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Old 12-30-2018, 06:04 AM   #1
oneiros
Junior Member
oneiros began at the beginning.
 
Posts: 1
Karma: 10
Join Date: Dec 2018
Device: Kindle
sharing to kidle problems

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]
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