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I was looking back at a few old memes recently, and I noticed how memes used to have a lot more images uploaded to their respective galleries, whereas when most memes get pages today not enough people make an effort to upload images.

I was wondering if mass-uploading images was possible on this site. If so, what permissions do I need to do it?

There is a Batch Upload option indeed, although if I recall correctly it's something reserved to mods and admins. Which makes sense, as otherwise anyone could spam the galleries on a malicious whim.