Since the Recordings beta, when I share a sub-60-second video clip with my friends on their chat windows, it will show a blue "uploading" bar that will finish, as if the file is about to be sent, but then nothing will happen and I have to repeat the operation for the file to actually be sent. This also happens when sharing screenshots, even random images from my computer that I drag & drop in the chat window. This has happened several times now.