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Right now when you upload a bunch of images to the gallery, it asks you if you want to link a web page. This is a little backwards in practice; if I want to make a showcase thread, that is the URL I want to use. However I can't make the showcase thread without the images, so it's a deadlock.

I sometimes have posted a placeholder thread in the showcase, posted my images, arranged them, and then edited the placeholder to get the images in place. That is a kinda crappy hack though. Doing it one by one after fact is pretty crappy too.

What I would like to see is an option to mass update a gallery with a URL. I don't know how difficult that would be, but there already IS functionality similar to allow for disabling voting, mass tagging, and editing the gallery name, so it seems feasible.

Yeah, currently the URL field is intended more for including links to somewhere off-site. It's a good idea, though.