diff --git a/apps/app_dial.c b/apps/app_dial.c
index 95757e38b9..c7d4f425a7 100644
--- a/apps/app_dial.c
+++ b/apps/app_dial.c
@@ -1590,8 +1590,14 @@ static int dial_exec_full(struct ast_channel *chan, void *data, struct ast_flags
 	time(&start_time);
 	peer = wait_for_answer(chan, outgoing, &to, peerflags, &pa, &num, &result);
 
-	ast_channel_datastore_remove(chan, datastore);
-	ast_channel_datastore_free(datastore);
+	/* The ast_channel_datastore_remove() function could fail here if the
+	 * datastore was moved to another channel during a masquerade. If this is
+	 * the case, don't free the datastore here because later, when the channel
+	 * to which the datastore was moved hangs up, it will attempt to free this
+	 * datastore again, causing a crash
+	 */
+	if (!ast_channel_datastore_remove(chan, datastore))
+		ast_channel_datastore_free(datastore);
 	if (!peer) {
 		if (result) {
 			res = result;
diff --git a/apps/app_queue.c b/apps/app_queue.c
index 37c94f76f8..ca1e05c163 100644
--- a/apps/app_queue.c
+++ b/apps/app_queue.c
@@ -3243,8 +3243,13 @@ static int try_calling(struct queue_ent *qe, const char *options, char *announce
 	if (use_weight)
 		ao2_unlock(queues);
 	lpeer = wait_for_answer(qe, outgoing, &to, &digit, numbusies, ast_test_flag(&(bridge_config.features_caller), AST_FEATURE_DISCONNECT), forwardsallowed);
-	if (datastore) {
-		ast_channel_datastore_remove(qe->chan, datastore);
+	/* The ast_channel_datastore_remove() function could fail here if the
+	 * datastore was moved to another channel during a masquerade. If this is
+	 * the case, don't free the datastore here because later, when the channel
+	 * to which the datastore was moved hangs up, it will attempt to free this
+	 * datastore again, causing a crash
+	 */
+	if (datastore && !ast_channel_datastore_remove(qe->chan, datastore)) {
 		ast_channel_datastore_free(datastore);
 	}
 	ao2_lock(qe->parent);