diff --git a/selfprivacy_api/services/service.py b/selfprivacy_api/services/service.py
index e01501b..0f018b6 100644
--- a/selfprivacy_api/services/service.py
+++ b/selfprivacy_api/services/service.py
@@ -284,17 +284,23 @@ class StoppedService:
     def __enter__(self) -> Service:
         self.original_status = self.service.get_status()
         if self.original_status not in [ServiceStatus.INACTIVE, ServiceStatus.FAILED]:
-            self.service.stop()
-            wait_until_true(
-                lambda: self.service.get_status() == ServiceStatus.INACTIVE,
-                timeout_sec=DEFAULT_START_STOP_TIMEOUT,
-            )
+            try:
+                self.service.stop()
+                wait_until_true(
+                    lambda: self.service.get_status() == ServiceStatus.INACTIVE,
+                    timeout_sec=DEFAULT_START_STOP_TIMEOUT,
+                )
+            except TimeoutError as e:
+                raise TimeoutError(f"timed out waiting for {self.service.get_display_name()} to stop")
         return self.service
 
     def __exit__(self, type, value, traceback):
         if self.original_status in [ServiceStatus.ACTIVATING, ServiceStatus.ACTIVE]:
-            self.service.start()
-            wait_until_true(
-                lambda: self.service.get_status() == ServiceStatus.ACTIVE,
-                timeout_sec=DEFAULT_START_STOP_TIMEOUT,
-            )
+            try:
+                self.service.start()
+                wait_until_true(
+                    lambda: self.service.get_status() == ServiceStatus.ACTIVE,
+                    timeout_sec=DEFAULT_START_STOP_TIMEOUT,
+                )
+            except TimeoutError as e:
+                raise TimeoutError(f"timed out waiting for {self.service.get_display_name()} to start")