diff --git a/include/mosquitto_broker.h b/include/mosquitto_broker.h
index e497a195..b171db70 100644
--- a/include/mosquitto_broker.h
+++ b/include/mosquitto_broker.h
@@ -1045,10 +1045,8 @@ int mosquitto_subscription_delete(const char *client_id, const char *topic);
  * message for an existing topic first.
  *
  * Parameters:
- *   msg->plugin_topic - the topic that the message references
- *          The broker will *not* modify this string and it remains the
- *          property of the plugin.
- *   msg->store_id - the store id of the stored message that is to be retained
+ *   topic - the topic that the message references
+ *   store_id - the store id of the stored message that is to be retained
  *
  * Returns:
  *   MOSQ_ERR_SUCCESS - on success
@@ -1056,7 +1054,7 @@ int mosquitto_subscription_delete(const char *client_id, const char *topic);
  *   MOSQ_ERR_NOT_FOUND - the referenced stored message was not found
  *   MOSQ_ERR_NOMEM - on out of memory
  */
-int mosquitto_persist_retain_add(struct mosquitto_evt_persist_retain *retain);
+int mosquitto_persist_retain_add(const char *topic, uint64_t store_id);
 
 
 /* Function: mosquitto_persist_retain_delete
@@ -1064,9 +1062,7 @@ int mosquitto_persist_retain_add(struct mosquitto_evt_persist_retain *retain);
  * Use to delete a retained message.
  *
  * Parameters:
- *   msg->plugin_topic - the topic that the message references
- *          The broker will *not* modify this string and it remains the
- *          property of the plugin.
+ *   topic - the topic that the message references
  *
  * Returns:
  *   MOSQ_ERR_SUCCESS - on success
diff --git a/lib/send_publish.c b/lib/send_publish.c
index 5c7cd8ad..2100bf98 100644
--- a/lib/send_publish.c
+++ b/lib/send_publish.c
@@ -248,7 +248,7 @@ int send__real_publish(struct mosquitto *mosq, uint16_t mid, const char *topic,
 	}
 
 	/* Payload */
-	if(payloadlen){
+	if(payloadlen && payload){
 		packet__write_bytes(packet, payload, payloadlen);
 	}
 
diff --git a/src/database.c b/src/database.c
index 731b9034..fe5154df 100644
--- a/src/database.c
+++ b/src/database.c
@@ -281,8 +281,8 @@ void db__msg_store_remove(struct mosquitto_msg_store *store, bool notify)
 	HASH_DELETE(hh, db.msg_store, store);
 	db.msg_store_count--;
 	db.msg_store_bytes -= store->payloadlen;
-	if(db.shutdown == false || notify == true){
-		plugin_persist__handle_msg_delete(store);
+	if(notify == true){
+		plugin_persist__handle_msg_remove(store);
 	}
 	db__msg_store_free(store);
 }
diff --git a/src/linker-macosx.syms b/src/linker-macosx.syms
index 433dd5f6..f58e4780 100644
--- a/src/linker-macosx.syms
+++ b/src/linker-macosx.syms
@@ -21,10 +21,10 @@ _mosquitto_kick_client_by_username
 _mosquitto_log_printf
 _mosquitto_malloc
 _mosquitto_persist_client_add
+_mosquitto_persist_client_delete
 _mosquitto_persist_client_msg_add
 _mosquitto_persist_client_msg_delete
 _mosquitto_persist_client_msg_update
-_mosquitto_persist_client_delete
 _mosquitto_persist_client_update
 _mosquitto_persist_msg_add
 _mosquitto_persist_msg_delete
@@ -53,6 +53,7 @@ _mosquitto_pub_topic_check
 _mosquitto_realloc
 _mosquitto_set_username
 _mosquitto_strdup
+_mosquitto_string_to_property_info
 _mosquitto_sub_matches_acl
 _mosquitto_sub_matches_acl_with_pattern
 _mosquitto_sub_topic_check
diff --git a/src/linker.syms b/src/linker.syms
index a3cdcd99..4ed85fe6 100644
--- a/src/linker.syms
+++ b/src/linker.syms
@@ -54,6 +54,7 @@
 	mosquitto_realloc;
 	mosquitto_set_username;
 	mosquitto_strdup;
+	mosquitto_string_to_property_info;
 	mosquitto_sub_matches_acl;
 	mosquitto_sub_matches_acl_with_pattern;
 	mosquitto_sub_topic_check;
diff --git a/src/plugin_persist.c b/src/plugin_persist.c
index 7a9135f4..6d420bd0 100644
--- a/src/plugin_persist.c
+++ b/src/plugin_persist.c
@@ -90,6 +90,9 @@ void plugin_persist__handle_client_update(struct mosquitto *context)
 	if(db.shutdown) return;
 
 	UNUSED(will); /* FIXME */
+
+	if(db.shutdown) return;
+
 	opts = &db.config->security_options;
 	memset(&event_data, 0, sizeof(event_data));
 	event_data.client_id = context->id;
diff --git a/src/plugin_public.c b/src/plugin_public.c
index 4ed15dc7..532318f0 100644
--- a/src/plugin_public.c
+++ b/src/plugin_public.c
@@ -539,9 +539,13 @@ int mosquitto_persist_client_msg_add(struct mosquitto_evt_persist_client_msg *cl
 	struct mosquitto *context;
 	struct mosquitto_msg_store *stored;
 
-	if(client_msg == NULL || client_msg->plugin_client_id == NULL) return MOSQ_ERR_INVAL;
+	if(client_msg == NULL || client_msg->plugin_client_id == NULL){
+		free(client_msg->plugin_client_id);
+		return MOSQ_ERR_INVAL;
+	}
 
 	HASH_FIND(hh_id, db.contexts_by_id, client_msg->plugin_client_id, strlen(client_msg->plugin_client_id), context);
+	free(client_msg->plugin_client_id);
 	if(context == NULL){
 		return MOSQ_ERR_NOT_FOUND;
 	}
diff --git a/src/retain.c b/src/retain.c
index ee545a66..62a8f056 100644
--- a/src/retain.c
+++ b/src/retain.c
@@ -71,22 +71,22 @@ int retain__init(void)
 	return MOSQ_ERR_SUCCESS;
 }
 
-int mosquitto_persist_retain_add(struct mosquitto_evt_persist_retain *msg)
+int mosquitto_persist_retain_add(const char *topic, uint64_t store_id)
 {
 	struct mosquitto_msg_store *stored;
 	int rc = MOSQ_ERR_UNKNOWN;
 	char **split_topics = NULL;
 	char *local_topic = NULL;
 
-	if(msg == NULL || msg->plugin_topic == NULL) return MOSQ_ERR_INVAL;
+	if(topic == NULL) return MOSQ_ERR_INVAL;
 
-	HASH_FIND(hh, db.msg_store, &msg->store_id, sizeof(msg->store_id), stored);
+	HASH_FIND(hh, db.msg_store, &store_id, sizeof(store_id), stored);
 	if(stored){
-		if(sub__topic_tokenise(msg->plugin_topic, &local_topic, &split_topics, NULL)) return MOSQ_ERR_NOMEM;
+		if(sub__topic_tokenise(topic, &local_topic, &split_topics, NULL)) return MOSQ_ERR_NOMEM;
 
