diff --git a/src/chat_commands.c b/src/chat_commands.c
index f799abe..54100c7 100644
--- a/src/chat_commands.c
+++ b/src/chat_commands.c
@@ -166,7 +166,7 @@ void cmd_sendfile(WINDOW *window, ToxWindow *self, Tox *m, int argc, char (*argv
         if (!file_senders[i].active) {
             memcpy(file_senders[i].pathname, path, path_len + 1);
             file_senders[i].active = true;
-            file_senders[i].chatwin = window;
+            file_senders[i].toxwin = self;
             file_senders[i].file = file_to_send;
             file_senders[i].filenum = (uint8_t) filenum;
             file_senders[i].friendnum = self->num;
diff --git a/src/main.c b/src/main.c
index 6b808af..a9f1095 100644
--- a/src/main.c
+++ b/src/main.c
@@ -379,7 +379,13 @@ static void do_file_senders(Tox *m)
 
         /* If file transfer has timed out kill transfer and send kill control */
         if (timed_out(file_senders[i].timestamp, current_time, TIMEOUT_FILESENDER)) {
-            wprintw(file_senders[i].chatwin, "File transfer for '%s' timed out.\n", pathname);
+            ChatContext *ctx = (ChatContext *) file_senders[i].toxwin->chatwin;
+
+            if (ctx != NULL) {
+                wprintw(ctx->history, "File transfer for '%s' timed out.\n", pathname);
+                alert_window(file_senders[i].toxwin);
+            }
+
             tox_file_sendcontrol(m, friendnum, 0, filenum, TOX_FILECONTROL_KILL, 0, 0);
             close_file_sender(i);
             continue;
@@ -397,7 +403,13 @@ static void do_file_senders(Tox *m)
                                              tox_filedata_size(m, friendnum), fp);
 
             if (file_senders[i].piecelen == 0) {
-                wprintw(file_senders[i].chatwin, "File '%s' successfuly sent.\n", pathname);
+                ChatContext *ctx = (ChatContext *) file_senders[i].toxwin->chatwin;
+
+                if (ctx != NULL) {
+                    wprintw(ctx->history, "File '%s' successfuly sent.\n", pathname);
+                    alert_window(file_senders[i].toxwin);
+                }
+
                 tox_file_sendcontrol(m, friendnum, 0, filenum, TOX_FILECONTROL_FINISHED, 0, 0);
                 close_file_sender(i);
                 break;
diff --git a/src/toxic_windows.h b/src/toxic_windows.h
index f2d5cad..8b92ec7 100644
--- a/src/toxic_windows.h
+++ b/src/toxic_windows.h
@@ -107,7 +107,7 @@ typedef struct {
 
 typedef struct {
     FILE *file;
-    WINDOW *chatwin;
+    ToxWindow *toxwin;
     int friendnum;
     bool active;
     uint8_t filenum;