diff --git a/res/res_rtp_asterisk.c b/res/res_rtp_asterisk.c
index a07c056..4fdd04a 100644
--- a/res/res_rtp_asterisk.c
+++ b/res/res_rtp_asterisk.c
@@ -2101,6 +2101,8 @@ static int __rtp_recvfrom(struct ast_rtp_instance *instance, void *buf, size_t s
                        SSL_set_accept_state(dtls->ssl);
                }

+               ast_mutex_lock(&dtls->lock);
+
                dtls_srtp_check_pending(instance, rtp, rtcp);

                BIO_write(dtls->read_bio, buf, len);
@@ -2111,6 +2113,7 @@ static int __rtp_recvfrom(struct ast_rtp_instance *instance, void *buf, size_t s
                        unsigned long error = ERR_get_error();
                        ast_log(LOG_ERROR, "DTLS failure occurred on RTP instance '%p' due to reason '%s', terminating\n",
                                instance, ERR_reason_error_string(error));
+                       ast_mutex_unlock(&dtls->lock);
                        return -1;
                }

@@ -2125,11 +2128,11 @@ static int __rtp_recvfrom(struct ast_rtp_instance *instance, void *buf, size_t s
                        }
                } else {
                        /* Since we've sent additional traffic start the timeout timer for retransmission */
-                       ast_mutex_lock(&dtls->lock);
                        dtls_srtp_start_timeout_timer(instance, rtp, rtcp);
-                       ast_mutex_unlock(&dtls->lock);
                }

+               ast_mutex_unlock(&dtls->lock);
+
                return res;
        }
 #endif
@@ -4678,6 +4681,9 @@ static int ast_rtp_fd(struct ast_rtp_instance *instance, int rtcp)
 static void ast_rtp_remote_address_set(struct ast_rtp_instance *instance, struct ast_sockaddr *addr)
 {
        struct ast_rtp *rtp = ast_rtp_instance_get_data(instance);
+#ifdef HAVE_OPENSSL_SRTP
+       struct dtls_details *dtls;
+#endif

        if (rtp->rtcp) {
                ast_debug(1, "Setting RTCP address on RTP instance '%p'\n", instance);
@@ -4695,6 +4701,26 @@ static void ast_rtp_remote_address_set(struct ast_rtp_instance *instance, struct
                rtp_learning_seq_init(&rtp->rtp_source_learn, rtp->seqno);
        }

+#ifdef HAVE_OPENSSL_SRTP
+       /* Trigger pending outbound DTLS packets received before the address was set.  Avoid unnecessary locking
+        * by checking if we're passive. Without this, we only send the pending packets once a new SSL packet is
+        * received in __rtp_recvfrom.
+        */
+       dtls = &rtp->dtls;
+       if (dtls->dtls_setup == AST_RTP_DTLS_SETUP_PASSIVE) {
+               ast_mutex_lock(&dtls->lock);
+               dtls_srtp_check_pending(instance, rtp, 0);
+               ast_mutex_unlock(&dtls->lock);
+       }
+
+       dtls = &rtp->rtcp->dtls;
+       if (dtls->dtls_setup == AST_RTP_DTLS_SETUP_PASSIVE) {
+               ast_mutex_lock(&dtls->lock);
+               dtls_srtp_check_pending(instance, rtp, 1);
+               ast_mutex_unlock(&dtls->lock);
+       }
+#endif
+
        return;
 }