diff --git a/ssl/d1_lib.c b/ssl/d1_lib.c
index be4ff02a89..1ac0975d0a 100644
--- a/ssl/d1_lib.c
+++ b/ssl/d1_lib.c
@@ -130,6 +130,17 @@ void dtls1_clear_sent_buffer(SSL_CONNECTION *s)
 
     while ((item = pqueue_pop(s->d1->sent_messages)) != NULL) {
         frag = (hm_fragment *)item->data;
+
+        if (frag->msg_header.is_ccs
+                && frag->msg_header.saved_retransmit_state.wrlmethod != NULL
+                && s->rlayer.wrl != frag->msg_header.saved_retransmit_state.wrl) {
+            /*
+             * If we're freeing the CCS then we're done with the old wrl and it
+             * can bee freed
+             */
+            frag->msg_header.saved_retransmit_state.wrlmethod->free(frag->msg_header.saved_retransmit_state.wrl);
+        }
+
         dtls1_hm_fragment_free(frag);
         pitem_free(item);
     }
@@ -143,16 +154,16 @@ void dtls1_free(SSL *ssl)
     if (s == NULL)
         return;
 
-    DTLS_RECORD_LAYER_free(&s->rlayer);
-
-    ssl3_free(ssl);
-
     if (s->d1 != NULL) {
         dtls1_clear_queues(s);
         pqueue_free(s->d1->buffered_messages);
         pqueue_free(s->d1->sent_messages);
     }
 
+    DTLS_RECORD_LAYER_free(&s->rlayer);
+
+    ssl3_free(ssl);
+
     OPENSSL_free(s->d1);
     s->d1 = NULL;
 }
diff --git a/ssl/statem/statem_dtls.c b/ssl/statem/statem_dtls.c
index 97d9f4591c..c674ddfb54 100644
--- a/ssl/statem/statem_dtls.c
+++ b/ssl/statem/statem_dtls.c
@@ -94,14 +94,7 @@ void dtls1_hm_fragment_free(hm_fragment *frag)
 {
     if (!frag)
         return;
-    if (frag->msg_header.is_ccs) {
-        /*
-         * If we're freeing the CCS then we're done with the old wrl and it
-         * can bee freed
-         */
-        if (frag->msg_header.saved_retransmit_state.wrlmethod != NULL)
-            frag->msg_header.saved_retransmit_state.wrlmethod->free(frag->msg_header.saved_retransmit_state.wrl);
-    }
+
     OPENSSL_free(frag->fragment);
     OPENSSL_free(frag->reassembly);
     OPENSSL_free(frag);