A job posting I'm interested in says to submit my resume and that no cover letter is required. Part of me thinks sending one shows initiative, but another part thinks it could look like I ignored what they asked for. Would you bother writing one anyway, or take that as a hint to skip it?

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If there's a an opportunity to submit a cover letter and you've got something to say you might as well write it. The purpose of a cover letter is to highlight things about yourself that may not be obvious from your resume, so if that's something you want to do, go for it. Of course, if it's a web form that has no place to attach the cover letter, that's an obvious hint not to bother.

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You are overthinking it already. If you have a cover letter ready to go, submit it, but you aren’t required to. If it said under no circumstances to include a cover letter, then that’s when I would say to skip it.

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