_playing})")
                     if not self.extra_button_playing:
                         # Play extra button sound in a separate thread to not block
+                        print(f"[BUTTON] Starting button sound thread...")
                         button_thread = threading.Thread(target=self.play_extra_button_sound, daemon=True)
                         button_thread.start()
                         time.sleep(0.5)  # Debounce
+                    else:
+                        print(f"[BUTTON] Button sound already playing, ignoring")
 
                 # Wait for handset pickup
                 if GPIO.input(HOOK_PIN) == HOOK_PRESSED and self.phone_status == "on_hook":