diff --git a/pyrit/executor/attack/component/adversarial_conversation_manager.py b/pyrit/executor/attack/component/adversarial_conversation_manager.py
index a8f766ac16..95e1fe0ea7 100644
--- a/pyrit/executor/attack/component/adversarial_conversation_manager.py
+++ b/pyrit/executor/attack/component/adversarial_conversation_manager.py
@@ -13,6 +13,7 @@
 from uuid import uuid4
 
 from pyrit.exceptions import (
+    BadRequestException,
     ComponentRole,
     InvalidJsonException,
     execution_context,
@@ -755,6 +756,7 @@ async def generate_adversarial_reply_async(
             AdversarialReply: ``next_message`` plus the parsed ``rationale`` / ``last_response_summary``.
 
         Raises:
+            BadRequestException: If the adversarial chat returns a blocked or otherwise errored response.
             ValueError: If no response is received from the adversarial chat.
             InvalidJsonException: If the reply is not valid JSON after the retry budget is exhausted.
         """
@@ -831,6 +833,7 @@ async def _send_and_parse_async(
             AdversarialReply: ``next_message`` plus the parsed ``rationale`` / ``last_response_summary``.
 
         Raises:
+            BadRequestException: If the adversarial chat returns a blocked or otherwise errored response.
             ValueError: If no response is received from the adversarial chat.
             InvalidJsonException: If the reply is not valid JSON after the retry budget is exhausted.
         """
@@ -853,6 +856,10 @@ async def _send_and_parse_async(
         schema = self._response_json_schema
 
         def _parse(response: Message) -> AdversarialReply:
+            if response.is_error():
+                raise BadRequestException(
+                    message=f"Adversarial chat returned a blocked or errored response: {response.get_value()}"
+                )
             return _parse_adversarial_reply(response.get_value(), schema=schema)
 
         with execution_context(
diff --git a/tests/unit/executor/attack/component/test_adversarial_conversation_manager.py b/tests/unit/executor/attack/component/test_adversarial_conversation_manager.py
index edddd5c34e..8fb7823eb3 100644
--- a/tests/unit/executor/attack/component/test_adversarial_conversation_manager.py
+++ b/tests/unit/executor/attack/component/test_adversarial_conversation_manager.py
@@ -1,13 +1,14 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
+import json
 import logging
 from types import SimpleNamespace
 from unittest.mock import AsyncMock, MagicMock
 
 import pytest
 
-from pyrit.exceptions import InvalidJsonException
+from pyrit.exceptions import BadRequestException, InvalidJsonException
 from pyrit.executor.attack.component.adversarial_conversation_manager import (
     _BLOCKED_FEEDBACK_TEXT,
     _DEFAULT_ADVERSARIAL_SCHEMA_NAME,
@@ -93,6 +94,18 @@ def _response_message(value: str = "target said hi", *, data_type: str = "text",
     return Message(message_pieces=[piece])
 
 
+def _blocked_adversarial_response(refusal: str = "I cannot assist with that request.") -> Message:
+    payload = json.dumps({"status_code": 200, "message": refusal})
+    piece = MessagePiece(
+        role="assistant",
+        original_value=payload,
+        original_value_data_type="error",
+        response_error="blocked",
+    )
+    piece.mark_as_structured_refusal(refusal=refusal)
+    return Message(message_pieces=[piece])
+
+
 def _seed_message(value: str = "seed prompt") -> Message:
     return Message(message_pieces=[MessagePiece(role="user", original_value=value, original_value_data_type="text")])
 
@@ -549,6 +562,36 @@ async def test_invalid_reply_raises(self):
         with pytest.raises(InvalidJsonException):
             await manager.get_next_message_async(turn_index=1, last_response=_response_message())
 
+    async def test_blocked_reply_does_not_retry_json_parsing(self) -> None:
+        normalizer = _normalizer(None)
+        normalizer.send_prompt_async.return_value = _blocked_adversarial_response()
+        manager = _manager(
+            adversarial_system_prompt=_system_prompt(schema=SCHEMA),
+            prompt_normalizer=normalizer,
+        )
+
+        with pytest.raises(BadRequestException, match="blocked or errored response"):
+            await manager.get_next_message_async(turn_index=1, last_response=_response_message())
+
+        normalizer.send_prompt_async.assert_awaited_once()
+
+    async def test_malformed_non_error_reply_retries_then_succeeds(self) -> None:
+        normalizer = _normalizer(None)
+        normalizer.send_prompt_async.side_effect = [
+            Message.from_prompt(prompt="totally not json", role="assistant"),
+            Message.from_prompt(prompt=VALID_JSON, role="assistant"),
+        ]
+        manager = _manager(
+            adversarial_system_prompt=_system_prompt(schema=SCHEMA),
+            prompt_normalizer=normalizer,
+        )
+
+        turn = await manager.get_next_message_async(turn_index=1, last_response=_response_message())
+
+        assert turn.reply is not None
+        assert turn.reply.next_message == "hello target"
+        assert normalizer.send_prompt_async.call_count == 2
+
     async def test_non_object_reply_retries_then_succeeds(self) -> None:
         normalizer = _normalizer(None)
         normalizer.send_prompt_async.side_effect = [