diff --git a/tests/integration/cli/test_ursula_cli_run.py b/tests/integration/cli/test_ursula_cli_run.py
new file mode 100644
index 000000000..dbf42ab1c
--- /dev/null
+++ b/tests/integration/cli/test_ursula_cli_run.py
@@ -0,0 +1,118 @@
+import json
+
+import pytest
+
+from nucypher.blockchain.eth.actors import Operator
+from nucypher.blockchain.eth.trackers.dkg import ActiveRitualTracker
+from nucypher.cli.commands import ursula
+from nucypher.cli.main import nucypher_cli
+from nucypher.config.base import CharacterConfiguration
+from tests.constants import FAKE_PASSWORD_CONFIRMED, MOCK_IP_ADDRESS
+
+
+@pytest.fixture
+def v4_config_file(tempfile_path, ursula_test_config):
+    config_dictionary = {
+        "federated_only": None,
+        "checksum_address": None,
+        "keystore_path": None,
+        "domain": str(ursula_test_config.domain),
+        "learn_on_same_thread": False,
+        "abort_on_learning_error": False,
+        "start_learning_now": False,
+        "save_metadata": False,
+        "node_storage": {"storage_type": ":memory:"},
+        "lonely": False,
+        "eth_provider_uri": ursula_test_config.eth_endpoint,
+        "poa": None,
+        "light": False,
+        "signer_uri": ursula_test_config.signer_uri,
+        "gas_strategy": "fast",
+        "max_gas_price": None,
+        "operator_address": ursula_test_config.operator_address,
+        "rest_host": MOCK_IP_ADDRESS,
+        "rest_port": ursula_test_config.rest_port,
+        "db_filepath": "/root/.local/share/nucypher/ursula.db",
+        "availability_check": False,
+        "payment_method": "SubscriptionManager",
+        "payment_provider": ursula_test_config.polygon_endpoint,
+        "payment_network": str(
+            ursula_test_config.domain
+        ),  # doesn't really matter what this is
+        "version": 4,
+    }
+    json.dump(config_dictionary, open(tempfile_path, "w"))
+    return tempfile_path
+
+
+def test_ursula_run_specified_config_file(
+    testerchain,
+    click_runner,
+    mocker,
+    ursulas,
+    monkeypatch,
+    v4_config_file,
+):
+    # migration spy
+    migration_spy = mocker.spy(ursula, "migrate")
+
+    # Mock DKG
+    mocker.patch.object(ActiveRitualTracker, "start", autospec=True)
+
+    # Mock Teacher Resolution
+    from nucypher.characters.lawful import Ursula
+
+    teacher = ursulas[0]
+    mocker.patch.object(Ursula, "from_teacher_uri", return_value=teacher)
+
+    # don't try unlocking keystore
+    mocker.patch("nucypher.cli.utils.unlock_nucypher_keystore", return_value=True)
+
+    # Mock worker qualification
+    staking_provider = ursulas[1]
+
+    def set_staking_provider_address(operator, *args, **kwargs):
+        operator.checksum_address = staking_provider.checksum_address
+        return True
+
+    monkeypatch.setattr(Operator, "block_until_ready", set_staking_provider_address)
+
+    # mock creation of non-dev ursula
+    mocker.patch(
+        "nucypher.cli.commands.ursula.make_cli_character", return_value=ursulas[1]
+    )
+
+    # skip preflight since not in dev mode
+    mocker.patch("nucypher.characters.lawful.validate_operator_ip", return_value=None)
+
+    # manual teacher
+    run_args = (
+        "ursula",
+        "run",
+        "--dry-run",
+        "--debug",
+        "--config-file",
+        str(v4_config_file.absolute()),
+        "--teacher",
+        teacher.rest_url(),
+        "--no-ip-checkup",
+    )
+
+    assert migration_spy.call_count == 0
+
+    result = click_runner.invoke(
+        nucypher_cli, run_args, catch_exceptions=False, input=FAKE_PASSWORD_CONFIRMED
+    )
+
+    # check that migration was indeed called
+    assert migration_spy.call_count == 1
+
+    # check that migration worked - updated to latest version
+    with open(v4_config_file.absolute(), "r") as file:
+        contents = file.read()
+    config = json.loads(contents)
+    config_version = config["version"]
+    assert config_version > 4, "migrated to newer version"
+    assert config_version == CharacterConfiguration.VERSION
+
+    assert result.exit_code == 0, result.output