diff --git a/openhands/cli/main.py b/openhands/cli/main.py
index d8c07ef63d..7247ce9ad7 100644
--- a/openhands/cli/main.py
+++ b/openhands/cli/main.py
@@ -77,7 +77,6 @@ async def cleanup_session(
     controller: AgentController,
 ) -> None:
     """Clean up all resources from the current session."""
-
     event_stream = runtime.event_stream
     end_state = controller.get_state()
     end_state.save_to_session(
@@ -434,7 +433,23 @@ async def main_with_loop(loop: asyncio.AbstractEventLoop) -> None:
         return
 
     # Read task from file, CLI args, or stdin
-    task_str = read_task(args, config.cli_multiline_input)
+    if args.file:
+        # For CLI usage, we want to enhance the file content with a prompt
+        # that instructs the agent to read and understand the file first
+        with open(args.file, 'r', encoding='utf-8') as file:
+            file_content = file.read()
+
+        # Create a prompt that instructs the agent to read and understand the file first
+        task_str = f"""The user has tagged a file '{args.file}'.
+Please read and understand the following file content first:
+
+```
+{file_content}
+```
+
+After reviewing the file, please ask the user what they would like to do with it."""
+    else:
+        task_str = read_task(args, config.cli_multiline_input)
 
     # Run the first session
     new_session_requested = await run_session(
diff --git a/tests/unit/test_cli.py b/tests/unit/test_cli.py
index 7013a90b4b..4355ecc331 100644
--- a/tests/unit/test_cli.py
+++ b/tests/unit/test_cli.py
@@ -345,6 +345,7 @@ async def test_main_without_task(
     mock_args.agent_cls = None
     mock_args.llm_config = None
     mock_args.name = None
+    mock_args.file = None
     mock_parse_args.return_value = mock_args
 
     # Mock config
@@ -427,6 +428,7 @@ async def test_main_with_task(
     mock_args = MagicMock()
     mock_args.agent_cls = 'custom-agent'
     mock_args.llm_config = 'custom-config'
+    mock_args.file = None
     mock_parse_args.return_value = mock_args
 
     # Mock config
@@ -523,6 +525,7 @@ async def test_main_with_session_name_passes_name_to_run_session(
     mock_args.agent_cls = None
     mock_args.llm_config = None
     mock_args.name = test_session_name  # Set the session name
+    mock_args.file = None
     mock_parse_args.return_value = mock_args
 
     # Mock config
@@ -831,3 +834,93 @@ async def test_config_loading_order(
 
     # Verify that run_session was called with the correct arguments
     mock_run_session.assert_called_once()
+
+
+@pytest.mark.asyncio
+@patch('openhands.cli.main.parse_arguments')
+@patch('openhands.cli.main.setup_config_from_args')
+@patch('openhands.cli.main.FileSettingsStore.get_instance')
+@patch('openhands.cli.main.check_folder_security_agreement')
+@patch('openhands.cli.main.run_session')
+@patch('openhands.cli.main.LLMSummarizingCondenserConfig')
+@patch('openhands.cli.main.NoOpCondenserConfig')
+@patch('builtins.open', new_callable=MagicMock)
+async def test_main_with_file_option(
+    mock_open,
+    mock_noop_condenser,
+    mock_llm_condenser,
+    mock_run_session,
+    mock_check_security,
+    mock_get_settings_store,
+    mock_setup_config,
+    mock_parse_args,
+):
+    """Test main function with a file option."""
+    loop = asyncio.get_running_loop()
+
+    # Mock arguments
+    mock_args = MagicMock()
+    mock_args.agent_cls = None
+    mock_args.llm_config = None
+    mock_args.name = None
+    mock_args.file = '/path/to/test/file.txt'
+    mock_args.task = None
+    mock_parse_args.return_value = mock_args
+
+    # Mock config
+    mock_config = MagicMock()
+    mock_config.workspace_base = '/test/dir'
+    mock_config.cli_multiline_input = False
+    mock_setup_config.return_value = mock_config
+
+    # Mock settings store
+    mock_settings_store = AsyncMock()
+    mock_settings = MagicMock()
+    mock_settings.agent = 'test-agent'
+    mock_settings.llm_model = 'test-model'
+    mock_settings.llm_api_key = 'test-api-key'
+    mock_settings.llm_base_url = 'test-base-url'
+    mock_settings.confirmation_mode = True
+    mock_settings.enable_default_condenser = True
+    mock_settings_store.load.return_value = mock_settings
+    mock_get_settings_store.return_value = mock_settings_store
+
+    # Mock condenser config to return a mock instead of validating
+    mock_llm_condenser_instance = MagicMock()
+    mock_llm_condenser.return_value = mock_llm_condenser_instance
+
+    # Mock security check
+    mock_check_security.return_value = True
+
+    # Mock file open
+    mock_file = MagicMock()
+    mock_file.__enter__.return_value.read.return_value = 'This is a test file content.'
+    mock_open.return_value = mock_file
+
+    # Mock run_session to return False (no new session requested)
+    mock_run_session.return_value = False
+
+    # Run the function
+    await cli.main_with_loop(loop)
+
+    # Assertions
+    mock_parse_args.assert_called_once()
+    mock_setup_config.assert_called_once_with(mock_args)
+    mock_get_settings_store.assert_called_once()
+    mock_settings_store.load.assert_called_once()
+    mock_check_security.assert_called_once_with(mock_config, '/test/dir')
+
+    # Verify file was opened
+    mock_open.assert_called_once_with('/path/to/test/file.txt', 'r', encoding='utf-8')
+
+    # Check that run_session was called with expected arguments
+    mock_run_session.assert_called_once()
+    # Extract the task_str from the call
+    task_str = mock_run_session.call_args[0][4]
+    assert "The user has tagged a file '/path/to/test/file.txt'" in task_str
+    assert 'Please read and understand the following file content first:' in task_str
+    assert 'This is a test file content.' in task_str
+    assert (
+        'After reviewing the file, please ask the user what they would like to do with it.'
+        in task_str
+    )