diff --git a/ChangeLog.txt b/ChangeLog.txt
index d2e83a7f1c..f5fccfe8f7 100644
--- a/ChangeLog.txt
+++ b/ChangeLog.txt
@@ -31,6 +31,8 @@ Broker:
   only a single plugin can interact with a unique $CONTROL topic. Using
   multiple instances of the plugin would produce duplicate entries in the
   config file. Closes #2601. Closes #2470.
+- Fix case where expired messages were causing queued messages not to be
+  delivered. Closes #2609.
 
 Client library:
 - Fix threads library detection on Windows under cmake. Bumps the minimum
diff --git a/src/database.c b/src/database.c
index 21f9357d26..5e77a281d1 100644
--- a/src/database.c
+++ b/src/database.c
@@ -356,6 +356,22 @@ static void db__message_remove_from_inflight(struct mosquitto_msg_data *msg_data
 }
 
 
+static void db__message_remove_from_queued(struct mosquitto_msg_data *msg_data, struct mosquitto_client_msg *item)
+{
+	if(!msg_data || !item){
+		return;
+	}
+
+	DL_DELETE(msg_data->queued, item);
+	if(item->store){
+		db__msg_store_ref_dec(&item->store);
+	}
+
+	mosquitto_property_free_all(&item->properties);
+	mosquitto__free(item);
+}
+
+
 void db__message_dequeue_first(struct mosquitto *context, struct mosquitto_msg_data *msg_data)
 {
 	struct mosquitto_client_msg *msg;
@@ -1021,6 +1037,40 @@ int db__message_release_incoming(struct mosquitto *context, uint16_t mid)
 	}
 }
 
+
+void db__expire_all_messages(struct mosquitto *context)
+{
+	struct mosquitto_client_msg *msg, *tmp;
+
+	DL_FOREACH_SAFE(context->msgs_out.inflight, msg, tmp){
+		if(msg->store->message_expiry_time && db.now_real_s > msg->store->message_expiry_time){
+			if(msg->qos > 0){
+				util__increment_send_quota(context);
+			}
+			db__message_remove_from_inflight(&context->msgs_out, msg);
+		}
+	}
+	DL_FOREACH_SAFE(context->msgs_out.queued, msg, tmp){
+		if(msg->store->message_expiry_time && db.now_real_s > msg->store->message_expiry_time){
+			db__message_remove_from_queued(&context->msgs_out, msg);
+		}
+	}
+	DL_FOREACH_SAFE(context->msgs_in.inflight, msg, tmp){
+		if(msg->store->message_expiry_time && db.now_real_s > msg->store->message_expiry_time){
+			if(msg->qos > 0){
+				util__increment_receive_quota(context);
+			}
+			db__message_remove_from_inflight(&context->msgs_in, msg);
+		}
+	}
+	DL_FOREACH_SAFE(context->msgs_in.queued, msg, tmp){
+		if(msg->store->message_expiry_time && db.now_real_s > msg->store->message_expiry_time){
+			db__message_remove_from_queued(&context->msgs_in, msg);
+		}
+	}
+}
+
+
 static int db__message_write_inflight_out_single(struct mosquitto *context, struct mosquitto_client_msg *msg)
 {
 	mosquitto_property *cmsg_props = NULL, *store_props = NULL;
diff --git a/src/handle_connect.c b/src/handle_connect.c
index 790c88a2b0..21405adff7 100644
--- a/src/handle_connect.c
+++ b/src/handle_connect.c
@@ -318,6 +318,7 @@ int connect__on_authorised(struct mosquitto *context, void *auth_data_out, uint1
 	rc = send__connack(context, connect_ack, CONNACK_ACCEPTED, connack_props);
 	mosquitto_property_free_all(&connack_props);
 	if(rc) return rc;
+	db__expire_all_messages(context);
 	rc = db__message_write_queued_out(context);
 	if(rc) return rc;
 	rc = db__message_write_inflight_out_all(context);
diff --git a/src/mosquitto_broker_internal.h b/src/mosquitto_broker_internal.h
index 8f2ad0b25c..c28eaa2a57 100644
--- a/src/mosquitto_broker_internal.h
+++ b/src/mosquitto_broker_internal.h
@@ -670,6 +670,7 @@ int db__message_write_queued_out(struct mosquitto *context);
 int db__message_write_queued_in(struct mosquitto *context);
 void db__msg_add_to_inflight_stats(struct mosquitto_msg_data *msg_data, struct mosquitto_client_msg *msg);
 void db__msg_add_to_queued_stats(struct mosquitto_msg_data *msg_data, struct mosquitto_client_msg *msg);
+void db__expire_all_messages(struct mosquitto *context);
 
 /* ============================================================
  * Subscription functions