-		rc = retain__store(msg->plugin_topic, stored, split_topics, false);
-		mosquitto__FREE(split_topics);
-		mosquitto__FREE(local_topic);
+		rc = retain__store(topic, stored, split_topics, false);
+		mosquitto__free(split_topics);
+		mosquitto__free(local_topic);
 	}
 
 	return rc;
diff --git a/test/broker/15-persist-client-msg-in-v3-1-1.py b/test/broker/15-persist-client-msg-in-v3-1-1.py
index 47a5bdbf..32c2bcb2 100755
--- a/test/broker/15-persist-client-msg-in-v3-1-1.py
+++ b/test/broker/15-persist-client-msg-in-v3-1-1.py
@@ -24,11 +24,18 @@ qos = 2
 connect_packet = mosq_test.gen_connect(client_id, proto_ver=proto_ver, clean_session=False)
 connack_packet1 = mosq_test.gen_connack(rc=0, proto_ver=proto_ver)
 connack_packet2 = mosq_test.gen_connack(rc=0, flags=1, proto_ver=proto_ver)
+
 mid = 1
-publish_packet = mosq_test.gen_publish(topic=topic, qos=qos, payload="message", mid=mid, proto_ver=proto_ver)
-pubrec_packet = mosq_test.gen_pubrec(mid=mid, proto_ver=proto_ver)
-pubrel_packet = mosq_test.gen_pubrel(mid=mid, proto_ver=proto_ver)
-pubcomp_packet = mosq_test.gen_pubcomp(mid=mid, proto_ver=proto_ver)
+publish1_packet = mosq_test.gen_publish(topic=topic, qos=qos, payload="message1", mid=mid, proto_ver=proto_ver)
+pubrec1_packet = mosq_test.gen_pubrec(mid=mid, proto_ver=proto_ver)
+pubrel1_packet = mosq_test.gen_pubrel(mid=mid, proto_ver=proto_ver)
+pubcomp1_packet = mosq_test.gen_pubcomp(mid=mid, proto_ver=proto_ver)
+
+mid = 2
+publish2_packet = mosq_test.gen_publish(topic=topic, qos=qos, payload="message2", mid=mid, proto_ver=proto_ver)
+pubrec2_packet = mosq_test.gen_pubrec(mid=mid, proto_ver=proto_ver)
+pubrel2_packet = mosq_test.gen_pubrel(mid=mid, proto_ver=proto_ver)
+pubcomp2_packet = mosq_test.gen_pubcomp(mid=mid, proto_ver=proto_ver)
 
 connect_packet_helper = mosq_test.gen_connect(helper_id, proto_ver=proto_ver, clean_session=True)
 subscribe_packet = mosq_test.gen_subscribe(mid, topic, qos=qos, proto_ver=proto_ver)
@@ -39,8 +46,9 @@ broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=Tr
 con = None
 try:
     # Connect client, start flow, disconnect
-    sock = mosq_test.do_client_connect(connect_packet, connack_packet1, timeout=5, port=port)
-    mosq_test.do_send_receive(sock, publish_packet, pubrec_packet, "pubrec send")
+    sock = mosq_test.do_client_connect(connect_packet, connack_packet1, timeout=5, port=port, connack_error="connack 1")
+    mosq_test.do_send_receive(sock, publish1_packet, pubrec1_packet, "pubrec1 send")
+    mosq_test.do_send_receive(sock, publish2_packet, pubrec2_packet, "pubrec2 send")
     sock.close()
 
     # Kill broker
@@ -51,15 +59,21 @@ try:
     broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=True, port=port)
 
     # Connect helper and subscribe
-    helper = mosq_test.do_client_connect(connect_packet_helper, connack_packet1, timeout=5, port=port)
+    helper = mosq_test.do_client_connect(connect_packet_helper, connack_packet1, timeout=5, port=port, connack_error="helper connack")
     mosq_test.do_send_receive(helper, subscribe_packet, suback_packet, "suback helper")
 
     # Complete the flow
-    sock = mosq_test.do_client_connect(connect_packet, connack_packet2, timeout=5, port=port)
-    mosq_test.do_send_receive(sock, pubrel_packet, pubcomp_packet, "pubrel send")
+    sock = mosq_test.do_client_connect(connect_packet, connack_packet2, timeout=5, port=port, connack_error="connack 2")
+    mosq_test.do_send_receive(sock, pubrel1_packet, pubcomp1_packet, "pubrel1 send")
+    mosq_test.do_send_receive(sock, pubrel2_packet, pubcomp2_packet, "pubrel2 send")
 
-    mosq_test.do_receive_send(helper, publish_packet, pubrec_packet, "pubrec receive")
-    mosq_test.do_receive_send(helper, pubrel_packet, pubcomp_packet, "pubcomp receive")
+    mosq_test.expect_packet(helper, "publish1 receive", publish1_packet)
+    mosq_test.expect_packet(helper, "publish2 receive", publish2_packet)
+    helper.send(pubrec1_packet)
+    mosq_test.do_receive_send(helper, pubrel1_packet, pubcomp1_packet, "pubcomp1 receive")
+
+    helper.send(pubrec2_packet)
+    mosq_test.do_receive_send(helper, pubrel2_packet, pubcomp2_packet, "pubcomp2 receive")
 
