diff --git a/lelab/rollout.py b/lelab/rollout.py
index bdffdf1..5e2b013 100644
--- a/lelab/rollout.py
+++ b/lelab/rollout.py
@@ -153,6 +153,84 @@ def _format_cameras_arg(cameras: dict[str, dict[str, Any]]) -> str:
     return "{" + ", ".join(parts) + "}"
 
 
+# Exception lines at the tail of a Python traceback look like
+# "RuntimeError: ..." or "lerobot.errors.DeviceNotConnectedError: ...".
+_EXC_LINE_RE = re.compile(r"^[A-Za-z_][\w.]*(?:Error|Exception|Interrupt|Timeout|Failure)\b")
+
+
+def _extract_error_from_log(log_path: str | None) -> str | None:
+    """Pull the meaningful error out of a failed rollout's log so the UI can
+    show it directly instead of telling the user to open a file in the cache."""
+    if not log_path:
+        return None
+    try:
+        with open(log_path, encoding="utf-8", errors="replace") as fh:
+            lines = fh.readlines()
+    except OSError:
+        return None
+    tail = [ln.rstrip("\n") for ln in lines[-50:]]
+    # Prefer the last exception line + everything after it (the message body).
+    exc_idx = next((i for i in range(len(tail) - 1, -1, -1) if _EXC_LINE_RE.match(tail[i])), None)
+    if exc_idx is not None:
+        snippet = "\n".join(tail[exc_idx:]).strip()
+    else:
+        non_empty = [ln for ln in tail if ln.strip()]
+        snippet = "\n".join(non_empty[-6:]).strip()
+    snippet = re.sub(r"\n\s*\n+", "\n", snippet)
+    if len(snippet) > 500:
+        snippet = snippet[:500].rstrip() + "…"
+    return snippet or None
+
+
+def _friendly_hint(error_text: str | None) -> str | None:
+    """A plain-language, actionable headline for the common SO-101 failures."""
+    if not error_text:
+        return None
+    low = error_text.lower()
+    if "overload" in low or "torque_enable" in low:
+        return (
+            "A motor overloaded — usually the gripper holding an object too hard. Release the object / "
+            "open the gripper and power-cycle the arm before trying again."
+        )
+    if "missing motor ids" in low or "motor check failed" in low:
+        return (
+            "A follower motor isn't responding (often the gripper, id 6). If a skill was holding an object "
+            "it likely overloaded — remove it, power-cycle the arm, then try teleoperation first."
+        )
+    if "could not connect" in low or "failed to connect" in low or "not connected" in low:
+        return "Couldn't connect to the arm — make sure it's plugged in, powered on, and on the right port."
+    if "frame is too old" in low or "no frame" in low or "frame timeout" in low:
+        return (
+            "A camera can't keep up — frames are arriving too slowly. Lower its resolution/FPS, "
+            "set FOURCC=MJPG, and close other heavy apps, then try again."
+        )
+    if "failed to set capture_" in low or "actual_width" in low or "actual_height" in low:
+        return "A camera doesn't support the configured resolution — open camera settings and click Auto."
+    if "permission" in low and ("port" in low or "com" in low):
+        return "Couldn't open the serial port — close anything else using it, or run `lelab --stop`."
+    return None
+
+
+# Errors that mean the policy actually ran and only shutdown/cleanup tripped —
+# e.g. disabling torque on a gripper still holding an object.
+_CLEANUP_MARKERS = ("overload", "torque_enable", "disconnect", "not connected")
+
+
+def _classify_outcome(rc: int | None, rollout_started: bool, error_text: str | None) -> str:
+    """ok | ran_with_warning | failed.
+
+    A non-zero exit *after* the rollout main loop started, where the error is a
+    torque-disable/overload on shutdown, means the skill ran but a motor (usually
+    the loaded gripper) complained during cleanup — that's a warning, not a
+    failure, so the UI shouldn't call a working run "failed"."""
+    if not rc:
+        return "ok"
+    low = (error_text or "").lower()
+    if rollout_started and any(marker in low for marker in _CLEANUP_MARKERS):
+        return "ran_with_warning"
+    return "failed"
+
+
 def handle_start_inference(request: InferenceRequest) -> dict[str, Any]:
     """Start a one-shot rollout subprocess. Returns a dict — the route
     layer turns it into a JSON response or HTTPException as appropriate."""
@@ -308,10 +386,17 @@ def handle_inference_status() -> dict[str, Any]:
             _inference_started_at = None
             _inference_rollout_started_at = None
             _inference_meta = {}
+            # On failure, surface the real error from the log so the UI doesn't
+            # have to send the user digging through the cache.
+            error = _extract_error_from_log(finished_meta.get("log_path")) if rc else None
+            outcome = _classify_outcome(rc, finished_rollout_started is not None, error)
             return {
                 "inference_active": False,
                 "exited": True,
                 "exit_code": rc,
+                "outcome": outcome,
+                "error": error,
+                "hint": _friendly_hint(error),
                 "policy_ref": finished_meta.get("policy_ref"),
                 "duration_s": finished_meta.get("duration_s"),
                 "log_path": finished_meta.get("log_path"),
diff --git a/tests/test_rollout.py b/tests/test_rollout.py
index 3a061d0..224e465 100644
--- a/tests/test_rollout.py
+++ b/tests/test_rollout.py
@@ -261,3 +261,43 @@ def test_handle_start_inference_blocked_when_already_active(monkeypatch) -> None
     assert result["success"] is False
     assert result["status_code"] == 409
     assert "already active" in result["message"]
+
+
+def test_classify_outcome_ok_warns_and_fails() -> None:
+    from lelab.rollout import _classify_outcome
+
+    # rc 0/None => the run was fine.
+    assert _classify_outcome(0, True, "overload") == "ok"
+    assert _classify_outcome(None, True, None) == "ok"
+    # Non-zero AFTER the rollout started, with a torque-disable/overload on
+    # shutdown => the skill ran; only cleanup tripped.
+    assert _classify_outcome(1, True, "Motor 6 overload, torque_enable failed") == "ran_with_warning"
+    # Never started, or an unrelated error => a real failure.
+    assert _classify_outcome(1, False, "overload") == "failed"
+    assert _classify_outcome(1, True, "could not connect to the arm") == "failed"
+
+
+def test_friendly_hint_maps_common_failures() -> None:
+    from lelab.rollout import _friendly_hint
+
+    assert "gripper" in (_friendly_hint("Motor overload detected") or "").lower()
+    assert "connect" in (_friendly_hint("Failed to connect to the follower") or "").lower()
+    assert _friendly_hint("some unrecognised traceback") is None
+    assert _friendly_hint(None) is None
+
+
+def test_extract_error_from_log_pulls_exception_tail(tmp_path) -> None:
+    from lelab.rollout import _extract_error_from_log
+
+    log = tmp_path / "rollout.log"
+    log.write_text(
+        "INFO starting rollout\n"
+        "Traceback (most recent call last):\n"
+        '  File "x.py", line 1\n'
+        "RuntimeError: gripper overload during shutdown\n",
+        encoding="utf-8",
+    )
+    out = _extract_error_from_log(str(log))
+    assert out is not None and "RuntimeError: gripper overload during shutdown" in out
+    assert _extract_error_from_log(None) is None
+    assert _extract_error_from_log(str(tmp_path / "missing.log")) is None