diff --git a/agent/display.py b/agent/display.py
index cdfc88f46a3..d1460ea46fd 100644
--- a/agent/display.py
+++ b/agent/display.py
@@ -787,33 +787,65 @@ class KawaiiSpinner:
 # Cute tool message (completion line that replaces the spinner)
 # =========================================================================
 
+_ERROR_SUFFIX_MAX_LEN = 48
+
+
+def _trim_error(msg: str) -> str:
+    """Shrink an error message for inline display in a tool status line.
+
+    Strips overly long absolute paths down to just the filename so the
+    suffix stays readable on narrow terminals.
+    """
+    msg = msg.strip()
+    # Common case: "File not found: /very/long/absolute/path/foo.py"
+    if "File not found:" in msg:
+        _, _, tail = msg.partition("File not found:")
+        tail = tail.strip()
+        if "/" in tail:
+            msg = f"File not found: {tail.rsplit('/', 1)[-1]}"
+    if len(msg) > _ERROR_SUFFIX_MAX_LEN:
+        msg = msg[: _ERROR_SUFFIX_MAX_LEN - 3] + "..."
+    return msg
+
+
 def _detect_tool_failure(tool_name: str, result: str | None) -> tuple[bool, str]:
     """Inspect a tool result string for signs of failure.
 
-    Returns ``(is_failure, suffix)`` where *suffix* is an informational tag
-    like ``" [exit 1]"`` for terminal failures, or ``" [error]"`` for generic
-    failures.  On success, returns ``(False, "")``.
+    Returns ``(is_failure, suffix)`` where *suffix* is a short informational
+    tag like ``" [exit 1]"`` for terminal failures, ``" [full]"`` for memory
+    overflow, or a trimmed error message (``" [File not found: foo.py]"``).
+    On success returns ``(False, "")``.
     """
     if result is None:
         return False, ""
     if file_mutation_result_landed(tool_name, result):
         return False, ""
 
+    data = safe_json_loads(result)
+
+    # Terminal: non-zero exit code is the canonical failure signal.
     if tool_name == "terminal":
-        data = safe_json_loads(result)
         if isinstance(data, dict):
             exit_code = data.get("exit_code")
             if exit_code is not None and exit_code != 0:
+                err_msg = data.get("error")
+                if err_msg:
+                    return True, f" [{_trim_error(str(err_msg))}]"
                 return True, f" [exit {exit_code}]"
         return False, ""
 
-    # Memory-specific: distinguish "full" from real errors
+    # Memory: distinguish "store full" from real errors.
     if tool_name == "memory":
-        data = safe_json_loads(result)
         if isinstance(data, dict):
             if data.get("success") is False and "exceed the limit" in data.get("error", ""):
                 return True, " [full]"
 
+    # Structured error in JSON result (any tool that surfaces {"error": ...}).
+    if isinstance(data, dict):
+        err = data.get("error") or data.get("message")
+        if err and (data.get("success") is False or "error" in data):
+            return True, f" [{_trim_error(str(err))}]"
+
     # Generic heuristic for non-terminal tools
     # Multimodal tool results (dicts with _multimodal=True) are not strings —
     # treat them as successes since failures would be JSON-encoded strings.
diff --git a/agent/tool_executor.py b/agent/tool_executor.py
index e350994b4dc..438a6337074 100644
--- a/agent/tool_executor.py
+++ b/agent/tool_executor.py
@@ -388,6 +388,7 @@ def execute_tool_calls_concurrent(agent, assistant_message, messages: list, effe
                     agent.tool_progress_callback(
                         "tool.completed", function_name, None, None,
                         duration=tool_duration, is_error=is_error,
+                        result=function_result,
                     )
                 except Exception as cb_err:
                     logging.debug(f"Tool progress callback error: {cb_err}")
@@ -822,6 +823,7 @@ def execute_tool_calls_sequential(agent, assistant_message, messages: list, effe
                 agent.tool_progress_callback(
                     "tool.completed", function_name, None, None,
                     duration=tool_duration, is_error=_is_error_result,
+                    result=function_result,
                 )
             except Exception as cb_err:
                 logging.debug(f"Tool progress callback error: {cb_err}")
diff --git a/cli.py b/cli.py
index e20472c7623..53bf7bf5dea 100644
--- a/cli.py
+++ b/cli.py
@@ -10264,9 +10264,7 @@ class HermesCLI:
                 self._last_scrollback_tool = function_name
                 try:
                     from agent.display import get_cute_tool_message
-                    line = get_cute_tool_message(function_name, stored_args, duration)
-                    if is_error:
-                        line = f"{line} [error]"
+                    line = get_cute_tool_message(function_name, stored_args, duration, result=kwargs.get("result"))
                     _cprint(f"  {line}")
                 except Exception:
                     pass