diff --git a/vocode/streaming/output_device/twilio_output_device.py b/vocode/streaming/output_device/twilio_output_device.py
index 062d998dd..74e0e9c07 100644
--- a/vocode/streaming/output_device/twilio_output_device.py
+++ b/vocode/streaming/output_device/twilio_output_device.py
@@ -8,6 +8,7 @@
 
 from fastapi import WebSocket
 from fastapi.websockets import WebSocketState
+from loguru import logger
 from pydantic import BaseModel
 
 from vocode.streaming.output_device.abstract_output_device import AbstractOutputDevice
@@ -70,7 +71,7 @@ async def _process_mark_messages(self):
                 # mark messages are tagged with the chunk ID that is attached to the audio chunk
                 # but they are guaranteed to come in the same order as the audio chunks, and we
                 # don't need to build resiliency there
-                await self._mark_message_queue.get()
+                mark_message = await self._mark_message_queue.get()
                 item = await self._unprocessed_audio_chunks_queue.get()
             except asyncio.CancelledError:
                 return
@@ -78,6 +79,11 @@ async def _process_mark_messages(self):
             self.interruptible_event = item
             audio_chunk = item.payload
 
+            if mark_message.chunk_id != str(audio_chunk.chunk_id):
+                logger.error(
+                    f"Received a mark message out of order with chunk ID {mark_message.chunk_id}"
+                )
+
             if item.is_interrupted():
                 audio_chunk.on_interrupt()
                 audio_chunk.state = ChunkState.INTERRUPTED
diff --git a/vocode/streaming/output_device/vonage_output_device.py b/vocode/streaming/output_device/vonage_output_device.py
index 8385bfaaf..53234e67c 100644
--- a/vocode/streaming/output_device/vonage_output_device.py
+++ b/vocode/streaming/output_device/vonage_output_device.py
@@ -36,5 +36,5 @@ async def play(self, chunk: bytes):
             subchunk = chunk[i : i + VONAGE_CHUNK_SIZE]
             if len(subchunk) % 2 == 1:
                 subchunk += PCM_SILENCE_BYTE  # pad with silence, Vonage goes crazy otherwise
-            if self.ws and self.ws.application_state == WebSocketState.DISCONNECTED:
+            if self.ws and self.ws.application_state != WebSocketState.DISCONNECTED:
                 await self.ws.send_bytes(subchunk)
diff --git a/vocode/streaming/streaming_conversation.py b/vocode/streaming/streaming_conversation.py
index 0e84e4285..bdb563230 100644
--- a/vocode/streaming/streaming_conversation.py
+++ b/vocode/streaming/streaming_conversation.py
@@ -945,6 +945,7 @@ def _on_interrupt():
                 "on_interrupt",
                 create_on_interrupt_callback(processed_event),
             )
+            # Prevents the case where we send a chunk after the output device has been interrupted
             async with self.interrupt_lock:
                 self.output_device.consume_nonblocking(
                     InterruptibleEvent(