[python] PoC: AI Guard test under INTEGRATION_FRAMEWORKS

manifests/java.yml

@@ -3273,6 +3273,7 @@ manifest:
         "*": irrelevant
         spring-boot: v1.63.0
   tests/integration_frameworks/llm/anthropic/test_anthropic_llmobs.py::TestAnthropicLlmObsMessages::test_create_error: bug (MLOB-1234)
+  tests/integration_frameworks/llm/openai/test_openai_ai_guard.py: missing_feature (APPSEC-68977, AI Guard/OpenAI integration not yet wired into INTEGRATION_FRAMEWORKS)
   tests/integration_frameworks/llm/openai/test_openai_apm.py: v1.61.0
   tests/integration_frameworks/llm/openai/test_openai_llmobs.py: v1.61.0
   tests/integrations/crossed_integrations/test_kafka.py::Test_Kafka:

manifests/nodejs.yml

@@ -1748,6 +1748,7 @@ manifest:
   : bug (MLOB-5070)
   ? tests/integration_frameworks/llm/google_genai/test_google_genai_llmobs.py::TestGoogleGenAiGenerateContentWithTools::test_generate_content_with_tools
   : missing_feature (Node.js LLM Observability Google GenAI integration does not submit tool definitions)
+  tests/integration_frameworks/llm/openai/test_openai_ai_guard.py::TestOpenAiAiGuard: missing_feature (APPSEC-68977, AI Guard/OpenAI integration not yet wired into INTEGRATION_FRAMEWORKS)
   tests/integration_frameworks/llm/openai/test_openai_apm.py::TestOpenAiApmChatCompletions: *ref_5_76_0
   tests/integration_frameworks/llm/openai/test_openai_apm.py::TestOpenAiApmCompletions: *ref_5_76_0
   tests/integration_frameworks/llm/openai/test_openai_apm.py::TestOpenAiApmEmbeddings: *ref_5_76_0

manifests/python.yml

@@ -1362,6 +1362,7 @@ manifest:
   tests/integration_frameworks/llm/google_genai/test_google_genai_llmobs.py::TestGoogleGenAiGenerateContentWithTools: v3.13.0
   ? tests/integration_frameworks/llm/google_genai/test_google_genai_llmobs.py::TestGoogleGenAiGenerateContentWithTools::test_generate_content_with_tools
   : bug (MLOB-5071)
+  tests/integration_frameworks/llm/openai/test_openai_ai_guard.py::TestOpenAiAiGuard: v4.10.0
   tests/integration_frameworks/llm/openai/test_openai_apm.py::TestOpenAiApmChatCompletions: v3.13.0
   tests/integration_frameworks/llm/openai/test_openai_apm.py::TestOpenAiApmCompletions: v3.13.0
   tests/integration_frameworks/llm/openai/test_openai_apm.py::TestOpenAiApmEmbeddings: v3.13.0

