Or Use server = smtplib.SMTP(smtp.gmail.com:25) for normal connection. and if you want tls from port 25, simply add
@Meredith Usually its a content filter/proxy/firewall t mail.ruhat filters the SSL traffic in your network and uses the self signed certificate in order to decrypt all the secure traffic.
This is because of Execution Policy. This defines how powershell scripts will run. In Default windows desktops, it is Restricted, not allowing any scripts (signed or unsigned) only。
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