diff --git a/patroni/ha.py b/patroni/ha.py
index c0821bc2..9f84613f 100644
--- a/patroni/ha.py
+++ b/patroni/ha.py
@@ -316,8 +316,7 @@ class Ha(object):
             msg = 'running pg_rewind from ' + leader.name
             return self._async_executor.try_run_async(msg, self._rewind.execute, args=(leader,)) or msg
 
-        # remove_data_directory_on_diverged_timelines is set
-        if not self.is_standby_cluster():
+        if self._rewind.should_remove_data_directory_on_diverged_timelines and not self.is_standby_cluster():
             msg = 'reinitializing due to diverged timelines'
             return self._async_executor.try_run_async(msg, self._do_reinitialize, args=(self.cluster,)) or msg
 
diff --git a/patroni/postgresql/rewind.py b/patroni/postgresql/rewind.py
index 5a2e4a39..db7055df 100644
--- a/patroni/postgresql/rewind.py
+++ b/patroni/postgresql/rewind.py
@@ -46,9 +46,13 @@ class Rewind(object):
             return False
         return self.configuration_allows_rewind(self._postgresql.controldata())
 
+    @property
+    def should_remove_data_directory_on_diverged_timelines(self):
+        return self._postgresql.config.get('remove_data_directory_on_diverged_timelines')
+
     @property
     def can_rewind_or_reinitialize_allowed(self):
-        return self._postgresql.config.get('remove_data_directory_on_diverged_timelines') or self.can_rewind
+        return self.should_remove_data_directory_on_diverged_timelines or self.can_rewind
 
     def trigger_check_diverged_lsn(self):
         if self.can_rewind_or_reinitialize_allowed and self._state != REWIND_STATUS.NEED:
@@ -374,19 +378,22 @@ class Rewind(object):
 
         if self.pg_rewind(r):
             self._state = REWIND_STATUS.SUCCESS
-        elif not self.check_leader_is_not_in_recovery(r):
-            logger.warning('Failed to rewind because master %s become unreachable', leader.name)
         else:
-            logger.error('Failed to rewind from healty master: %s', leader.name)
-
-            for name in ('remove_data_directory_on_rewind_failure', 'remove_data_directory_on_diverged_timelines'):
-                if self._postgresql.config.get(name):
-                    logger.warning('%s is set. removing...', name)
-                    self._postgresql.remove_data_directory()
-                    self._state = REWIND_STATUS.INITIAL
-                    break
+            if not self.check_leader_is_not_in_recovery(r):
+                logger.warning('Failed to rewind because master %s become unreachable', leader.name)
+                if not self.can_rewind:  # It is possible that the previous attempt damaged pg_control file!
+                    self._state = REWIND_STATUS.FAILED
             else:
+                logger.error('Failed to rewind from healty master: %s', leader.name)
                 self._state = REWIND_STATUS.FAILED
+
+            if self.failed:
+                for name in ('remove_data_directory_on_rewind_failure', 'remove_data_directory_on_diverged_timelines'):
+                    if self._postgresql.config.get(name):
+                        logger.warning('%s is set. removing...', name)
+                        self._postgresql.remove_data_directory()
+                        self._state = REWIND_STATUS.INITIAL
+                        break
         return False
 
     def reset_state(self):
diff --git a/tests/test_ha.py b/tests/test_ha.py
index 56277f97..5ed4503d 100644
--- a/tests/test_ha.py
+++ b/tests/test_ha.py
@@ -314,6 +314,7 @@ class TestHa(PostgresInit):
             self.assertEqual(self.ha.run_cycle(), 'fake')
 
     @patch.object(Rewind, 'rewind_or_reinitialize_needed_and_possible', Mock(return_value=True))
+    @patch.object(Rewind, 'should_remove_data_directory_on_diverged_timelines', PropertyMock(return_value=True))
     @patch.object(Bootstrap, 'create_replica', Mock(return_value=1))
     def test_recover_with_reinitialize(self):
         self.p.is_running = false