     rc = 0
 finally:
diff --git a/test/broker/15-persist-client-msg-in-v5-0.py b/test/broker/15-persist-client-msg-in-v5-0.py
new file mode 100755
index 00000000..ea0929e2
--- /dev/null
+++ b/test/broker/15-persist-client-msg-in-v5-0.py
@@ -0,0 +1,92 @@
+#!/usr/bin/env python3
+
+# Connect a client, start a QoS 2 flow, disconnect, restore, carry on with the
+# QoS 2 flow. Is it received?
+
+from mosq_test_helper import *
+import persist_help
+
+port = mosq_test.get_port()
+conf_file = os.path.basename(__file__).replace('.py', '.conf')
+persist_help.write_config(conf_file, port)
+
+rc = 1
+
+persist_help.init(port)
+
+client_id = "persist-client-msg-in-v5-0"
+proto_ver = 5
+
+helper_id = "persist-client-msg-in-v5-0-helper"
+topic = "client-msg-in/2"
+qos = 2
+
+connect_props = mqtt5_props.gen_uint32_prop(mqtt5_props.PROP_SESSION_EXPIRY_INTERVAL, 60)
+connect_packet = mosq_test.gen_connect(client_id, proto_ver=proto_ver, clean_session=False, properties=connect_props)
+connack_packet1 = mosq_test.gen_connack(rc=0, proto_ver=proto_ver)
+connack_packet2 = mosq_test.gen_connack(rc=0, flags=1, proto_ver=proto_ver)
+
+mid = 1
+publish1_packet = mosq_test.gen_publish(topic=topic, qos=qos, payload="message1", mid=mid, proto_ver=proto_ver)
+pubrec1_packet = mosq_test.gen_pubrec(mid=mid, proto_ver=proto_ver)
+pubrel1_packet = mosq_test.gen_pubrel(mid=mid, proto_ver=proto_ver)
+pubcomp1_packet = mosq_test.gen_pubcomp(mid=mid, proto_ver=proto_ver)
+
+mid = 2
+publish2_packet = mosq_test.gen_publish(topic=topic, qos=qos, payload="message2", mid=mid, proto_ver=proto_ver)
+pubrec2_packet = mosq_test.gen_pubrec(mid=mid, proto_ver=proto_ver)
+pubrel2_packet = mosq_test.gen_pubrel(mid=mid, proto_ver=proto_ver)
+pubcomp2_packet = mosq_test.gen_pubcomp(mid=mid, proto_ver=proto_ver)
+
+connect_packet_helper = mosq_test.gen_connect(helper_id, proto_ver=proto_ver, clean_session=True)
+subscribe_packet = mosq_test.gen_subscribe(mid, topic, qos=qos, proto_ver=proto_ver)
+suback_packet = mosq_test.gen_suback(mid=mid, qos=qos, proto_ver=proto_ver)
+
+broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=True, port=port)
+
+con = None
+try:
+    # Connect client, start flow, disconnect
+    sock = mosq_test.do_client_connect(connect_packet, connack_packet1, timeout=5, port=port, connack_error="connack 1")
+    mosq_test.do_send_receive(sock, publish1_packet, pubrec1_packet, "pubrec1 send")
+    mosq_test.do_send_receive(sock, publish2_packet, pubrec2_packet, "pubrec2 send")
+    sock.close()
+
+    # Kill broker
+    broker.terminate()
+    broker.wait()
+
+    # Restart broker
+    broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=True, port=port)
+
+    # Connect helper and subscribe
+    helper = mosq_test.do_client_connect(connect_packet_helper, connack_packet1, timeout=5, port=port, connack_error="helper connack")
+    mosq_test.do_send_receive(helper, subscribe_packet, suback_packet, "suback helper")
+
+    # Complete the flow
+    sock = mosq_test.do_client_connect(connect_packet, connack_packet2, timeout=5, port=port, connack_error="connack 2")
+    mosq_test.do_send_receive(sock, pubrel1_packet, pubcomp1_packet, "pubrel1 send")
+    mosq_test.do_send_receive(sock, pubrel2_packet, pubcomp2_packet, "pubrel2 send")
+
+    mosq_test.expect_packet(helper, "publish1 receive", publish1_packet)
+    mosq_test.expect_packet(helper, "publish2 receive", publish2_packet)
+    helper.send(pubrec1_packet)
+    mosq_test.do_receive_send(helper, pubrel1_packet, pubcomp1_packet, "pubcomp1 receive")
+
+    helper.send(pubrec2_packet)
+    mosq_test.do_receive_send(helper, pubrel2_packet, pubcomp2_packet, "pubcomp2 receive")
+
+    rc = 0
+finally:
+    if broker is not None:
+        broker.terminate()
+        broker.wait()
+        (stdo, stde) = broker.communicate()
+    os.remove(conf_file)
+    rc += persist_help.cleanup(port)
+
+    if rc:
+        print(stde.decode('utf-8'))
+
+
+exit(rc)
diff --git a/test/broker/15-persist-client-msg-out-queue-v3-1-1.py b/test/broker/15-persist-client-msg-out-queue-v3-1-1.py
new file mode 100755
index 00000000..4b43b6ae
--- /dev/null
+++ b/test/broker/15-persist-client-msg-out-queue-v3-1-1.py
@@ -0,0 +1,102 @@
+#!/usr/bin/env python3
+
+# Connect a client, add a subscription, disconnect, send a message with a
+# different client, restore, reconnect, check it is received.
+
+from mosq_test_helper import *
+import persist_help
+
+port = mosq_test.get_port()
+conf_file = os.path.basename(__file__).replace('.py', '.conf')
+persist_help.write_config(conf_file, port)
+
+rc = 1
+
+persist_help.init(port)
+
+keepalive = 10
+client_id = "persist-client-msg-v3-1-1"
+proto_ver = 4
+
+helper_id = "persist-client-msg-v3-1-1-helper"
+topic0 = "client-msg/0"
+topic1 = "client-msg/1"
+topic2 = "client-msg/2"
+
+connect_packet = mosq_test.gen_connect(client_id, keepalive=keepalive, proto_ver=proto_ver, clean_session=False)
+connack_packet1 = mosq_test.gen_connack(rc=0, proto_ver=proto_ver)
+connack_packet2 = mosq_test.gen_connack(rc=0, flags=1, proto_ver=proto_ver)
+mid = 1
+subscribe_packet0 = mosq_test.gen_subscribe(mid, topic0, qos=0, proto_ver=proto_ver)
+suback_packet0 = mosq_test.gen_suback(mid=mid, qos=0, proto_ver=proto_ver)
+subscribe_packet1 = mosq_test.gen_subscribe(mid, topic1, qos=1, proto_ver=proto_ver)
+suback_packet1 = mosq_test.gen_suback(mid=mid, qos=1, proto_ver=proto_ver)
+subscribe_packet2 = mosq_test.gen_subscribe(mid, topic2, qos=2, proto_ver=proto_ver)
+suback_packet2 = mosq_test.gen_suback(mid=mid, qos=2, proto_ver=proto_ver)
+
+connect_packet_helper = mosq_test.gen_connect(helper_id, keepalive=keepalive, proto_ver=proto_ver, clean_session=True)
+publish_packet0 = mosq_test.gen_publish(topic=topic0, qos=0, payload="message", proto_ver=proto_ver)
+mid = 1
+publish_packet1 = mosq_test.gen_publish(topic=topic1, qos=1, payload="message", mid=mid, proto_ver=proto_ver)
+puback_packet = mosq_test.gen_puback(mid=mid, proto_ver=proto_ver)
+mid = 2
+publish_packet2 = mosq_test.gen_publish(topic=topic2, qos=2, payload="message", mid=mid, proto_ver=proto_ver)
+pubrec_packet = mosq_test.gen_pubrec(mid=mid, proto_ver=proto_ver)
+pubrel_packet = mosq_test.gen_pubrel(mid=mid, proto_ver=proto_ver)
+pubcomp_packet = mosq_test.gen_pubcomp(mid=mid, proto_ver=proto_ver)
+
+
+broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=True, port=port)
+
+con = None
+try:
+    # Connect client, subscribe, disconnect
+    sock = mosq_test.do_client_connect(connect_packet, connack_packet1, timeout=5, port=port)
+    mosq_test.do_send_receive(sock, subscribe_packet0, suback_packet0, "suback 0")
+    mosq_test.do_send_receive(sock, subscribe_packet1, suback_packet1, "suback 1")
+    mosq_test.do_send_receive(sock, subscribe_packet2, suback_packet2, "suback 2")
+    sock.close()
+
+    # Connect helper and publish
+    helper = mosq_test.do_client_connect(connect_packet_helper, connack_packet1, timeout=5, port=port)
+    helper.send(publish_packet0)
+    mosq_test.do_send_receive(helper, publish_packet1, puback_packet, "puback helper")
+    mosq_test.do_send_receive(helper, publish_packet2, pubrec_packet, "pubrec helper")
+    mosq_test.do_send_receive(helper, pubrel_packet, pubcomp_packet, "pubcomp helper")
+    helper.close()
+
+    # Kill broker
+    broker.terminate()
+    broker.wait()
+
+    # Restart broker
+    broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=True, port=port)
+
+    # Connect client again, it should have a session
+    sock = mosq_test.do_client_connect(connect_packet, connack_packet2, timeout=5, port=port)
+
+    # Does the client get the messages
