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Hola Amigo, yo estoy teniendo un problema similar:
Traceback (most recent call last):
File "site-packages\calibre\gui2\wizard\send_email.py", line 209, in test_email_settings
File "site-packages\calibre\utils\smtp.py", line 177, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 667, in starttls
SMTPException: STARTTLS extension not supported by server.
Log:
connect: (u'smtp.live.com', 587)
connect: (u'smtp.live.com', 587)
reply: '220 DESKTOPNHJDI66 AVG SMTP proxy ready.\r\n'
reply: retcode (220); Msg: DESKTOPNHJDI66 AVG SMTP proxy ready.
connect: DESKTOPNHJDI66 AVG SMTP proxy ready.
send: u'ehlo [192.168.0.13]\r\n'
reply: '250-DESKTOPNHJDI66\r\n'
reply: '250-AUTH=LOGIN\r\n'
reply: '250 AUTH LOGIN PLAIN\r\n'
reply: retcode (250); Msg: DESKTOPNHJDI66
AUTH=LOGIN
AUTH LOGIN PLAIN
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