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knowles03 · 08-04-2020, 01:02 AM

I've always been able to send books to my Mom through Calibre. But I tried last night with no success and keep getting the same failure. I'm wondering if anyone has any suggestions. I tried turning off my firewall but haven't had to do that before. Also tried plugging in her kindle to my laptop and transferring it directly but Calibre would freeze up when scanning her device for books. Any help would be appreciated. Below is the error text from trying to email a book to her.

Code:

Starting job: Email Salvatore, R.A - Icewind Dale 02 - Streams of Silver to bknowles621_710@kindle.com 
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 CH2PR14CA0007.outlook.office365.com Microsoft ESMTP MAIL Service ready at Tue, 4 Aug 2020 04:46:45 +0000\r\n' 
reply: retcode (220); Msg: CH2PR14CA0007.outlook.office365.com Microsoft ESMTP MAIL Service ready at Tue, 4 Aug 2020 04:46:45 +0000 
connect: CH2PR14CA0007.outlook.office365.com Microsoft ESMTP MAIL Service ready at Tue, 4 Aug 2020 04:46:45 +0000 
send: u'ehlo [192.168.254.68]\r\n' 
reply: '250-CH2PR14CA0007.outlook.office365.com Hello [98.23.3.6]\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: CH2PR14CA0007.outlook.office365.com Hello [98.23.3.6]
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: u'ehlo [192.168.254.68]\r\n' 
reply: '250-CH2PR14CA0007.outlook.office365.com Hello [98.23.3.6]\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: CH2PR14CA0007.outlook.office365.com Hello [98.23.3.6]
SIZE 157286400
PIPELINING
DSN
ENHANCEDSTATUSCODES
AUTH LOGIN XOAUTH2
8BITMIME
BINARYMIME
CHUNKING
SMTPUTF8 
send: AUTH <censored> 
reply: '334 UGFzc3dvcmQ6\r\n' 
reply: retcode (334); Msg: UGFzc3dvcmQ6 
send: 'ajF1akhDVDA=\r\n' 
reply: '535 5.7.3 Authentication unsuccessful [CH2PR14CA0007.namprd14.prod.outlook.com]\r\n' 
reply: retcode (535); Msg: 5.7.3 Authentication unsuccessful [CH2PR14CA0007.namprd14.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 182, in sendmail
  File "site-packages\calibre\utils\smtplib.py", line 645, in login
SMTPAuthenticationError: (535, '5.7.3 Authentication unsuccessful [CH2PR14CA0007.namprd14.prod.outlook.com]')
 

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 CH2PR14CA0051.outlook.office365.com Microsoft ESMTP MAIL Service ready at Tue, 4 Aug 2020 04:51:52 +0000\r\n' 
reply: retcode (220); Msg: CH2PR14CA0051.outlook.office365.com Microsoft ESMTP MAIL Service ready at Tue, 4 Aug 2020 04:51:52 +0000 
connect: CH2PR14CA0051.outlook.office365.com Microsoft ESMTP MAIL Service ready at Tue, 4 Aug 2020 04:51:52 +0000 
send: u'ehlo [192.168.254.68]\r\n' 
reply: '250-CH2PR14CA0051.outlook.office365.com Hello [98.23.3.6]\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: CH2PR14CA0051.outlook.office365.com Hello [98.23.3.6]
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: u'ehlo [192.168.254.68]\r\n' 
reply: '250-CH2PR14CA0051.outlook.office365.com Hello [98.23.3.6]\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: CH2PR14CA0051.outlook.office365.com Hello [98.23.3.6]
SIZE 157286400
PIPELINING
DSN
ENHANCEDSTATUSCODES
AUTH LOGIN XOAUTH2
8BITMIME
BINARYMIME
CHUNKING
SMTPUTF8 
send: AUTH <censored> 
reply: '334 UGFzc3dvcmQ6\r\n' 
reply: retcode (334); Msg: UGFzc3dvcmQ6 
send: 'ajF1akhDVDA=\r\n' 
reply: '535 5.7.3 Authentication unsuccessful [CH2PR14CA0051.namprd14.prod.outlook.com]\r\n' 
reply: retcode (535); Msg: 5.7.3 Authentication unsuccessful [CH2PR14CA0051.namprd14.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 182, in sendmail
  File "site-packages\calibre\utils\smtplib.py", line 645, in login
SMTPAuthenticationError: (535, '5.7.3 Authentication unsuccessful [CH2PR14CA0051.namprd14.prod.outlook.com]')
 
Job: "Email Salvatore, R.A - Icewind Dale 02 - Streams of Silver to bknowles621_710@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 [CH2PR14CA0051.namprd14.prod.outlook.com]')
 
Called with args: (u'C:\\Users\\sknow\\AppData\\Local\\Temp\\calibre_cs_g13\\n5ox4bcaltmpfmt.mobi', u'Salvatore, R.A - Icewind Dale 02 - Streams of Silver - Salvatore, R.A.mobi', u'bknowles621_710@kindle.com', u'E-book: Salvatore, R.A - Icewind Dale 02 - Streams of Silver', u'Attached, you will find the e-book\n\nSalvatore, R.A - Icewind Dale 02 - Streams of Silver\n\tby Salvatore, R.A\n\nin the MOBI format.') {u'abort': <threading._Event object at 0x000001BE0039EA48>, u'log': <calibre.utils.logging.GUILog object at 0x000001BE0039EB48>, u'notifications': <Queue.Queue instance at 0x000001BE0039E948>}