Cannot send books to kindle by email from Calibre

[Jonno34]

I used to send books to my kindle library by email from Calibre. Unfortunately it seems to have stopped working. I have updated Calibre, rebooted my computer and still no success.

I have altered the mail address but this is the message I get.
Please help!

Spoiler:

Starting job: Email Storm to xxxxxx44f90@kindle.com
connect: (u'smtp.live.com', 587)
connect: (u'smtp.live.com', 587)

Sending failed...

Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 45, in run
File "site-packages\calibre\gui2\email.py", line 135, in sendmail
File "site-packages\calibre\utils\smtp.py", line 159, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 338, in connect
File "site-packages\calibre\utils\smtplib.py", line 312, in _get_socket
File "socket.py", line 557, in create_connection
gaierror: [Errno 11001] getaddrinfo failed


Retrying in 301 seconds...

Waiting 301 seconds before sending, to avoid being marked as spam.
You can control this delay via Preferences->Tweaks
connect: (u'smtp.live.com', 587)
connect: (u'smtp.live.com', 587)
reply: '220 VI1PR04CA0099.outlook.office365.com Microsoft ESMTP MAIL Service ready at Fri, 26 Jul 2019 11:30:13 +0000\r\n'
reply: retcode (220); Msg: VI1PR04CA0099.outlook.office365.com Microsoft ESMTP MAIL Service ready at Fri, 26 Jul 2019 11:30:13 +0000
connect: VI1PR04CA0099.outlook.office365.com Microsoft ESMTP MAIL Service ready at Fri, 26 Jul 2019 11:30:13 +0000
send: u'ehlo [192.168.5.8]\r\n'
reply: '250-VI1PR04CA0099.outlook.office365.com Hello [31.209.106.183]\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 SMTPUTF8\r\n'
reply: retcode (250); Msg: VI1PR04CA0099.outlook.office365.com Hello [31.209.106.183]
SIZE 157286400
PIPELINING
DSN
ENHANCEDSTATUSCODES
STARTTLS
8BITMIME
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: u'ehlo [192.168.5.8]\r\n'
reply: '250-VI1PR04CA0099.outlook.office365.com Hello [31.209.106.183]\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 SMTPUTF8\r\n'
reply: retcode (250); Msg: VI1PR04CA0099.outlook.office365.com Hello [31.209.106.183]
SIZE 157286400
PIPELINING
DSN
ENHANCEDSTATUSCODES
AUTH LOGIN XOAUTH2
8BITMIME
SMTPUTF8
send: AUTH <censored>
reply: '334 UGFzc3dvcmQ6\r\n'
reply: retcode (334); Msg: UGFzc3dvcmQ6
send: 'RGVmbmU4MDQ=\r\n'
reply: '535 5.7.3 Authentication unsuccessful [VI1PR04CA0099.eurprd04.prod.outlook.com]\r\n'
reply: retcode (535); Msg: 5.7.3 Authentication unsuccessful [VI1PR04CA0099.eurprd04.prod.outlook.com]

Sending failed...

Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 45, in run
File "site-packages\calibre\gui2\email.py", line 135, in sendmail
File "site-packages\calibre\utils\smtp.py", line 170, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 645, in login
SMTPAuthenticationError: (535, '5.7.3 Authentication unsuccessful [VI1PR04CA0099.eurprd04.prod.outlook.com]')

Job: "Email Storm to xxxxxx44f90@kindle.com" failed with error:
Traceback (most recent call last):
File "site-packages\calibre\gui2\threaded_jobs.py", line 83, in start_work
File "site-packages\calibre\gui2\email.py", line 102, in __call__
SMTPAuthenticationError: (535, '5.7.3 Authentication unsuccessful [VI1PR04CA0099.eurprd04.prod.outlook.com]')

Called with args: (u'C:\\Users\\Jonathan\\AppData\\Local\\Temp\\cali bre_6svayt\\uufozqcaltmpfmt.mobi', u'Storm - Clive Cussler.mobi', u'xxxxxs_e44f90@kindle.com', u'E-book: Storm', u'Attached, you will find the e-book\n\nStorm\n\tby Clive Cussler\n\nin the MOBI format.') {u'log': <calibre.utils.logging.GUILog object at 0x0884B110>, u'notifications': <Queue.Queue instance at 0x0884A378>, u'abort': <threading._Event object at 0x0884B1D0>}

[theducks]

The line

SMTPAuthenticationError: (535, '5.7.3 Authentication unsuccessful [VI1PR04CA0099.eurprd04.prod.outlook.com]'

says it.

Your send MAIL user logon is failing