@Meredith Usually its a content filter/proxy/firewall that filters the SSL traffic in your network and uses the self signed certificate in order to decrypt all the secure traffic.
Or Use server = smtplib.SMTP(smtp.gmail.com:25) for normal connection. and if you want tls from port 25, simply add
If youre using macOS, just simply follow these steps: Go to this link: (Profile -> settings -> developers setting -> personal access tokens).
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