diff --git a/plinth/setup.py b/plinth/setup.py
index a7fcef3e6..a90e3f3f4 100644
--- a/plinth/setup.py
+++ b/plinth/setup.py
@@ -469,12 +469,6 @@ class ForceUpgrader():
 
         """
         for _ in range(self.UPGRADE_ATTEMPTS):
-            logger.info('Waiting for %s seconds before attempting upgrade',
-                        self.UPGRADE_ATTEMPT_WAIT_SECONDS)
-            if self._wait_event.wait(self.UPGRADE_ATTEMPT_WAIT_SECONDS):
-                logger.info('Stopping upgrade attempts due to shutdown')
-                return
-
             try:
                 logger.info('Attempting to perform upgrade')
                 self._attempt_upgrade()
@@ -489,6 +483,12 @@ class ForceUpgrader():
                 # Assume all other errors are temporary
                 logger.exception('Unknown exception: %s', exception)
 
+            logger.info('Waiting for %s seconds before attempting upgrade',
+                        self.UPGRADE_ATTEMPT_WAIT_SECONDS)
+            if self._wait_event.wait(self.UPGRADE_ATTEMPT_WAIT_SECONDS):
+                logger.info('Stopping upgrade attempts due to shutdown')
+                return
+
         logger.info('Giving up on upgrade after too many retries')
 
     def shutdown(self):
@@ -748,14 +748,6 @@ class DpkgHandler:
         This method is guaranteed to not to run more than once simultaneously.
         """
         for _ in range(self.HANDLE_ATTEMPTS):
-            logger.info(
-                'Waiting for %s seconds before attempting post-dpkg '
-                'operations', self.HANDLE_ATTEMPT_WAIT_SECONDS)
-            if self._wait_event.wait(self.HANDLE_ATTEMPT_WAIT_SECONDS):
-                logger.info(
-                    'Stopping post-dpkg operation attempts due to shutdown')
-                return
-
             try:
                 logger.info('Attempting to perform post-dpkg operations')
                 self._attempt_post_invoke()
@@ -771,6 +763,14 @@ class DpkgHandler:
                 # Assume all other errors are temporary
                 logger.exception('Unknown exception: %s', exception)
 
+            logger.info(
+                'Waiting for %s seconds before attempting post-dpkg '
+                'operations', self.HANDLE_ATTEMPT_WAIT_SECONDS)
+            if self._wait_event.wait(self.HANDLE_ATTEMPT_WAIT_SECONDS):
+                logger.info(
+                    'Stopping post-dpkg operation attempts due to shutdown')
+                return
+
         logger.info('Giving up on post-dpkg operations after too many retries')
 
     def _attempt_post_invoke(self) -> None: