sharing to kidle problems

[oneiros]

Hello, after one hour fiddling with settings and looking around the web for solutions it seems I'm dealing with some odd email sharing issue.
So I have tried with two different email accounts (outlook and gmail) from two different Windows 10 computers. In both cases I keep getting a "authentication error".

- Calibre is up to date to latest version
- Both PCs have antivirus/firewall properly configured to give free access to Calibre
- Emails/passwords are verified and correct
- Both email addresses are authorized in amazon/kindle preferences

Since the outlook email is my default one I'm posting only the log for the outlook account error.

It may be due to the two step authentication log-in enabled?

Traceback (most recent call last):
File "site-packages\calibre\gui2\wizard\send_email.py", line 207, in test_email_settings
File "site-packages\calibre\utils\smtp.py", line 159, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 648, in login
SMTPAuthenticationError: (535, '5.7.3 Authentication unsuccessful [PR0P264CA0047.FRAP264.PROD.OUTLOOK.COM]')


Log:
connect: (u'smtp.live.com', 587)
connect: (u'smtp.live.com', 587)
reply: '220 PR0P264CA0047.outlook.office365.com Microsoft ESMTP MAIL Service ready at Sun, 30 Dec 2018 11:02:57 +0000\r\n'
reply: retcode (220); Msg: PR0P264CA0047.outlook.office365.com Microsoft ESMTP MAIL Service ready at Sun, 30 Dec 2018 11:02:57 +0000
connect: PR0P264CA0047.outlook.office365.com Microsoft ESMTP MAIL Service ready at Sun, 30 Dec 2018 11:02:57 +0000
send: 'ehlo WIN10.station\r\n'
reply: '250-PR0P264CA0047.outlook.office365.com Hello [5.95.24.182]\r\n'
reply: '250-SIZE 157286400\r\n'
reply: '250-PIPELINING\r\n'
reply: '250-DSN\r\n'
reply: '250-ENHANCEDSTATUSCODES\r\n'
reply: '250-STARTTLS\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-BINARYMIME\r\n'
reply: '250-CHUNKING\r\n'
reply: '250 SMTPUTF8\r\n'
reply: retcode (250); Msg: PR0P264CA0047.outlook.office365.com Hello [5.95.24.182]
SIZE 157286400
PIPELINING
DSN
ENHANCEDSTATUSCODES
STARTTLS
8BITMIME
BINARYMIME
CHUNKING
SMTPUTF8
send: 'STARTTLS\r\n'
reply: '220 2.0.0 SMTP server ready\r\n'
reply: retcode (220); Msg: 2.0.0 SMTP server ready
send: 'ehlo WIN10.station\r\n'
reply: '250-PR0P264CA0047.outlook.office365.com Hello [5.95.24.182]\r\n'
reply: '250-SIZE 157286400\r\n'
reply: '250-PIPELINING\r\n'
reply: '250-DSN\r\n'
reply: '250-ENHANCEDSTATUSCODES\r\n'
reply: '250-AUTH LOGIN XOAUTH2\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-BINARYMIME\r\n'
reply: '250-CHUNKING\r\n'
reply: '250 SMTPUTF8\r\n'
reply: retcode (250); Msg: PR0P264CA0047.outlook.office365.com Hello [5.95.24.182]
SIZE 157286400
PIPELINING
DSN
ENHANCEDSTATUSCODES
AUTH LOGIN XOAUTH2
8BITMIME
BINARYMIME
CHUNKING
SMTPUTF8
send: 'AUTH LOGIN bWFydjczQG91dGxvb2suY29t\r\n'
reply: '334 UGFzc3dvcmQ6\r\n'
reply: retcode (334); Msg: UGFzc3dvcmQ6
send: 'X1RoeDExMzgtTHVoMzQxN18=\r\n'
reply: '535 5.7.3 Authentication unsuccessful [PR0P264CA0047.FRAP264.PROD.OUTLOOK.COM]\r\n'
reply: retcode (535); Msg: 5.7.3 Authentication unsuccessful [PR0P264CA0047.FRAP264.PROD.OUTLOOK.COM]

[kovidgoyal]

that's an authentication error which means the server rejected your username and password. Either they are incorrect or you need to tell the server to allow smtp clients, many mail services disable them by default, see https://manual.calibre-ebook.com/faq...-using-calibre