Hello @HopeandCope ,
If you only delete the contact, then yes uploading a file with that contact info will re-add them and update any new info if provided in the upload.
If you're wanting to get rid of contacts, and not have them be able to be re-added without explicitly going through a sign up form or other method of overwriting their permissions, then I'd advise also unsubscribing them.
You can upload lists of contacts to mass-unsubscribe at one time, if you have advanced permissions turned on for your account.
You can unsubscribe bounces while deleting them, if doing so via an email's bounces report.
Otherwise, you'll need to go through your files and remove the contacts that you don't want re-imported.
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