diff --git a/.github/workflows/test_and_build.yml b/.github/workflows/test_and_build.yml
index bc0efbe0..465fa711 100644
--- a/.github/workflows/test_and_build.yml
+++ b/.github/workflows/test_and_build.yml
@@ -46,7 +46,7 @@ jobs:
           COGNITE_PROJECT: extractor-tests
           COGNITE_BASE_URL: https://greenfield.cognitedata.com
           COGNITE_DEV_PROJECT: extractor-aws-dub-dev-testing
-          COGNITE_DEV_BASE_URL: https://aws-dub-dev.cognitedata.com/
+          COGNITE_DEV_BASE_URL: https://aws-dub-dev.cognitedata.com
           COGNITE_DEV_TOKEN_SCOPES: https://aws-dub-dev.cognitedata.com/.default
           COGNITE_INTEGRATION: pythonutils-test
         run: |
diff --git a/cognite/extractorutils/unstable/core/checkin_worker.py b/cognite/extractorutils/unstable/core/checkin_worker.py
index 2b83ecf7..a65a9c31 100644
--- a/cognite/extractorutils/unstable/core/checkin_worker.py
+++ b/cognite/extractorutils/unstable/core/checkin_worker.py
@@ -96,6 +96,18 @@ def active_revision(self, value: ConfigRevision) -> None:
         with self._lock:
             self._active_revision = value
 
+    def reset_startup(self) -> None:
+        """
+        Reset startup.
+
+        This will reset startup if and when the extractor restarts either
+        due to changes in the config or the extractor just starting for the first time.
+
+        """
+        with self._lock:
+            self._is_running = False
+            self._has_reported_startup = False
+
     def set_on_revision_change_handler(self, on_revision_change: Callable[[int], None]) -> None:
         """
         Set the handler for when the configuration revision changes.
diff --git a/cognite/extractorutils/unstable/core/runtime.py b/cognite/extractorutils/unstable/core/runtime.py
index 30d7d2fa..da0a2068 100644
--- a/cognite/extractorutils/unstable/core/runtime.py
+++ b/cognite/extractorutils/unstable/core/runtime.py
@@ -525,6 +525,8 @@ def _main_runtime(self, args: Namespace) -> None:
                 message = self._message_queue.get_nowait()
                 match message:
                     case RuntimeMessage.RESTART:
+                        self.logger.info("Extractor restart detected. Restarting extractor.")
+                        checkin_worker.reset_startup()
                         continue
 
                     case _:
diff --git a/pyproject.toml b/pyproject.toml
index 7566ee58..37c4db12 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -123,5 +123,8 @@ only-include = ["cognite"]
 requires = ["hatchling"]
 build-backend = "hatchling.build"
 
+[dependency-groups]
+dev = []
+
 [project.scripts]
 simple-extractor = "cognite.examples.unstable.extractors.simple_extractor.main:main"
diff --git a/tests/test_unstable/conftest.py b/tests/test_unstable/conftest.py
index bd5001b5..d143f0ff 100644
--- a/tests/test_unstable/conftest.py
+++ b/tests/test_unstable/conftest.py
@@ -151,7 +151,7 @@ def json_callback(request: Any, context: Any) -> dict:
 
         requests_mock.register_uri(
             method="POST",
-            url=f"{connection_config.base_url}api/v1/projects/{connection_config.project}/integrations/startup",
+            url=f"{connection_config.base_url}/api/v1/projects/{connection_config.project}/integrations/startup",
             json=json_callback,
             status_code=status_code,
         )
@@ -177,7 +177,7 @@ def json_callback(request: Any, context: Any) -> dict:
 
         requests_mock.register_uri(
             method="POST",
-            url=f"{connection_config.base_url}api/v1/projects/{connection_config.project}/integrations/checkin",
+            url=f"{connection_config.base_url}/api/v1/projects/{connection_config.project}/integrations/checkin",
             json=json_callback,
             status_code=status_code,
         )
diff --git a/tests/test_unstable/test_checkin_worker.py b/tests/test_unstable/test_checkin_worker.py
index 9bc484d3..2711aca8 100644
--- a/tests/test_unstable/test_checkin_worker.py
+++ b/tests/test_unstable/test_checkin_worker.py
@@ -157,6 +157,71 @@ def test_run_report_periodic(
     assert "taskEvents" in checkin_bag[1]
 
 
+def test_run_report_periodic_reset_startup(
+    connection_config: ConnectionConfig,
+    application_config: TestConfig,
+    requests_mock: requests_mock.Mocker,
+    mock_checkin_request: Callable[[requests_mock.Mocker], None],
+    mock_startup_request: Callable[[requests_mock.Mocker], None],
+    faker: faker.Faker,
+    checkin_bag: list,
+) -> None:
+    requests_mock.real_http = True
+    mock_startup_request(requests_mock)
+    mock_checkin_request(requests_mock)
+    cognite_client = connection_config.get_cognite_client("test_checkin")
+    cancellation_token = CancellationToken()
+    worker = CheckinWorker(
+        cognite_client,
+        connection_config.integration.external_id,
+        logging.getLogger(__name__),
+    )
+
+    test_extractor = TestExtractor(
+        FullConfig(
+            connection_config=connection_config, application_config=application_config, current_config_revision=1
+        ),
+        worker,
+    )
+    test_extractor._start_time = datetime.fromtimestamp(int(now() / 1000), tz=timezone.utc)
+    message_queue: Queue = Queue()
+    mp_cancel_event = Event()
+    test_extractor._attach_runtime_controls(cancel_event=mp_cancel_event, message_queue=message_queue)
+
+    worker.report_task_end("task1", faker.sentence())
+    worker.report_task_start("task1", faker.sentence())
+    worker.report_error(
+        Error(
+            level=ErrorLevel.error,
+            description=faker.sentence(),
+            task_name="task1",
+            extractor=test_extractor,
+            details=None,
+        )
+    )
+
+    process = Thread(
+        target=worker.run_periodic_checkin,
+        args=(cancellation_token, test_extractor._get_startup_request(), 2.0),
+    )
+    process.start()
+    worker.reset_startup()
+    process.join(timeout=3)
+    cancellation_token.cancel()
+
+    cancellation_token = CancellationToken()
+    process = Thread(
+        target=worker.run_periodic_checkin,
+        args=(cancellation_token, test_extractor._get_startup_request(), 2.0),
+    )
+    process.start()
+    worker.reset_startup()
+    process.join(timeout=3)
+    cancellation_token.cancel()
+
+    assert len(checkin_bag) >= 3
+
+
 def test_run_report_periodic_ensure_reorder(
     connection_config: ConnectionConfig,
     application_config: TestConfig,