diff --git a/coreapi/chat.c b/coreapi/chat.c
index b7ecd439b..2d0a9dc18 100644
--- a/coreapi/chat.c
+++ b/coreapi/chat.c
@@ -117,13 +117,14 @@ void linphone_chat_message_cbs_set_file_transfer_progress_indication(
 BELLE_SIP_DECLARE_NO_IMPLEMENTED_INTERFACES(LinphoneChatMessage);
 
 static void _linphone_chat_room_destroy(LinphoneChatRoom *cr) {
-	bctbx_list_free_with_data(cr->transient_messages, (void (*)(void *))linphone_chat_message_release);
-	if (cr->received_rtt_characters) {
-		cr->received_rtt_characters = bctbx_list_free_with_data(cr->received_rtt_characters, (void (*)(void *))ms_free);
-	}
 	linphone_chat_room_delete_composing_idle_timer(cr);
 	linphone_chat_room_delete_composing_refresh_timer(cr);
 	linphone_chat_room_delete_remote_composing_refresh_timer(cr);
+	bctbx_list_free_with_data(cr->transient_messages, (bctbx_list_free_func)linphone_chat_message_release);
+	if (cr->weak_messages != NULL) bctbx_list_free(cr->weak_messages);
+	if (cr->received_rtt_characters) {
+		cr->received_rtt_characters = bctbx_list_free_with_data(cr->received_rtt_characters, (bctbx_list_free_func)ms_free);
+	}
 	if (cr->lc != NULL) {
 		if (bctbx_list_find(cr->lc->chatrooms, cr)) {
 			ms_error("LinphoneChatRoom[%p] is destroyed while still being used by the LinphoneCore. This is abnormal."
@@ -138,7 +139,6 @@ static void _linphone_chat_room_destroy(LinphoneChatRoom *cr) {
 	if (cr->pending_message)
 		linphone_chat_message_destroy(cr->pending_message);
 	ms_free(cr->peer);
-	if (cr->weak_messages != NULL) bctbx_list_free(cr->weak_messages);
 }
 
 void linphone_chat_message_set_state(LinphoneChatMessage *msg, LinphoneChatMessageState state) {
@@ -313,6 +313,7 @@ void linphone_chat_room_release(LinphoneChatRoom *cr) {
 	linphone_chat_room_delete_composing_refresh_timer(cr);
 	linphone_chat_room_delete_remote_composing_refresh_timer(cr);
 	bctbx_list_for_each(cr->weak_messages, (bctbx_list_iterate_func)linphone_chat_message_deactivate);
+	bctbx_list_for_each(cr->transient_messages, (bctbx_list_iterate_func)linphone_chat_message_deactivate);
 	cr->lc = NULL;
 	linphone_chat_room_unref(cr);
 }
@@ -1717,11 +1718,11 @@ void linphone_chat_message_unref(LinphoneChatMessage *msg) {
 }
 
 static void linphone_chat_message_deactivate(LinphoneChatMessage *msg){
+	if (msg->file_transfer_information != NULL) {
+		_linphone_chat_message_cancel_file_transfer(msg, FALSE);
+	}
 	/*mark the chat msg as orphan (it has no chat room anymore)*/
 	msg->chat_room = NULL;
-	if (msg->file_transfer_information != NULL) {
-		linphone_chat_message_cancel_file_transfer(msg);
-	}
 }
 
 static void linphone_chat_message_release(LinphoneChatMessage *msg) {
diff --git a/coreapi/chat_file_transfer.c b/coreapi/chat_file_transfer.c
index 3d5e69378..c1fd37984 100644
--- a/coreapi/chat_file_transfer.c
+++ b/coreapi/chat_file_transfer.c
@@ -613,7 +613,7 @@ void linphone_chat_message_start_file_download(LinphoneChatMessage *msg,
 	linphone_chat_message_download_file(msg);
 }
 
-void linphone_chat_message_cancel_file_transfer(LinphoneChatMessage *msg) {
+void _linphone_chat_message_cancel_file_transfer(LinphoneChatMessage *msg, bool_t unref) {
 	if (msg->http_request) {
 		if (msg->state == LinphoneChatMessageStateInProgress) {
 			linphone_chat_message_set_state(msg, LinphoneChatMessageStateNotDelivered);
@@ -625,7 +625,7 @@ void linphone_chat_message_cancel_file_transfer(LinphoneChatMessage *msg) {
 								, msg
 								, msg->chat_room);
 				belle_http_provider_cancel_request(msg->chat_room->lc->http_provider, msg->http_request);
-				if (msg->dir == LinphoneChatMessageOutgoing) {
+				if ((msg->dir == LinphoneChatMessageOutgoing) && unref) {
 					// must release it
 					linphone_chat_message_unref(msg);
 				}
@@ -639,6 +639,10 @@ void linphone_chat_message_cancel_file_transfer(LinphoneChatMessage *msg) {
 	}
 }
 
+void linphone_chat_message_cancel_file_transfer(LinphoneChatMessage *msg) {
+	_linphone_chat_message_cancel_file_transfer(msg, TRUE);
+}
+
 void linphone_chat_message_set_file_transfer_filepath(LinphoneChatMessage *msg, const char *filepath) {
 	if (msg->file_transfer_filepath != NULL) {
 		ms_free(msg->file_transfer_filepath);
diff --git a/coreapi/private.h b/coreapi/private.h
index 33d8b9710..a43cb2713 100644
--- a/coreapi/private.h
+++ b/coreapi/private.h
@@ -657,6 +657,7 @@ void linphone_chat_message_set_state(LinphoneChatMessage *msg, LinphoneChatMessa
 void linphone_chat_message_set_is_secured(LinphoneChatMessage *msg, bool_t secured);
 void linphone_chat_message_send_delivery_notification(LinphoneChatMessage *cm, LinphoneReason reason);
 void linphone_chat_message_send_display_notification(LinphoneChatMessage *cm);
+void _linphone_chat_message_cancel_file_transfer(LinphoneChatMessage *msg, bool_t unref);
 int linphone_chat_room_upload_file(LinphoneChatMessage *msg);
 void _linphone_chat_room_send_message(LinphoneChatRoom *cr, LinphoneChatMessage *msg);
 LinphoneChatMessageCbs *linphone_chat_message_cbs_new(void);
diff --git a/tester/message_tester.c b/tester/message_tester.c
index 3f4616c38..cece23af6 100644
--- a/tester/message_tester.c
+++ b/tester/message_tester.c
@@ -1793,9 +1793,8 @@ void file_transfer_io_error_base(char *server_url, bool_t destroy_room) {
 	linphone_chat_room_send_chat_message(chatroom, msg);
 	BC_ASSERT_TRUE(wait_for_until(marie->lc, NULL, &marie->stat.number_of_LinphoneMessageInProgress, 1, 1000));
 	if (destroy_room) {
-		//since message is orphan, we do not expect to be notified of state change
 		linphone_core_delete_chat_room(marie->lc, chatroom);
-		BC_ASSERT_FALSE(wait_for_until(marie->lc, NULL, &marie->stat.number_of_LinphoneMessageNotDelivered, 1, 1000));
+		BC_ASSERT_TRUE(wait_for_until(marie->lc, NULL, &marie->stat.number_of_LinphoneMessageNotDelivered, 1, 1000));
 	} else {
 		BC_ASSERT_TRUE(wait_for_until(marie->lc, NULL, &marie->stat.number_of_LinphoneMessageNotDelivered, 1, 3000));
 	}