+    mosq_test.do_receive_send(sock, publish_packet1, puback_packet, "publish 1")
+    mosq_test.do_receive_send(sock, publish_packet2, pubrec_packet, "publish 2")
+    mosq_test.do_receive_send(sock, pubrel_packet, pubcomp_packet, "pubrel 2")
+    sock.close()
+
+    # Connect client again, it should have a session
+    sock = mosq_test.do_client_connect(connect_packet, connack_packet2, timeout=5, port=port)
+    # If there are messages, the ping will fail
+    mosq_test.do_ping(sock)
+
+    rc = 0
+finally:
+    if broker is not None:
+        broker.terminate()
+        broker.wait()
+        (stdo, stde) = broker.communicate()
+    os.remove(conf_file)
+    rc += persist_help.cleanup(port)
+
+    if rc:
+        print(stde.decode('utf-8'))
+
+
+exit(rc)
diff --git a/test/broker/15-persist-client-msg-out-v5-0.py b/test/broker/15-persist-client-msg-out-v5-0.py
new file mode 100755
index 00000000..301ebc5c
--- /dev/null
+++ b/test/broker/15-persist-client-msg-out-v5-0.py
@@ -0,0 +1,102 @@
+#!/usr/bin/env python3
+
+# Connect a client, add a subscription, disconnect, send a message with a
+# different client, restore, reconnect, check it is received.
+
+from mosq_test_helper import *
+import persist_help
+
+port = mosq_test.get_port()
+conf_file = os.path.basename(__file__).replace('.py', '.conf')
+persist_help.write_config(conf_file, port)
+
+rc = 1
+
+persist_help.init(port)
+
+client_id = "persist-client-msg-v5-0"
+proto_ver = 5
+
+helper_id = "persist-client-msg-v5-0-helper"
+topic0 = "client-msg/0"
+topic1 = "client-msg/1"
+topic2 = "client-msg/2"
+
+connect_props = mqtt5_props.gen_uint32_prop(mqtt5_props.PROP_SESSION_EXPIRY_INTERVAL, 60)
+connect_packet = mosq_test.gen_connect(client_id, proto_ver=proto_ver, clean_session=False, properties=connect_props)
+connack_packet1 = mosq_test.gen_connack(rc=0, proto_ver=proto_ver)
+connack_packet2 = mosq_test.gen_connack(rc=0, flags=1, proto_ver=proto_ver)
+mid = 1
+subscribe_packet0 = mosq_test.gen_subscribe(mid, topic0, qos=0, proto_ver=proto_ver)
+suback_packet0 = mosq_test.gen_suback(mid=mid, qos=0, proto_ver=proto_ver)
+subscribe_packet1 = mosq_test.gen_subscribe(mid, topic1, qos=1, proto_ver=proto_ver)
+suback_packet1 = mosq_test.gen_suback(mid=mid, qos=1, proto_ver=proto_ver)
+subscribe_packet2 = mosq_test.gen_subscribe(mid, topic2, qos=2, proto_ver=proto_ver)
+suback_packet2 = mosq_test.gen_suback(mid=mid, qos=2, proto_ver=proto_ver)
+
+connect_packet_helper = mosq_test.gen_connect(helper_id, proto_ver=proto_ver, clean_session=True)
+publish_packet0 = mosq_test.gen_publish(topic=topic0, qos=0, payload="message", proto_ver=proto_ver)
+mid = 1
+publish_packet1 = mosq_test.gen_publish(topic=topic1, qos=1, payload="message", mid=mid, proto_ver=proto_ver)
+puback_packet = mosq_test.gen_puback(mid=mid, proto_ver=proto_ver)
+mid = 2
+publish_packet2 = mosq_test.gen_publish(topic=topic2, qos=2, payload="message", mid=mid, proto_ver=proto_ver)
+pubrec_packet = mosq_test.gen_pubrec(mid=mid, proto_ver=proto_ver)
+pubrel_packet = mosq_test.gen_pubrel(mid=mid, proto_ver=proto_ver)
+pubcomp_packet = mosq_test.gen_pubcomp(mid=mid, proto_ver=proto_ver)
+
+
+broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=True, port=port)
+
+con = None
+try:
+    # Connect client, subscribe, disconnect
+    sock = mosq_test.do_client_connect(connect_packet, connack_packet1, timeout=5, port=port, connack_error="connack 1")
+    mosq_test.do_send_receive(sock, subscribe_packet0, suback_packet0, "suback 0")
+    mosq_test.do_send_receive(sock, subscribe_packet1, suback_packet1, "suback 1")
+    mosq_test.do_send_receive(sock, subscribe_packet2, suback_packet2, "suback 2")
+    sock.close()
+
+    # Connect helper and publish
+    helper = mosq_test.do_client_connect(connect_packet_helper, connack_packet1, timeout=5, port=port, connack_error="helper connack")
+    helper.send(publish_packet0)
+    mosq_test.do_send_receive(helper, publish_packet1, puback_packet, "puback helper")
+    mosq_test.do_send_receive(helper, publish_packet2, pubrec_packet, "pubrec helper")
+    mosq_test.do_send_receive(helper, pubrel_packet, pubcomp_packet, "pubcomp helper")
+    helper.close()
+
+    # Kill broker
+    broker.terminate()
+    broker.wait()
+
+    # Restart broker
+    broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=True, port=port)
+
+    # Connect client again, it should have a session
+    sock = mosq_test.do_client_connect(connect_packet, connack_packet2, timeout=5, port=port, connack_error="connack 2")
+
+    # Does the client get the messages
+    mosq_test.do_receive_send(sock, publish_packet1, puback_packet, "publish 1")
+    mosq_test.do_receive_send(sock, publish_packet2, pubrec_packet, "publish 2")
+    mosq_test.do_receive_send(sock, pubrel_packet, pubcomp_packet, "pubrel 2")
+    sock.close()
+
+    # Connect client again, it should have a session
+    sock = mosq_test.do_client_connect(connect_packet, connack_packet2, timeout=5, port=port, connack_error="connack 3")
+    # If there are messages, the ping will fail
+    mosq_test.do_ping(sock)
+
+    rc = 0
+finally:
+    if broker is not None:
+        broker.terminate()
+        broker.wait()
+        (stdo, stde) = broker.communicate()
+    os.remove(conf_file)
+    rc += persist_help.cleanup(port)
+
+    if rc:
+        print(stde.decode('utf-8'))
+
+
+exit(rc)
diff --git a/test/broker/15-persist-client-v3-1-1.conf b/test/broker/15-persist-client-v3-1-1.conf
new file mode 100644
index 00000000..e69de29b
diff --git a/test/broker/15-persist-client-v5.0.py b/test/broker/15-persist-client-v5.0.py
new file mode 100755
index 00000000..3eeadeb5
--- /dev/null
+++ b/test/broker/15-persist-client-v5.0.py
@@ -0,0 +1,83 @@
+#!/usr/bin/env python3
+
+# Connect a client, check it is restored, clear the client, check it is not there.
+
+from mosq_test_helper import *
+import persist_help
+
+port = mosq_test.get_port()
+conf_file = os.path.basename(__file__).replace('.py', '.conf')
+persist_help.write_config(conf_file, port)
+
+rc = 1
+
+persist_help.init(port)
+
+keepalive = 10
+client_id = "persist-client-v5-0"
+proto_ver = 5
+
+connect_props = mqtt5_props.gen_uint32_prop(mqtt5_props.PROP_SESSION_EXPIRY_INTERVAL, 60)
+connect_packet = mosq_test.gen_connect(client_id, keepalive=keepalive, proto_ver=proto_ver, clean_session=False, properties=connect_props)
+connack_packet1 = mosq_test.gen_connack(rc=0, proto_ver=proto_ver)
+connack_packet2 = mosq_test.gen_connack(rc=0, flags=1, proto_ver=proto_ver)
+
+connect_packet_clean = mosq_test.gen_connect(client_id, keepalive=keepalive, proto_ver=proto_ver, clean_session=True)
+
+broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=True, port=port)
+
+con = None
+try:
+    # Connect client
+    sock = mosq_test.do_client_connect(connect_packet, connack_packet1, timeout=5, port=port, connack_error="connack 1")
+    mosq_test.do_ping(sock)
+    sock.close()
+
+    # Kill broker
+    broker.terminate()
+    broker.wait()
+
+    # Restart broker
+    broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=True, port=port)
+
+    # Connect client again, it should have a session
+    sock = mosq_test.do_client_connect(connect_packet, connack_packet2, timeout=5, port=port, connack_error="connack 2")
+    mosq_test.do_ping(sock)
+    sock.close()
+
+    # Clear the client
+    sock = mosq_test.do_client_connect(connect_packet_clean, connack_packet1, timeout=5, port=port, connack_error="connack 3")
+    mosq_test.do_ping(sock)
+    sock.close()
+
+    # Connect client, it should not have a session
+    sock = mosq_test.do_client_connect(connect_packet_clean, connack_packet1, timeout=5, port=port, connack_error="connack 4")
