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There are some instances where I'd like to add multiple articles to a category on a MediaWiki site such as Wikimedia Commons (for example, adding multiple images of airplanes to the category "Airplanes.") Is it possible to add multiple articles to a single category without manually editing each page and copying and pasting the category into the page's source?
(By any chance, does AutoWikiBot or a similar tool help to automate this process?)
Yes, if you have a list of pages that you want to add to some category, AutoWikiBrowser can help you do that. But, as with any other mass change, you should have a consensus to do so, or the change should be uncontroversial.
Also, to be able to use AWB on Commons, you need to be approved first, see Commons:AutoWikiBrowser for more information.
