diff --git a/src/cleveragents/cli.py b/src/cleveragents/cli.py
index 91089ff51..00fa8ffaa 100644
--- a/src/cleveragents/cli.py
+++ b/src/cleveragents/cli.py
@@ -87,9 +87,40 @@ def run(
         sys.exit(1)
 
     if output:
-        with output.open("w") as f:
-            f.write(result)
-        click.echo(f"Output written to {output}")
+        # Validate and safely write output file
+        try:
+            output_path = output.resolve()
+
+            # Block system directories
+            system_dirs = ['/etc', '/sys', '/proc', '/dev', '/boot', '/root']
+            for sys_dir in system_dirs:
+                if str(output_path).startswith(sys_dir):
+                    click.echo(
+                        f"Error: Cannot write to system directory: {sys_dir}",
+                        err=True
+                    )
+                    sys.exit(1)
+
+            # Confirm overwrite if file exists
+            if output_path.exists():
+                if not click.confirm(
+                    f"File '{output_path}' already exists. Overwrite?",
+                    default=False
+                ):
+                    click.echo("Cancelled.")
+                    sys.exit(0)
+
+            # Create parent directory if needed
+            output_path.parent.mkdir(parents=True, exist_ok=True)
+
+            # Write file
+            with output.open("w") as f:
+                f.write(result)
+            click.echo(f"Output written to {output}")
+
+        except Exception as e:
+            click.echo(f"Error writing output file: {e}", err=True)
+            sys.exit(1)
     else:
         click.echo(result)
 
diff --git a/tests/unit/test_cli.py b/tests/unit/test_cli.py
index c16303f1f..94323289d 100644
--- a/tests/unit/test_cli.py
+++ b/tests/unit/test_cli.py
@@ -4,9 +4,10 @@ Unit tests for cli.py module
 Tests the command-line interface for CleverAgents.
 """
 
+import os
 import pytest
 from pathlib import Path
-from unittest.mock import Mock, patch, AsyncMock, MagicMock
+from unittest.mock import Mock, patch
 from click.testing import CliRunner
 import tempfile
 
@@ -157,8 +158,8 @@ class TestRunCommand:
         mock_app_class.return_value = mock_app
         mock_asyncio_run.return_value = "Test result"
 
-        with tempfile.NamedTemporaryFile(mode='w', prefix='cleveragent_', delete=False) as output_file:
-            output_path = Path(output_file.name)
+        # Generate path to a non-existent file to avoid overwrite confirmation prompt
+        output_path = Path(tempfile.gettempdir()) / f'cleveragent_test_{os.getpid()}_{id(self)}.txt'
 
         try:
             result = runner.invoke(run, [