+    mosq_test.do_ping(sock)
+    sock.close()
+
+    # Kill broker
+    broker.terminate()
+    broker.wait()
+
+    # Restart broker
+    broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=True, port=port)
+
+    # Connect client, it should not have a session
+    sock = mosq_test.do_client_connect(connect_packet_clean, connack_packet1, timeout=5, port=port, connack_error="connack 5")
+    mosq_test.do_ping(sock)
+    sock.close()
+
+    rc = 0
+finally:
+    if broker is not None:
+        broker.terminate()
+        broker.wait()
+        (stdo, stde) = broker.communicate()
+    os.remove(conf_file)
+    rc += persist_help.cleanup(port)
+
+    if rc:
+        print(stde.decode('utf-8'))
+
+
+exit(rc)
diff --git a/test/broker/15-persist-publish-properties-v5-0.py b/test/broker/15-persist-publish-properties-v5-0.py
new file mode 100755
index 00000000..aff97b73
--- /dev/null
+++ b/test/broker/15-persist-publish-properties-v5-0.py
@@ -0,0 +1,86 @@
+#!/usr/bin/env python3
+
+# Publish a retained messages, check they are restored, with properties attached
+
+from mosq_test_helper import *
+import persist_help
+
+port = mosq_test.get_port()
+conf_file = os.path.basename(__file__).replace('.py', '.conf')
+persist_help.write_config(conf_file, port)
+
+rc = 1
+
+persist_help.init(port)
+
+topic = "test/retainprop"
+source_id = "persist-retain-properties-v5-0"
+qos = 0
+proto_ver = 5
+connect_packet = mosq_test.gen_connect(source_id, proto_ver=proto_ver, clean_session=True)
+connack_packet = mosq_test.gen_connack(rc=0, proto_ver=proto_ver)
+
+props = mqtt5_props.gen_byte_prop(mqtt5_props.PROP_PAYLOAD_FORMAT_INDICATOR, 1)
+props += mqtt5_props.gen_string_prop(mqtt5_props.PROP_CONTENT_TYPE, "plain/text")
+props += mqtt5_props.gen_string_prop(mqtt5_props.PROP_RESPONSE_TOPIC, "/dev/null")
+#props += mqtt5_props.gen_string_prop(mqtt5_props.PROP_CORRELATION_DATA, "2357289375902345")
+props += mqtt5_props.gen_string_pair_prop(mqtt5_props.PROP_USER_PROPERTY, "name", "value")
+props += mqtt5_props.gen_string_pair_prop(mqtt5_props.PROP_USER_PROPERTY, "name", "value")
+props += mqtt5_props.gen_string_pair_prop(mqtt5_props.PROP_USER_PROPERTY, "name", "value")
+props += mqtt5_props.gen_string_pair_prop(mqtt5_props.PROP_USER_PROPERTY, "name", "value")
+publish_packet = mosq_test.gen_publish(topic, qos=qos, payload="retained message 1", retain=True, proto_ver=proto_ver, properties=props)
+
+mid = 1
+subscribe_packet = mosq_test.gen_subscribe(mid, "test/retainprop", 0, proto_ver=proto_ver)
+suback_packet = mosq_test.gen_suback(mid, qos=0, proto_ver=proto_ver)
+
+mid = 2
+unsubscribe_packet = mosq_test.gen_unsubscribe(mid, "test/retainprop", proto_ver=proto_ver)
+unsuback_packet = mosq_test.gen_unsuback(mid, proto_ver=proto_ver)
+
+broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=True, port=port)
+
+try:
+    # Connect client
+    sock = mosq_test.do_client_connect(connect_packet, connack_packet, timeout=5, port=port)
+    # Check no retained messages exist
+    mosq_test.do_send_receive(sock, subscribe_packet, suback_packet, "suback")
+    # Ping will fail if a PUBLISH is received
+    mosq_test.do_ping(sock)
+    # Unsubscribe, so we don't receive the messages
+    mosq_test.do_send_receive(sock, unsubscribe_packet, unsuback_packet, "unsuback")
+
+    # Send some retained messages
+    sock.send(publish_packet)
+    mosq_test.do_ping(sock)
+    sock.close()
+
+    # Kill broker
+    broker.terminate()
+    broker.wait()
+
+    # Restart broker
+    broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=True, port=port)
+
+    # Connect client
+    sock = mosq_test.do_client_connect(connect_packet, connack_packet, timeout=5, port=port)
+    # Subscribe
+    mosq_test.do_send_receive(sock, subscribe_packet, suback_packet, "suback")
+    # Check retained messages exist
+    mosq_test.expect_packet(sock, "publish", publish_packet)
+    mosq_test.do_ping(sock)
+
+    rc = 0
+finally:
+    if broker is not None:
+        broker.terminate()
+        broker.wait()
+        (stdo, stde) = broker.communicate()
+    os.remove(conf_file)
+    rc += persist_help.cleanup(port)
+
+    if rc:
+        print(stde.decode('utf-8'))
+
+
+exit(rc)
diff --git a/test/broker/15-persist-retain-v5-0.py b/test/broker/15-persist-retain-v5-0.py
new file mode 100755
index 00000000..c33911d4
--- /dev/null
+++ b/test/broker/15-persist-retain-v5-0.py
@@ -0,0 +1,88 @@
+#!/usr/bin/env python3
+
+# Publish a retained messages, check they are restored
+
+from mosq_test_helper import *
+import persist_help
+
+port = mosq_test.get_port()
+conf_file = os.path.basename(__file__).replace('.py', '.conf')
+persist_help.write_config(conf_file, port)
+
+rc = 1
+
+persist_help.init(port)
+
+topic1 = "test/retain1"
+topic2 = "test/retain2"
+topic3 = "test/retain3"
+source_id = "persist-retain-v5-0"
+qos = 0
+payload2 = "retained message 2"
+payload3 = "retained message 3"
+proto_ver = 5
+connect_packet = mosq_test.gen_connect(source_id, proto_ver=proto_ver, clean_session=True)
+connack_packet = mosq_test.gen_connack(rc=0, proto_ver=proto_ver)
+
+publish1_packet = mosq_test.gen_publish(topic1, qos=qos, payload="retained message 1", retain=True, proto_ver=proto_ver)
+publish2_packet = mosq_test.gen_publish(topic2, qos=qos, payload=payload2, retain=False, proto_ver=proto_ver)
+publish3_packet = mosq_test.gen_publish(topic3, qos=qos, payload=payload3, retain=True, proto_ver=proto_ver)
+
+mid = 1
+subscribe_packet = mosq_test.gen_subscribe(mid, "#", 0, proto_ver=proto_ver)
+suback_packet = mosq_test.gen_suback(mid, qos=0, proto_ver=proto_ver)
+
+mid = 2
+unsubscribe_packet = mosq_test.gen_unsubscribe(mid, "#", proto_ver=proto_ver)
+unsuback_packet = mosq_test.gen_unsuback(mid, proto_ver=proto_ver)
+
+broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=True, port=port)
+
+try:
+    # Connect client
+    sock = mosq_test.do_client_connect(connect_packet, connack_packet, timeout=5, port=port)
+    # Check no retained messages exist
+    mosq_test.do_send_receive(sock, subscribe_packet, suback_packet, "suback")
+    # Ping will fail if a PUBLISH is received
+    mosq_test.do_ping(sock)
+    # Unsubscribe, so we don't receive the messages
+    mosq_test.do_send_receive(sock, unsubscribe_packet, unsuback_packet, "unsuback")
+
+    # Send some retained messages
+    sock.send(publish1_packet)
+    mosq_test.do_ping(sock)
+    sock.send(publish2_packet) # Not retained
+    mosq_test.do_ping(sock)
+    sock.send(publish3_packet)
+    mosq_test.do_ping(sock)
+    sock.close()
+
+    # Kill broker
+    broker.terminate()
+    broker.wait()
+
+    # Restart broker
+    broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=True, port=port)
+
+    # Connect client
+    sock = mosq_test.do_client_connect(connect_packet, connack_packet, timeout=5, port=port)
+    # Subscribe
+    mosq_test.do_send_receive(sock, subscribe_packet, suback_packet, "suback")
+    # Check retained messages exist
+    mosq_test.receive_unordered(sock, publish1_packet, publish3_packet, "publish 1 / 3")
+    mosq_test.do_ping(sock)
+
+    rc = 0
+finally:
+    if broker is not None:
+        broker.terminate()
+        broker.wait()
+        (stdo, stde) = broker.communicate()
+    os.remove(conf_file)
+    rc += persist_help.cleanup(port)
+
+    if rc:
+        print(stde.decode('utf-8'))
+
+
+exit(rc)
diff --git a/test/broker/15-persist-subscription-v3-1-1.py b/test/broker/15-persist-subscription-v3-1-1.py
index 7ac7ecd4..748a2ea1 100755
--- a/test/broker/15-persist-subscription-v3-1-1.py
+++ b/test/broker/15-persist-subscription-v3-1-1.py
@@ -6,6 +6,18 @@
 from mosq_test_helper import *
 import persist_help
 
