diff --git a/tests/cli/test_alice.py b/tests/cli/test_alice.py
new file mode 100644
index 000000000..59ca8951e
--- /dev/null
+++ b/tests/cli/test_alice.py
@@ -0,0 +1,89 @@
+import os
+
+from nucypher.cli.main import nucypher_cli
+from nucypher.config.characters import AliceConfiguration
+from nucypher.utilities.sandbox.constants import MOCK_URSULA_STARTING_PORT, INSECURE_DEVELOPMENT_PASSWORD, \
+    MOCK_IP_ADDRESS, MOCK_CUSTOM_INSTALLATION_PATH
+
+
+def test_initialize_alice_defaults(click_runner, mocker):
+    # Mock out filesystem writes
+    mocker.patch.object(AliceConfiguration, 'initialize', autospec=True)
+    mocker.patch.object(AliceConfiguration, 'to_configuration_file', autospec=True)
+
+    # Use default ursula init args
+    init_args = ('alice', 'init', '--federated-only')
+    user_input = '{password}\n{password}\n'.format(password=INSECURE_DEVELOPMENT_PASSWORD)
+    result = click_runner.invoke(nucypher_cli, init_args, input=user_input, catch_exceptions=False)
+    assert result.exit_code == 0
+
+    # REST Host
+    assert "nucypher alice run" in result.output
+
+    # Auth
+    assert 'Enter keyring password:' in result.output, 'WARNING: User was not prompted for password'
+    assert 'Repeat for confirmation:' in result.output, 'User was not prompted to confirm password'
+
+
+def test_alice_control_starts_mocked(click_runner, mocker):
+    class MockKeyring:
+        is_unlocked = False
+
+        @classmethod
+        def unlock(cls, password, *args, **kwargs):
+            assert password == INSECURE_DEVELOPMENT_PASSWORD
+            cls.is_unlocked = True
+
+    good_enough_config = AliceConfiguration(dev_mode=True, federated_only=True, keyring=MockKeyring)
+
+    mocker.patch.object(AliceConfiguration, "from_configuration_file", return_value=good_enough_config)
+    init_args = ('alice', 'run', '-x')
+
+    user_input = '{password}\n{password}\n'.format(password=INSECURE_DEVELOPMENT_PASSWORD)
+    result = click_runner.invoke(nucypher_cli, init_args, input=user_input)
+    assert result.exit_code == 0
+    assert MockKeyring.is_unlocked
+    assert 'Starting Alice Character Control' in result.output
+
+
+def test_initialize_alice_with_custom_configuration_root(custom_filepath, click_runner):
+
+    # Use a custom local filepath for configuration
+    init_args = ('alice', 'init',
+                 '--federated-only',
+                 '--config-root', custom_filepath)
+
+    user_input = '{password}\n{password}'.format(password=INSECURE_DEVELOPMENT_PASSWORD, ip=MOCK_IP_ADDRESS)
+    result = click_runner.invoke(nucypher_cli, init_args, input=user_input, catch_exceptions=False)
+    assert result.exit_code == 0
+
+    # CLI Output
+    assert MOCK_CUSTOM_INSTALLATION_PATH in result.output, "Configuration not in system temporary directory"
+    assert "nucypher alice run" in result.output, 'Help message is missing suggested command'
+    assert 'IPv4' not in result.output
+
+    # Files and Directories
+    assert os.path.isdir(custom_filepath), 'Configuration file does not exist'
+    assert os.path.isdir(os.path.join(custom_filepath, 'keyring')), 'Keyring does not exist'
+    assert os.path.isdir(os.path.join(custom_filepath, 'known_nodes')), 'known_nodes directory does not exist'
+
+    custom_config_filepath = os.path.join(custom_filepath, AliceConfiguration.CONFIG_FILENAME)
+    assert os.path.isfile(custom_config_filepath), 'Configuration file does not exist'
+
+    # Auth
+    assert 'Enter keyring password:' in result.output, 'WARNING: User was not prompted for password'
+    assert 'Repeat for confirmation:' in result.output, 'User was not prompted to confirm password'
+
+
+def test_alice_control_starts_with_preexisting_configuration(click_runner, custom_filepath):
+
+    custom_config_filepath = os.path.join(custom_filepath, AliceConfiguration.CONFIG_FILENAME)
+
+    init_args = ('alice', 'run',
+                 '--dry-run',
+                 '--config-file', custom_config_filepath)
+
+    user_input = '{password}\n{password}\n'.format(password=INSECURE_DEVELOPMENT_PASSWORD)
+    result = click_runner.invoke(nucypher_cli, init_args, input=user_input)
+    assert result.exit_code == 0
+    assert 'Starting Alice Character Control' in result.output