Stéphane Wirtel <steph...@wirtel.be> added the comment:

@lidayan

I have checked the code of your PR, and I think there is an issue with your 
code.

1. When you specify the secure flag to the SMTPHandler, it's because you will 
start the TLS connection if the SMTP server supports the STARTTLS. Firstly in 
plaintext mode and if STARTTLS is supported then we move to the TLS encryption.

2. If you use SSL + SMTP, it's not the same behavior because you support that 
your SMTP server will support a socket + ssl.

For my part, I suggest you the creation of a SMTPSSLHandler and use the 
SMTP_SSL class.

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Python tracker <rep...@bugs.python.org>
<https://bugs.python.org/issue35995>
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