What is the max size jpeg I can upload to a WIP post?
I was able to find this in the FAQs but I don't see any more information in the attachments window. I'm sure this is user error but help would be appreciated none the less.
What files types can I use? How large can attachments be?

In the attachment window you will find a list of the allowed file types and their maximum sizes. Files that are larger than these sizes will be rejected. There may also be an overall quota limit to the number of attachments you can post to the board.