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I'm getting a similar result, failing to send email. I'm using a gmx account and have smtp enabled in their security settings. I also have added an exception for calibre & calibre_parallel in my antivirus and firewall.
This is the log:
connect: (u'mail.gmx.com', 587)
connect: (u'mail.gmx.com', 587)
reply: '220 gmx.com (mrgmx001) Nemesis ESMTP Service ready\r\n'
reply: retcode (220); Msg: gmx.com (mrgmx001) Nemesis ESMTP Service ready
connect: gmx.com (mrgmx001) Nemesis ESMTP Service ready
send: 'ehlo [192.168.0.12]\r\n'
reply: '250-gmx.com Hello [192.168.0.12] [208.96.85.190]\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-AUTH LOGIN PLAIN\r\n'
reply: '250-SIZE 69920427\r\n'
reply: '250 STARTTLS\r\n'
reply: retcode (250); Msg: gmx.com Hello [192.168.0.12] [208.96.85.190]
8BITMIME
AUTH LOGIN PLAIN
SIZE 69920427
STARTTLS
send: AUTH
reply: '530 Must issue a STARTTLS command first\r\n'
reply: retcode (530); Msg: Must issue a STARTTLS command first
Any ideas?
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