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I don't think it's too complicated to get around this. Following advice I found elsewhere, I simply generated an application-specific password for Calibre through my Gmail account (which is set to 2-step verification), then copied that password, went to Calibre -> preferences -> sharing -> sharing books by email, and put it into the password box instead of my usual Gmail password. hey presto, and I could send ebooks to my Kindle via Calibre again.
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