diff --git a/src/loop.c b/src/loop.c
index 67b41e77..51f0acc1 100644
--- a/src/loop.c
+++ b/src/loop.c
@@ -206,6 +206,7 @@ int mosquitto_main_loop(struct mosquitto__listener_sock *listensock, int listens
 		plugin__handle_tick();
 		session_expiry__check();
 		will_delay__check();
+		plugin_persist__process_retain_events(false);
 
 		rc = mux__handle(listensock, listensock_count);
 		if(rc) return rc;
diff --git a/src/mosquitto.c b/src/mosquitto.c
index a5586051..19ac12f1 100644
--- a/src/mosquitto.c
+++ b/src/mosquitto.c
@@ -346,13 +346,6 @@ int main(int argc, char *argv[])
 
 	g_run = 1;
 	rc = mosquitto_main_loop(g_listensock, g_listensock_count);
-	db.shutdown = true;
-
-	log__printf(NULL, MOSQ_LOG_INFO, "mosquitto version %s terminating", VERSION);
-
-#ifdef WITH_CJSON
-	broker_control__cleanup();
-#endif
 
 	/* FIXME - this isn't quite right, all wills with will delay zero should be
 	 * sent now, but those with positive will delay should be persisted and
@@ -362,6 +355,16 @@ int main(int argc, char *argv[])
 	}
 	will_delay__send_all();
 
+	plugin_persist__process_retain_events(true);
+
+	/* Set to true only after persistence events have been processed */
+	db.shutdown = true;
+	log__printf(NULL, MOSQ_LOG_INFO, "mosquitto version %s terminating", VERSION);
+
+#ifdef WITH_CJSON
+	broker_control__cleanup();
+#endif
+
 #ifdef WITH_PERSISTENCE
 	persist__backup(true);
 #endif
diff --git a/src/mosquitto_broker_internal.h b/src/mosquitto_broker_internal.h
index 5274f305..0b931524 100644
--- a/src/mosquitto_broker_internal.h
+++ b/src/mosquitto_broker_internal.h
@@ -478,6 +478,11 @@ struct mosquitto__message_v5{
 	bool retain;
 };
 
+struct persist_retain_event{
+	UT_hash_handle hh;
+	struct mosquitto_base_msg *msg;
+	int event;
+};
 
 struct mosquitto_db{
 	dbid_t last_db_id;
@@ -488,6 +493,7 @@ struct mosquitto_db{
 	struct mosquitto *contexts_by_sock;
 	struct mosquitto *contexts_by_id_delayed_auth;
 	struct mosquitto *contexts_for_free;
+	struct persist_retain_event *persist_retain_events;
 #ifdef WITH_BRIDGE
 	struct mosquitto **bridges;
 	int bridge_count;
@@ -873,6 +879,8 @@ void plugin_persist__handle_base_msg_add(struct mosquitto_base_msg *base_msg);
 void plugin_persist__handle_base_msg_delete(struct mosquitto_base_msg *base_msg);
 void plugin_persist__handle_retain_msg_set(struct mosquitto_base_msg *base_msg);
 void plugin_persist__handle_retain_msg_delete(struct mosquitto_base_msg *base_msg);
+void plugin_persist__process_retain_events(bool force);
+void plugin_persist__queue_retain_event(struct mosquitto_base_msg *msg, int event);
 
 /* ============================================================
  * Property related functions
diff --git a/src/plugin_persist.c b/src/plugin_persist.c
index c055db0e..046aeb42 100644
--- a/src/plugin_persist.c
+++ b/src/plugin_persist.c
@@ -349,6 +349,54 @@ void plugin_persist__handle_base_msg_delete(struct mosquitto_base_msg *msg)
 }
 
 
+void plugin_persist__process_retain_events(bool force)
+{
+	struct persist_retain_event *evt, *evt_tmp;
+	static time_t last_run = 0;
+
+	if(db.now_real_s > last_run + 10 || force){
+		HASH_ITER(hh, db.persist_retain_events, evt, evt_tmp){
+			HASH_DELETE(hh, db.persist_retain_events, evt);
+			if(evt->event == MOSQ_EVT_PERSIST_RETAIN_MSG_SET){
+				plugin_persist__handle_base_msg_add(evt->msg);
+				plugin_persist__handle_retain_msg_set(evt->msg);
+			}else if(evt->event == MOSQ_EVT_PERSIST_RETAIN_MSG_DELETE){
+				plugin_persist__handle_retain_msg_delete(evt->msg);
+			}
+			db__msg_store_ref_dec(&evt->msg);
+			SAFE_FREE(evt);
+		}
+		last_run = db.now_real_s;
+	}
+}
+
+
+/* The retain event queue is used to store retain persistence events and periodically apply them.
+ * There can only be one event per topic queued at any one time, and this means that we
+ * can potentially remove a lot of set/delete persist events if a topic is
+ * being updated frequently. */
+void plugin_persist__queue_retain_event(struct mosquitto_base_msg *msg, int event)
+{
+	struct persist_retain_event *evt;
+
+	HASH_FIND(hh, db.persist_retain_events, msg->topic, strlen(msg->topic), evt);
+	if(evt){
+		db__msg_store_ref_dec(&evt->msg);
+		HASH_DELETE(hh, db.persist_retain_events, evt);
+	}else{
+		evt = mosquitto__calloc(1, sizeof(struct persist_retain_event));
+		if(!evt){
+			return;
+		}
+	}
+
+	evt->event = event;
+	evt->msg = msg;
+	db__msg_store_ref_inc(msg);
+	HASH_ADD_KEYPTR(hh, db.persist_retain_events, evt->msg->topic, strlen(evt->msg->topic), evt);
+}
+
+
 void plugin_persist__handle_retain_msg_set(struct mosquitto_base_msg *msg)
 {
 	struct mosquitto_evt_persist_retain_msg event_data;
diff --git a/src/plugin_public.c b/src/plugin_public.c
index bd67f2dd..4287efd6 100644
--- a/src/plugin_public.c
+++ b/src/plugin_public.c
@@ -682,6 +682,7 @@ int mosquitto_persist_base_msg_add(struct mosquitto_evt_persist_base_msg *msg)
 	uint32_t message_expiry_interval;
 	time_t message_expiry_interval_tt;
 	int i;
+	int rc;
 
