The sending email via curl is working for me properly on the _same_ machine.

some debug info:

...

> STARTTLS < 220 2.0.0 SMTP server ready

  * successfully set certificate verify locations:
  * CAfile: none CApath: /etc/ssl/certs
  * SSLv3, TLS handshake, Client hello (1):



} [data not shown]

  * SSLv3, TLS handshake, Server hello (2):



{ [data not shown]

  * SSLv3, TLS handshake, CERT (11):



{ [data not shown]

  * SSLv3, TLS handshake, Server key exchange (12):



{ [data not shown]

  * SSLv3, TLS handshake, Request CERT (13):



{ [data not shown]

  * SSLv3, TLS handshake, Server finished (14):



{ [data not shown]

  * SSLv3, TLS handshake, CERT (11):



} [data not shown]

  * SSLv3, TLS handshake, Client key exchange (16):



} [data not shown]

  * SSLv3, TLS change cipher, Client hello (1):



} [data not shown]

  * SSLv3, TLS handshake, Finished (20):



} [data not shown]

  * SSLv3, TLS change cipher, Client hello (1):



{ [data not shown]

  * SSLv3, TLS handshake, Finished (20):



{ [data not shown]

  * SSL connection using ECDHE-RSA-AES256-GCM-SHA384
  * Server certificate:
  * subject: C=US; ST=Washington; L=Redmond; O=Microsoft Corporation; 
CN=outlook.com
  * start date: 2017-09-13 00:00:00 GMT
  * expire date: 2018-09-13 12:00:00 GMT
  * issuer: C=US; O=DigiCert Inc; CN=DigiCert Cloud Services CA-1
  * SSL certificate verify ok.



...

CURL sends the STARTTLS command to server then starting TLS negotiation 
proceeds.

STARTTLS doesn't exist in smtp.nim.

Also I think STARTTLS and TLS negotiation proceeds is not implemented yet in 
smtp nim module. 

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