+def helper(port, packets):
+    helper_id = "persist-subscription-v3-1-1-helper"
+    connect_packet_helper = mosq_test.gen_connect(helper_id, proto_ver=4, clean_session=True)
+
+    # Connect helper and publish
+    helper = mosq_test.do_client_connect(connect_packet_helper, packets["connack1"], timeout=5, port=port)
+    helper.send(packets["publish0"])
+    mosq_test.do_send_receive(helper, packets["publish1"], packets["puback1"], "puback helper")
+    mosq_test.do_send_receive(helper, packets["publish2"], packets["pubrec2"], "pubrec helper")
+    mosq_test.do_send_receive(helper, packets["pubrel2"], packets["pubcomp2"], "pubcomp helper")
+    helper.close()
+
 port = mosq_test.get_port()
 conf_file = os.path.basename(__file__).replace('.py', '.conf')
 persist_help.write_config(conf_file, port)
@@ -17,35 +29,34 @@ persist_help.init(port)
 client_id = "persist-subscription-v3-1-1"
 proto_ver = 4
 
-helper_id = "persist-subscription-v3-1-1-helper"
 topic0 = "subscription/0"
 topic1 = "subscription/1"
 topic2 = "subscription/2"
 
-connect_packet = mosq_test.gen_connect(client_id, proto_ver=proto_ver, clean_session=False)
-connack_packet1 = mosq_test.gen_connack(rc=0, proto_ver=proto_ver)
-connack_packet2 = mosq_test.gen_connack(rc=0, flags=1, proto_ver=proto_ver)
+packets = {}
+packets["connect"] = mosq_test.gen_connect(client_id, proto_ver=proto_ver, clean_session=False)
+packets["connack1"] = mosq_test.gen_connack(rc=0, proto_ver=proto_ver)
+packets["connack2"] = mosq_test.gen_connack(rc=0, flags=1, proto_ver=proto_ver)
 mid = 1
-subscribe_packet0 = mosq_test.gen_subscribe(mid, topic0, qos=0, proto_ver=proto_ver)
-suback_packet0 = mosq_test.gen_suback(mid=mid, qos=0, proto_ver=proto_ver)
-subscribe_packet1 = mosq_test.gen_subscribe(mid, topic1, qos=1, proto_ver=proto_ver)
-suback_packet1 = mosq_test.gen_suback(mid=mid, qos=1, proto_ver=proto_ver)
-subscribe_packet2 = mosq_test.gen_subscribe(mid, topic2, qos=2, proto_ver=proto_ver)
-suback_packet2 = mosq_test.gen_suback(mid=mid, qos=2, proto_ver=proto_ver)
+packets["subscribe0"] = mosq_test.gen_subscribe(mid, topic0, qos=0, proto_ver=proto_ver)
+packets["suback0"] = mosq_test.gen_suback(mid=mid, qos=0, proto_ver=proto_ver)
+packets["subscribe1"] = mosq_test.gen_subscribe(mid, topic1, qos=1, proto_ver=proto_ver)
+packets["suback1"] = mosq_test.gen_suback(mid=mid, qos=1, proto_ver=proto_ver)
+packets["subscribe2"] = mosq_test.gen_subscribe(mid, topic2, qos=2, proto_ver=proto_ver)
+packets["suback2"] = mosq_test.gen_suback(mid=mid, qos=2, proto_ver=proto_ver)
 
-unsubscribe_packet2 = mosq_test.gen_unsubscribe(mid, topic2, proto_ver=proto_ver)
-unsuback_packet2 = mosq_test.gen_unsuback(mid=mid, proto_ver=proto_ver)
+packets["unsubscribe2"] = mosq_test.gen_unsubscribe(mid, topic2, proto_ver=proto_ver)
+packets["unsuback2"] = mosq_test.gen_unsuback(mid=mid, proto_ver=proto_ver)
 
-connect_packet_helper = mosq_test.gen_connect(helper_id, proto_ver=proto_ver, clean_session=True)
-publish_packet0 = mosq_test.gen_publish(topic=topic0, qos=0, payload="message", proto_ver=proto_ver)
+packets["publish0"] = mosq_test.gen_publish(topic=topic0, qos=0, payload="message", proto_ver=proto_ver)
 mid = 1
-publish_packet1 = mosq_test.gen_publish(topic=topic1, qos=1, payload="message", mid=mid, proto_ver=proto_ver)
-puback_packet = mosq_test.gen_puback(mid=mid, proto_ver=proto_ver)
+packets["publish1"] = mosq_test.gen_publish(topic=topic1, qos=1, payload="message", mid=mid, proto_ver=proto_ver)
+packets["puback1"] = mosq_test.gen_puback(mid=mid, proto_ver=proto_ver)
 mid = 2
-publish_packet2 = mosq_test.gen_publish(topic=topic2, qos=2, payload="message", mid=mid, proto_ver=proto_ver)
-pubrec_packet = mosq_test.gen_pubrec(mid=mid, proto_ver=proto_ver)
-pubrel_packet = mosq_test.gen_pubrel(mid=mid, proto_ver=proto_ver)
-pubcomp_packet = mosq_test.gen_pubcomp(mid=mid, proto_ver=proto_ver)
+packets["publish2"] = mosq_test.gen_publish(topic=topic2, qos=2, payload="message", mid=mid, proto_ver=proto_ver)
+packets["pubrec2"] = mosq_test.gen_pubrec(mid=mid, proto_ver=proto_ver)
+packets["pubrel2"] = mosq_test.gen_pubrel(mid=mid, proto_ver=proto_ver)
+packets["pubcomp2"] = mosq_test.gen_pubcomp(mid=mid, proto_ver=proto_ver)
 