tests/integration_frameworks/llm/openai/test_openai_ai_guard.py

@@ -0,0 +1,118 @@
+"""AI Guard <-> OpenAI integration tests, run under the INTEGRATION_FRAMEWORKS scenario.
+
+Investigation task: https://datadoghq.atlassian.net/browse/APPSEC-68977
+
+Unlike ``tests/ai_guard/test_ai_guard_sdk.py`` (which drives the AI Guard SDK directly via
+``/ai_guard/evaluate``), this suite exercises the *integration* between AI Guard and the
+OpenAI client, the same way the LLM Observability suite does: it calls the OpenAI SDK
+directly through the existing weblog endpoints (``/chat/completions``). When
+``DD_AI_GUARD_ENABLED=true``, ``ai_guard_listen()`` auto-wires into the OpenAI SDK, so AI
+Guard evaluates the call at three points with no manual ``evaluate()`` call:
+
+- **before-model**: the request/prompt is evaluated before the model is called;
+- **after-model**: the model response is evaluated (streamed responses require
+  ``DD_AI_GUARD_ANALYZE_STREAM_RESPONSES_ENABLED=true``, which buffers and reconstructs
+  the response before running the evaluation);
+- **tool-call**: tool calls produced by the model are evaluated.
+
+We assert only that the integration wires each evaluation point and emits an ``ai_guard``
+span attached to the OpenAI trace. The evaluation *outcome* (ALLOW / DENY / ABORT) is
+already covered by the ``AI_GUARD`` scenario and is intentionally not re-asserted here.
+"""
+
+import os
+
+import pytest
+
+from utils import features, scenarios
+from utils.docker_fixtures import FrameworkTestClientApi, TestAgentAPI
+
+from .utils import TOOLS, BaseOpenaiTest
+
+
+@pytest.fixture
+def library_env(request: pytest.FixtureRequest) -> dict[str, str]:
+    env = {
+        "DD_AI_GUARD_ENABLED": "true",
+        # after-model evaluation of streamed responses is opt-in
+        "DD_AI_GUARD_ANALYZE_STREAM_RESPONSES_ENABLED": "true",
+    }
+    # The AI Guard client needs an API key + app key. Real keys are required when recording
+    # cassettes (the client calls the real AI Guard API); mock keys are fine on replay since
+    # the VCR proxy matches on the request, not on auth.
+    if request.config.option.generate_cassettes:
+        env["DD_API_KEY"] = os.environ["DD_API_KEY"]
+        env["DD_APP_KEY"] = os.environ["DD_APP_KEY"]
+    else:
+        env["DD_API_KEY"] = "mock_api_key"
+        env["DD_APP_KEY"] = "mock_app_key"
+    return env
+
+
+def _ai_guard_spans(traces: list[list[dict]]) -> list[dict]:
+    return [span for trace in traces for span in trace if span.get("resource") == "ai_guard"]
+
+
+@features.ai_guard
+@scenarios.integration_frameworks
+class TestOpenAiAiGuard(BaseOpenaiTest):
+    """AI Guard evaluation triggered through the auto-instrumented OpenAI integration."""
+
+    def test_before_model_validation(self, test_agent: TestAgentAPI, test_client: FrameworkTestClientApi):
+        """The prompt is evaluated by AI Guard before the OpenAI model is called."""
+        with test_agent.vcr_context():
+            test_client.request(
+                "POST",
+                "/chat/completions",
+                dict(
+                    model="gpt-4o-mini",
+                    messages=[{"role": "user", "content": "What is the weather like today?"}],
+                    parameters=dict(max_tokens=35),
+                ),
+            )
+
+        guard_spans = _ai_guard_spans(test_agent.wait_for_num_traces(num=1))
+        assert guard_spans, "expected an ai_guard span from the before-model evaluation"
+        assert any(span["meta"].get("ai_guard.target") == "prompt" for span in guard_spans), (
+            "expected a before-model ai_guard span with target 'prompt'"
+        )
+
+    def test_after_model_validation(self, test_agent: TestAgentAPI, test_client: FrameworkTestClientApi):
+        """The streamed model response is evaluated by AI Guard after the model returns."""
+        with test_agent.vcr_context(stream=True):
+            test_client.request(
+                "POST",
+                "/chat/completions",
+                dict(
+                    model="gpt-4o-mini",
+                    messages=[{"role": "user", "content": "Tell me a short story about a robot."}],
+                    parameters=dict(max_tokens=35, stream=True),
+                ),
+            )
+
+        guard_spans = _ai_guard_spans(test_agent.wait_for_num_traces(num=1))
+        assert guard_spans, "expected an ai_guard span from the after-model (streamed) evaluation"
+
+    def test_tool_call_validation(self, test_agent: TestAgentAPI, test_client: FrameworkTestClientApi):
+        """Tool calls produced by the model are evaluated by AI Guard."""
+        with test_agent.vcr_context():
+            test_client.request(
+                "POST",
+                "/chat/completions",
+                dict(
+                    model="gpt-4o-mini",
+                    messages=[
+                        {
+                            "role": "user",
+                            "content": "Bob is a student at Stanford University. He is studying computer science.",
+                        }
+                    ],
+                    parameters=dict(tool_choice="auto", tools=TOOLS),
+                ),
+            )
+
+        guard_spans = _ai_guard_spans(test_agent.wait_for_num_traces(num=1))
+        assert guard_spans, "expected an ai_guard span from the tool-call evaluation"
+        assert any(span["meta"].get("ai_guard.target") == "tool" for span in guard_spans), (
+            "expected a tool-call ai_guard span with target 'tool'"
+        )

tests/integration_frameworks/utils/vcr-cassettes/aiguard/test_after_model_validation_stream_True_aiguard_evaluate_post_5dec5d6a.json

@@ -0,0 +1,38 @@
+{
+  "request": {
+    "method": "POST",
+    "url": "https://app.datadoghq.com/api/v2/ai-guard/evaluate",
+    "headers": {
+      "Accept-Encoding": "identity",
+      "Content-Length": "153",
+      "Content-Type": "application/json",
+      "DD-AI-GUARD-VERSION": "4.10.6",
+      "DD-AI-GUARD-SOURCE": "SDK",
+      "DD-AI-GUARD-LANGUAGE": "python",
+      "Datadog-Entity-ID": "in-115544"
+    },
+    "body": "{\"data\": {\"attributes\": {\"messages\": [{\"role\": \"user\", \"content\": \"Tell me a short story about a robot.\"}], \"meta\": {\"service\": \"openai\", \"env\": null}}}}"
+  },
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+    },
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+  }
+}

tests/integration_frameworks/utils/vcr-cassettes/aiguard/test_before_model_validation_aiguard_evaluate_post_ca44130a.json

@@ -0,0 +1,38 @@
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+  }
+}

tests/integration_frameworks/utils/vcr-cassettes/aiguard/test_before_model_validation_aiguard_evaluate_post_d13cc790.json

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+}

tests/integration_frameworks/utils/vcr-cassettes/aiguard/test_tool_call_validation_aiguard_evaluate_post_9e556a11.json

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+  }
+}

tests/integration_frameworks/utils/vcr-cassettes/aiguard/test_tool_call_validation_aiguard_evaluate_post_a304603c.json

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+}