diff --git a/py/src/braintrust/wrappers/pydantic_ai.py b/py/src/braintrust/wrappers/pydantic_ai.py
index c932c91a..9ed61462 100644
--- a/py/src/braintrust/wrappers/pydantic_ai.py
+++ b/py/src/braintrust/wrappers/pydantic_ai.py
@@ -127,6 +127,26 @@ def agent_run_sync_wrapper(wrapped: Any, instance: Any, args: Any, kwargs: Any):
 
     wrap_function_wrapper(Agent, "run_sync", agent_run_sync_wrapper)
 
+    def agent_to_cli_sync_wrapper(wrapped: Any, instance: Any, args: Any, kwargs: Any):
+        _ensure_model_wrapped(instance)
+        input_data, metadata = _build_agent_input_and_metadata(args, kwargs, instance)
+
+        with start_span(
+            name=f"agent_to_cli_sync [{instance.name}]"
+            if hasattr(instance, "name") and instance.name
+            else "agent_to_cli_sync",
+            type=SpanTypeAttribute.LLM,
+            input=input_data if input_data else None,
+            metadata=metadata,
+        ) as agent_span:
+            start_time = time.time()
+            result = wrapped(*args, **kwargs)
+            end_time = time.time()
+            agent_span.log(metrics={"start": start_time, "end": end_time, "duration": end_time - start_time})
+            return result
+
+    wrap_function_wrapper(Agent, "to_cli_sync", agent_to_cli_sync_wrapper)
+
     def agent_run_stream_wrapper(wrapped: Any, instance: Any, args: Any, kwargs: Any):
         _ensure_model_wrapped(instance)
         input_data, metadata = _build_agent_input_and_metadata(args, kwargs, instance)
diff --git a/py/src/braintrust/wrappers/test_pydantic_ai_integration.py b/py/src/braintrust/wrappers/test_pydantic_ai_integration.py
index 4a6ad2ae..14088f74 100644
--- a/py/src/braintrust/wrappers/test_pydantic_ai_integration.py
+++ b/py/src/braintrust/wrappers/test_pydantic_ai_integration.py
@@ -3,6 +3,7 @@
 # pyright: reportUnknownParameterType=false
 # pyright: reportPrivateUsage=false
 import asyncio
+import inspect
 import time
 
 import pytest
@@ -13,6 +14,7 @@
 from pydantic import BaseModel
 from pydantic_ai import Agent, ModelSettings
 from pydantic_ai.messages import ModelRequest, UserPromptPart
+from pydantic_ai.usage import UsageLimits
 
 PROJECT_NAME = "test-pydantic-ai-integration"
 MODEL = "openai:gpt-4o-mini"  # Use cheaper model for tests
@@ -168,6 +170,71 @@ def is_descendant(child_span, ancestor_id):
     assert "completion_tokens" in agent_sync_span["metrics"]
 
 
+def test_agent_to_cli_sync(memory_logger, monkeypatch):
+    """Test Agent.to_cli_sync() records a CLI session span."""
+    assert not memory_logger.pop()
+
+    cli_signature = inspect.signature(Agent.to_cli_sync)
+    message_history = [ModelRequest(parts=[UserPromptPart(content="Previous question")])]
+    agent = Agent(MODEL, name="cli-agent", model_settings=ModelSettings(max_tokens=50))
+    captured = {}
+
+    async def fake_run_chat(
+        *,
+        stream,
+        agent,
+        deps,
+        console,
+        code_theme,
+        prog_name,
+        message_history,
+        model_settings=None,
+        usage_limits=None,
+    ):
+        assert stream is True
+        assert prog_name == "braintrust-cli"
+        assert message_history is not None
+        captured["model_settings"] = model_settings
+        captured["usage_limits"] = usage_limits
+        return 0
+
+    monkeypatch.setattr("pydantic_ai._cli.run_chat", fake_run_chat)
+
+    cli_kwargs = {
+        "prog_name": "braintrust-cli",
+        "message_history": message_history,
+    }
+    # pydantic_ai 1.10.0 exposes a smaller to_cli_sync API; newer versions add
+    # model_settings and usage_limits, so assert those fields only when present.
+    if "model_settings" in cli_signature.parameters:
+        cli_kwargs["model_settings"] = ModelSettings(max_tokens=20, temperature=0.2)
+    if "usage_limits" in cli_signature.parameters:
+        cli_kwargs["usage_limits"] = UsageLimits(request_limit=3)
+
+    start = time.time()
+    agent.to_cli_sync(**cli_kwargs)
+    end = time.time()
+
+    spans = memory_logger.pop()
+    assert len(spans) == 1, f"Expected 1 CLI span, got {len(spans)}"
+
+    cli_span = spans[0]
+    assert cli_span["span_attributes"]["type"] == SpanTypeAttribute.LLM
+    assert cli_span["span_attributes"]["name"] == "agent_to_cli_sync [cli-agent]"
+    assert cli_span["metadata"]["model"] == "gpt-4o-mini"
+    assert cli_span["metadata"]["provider"] == "openai"
+    assert cli_span["input"]["prog_name"] == "braintrust-cli"
+    assert "message_history" in cli_span["input"]
+    if "model_settings" in cli_signature.parameters:
+        assert captured["model_settings"] is not None
+        assert cli_span["input"]["model_settings"]["max_tokens"] == 20
+        assert cli_span["input"]["model_settings"]["temperature"] == 0.2
+    if "usage_limits" in cli_signature.parameters:
+        assert captured["usage_limits"] is not None
+        assert cli_span["input"]["usage_limits"]["request_limit"] == 3
+    _assert_metrics_are_valid(cli_span["metrics"], start, end)
+
+
 @pytest.mark.vcr
 @pytest.mark.asyncio
 async def test_multiple_identical_sequential_streams(memory_logger):