Gmail pop3 error “Leaf certificate is expired”

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The issue I was having was that while my certificates had updated, my dovecot server had not reloaded and was still using the old certificates. Restarting my dovecot server solved the problem.

Sounds like you need to restart/reload your dovecot after each renewal OR on a regular schedule [like weekly].

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Unfortunately, OP did not provide much information, such as which ACME client is being used. E.g., Certbot provides a --deploy-hook option which is perfect for such reloading tasks.

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