diff --git a/ra_aid/console/cowboy_messages.py b/ra_aid/console/cowboy_messages.py
new file mode 100644
index 0000000..e881c72
--- /dev/null
+++ b/ra_aid/console/cowboy_messages.py
@@ -0,0 +1,17 @@
+import random
+
+COWBOY_MESSAGES = [
+    "Yeeehaw! 🤠",
+    "Yippee ki yay motherfucker! 🤠",
+    "Saddle up partner! 🤠",
+    "This ain't my first rodeo! 🤠",
+    "Lock and load, partner! 🤠"
+]
+
+def get_cowboy_message() -> str:
+    """Randomly select and return a cowboy message.
+    
+    Returns:
+        str: A randomly selected cowboy message
+    """
+    return random.choice(COWBOY_MESSAGES)
diff --git a/ra_aid/tools/shell.py b/ra_aid/tools/shell.py
index 2dc8826..7dc3527 100644
--- a/ra_aid/tools/shell.py
+++ b/ra_aid/tools/shell.py
@@ -6,6 +6,7 @@ from rich.prompt import Confirm
 from ra_aid.tools.memory import _global_memory
 from ra_aid.proc.interactive import run_interactive_command
 from ra_aid.text.processing import truncate_output
+from ra_aid.console.cowboy_messages import get_cowboy_message
 
 console = Console()
 
@@ -45,6 +46,9 @@ def run_shell_command(command: str) -> Dict[str, Union[str, int, bool]]:
     # Check if we need approval
     cowboy_mode = _global_memory.get('config', {}).get('cowboy_mode', False)
     
+    if cowboy_mode:
+        console.print(get_cowboy_message())
+    
     if not cowboy_mode:
         if not Confirm.ask("Execute this command?", default=True):
             return {
diff --git a/tests/ra_aid/console/test_cowboy_messages.py b/tests/ra_aid/console/test_cowboy_messages.py
new file mode 100644
index 0000000..cbcf156
--- /dev/null
+++ b/tests/ra_aid/console/test_cowboy_messages.py
@@ -0,0 +1,18 @@
+import pytest
+from ra_aid.console.cowboy_messages import get_cowboy_message, COWBOY_MESSAGES
+
+def test_get_cowboy_message_returns_string():
+    """Test that get_cowboy_message returns a non-empty string"""
+    message = get_cowboy_message()
+    assert isinstance(message, str)
+    assert len(message) > 0
+
+def test_cowboy_message_contains_emoji():
+    """Test that returned message contains the cowboy emoji"""
+    message = get_cowboy_message()
+    assert '🤠' in message
+
+def test_message_from_predefined_list():
+    """Test that returned message is from our predefined list"""
+    message = get_cowboy_message()
+    assert message in COWBOY_MESSAGES
diff --git a/tests/ra_aid/tools/test_shell.py b/tests/ra_aid/tools/test_shell.py
index 231b39b..878fe63 100644
--- a/tests/ra_aid/tools/test_shell.py
+++ b/tests/ra_aid/tools/test_shell.py
@@ -30,6 +30,18 @@ def test_shell_command_cowboy_mode(mock_console, mock_confirm, mock_run_interact
     assert "test output" in result['output']
     mock_confirm.ask.assert_not_called()
 
+def test_shell_command_cowboy_message(mock_console, mock_confirm, mock_run_interactive):
+    """Test that cowboy mode displays a cowboy message"""
+    _global_memory['config'] = {'cowboy_mode': True}
+    
+    with patch('ra_aid.tools.shell.get_cowboy_message') as mock_get_message:
+        mock_get_message.return_value = '🤠 Test cowboy message!'
+        result = run_shell_command("echo test")
+    
+    assert result['success'] is True
+    mock_console.print.assert_any_call('🤠 Test cowboy message!')
+    mock_get_message.assert_called_once()
+
 def test_shell_command_interactive_approved(mock_console, mock_confirm, mock_run_interactive):
     """Test shell command execution with interactive approval"""
     _global_memory['config'] = {'cowboy_mode': False}