 	memset(&context, 0, sizeof(context));
 
@@ -725,7 +726,10 @@ int mosquitto_persist_base_msg_add(struct mosquitto_evt_persist_base_msg *msg)
 			}
 		}
 	}
-	return db__message_store(&context, base_msg, message_expiry_interval, msg->store_id, mosq_mo_broker);
+	rc = db__message_store(&context, base_msg, message_expiry_interval, msg->store_id, mosq_mo_broker);
+	free(context.id);
+	free(context.username);
+	return rc;
 
 error:
 	mosquitto_property_free_all(&msg->plugin_properties);
diff --git a/src/retain.c b/src/retain.c
index 1e2db194..cccc2aea 100644
--- a/src/retain.c
+++ b/src/retain.c
@@ -159,7 +159,7 @@ int retain__store(const char *topic, struct mosquitto_base_msg *base_msg, char *
 	if(retainhier->retained){
 		if(persist && retainhier->retained->topic[0] != '$' && base_msg->payloadlen == 0){
 			/* Only delete if another retained message isn't replacing this one */
-			plugin_persist__handle_retain_msg_delete(retainhier->retained);
+			plugin_persist__queue_retain_event(retainhier->retained, MOSQ_EVT_PERSIST_RETAIN_MSG_DELETE);
 		}
 		db__msg_store_ref_dec(&retainhier->retained);
 #ifdef WITH_SYS_TREE
@@ -173,8 +173,7 @@ int retain__store(const char *topic, struct mosquitto_base_msg *base_msg, char *
 		retainhier->retained = base_msg;
 		db__msg_store_ref_inc(retainhier->retained);
 		if(persist && retainhier->retained->topic[0] != '$'){
-			plugin_persist__handle_base_msg_add(retainhier->retained);
-			plugin_persist__handle_retain_msg_set(retainhier->retained);
+			plugin_persist__queue_retain_event(retainhier->retained, MOSQ_EVT_PERSIST_RETAIN_MSG_SET);
 		}
 #ifdef WITH_SYS_TREE
 		db.retained_count++;
diff --git a/test/unit/persist_read_stubs.c b/test/unit/persist_read_stubs.c
index 25ffc869..4f1da80e 100644
--- a/test/unit/persist_read_stubs.c
+++ b/test/unit/persist_read_stubs.c
@@ -239,3 +239,14 @@ void plugin_persist__handle_base_msg_add(struct mosquitto_base_msg *msg)
 {
 	UNUSED(msg);
 }
+
+void plugin_persist__process_retain_events(bool force)
+{
+	UNUSED(force);
+}
+
+void plugin_persist__queue_retain_event(struct mosquitto_base_msg *msg, int event)
+{
+	UNUSED(msg);
+	UNUSED(event);
+}
diff --git a/test/unit/persist_write_stubs.c b/test/unit/persist_write_stubs.c
index cdb6aa49..56100e22 100644
--- a/test/unit/persist_write_stubs.c
+++ b/test/unit/persist_write_stubs.c
@@ -211,3 +211,14 @@ void plugin_persist__handle_subscription_delete(struct mosquitto *context, const
 	UNUSED(context);
 	UNUSED(sub);
 }
+
+void plugin_persist__process_retain_events(bool force)
+{
+	UNUSED(force);
+}
+
+void plugin_persist__queue_retain_event(struct mosquitto_base_msg *msg, int event)
+{
+	UNUSED(msg);
+	UNUSED(event);
+}
diff --git a/test/unit/stubs.c b/test/unit/stubs.c
index 660dfe0f..5229d491 100644
--- a/test/unit/stubs.c
+++ b/test/unit/stubs.c
@@ -104,3 +104,14 @@ void plugin_persist__handle_retain_remove(struct mosquitto_base_msg *msg)
 {
 	UNUSED(msg);
 }
+
+void plugin_persist__process_retain_events(bool force)
+{
+	UNUSED(force);
+}
+
+void plugin_persist__queue_retain_event(struct mosquitto_base_msg *msg, int event)
+{
+	UNUSED(msg);
+	UNUSED(event);
+}