 
 broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=True, port=port)
@@ -53,10 +64,10 @@ broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=Tr
 con = None
 try:
     # Connect client
-    sock = mosq_test.do_client_connect(connect_packet, connack_packet1, timeout=5, port=port)
-    mosq_test.do_send_receive(sock, subscribe_packet0, suback_packet0, "suback 0")
-    mosq_test.do_send_receive(sock, subscribe_packet1, suback_packet1, "suback 1")
-    mosq_test.do_send_receive(sock, subscribe_packet2, suback_packet2, "suback 2")
+    sock = mosq_test.do_client_connect(packets["connect"], packets["connack1"], timeout=5, port=port)
+    mosq_test.do_send_receive(sock, packets["subscribe0"], packets["suback0"], "suback 0")
+    mosq_test.do_send_receive(sock, packets["subscribe1"], packets["suback1"], "suback 1")
+    mosq_test.do_send_receive(sock, packets["subscribe2"], packets["suback2"], "suback 2")
     sock.close()
 
     # Kill broker
@@ -67,25 +78,19 @@ try:
     broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=True, port=port)
 
     # Connect client again, it should have a session
-    sock = mosq_test.do_client_connect(connect_packet, connack_packet2, timeout=5, port=port)
+    sock = mosq_test.do_client_connect(packets["connect"], packets["connack2"], timeout=5, port=port)
     mosq_test.do_ping(sock)
 
-    # Connect helper and publish
-    helper = mosq_test.do_client_connect(connect_packet_helper, connack_packet1, timeout=5, port=port)
-    helper.send(publish_packet0)
-    mosq_test.do_send_receive(helper, publish_packet1, puback_packet, "puback helper")
-    mosq_test.do_send_receive(helper, publish_packet2, pubrec_packet, "pubrec helper")
-    mosq_test.do_send_receive(helper, pubrel_packet, pubcomp_packet, "pubcomp helper")
-    helper.close()
+    helper(port, packets)
 
     # Does the client get the messages
-    mosq_test.expect_packet(sock, "publish 0", publish_packet0)
-    mosq_test.do_receive_send(sock, publish_packet1, puback_packet, "publish 1")
-    mosq_test.do_receive_send(sock, publish_packet2, pubrec_packet, "publish 2")
-    mosq_test.do_receive_send(sock, pubrel_packet, pubcomp_packet, "pubrel 2")
+    mosq_test.expect_packet(sock, "publish 0", packets["publish0"])
+    mosq_test.do_receive_send(sock, packets["publish1"], packets["puback1"], "publish 1")
+    mosq_test.do_receive_send(sock, packets["publish2"], packets["pubrec2"], "publish 2")
+    mosq_test.do_receive_send(sock, packets["pubrel2"], packets["pubcomp2"], "pubrel 2")
 
     # Unsubscribe
-    mosq_test.do_send_receive(sock, unsubscribe_packet2, unsuback_packet2, "unsuback 2")
+    mosq_test.do_send_receive(sock, packets["unsubscribe2"], packets["unsuback2"], "unsuback 2")
     sock.close()
 
     # Kill broker
@@ -96,20 +101,15 @@ try:
     broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=True, port=port)
 
     # Connect client again, it should have a session
-    sock = mosq_test.do_client_connect(connect_packet, connack_packet2, timeout=5, port=port)
+    sock = mosq_test.do_client_connect(packets["connect"], packets["connack2"], timeout=5, port=port)
     mosq_test.do_ping(sock)
 
     # Connect helper and publish
-    helper = mosq_test.do_client_connect(connect_packet_helper, connack_packet1, timeout=5, port=port)
-    helper.send(publish_packet0)
-    mosq_test.do_send_receive(helper, publish_packet1, puback_packet, "puback helper")
-    mosq_test.do_send_receive(helper, publish_packet2, pubrec_packet, "pubrec helper")
-    mosq_test.do_send_receive(helper, pubrel_packet, pubcomp_packet, "pubcomp helper")
-    helper.close()
+    helper(port, packets)
 
     # Does the client get the messages
-    mosq_test.expect_packet(sock, "publish 0", publish_packet0)
-    mosq_test.do_receive_send(sock, publish_packet1, puback_packet, "publish 1")
+    mosq_test.expect_packet(sock, "publish 0", packets["publish0"])
+    mosq_test.do_receive_send(sock, packets["publish1"], packets["puback1"], "publish 1")
     mosq_test.do_ping(sock)
 
