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I've been having the same problem. I've tried different emails but still can't get it to work. I've tried to be sure that my firewall is allowing the program. Here is my error message for gmx:
Traceback (most recent call last):
File "site-packages\calibre\gui2\wizard\send_email.py", line 174, in test_email_settings
File "site-packages\calibre\utils\smtp.py", line 135, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 617, in login
SMTPAuthenticationError: (535, 'Authentication credentials invalid')
Log:
connect: (u'mail.gmx.com', 587)
connect: (u'mail.gmx.com', 587)
reply: '220 gmx.com (mrgmx002) Nemesis ESMTP Service ready\r\n'
reply: retcode (220); Msg: gmx.com (mrgmx002) Nemesis ESMTP Service ready
connect: gmx.com (mrgmx002) Nemesis ESMTP Service ready
send: 'ehlo [192.168.1.10]\r\n'
reply: '250-gmx.com Hello [192.168.1.10] [209.6.119.163]\r\n'
reply: '250-SIZE 69920427\r\n'
reply: '250-AUTH LOGIN PLAIN\r\n'
reply: '250 STARTTLS\r\n'
reply: retcode (250); Msg: gmx.com Hello [192.168.1.10] [209.6.119.163]
SIZE 69920427
AUTH LOGIN PLAIN
STARTTLS
send: 'STARTTLS\r\n'
reply: '220 OK\r\n'
reply: retcode (220); Msg: OK
send: 'ehlo [192.168.1.10]\r\n'
reply: '250-gmx.com Hello [192.168.1.10] [209.6.119.163]\r\n'
reply: '250-SIZE 69920427\r\n'
reply: '250 AUTH LOGIN PLAIN\r\n'
reply: retcode (250); Msg: gmx.com Hello [192.168.1.10] [209.6.119.163]
SIZE 69920427
AUTH LOGIN PLAIN
send: 'AUTH PLAIN AGpmcmVuY2g1NUBnbXguY29tADIzNDZCb29rcw==\r\n'
reply: '535 Authentication credentials invalid\r\n'
reply: retcode (535); Msg: Authentication credentials invalid
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