diff --git a/selfprivacy_api/utils/waitloop.py b/selfprivacy_api/utils/waitloop.py
index a375b8e..9f71a37 100644
--- a/selfprivacy_api/utils/waitloop.py
+++ b/selfprivacy_api/utils/waitloop.py
@@ -2,14 +2,19 @@ from time import sleep
 from typing import Callable
 from typing import Optional
 
-def wait_until_true(readiness_checker: Callable[[],bool],*,interval: float =0.1, timeout_sec: Optional[float] = None):
+
+def wait_until_true(
+    readiness_checker: Callable[[], bool],
+    *,
+    interval: float = 0.1,
+    timeout_sec: Optional[float] = None
+):
     elapsed = 0.0
     if timeout_sec is None:
         timeout_sec = 10e16
-    while not readiness_checker or elapsed > timeout_sec:
+
+    while (not readiness_checker()) and elapsed < timeout_sec:
         sleep(interval)
         elapsed += interval
     if elapsed > timeout_sec:
         raise TimeoutError()
-
-        
diff --git a/tests/test_graphql/test_backup.py b/tests/test_graphql/test_backup.py
index e54be85..573480c 100644
--- a/tests/test_graphql/test_backup.py
+++ b/tests/test_graphql/test_backup.py
@@ -52,7 +52,7 @@ def backups_backblaze(generic_userdata):
 
 
 @pytest.fixture()
-def raw_dummy_service(tmpdir, backups):
+def raw_dummy_service(tmpdir):
     dirnames = ["test_service", "also_test_service"]
     service_dirs = []
     for d in dirnames:
@@ -578,13 +578,13 @@ def test_services_to_back_up(backups, dummy_service):
 def test_sync(dummy_service):
     src = dummy_service.get_folders()[0]
     dst = dummy_service.get_folders()[1]
-    old_files_src = listdir(src)
-    old_files_dst = listdir(dst)
+    old_files_src = set(listdir(src))
+    old_files_dst = set(listdir(dst))
     assert old_files_src != old_files_dst
 
     sync(src, dst)
-    new_files_src = listdir(src)
-    new_files_dst = listdir(dst)
+    new_files_src = set(listdir(src))
+    new_files_dst = set(listdir(dst))
     assert new_files_src == old_files_src
     assert new_files_dst == new_files_src
 
diff --git a/tests/test_services.py b/tests/test_services.py
index 5816140..4d4c8f4 100644
--- a/tests/test_services.py
+++ b/tests/test_services.py
@@ -9,7 +9,10 @@ from selfprivacy_api.services.owned_path import OwnedPath
 from selfprivacy_api.services.generic_service_mover import FolderMoveNames
 
 from selfprivacy_api.services.test_service import DummyService
-from selfprivacy_api.services.service import Service
+from selfprivacy_api.services.service import Service, ServiceStatus
+from selfprivacy_api.utils.waitloop import wait_until_true
+
+from tests.test_graphql.test_backup import raw_dummy_service
 
 
 def test_unimplemented_folders_raises():
@@ -25,6 +28,20 @@ def test_unimplemented_folders_raises():
     assert owned_folders is not None
 
 
+def test_delayed_start_stop(raw_dummy_service):
+    dummy = raw_dummy_service
+
+    dummy.stop(delay=0.3)
+    assert dummy.get_status() == ServiceStatus.DEACTIVATING
+    wait_until_true(lambda: dummy.get_status() == ServiceStatus.INACTIVE)
+    assert dummy.get_status() == ServiceStatus.INACTIVE
+
+    dummy.start(delay=0.3)
+    assert dummy.get_status() == ServiceStatus.ACTIVATING
+    wait_until_true(lambda: dummy.get_status() == ServiceStatus.ACTIVE)
+    assert dummy.get_status() == ServiceStatus.ACTIVE
+
+
 def test_owned_folders_from_not_owned():
     assert Bitwarden.get_owned_folders() == [
         OwnedPath(