diff --git a/gptme/message.py b/gptme/message.py
index 48b7db081..9b0bddf7c 100644
--- a/gptme/message.py
+++ b/gptme/message.py
@@ -211,6 +211,15 @@ def format_msgs(
         if highlight:
             color = ROLE_COLOR[msg.role]
             userprefix = f"[bold {color}]{userprefix}[/bold {color}]"
+        if msg.role == "system":
+            first_line = msg.content.split("\n", 1)[0].lower()
+            isSuccess = first_line.startswith(("saved", "appended", "patch successfully", "ran"))
+            isError = first_line.startswith(("error", "failed"))
+            if isSuccess:
+                userprefix = f"{userprefix} ✅"
+            elif isError:
+                userprefix = f"{userprefix} ❌"
+                
         # get terminal width
         max_len = shutil.get_terminal_size().columns - len(userprefix)
         output = ""
diff --git a/gptme/tools/patch.py b/gptme/tools/patch.py
index 15febd0de..25c3094fd 100644
--- a/gptme/tools/patch.py
+++ b/gptme/tools/patch.py
@@ -257,7 +257,7 @@ def execute_patch(
         code = kwargs.get("patch", code)
 
     if not code:
-        yield Message("system", "No patch provided by the assistant")
+        yield Message("system", "Error: No patch provided by the assistant")
         return
 
     yield from execute_with_confirmation(
diff --git a/gptme/tools/shell.py b/gptme/tools/shell.py
index e8043b90f..a94599fb2 100644
--- a/gptme/tools/shell.py
+++ b/gptme/tools/shell.py
@@ -289,13 +289,15 @@ def execute_shell_impl(
 
     stdout = _shorten_stdout(stdout.strip(), pre_tokens=2000, post_tokens=8000)
     stderr = _shorten_stdout(stderr.strip(), pre_tokens=2000, post_tokens=2000)
-
     msg = (
-        _format_block_smart(
-            f"Ran {'allowlisted ' if allowlisted else ''}command", cmd, lang="bash"
-        )
-        + "\n\n"
+    _format_block_smart(
+        f"{'Failed to run' if returncode else 'Ran'} "
+        f"{'allowlisted ' if allowlisted else ''}command",
+        cmd,
+        lang="bash"
     )
+    + "\n\n"
+)
     if stdout:
         msg += _format_block_smart("", stdout, "stdout") + "\n\n"
     if stderr:
diff --git a/gptme/tools/tmux.py b/gptme/tools/tmux.py
index 5b0699913..75e6142cd 100644
--- a/gptme/tools/tmux.py
+++ b/gptme/tools/tmux.py
@@ -223,7 +223,7 @@ def execute_tmux(
             continue
 
         if len(parts) < 2:
-            yield Message("system", f"Missing arguments for command: {command}")
+            yield Message("system", f"Error: Missing arguments for command: {command}")
             continue
 
         _args = parts[1]
@@ -237,7 +237,7 @@ def execute_tmux(
         elif command == "kill_session":
             yield kill_session(_args)
         else:
-            yield Message("system", f"Unknown command: {command}")
+            yield Message("system", f"Error: Unknown command: {command}")
 
 
 instructions = """