I've had trouble in the past but there seems to be two ways to upload. You can use the basic or advanced version. I use the basic version to manage attachments. There is no clearly defined way to know that your file has uploaded from the attachments window other than to look at post you're trying to upload and see if your file is showing on it before posting. Videos take longer so be patient. I'm anxious to see some new videos from other Ladies of OCC members