diff --git a/rotary_phone_web.py b/rotary_phone_web.py
index 27751c8..89b1cea 100644
--- a/rotary_phone_web.py
+++ b/rotary_phone_web.py
@@ -181,8 +181,14 @@ class RotaryPhone:
         wf.close()
         print(f"Default dial tone saved to {DIALTONE_FILE}")
     
-    def play_sound_file(self, filepath):
-        """Play a WAV file with volume control"""
+    def play_sound_file(self, filepath, check_hook_status=True):
+        """Play a WAV file with volume control
+
+        Args:
+            filepath: Path to WAV file
+            check_hook_status: If True, only play while off-hook (for greeting).
+                             If False, play completely regardless of hook (for button)
+        """
         if not os.path.exists(filepath):
             print(f"Sound file not found: {filepath}")
             return False
@@ -207,7 +213,11 @@ class RotaryPhone:
 
             # Play the sound with volume control
             data = wf.readframes(CHUNK)
-            while data and self.phone_status == "off_hook":
+            while data:
+                # For greeting sounds, stop if handset is hung up
+                if check_hook_status and self.phone_status != "off_hook":
+                    break
+
                 # Apply volume by converting to numpy array and scaling
                 if volume < 1.0:
                     audio_data = np.frombuffer(data, dtype=np.int16)
@@ -295,10 +305,15 @@ class RotaryPhone:
         }
     
     def play_extra_button_sound(self):
-        """Play sound when extra button is pressed"""
+        """Play sound when extra button is pressed (only when on-hook)"""
         if not EXTRA_BUTTON_ENABLED:
             return
 
+        # Only play if phone is on hook (not in use)
+        if self.phone_status != "on_hook":
+            print("Extra button ignored - phone is off hook")
+            return
+
         button_sound = self.get_extra_button_sound_path()
         if not os.path.exists(button_sound):
             print(f"Extra button sound not found: {button_sound}")
@@ -306,7 +321,8 @@ class RotaryPhone:
 
         print(f"\n=== Extra button pressed ===")
         self.extra_button_playing = True
-        self.play_sound_file(button_sound)
+        # Play without checking hook status - play entire sound
+        self.play_sound_file(button_sound, check_hook_status=False)
         self.extra_button_playing = False
 
     def phone_loop(self):