I spent a lot of time taking screenshots via an annotation tool like Skitch, adding them to a Confluence page and resizing them to thumbnails.

Only when I was showing the page to other people did I realise that Confluence chose to overwrite all the images with the same one.

I've talked to me team and everyone has gotten burnt by this. Confluence should ask if I want to overwrite the existing image or generate an incremental suffix - just like any file explorer/finder.