diff --git a/ChangeLog.txt b/ChangeLog.txt
index 18c5514d..50f02d9c 100644
--- a/ChangeLog.txt
+++ b/ChangeLog.txt
@@ -1,3 +1,11 @@
+1.5.4 - 201810xx
+================
+
+Library:
+- Fix memory leak that occurred if mosquitto_reconnect() was used when TLS
+errors were present. Closes #592.
+
+
 1.5.3 - 20180925
 ================
 
diff --git a/lib/net_mosq.c b/lib/net_mosq.c
index 5494abae..4efda3d2 100644
--- a/lib/net_mosq.c
+++ b/lib/net_mosq.c
@@ -596,6 +596,9 @@ int net__socket_connect_step3(struct mosquitto *mosq, const char *host, uint16_t
 	if(rc) return rc;
 
 	if(mosq->ssl_ctx){
+		if(mosq->ssl){
+			SSL_free(mosq->ssl);
+		}
 		mosq->ssl = SSL_new(mosq->ssl_ctx);
 		if(!mosq->ssl){
 			COMPAT_CLOSE(mosq->sock);