     rc = 0
diff --git a/test/broker/15-persist-subscription-v5-0.py b/test/broker/15-persist-subscription-v5-0.py
new file mode 100755
index 00000000..67ad45b4
--- /dev/null
+++ b/test/broker/15-persist-subscription-v5-0.py
@@ -0,0 +1,139 @@
+#!/usr/bin/env python3
+
+# Connect a client, add a subscription, disconnect, restore, reconnect, send a
+# message with a different client, check it is received.
+
+from mosq_test_helper import *
+import persist_help
+
+def helper(port, packets):
+    helper_id = "persist-subscription-v5-0-helper"
+    connect_packet_helper = mosq_test.gen_connect(helper_id, proto_ver=5, clean_session=True)
+    connack_packet_helper = mosq_test.gen_connack(rc=0, proto_ver=5)
+
+    # Connect helper and publish
+    helper = mosq_test.do_client_connect(connect_packet_helper, connack_packet_helper, timeout=5, port=port, connack_error="helper connack")
+    helper.send(packets["publish0-helper"])
+    mosq_test.do_send_receive(helper, packets["publish1-helper"], packets["puback1"], "puback helper")
+    mosq_test.do_send_receive(helper, packets["publish2-helper"], packets["pubrec2"], "pubrec helper")
+    mosq_test.do_send_receive(helper, packets["pubrel2"], packets["pubcomp2"], "pubcomp helper")
+    helper.close()
+
+port = mosq_test.get_port()
+conf_file = os.path.basename(__file__).replace('.py', '.conf')
+persist_help.write_config(conf_file, port)
+
+rc = 1
+
+persist_help.init(port)
+
+client_id = "persist-subscription-v5-0"
+proto_ver = 5
+
+topic0 = "subscription/0"
+topic1 = "subscription/1"
+topic2 = "subscription/2"
+
+packets = {}
+connect_props = mqtt5_props.gen_uint32_prop(mqtt5_props.PROP_SESSION_EXPIRY_INTERVAL, 60)
+packets["connect"] = mosq_test.gen_connect(client_id, proto_ver=proto_ver, clean_session=False, properties=connect_props)
+packets["connack1"] = mosq_test.gen_connack(rc=0, proto_ver=proto_ver)
+packets["connack2"] = mosq_test.gen_connack(rc=0, flags=1, proto_ver=proto_ver)
+mid = 1
+
+publish_props0 = mqtt5_props.gen_varint_prop(mqtt5_props.PROP_SUBSCRIPTION_IDENTIFIER, 100)
+packets["subscribe0"] = mosq_test.gen_subscribe(mid, topic0, qos=0, proto_ver=proto_ver, properties=publish_props0)
+packets["suback0"] = mosq_test.gen_suback(mid=mid, qos=0, proto_ver=proto_ver)
+
+publish_props1 = mqtt5_props.gen_varint_prop(mqtt5_props.PROP_SUBSCRIPTION_IDENTIFIER, 101)
+packets["subscribe1"] = mosq_test.gen_subscribe(mid, topic1, qos=1, proto_ver=proto_ver, properties=publish_props1)
+packets["suback1"] = mosq_test.gen_suback(mid=mid, qos=1, proto_ver=proto_ver)
+
+publish_props2 = mqtt5_props.gen_varint_prop(mqtt5_props.PROP_SUBSCRIPTION_IDENTIFIER, 102)
+packets["subscribe2"] = mosq_test.gen_subscribe(mid, topic2, qos=2, proto_ver=proto_ver, properties=publish_props2)
+packets["suback2"] = mosq_test.gen_suback(mid=mid, qos=2, proto_ver=proto_ver)
+
+packets["unsubscribe2"] = mosq_test.gen_unsubscribe(mid, topic2, proto_ver=proto_ver)
+packets["unsuback2"] = mosq_test.gen_unsuback(mid=mid, proto_ver=proto_ver)
+
+packets["publish0-helper"] = mosq_test.gen_publish(topic=topic0, qos=0, payload="message", proto_ver=proto_ver)
+packets["publish0"] = mosq_test.gen_publish(topic=topic0, qos=0, payload="message", proto_ver=proto_ver, properties=publish_props0)
+mid = 1
+packets["publish1-helper"] = mosq_test.gen_publish(topic=topic1, qos=1, payload="message", mid=mid, proto_ver=proto_ver)
+packets["publish1"] = mosq_test.gen_publish(topic=topic1, qos=1, payload="message", mid=mid, proto_ver=proto_ver, properties=publish_props1)
+packets["puback1"] = mosq_test.gen_puback(mid=mid, proto_ver=proto_ver)
+mid = 2
+packets["publish2-helper"] = mosq_test.gen_publish(topic=topic2, qos=2, payload="message", mid=mid, proto_ver=proto_ver)
+packets["publish2"] = mosq_test.gen_publish(topic=topic2, qos=2, payload="message", mid=mid, proto_ver=proto_ver, properties=publish_props2)
+packets["pubrec2"] = mosq_test.gen_pubrec(mid=mid, proto_ver=proto_ver)
+packets["pubrel2"] = mosq_test.gen_pubrel(mid=mid, proto_ver=proto_ver)
+packets["pubcomp2"] = mosq_test.gen_pubcomp(mid=mid, proto_ver=proto_ver)
+
+
+broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=True, port=port)
+
+con = None
+try:
+    # Connect client
+    sock = mosq_test.do_client_connect(packets["connect"], packets["connack1"], timeout=5, port=port, connack_error="connack1")
+    mosq_test.do_send_receive(sock, packets["subscribe0"], packets["suback0"], "suback 0")
+    mosq_test.do_send_receive(sock, packets["subscribe1"], packets["suback1"], "suback 1")
+    mosq_test.do_send_receive(sock, packets["subscribe2"], packets["suback2"], "suback 2")
+    sock.close()
+
+    # Kill broker
+    broker.terminate()
+    broker.wait()
+
+    # Restart broker
+    broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=True, port=port)
+
+    # Connect client again, it should have a session
+    sock = mosq_test.do_client_connect(packets["connect"], packets["connack2"], timeout=5, port=port)
+    mosq_test.do_ping(sock)
+
+    helper(port, packets)
+
+    # Does the client get the messages
+    mosq_test.expect_packet(sock, "publish 0", packets["publish0"])
+    mosq_test.do_receive_send(sock, packets["publish1"], packets["puback1"], "publish 1")
+    mosq_test.do_receive_send(sock, packets["publish2"], packets["pubrec2"], "publish 2")
+    mosq_test.do_receive_send(sock, packets["pubrel2"], packets["pubcomp2"], "pubrel 2")
+
+    # Unsubscribe
+    mosq_test.do_send_receive(sock, packets["unsubscribe2"], packets["unsuback2"], "unsuback 2")
+    sock.close()
+
+    # Kill broker
+    broker.terminate()
+    broker.wait()
+
+    # Restart broker
+    broker = mosq_test.start_broker(filename=os.path.basename(__file__), use_conf=True, port=port)
+
+    # Connect client again, it should have a session
+    sock = mosq_test.do_client_connect(packets["connect"], packets["connack2"], timeout=5, port=port, connack_error="connack2")
+    mosq_test.do_ping(sock)
+
+    # Connect helper and publish
+    helper(port, packets)
+
+    # Does the client get the messages
+    mosq_test.expect_packet(sock, "publish 0", packets["publish0"])
+    mosq_test.do_receive_send(sock, packets["publish1"], packets["puback1"], "publish 1")
+    mosq_test.do_ping(sock)
+
+    rc = 0
+finally:
+    if broker is not None:
+        broker.terminate()
+        broker.wait()
+        (stdo, stde) = broker.communicate()
+    os.remove(conf_file)
+    rc += persist_help.cleanup(port)
+
+    if rc:
+        print(stde.decode('utf-8'))
+
+
+exit(rc)
diff --git a/test/broker/Makefile b/test/broker/Makefile
index cfb6ef1e..1005ef4c 100644
--- a/test/broker/Makefile
+++ b/test/broker/Makefile
@@ -253,11 +253,17 @@ endif
 endif
 
 15 :
-	./15-persist-client-v3-1-1.py
-	./15-persist-subscription-v3-1-1.py
-	./15-persist-retain-v3-1-1.py
-	./15-persist-client-msg-in-v3-1-1.py
-	./15-persist-client-msg-out-v3-1-1.py
+	#./15-persist-client-msg-in-v5-0.py
+	#./15-persist-client-msg-out-queue-v3-1-1.py
+	#./15-persist-client-msg-out-v3-1-1.py
+	#./15-persist-client-msg-out-v5-0.py
+	#./15-persist-client-v3-1-1.py
+	#./15-persist-client-v5.0.py
+	#./15-persist-publish-properties-v5-0.py
+	#./15-persist-retain-v3-1-1.py
+	#./15-persist-retain-v5-0.py
+	#./15-persist-subscription-v3-1-1.py
+	#./15-persist-subscription-v5-0.py
 
 16 :
 	./16-cmd-args.py
diff --git a/test/broker/test.py b/test/broker/test.py
index 71beb9e8..7ba45f4c 100755
--- a/test/broker/test.py
+++ b/test/broker/test.py
@@ -213,11 +213,17 @@ tests = [
     (1, './14-dynsec-role.py'),
     (1, './14-dynsec-role-invalid.py'),
 
-    #(1, './15-persist-client-msg-in-v3-1-1.py'),
+    #(1, './15-persist-client-msg-in-v5-0.py'),
+    #(1, './15-persist-client-msg-out-queue-v3-1-1.py'),
     #(1, './15-persist-client-msg-out-v3-1-1.py'),
+    #(1, './15-persist-client-msg-out-v5-0.py'),
     #(1, './15-persist-client-v3-1-1.py'),
+    #(1, './15-persist-client-v5.0.py'),
+    #(1, './15-persist-publish-properties-v5-0.py'),
     #(1, './15-persist-retain-v3-1-1.py'),
+    #(1, './15-persist-retain-v5-0.py'),
     #(1, './15-persist-subscription-v3-1-1.py'),
+    #(1, './15-persist-subscription-v5-0.py'),
 
     (1, './16-cmd-args.py'),
     (1, './16-config-includedir.py'),