FIX: Retry adversarial replies with non-object JSON roots

pyrit/executor/attack/component/adversarial_conversation_manager.py

@@ -235,15 +235,20 @@ def _parse_adversarial_reply(response_text: str, *, schema: JsonSchemaDefinition
         AdversarialReply: The parsed message and reasoning fields.
 
     Raises:
-        InvalidJsonException: If the reply is not valid JSON, is missing a required key, carries a
-            key the schema forbids, or omits ``next_message``.
+        InvalidJsonException: If the reply is not valid JSON, does not decode to an object, is
+            missing a required key, carries a key the schema forbids, or omits ``next_message``.
     """
     cleaned = remove_markdown_json(response_text)
     try:
         parsed = json.loads(cleaned)
     except json.JSONDecodeError as e:
         raise InvalidJsonException(message=f"Invalid JSON encountered: {cleaned}") from e
 
+    if not isinstance(parsed, dict):
+        raise InvalidJsonException(
+            message=(f"Adversarial-chat reply must be a JSON object, but decoded to {type(parsed).__name__}: {cleaned}")
+        )
+
     normalized = {_camel_to_snake(key): value for key, value in parsed.items()}
 
     if schema is not None:

tests/unit/executor/attack/component/test_adversarial_conversation_manager.py

@@ -171,6 +171,16 @@ def test_parse_reply_invalid_json_raises():
         _parse_adversarial_reply("not json at all", schema=SCHEMA)
 
 
+@pytest.mark.parametrize(
+    "response_text",
+    ["[]", "null", '"text"', "42"],
+    ids=["array", "null", "string", "number"],
+)
+def test_parse_reply_non_object_json_raises(response_text: str) -> None:
+    with pytest.raises(InvalidJsonException, match="must be a JSON object"):
+        _parse_adversarial_reply(response_text, schema=SCHEMA)
+
+
 def test_parse_reply_missing_key_raises():
     with pytest.raises(InvalidJsonException, match="Missing required keys"):
         _parse_adversarial_reply('{"next_message": "hi", "rationale": "r"}', schema=SCHEMA)
@@ -539,6 +549,23 @@ 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_non_object_reply_retries_then_succeeds(self) -> None:
+        normalizer = _normalizer(None)
+        normalizer.send_prompt_async.side_effect = [
+            Message.from_prompt(prompt="[]", 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
+
 
 # --- get_next_message_async: bypass path -------------------------------------