diff --git a/lelab/rollout.py b/lelab/rollout.py
index cfff79a8..0b34f31e 100644
--- a/lelab/rollout.py
+++ b/lelab/rollout.py
@@ -266,6 +266,11 @@ def handle_start_inference(request: InferenceRequest) -> dict[str, Any]:
         # Claim the slot now so a concurrent caller losing the race sees us.
         inference_active = True
 
+    # Opened partway through setup; the stdout pump thread takes ownership once
+    # it starts. Tracked here so a failure before that hand-off can close it
+    # instead of leaking the file handle (which on Windows also keeps the log
+    # locked).
+    log_handle = None
     try:
         # `setup_follower_calibration_file` returns the basename without the
         # .json extension. We need that stripped form for `--robot.id`,
@@ -323,9 +328,14 @@ def handle_start_inference(request: InferenceRequest) -> dict[str, Any]:
             name="inference-stdout-pump",
             daemon=True,
         ).start()
+        log_handle = None  # pump thread owns and closes it from here on
     except Exception as exc:
         logger.exception("Failed to start inference")
-        # Subprocess never started — release the slot.
+        # Startup failed before the pump thread took over (most often Popen
+        # itself). Release the slot and close the log file if we opened it before
+        # failing, so the handle isn't leaked.
+        if log_handle is not None:
+            log_handle.close()
         with _state_lock:
             inference_active = False
         return {"success": False, "status_code": 500, "message": f"Failed to start inference: {exc}"}
diff --git a/tests/test_rollout.py b/tests/test_rollout.py
index c0bb1f3d..5e445b70 100644
--- a/tests/test_rollout.py
+++ b/tests/test_rollout.py
@@ -263,6 +263,38 @@ def test_handle_start_inference_blocked_when_already_active(monkeypatch) -> None
     assert "already active" in result["message"]
 
 
+def test_handle_start_inference_closes_log_when_popen_fails(monkeypatch, tmp_path) -> None:
+    """If Popen fails after the log file is opened, the handle must be closed,
+    not leaked — on Windows a leaked handle also keeps the log file locked."""
+    from lelab import rollout
+
+    monkeypatch.setattr(rollout, "setup_follower_calibration_file", lambda cfg: "robot_a")
+    monkeypatch.setattr(rollout, "_resolve_policy_path", lambda ref: str(tmp_path / "model"))
+
+    opened: list = []
+    real_open = rollout.Path.open
+
+    def tracking_open(self, *args, **kwargs):
+        handle = real_open(self, *args, **kwargs)
+        opened.append(handle)
+        return handle
+
+    monkeypatch.setattr(rollout.Path, "open", tracking_open)
+
+    def boom(*args, **kwargs):
+        raise OSError("simulated Popen failure")
+
+    monkeypatch.setattr(rollout.subprocess, "Popen", boom)
+
+    result = rollout.handle_start_inference(_stub_request())
+
+    assert result["success"] is False
+    assert result["status_code"] == 500
+    assert opened, "expected the inference log file to have been opened"
+    assert all(handle.closed for handle in opened), "log handle leaked on Popen failure"
+    assert rollout.inference_active is False
+
+
 def test_classify_outcome_ok_warns_and_fails() -> None:
     from lelab.rollout import _classify_outcome