Here we are. It looks like it's something to do with my email now I'm looking at this log. No time to change it now but will come back to it later!
Starting job: Email Glenn Greenwald | guardian.co.uk to
username@kindle.com
connect: (u'smtp.gmail.com', 587)
connect: (u'smtp.gmail.com', 587)
reply: '220 mx.google.com ESMTP wu6sm19671227wjb.46 - gsmtp\r\n'
reply: retcode (220); Msg: mx.google.com ESMTP wu6sm19671227wjb.46 - gsmtp
connect: mx.google.com ESMTP wu6sm19671227wjb.46 - gsmtp
send: 'ehlo donnas-imac.home\r\n'
reply: '250-mx.google.com at your service, [86.139.211.82]\r\n'
reply: '250-SIZE 35882577\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-STARTTLS\r\n'
reply: '250-ENHANCEDSTATUSCODES\r\n'
reply: '250 CHUNKING\r\n'
reply: retcode (250); Msg: mx.google.com at your service, [86.139.211.82]
SIZE 35882577
8BITMIME
STARTTLS
ENHANCEDSTATUSCODES
CHUNKING
send: 'STARTTLS\r\n'
reply: '220 2.0.0 Ready to start TLS\r\n'
reply: retcode (220); Msg: 2.0.0 Ready to start TLS
send: 'ehlo donnas-imac.home\r\n'
reply: '250-mx.google.com at your service, [86.139.211.82]\r\n'
reply: '250-SIZE 35882577\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-AUTH LOGIN PLAIN XOAUTH XOAUTH2 PLAIN-CLIENTTOKEN\r\n'
reply: '250-ENHANCEDSTATUSCODES\r\n'
reply: '250 CHUNKING\r\n'
reply: retcode (250); Msg: mx.google.com at your service, [86.139.211.82]
SIZE 35882577
8BITMIME
AUTH LOGIN PLAIN XOAUTH XOAUTH2 PLAIN-CLIENTTOKEN
ENHANCEDSTATUSCODES
CHUNKING
send: AUTH <censored>
reply: '535-5.7.8 Username and Password not accepted. Learn more at\r\n'
reply: '535 5.7.8
http://support.google.com/mail/bin/a...y?answer=14257 wu6sm19671227wjb.46 - gsmtp\r\n'
reply: retcode (535); Msg: 5.7.8 Username and Password not accepted. Learn more at
5.7.8
http://support.google.com/mail/bin/a...y?answer=14257 wu6sm19671227wjb.46 - gsmtp
Sending failed...
Traceback (most recent call last):
File "site-packages/calibre/gui2/email.py", line 43, in run
File "site-packages/calibre/gui2/email.py", line 124, in sendmail
File "site-packages/calibre/utils/smtp.py", line 135, in sendmail
File "site-packages/calibre/utils/smtplib.py", line 617, in login
SMTPAuthenticationError: (535, '5.7.8 Username and Password not accepted. Learn more at\n5.7.8
http://support.google.com/mail/bin/a...y?answer=14257 wu6sm19671227wjb.46 - gsmtp')
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.gmail.com', 587)
connect: (u'smtp.gmail.com', 587)
reply: '220 mx.google.com ESMTP o3sm33640067wix.15 - gsmtp\r\n'
reply: retcode (220); Msg: mx.google.com ESMTP o3sm33640067wix.15 - gsmtp
connect: mx.google.com ESMTP o3sm33640067wix.15 - gsmtp
send: 'ehlo donnas-imac.home\r\n'
reply: '250-mx.google.com at your service, [86.139.211.82]\r\n'
reply: '250-SIZE 35882577\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-STARTTLS\r\n'
reply: '250-ENHANCEDSTATUSCODES\r\n'
reply: '250 CHUNKING\r\n'
reply: retcode (250); Msg: mx.google.com at your service, [86.139.211.82]
SIZE 35882577
8BITMIME
STARTTLS
ENHANCEDSTATUSCODES
CHUNKING
send: 'STARTTLS\r\n'
reply: '220 2.0.0 Ready to start TLS\r\n'
reply: retcode (220); Msg: 2.0.0 Ready to start TLS
send: 'ehlo donnas-imac.home\r\n'
reply: '250-mx.google.com at your service, [86.139.211.82]\r\n'
reply: '250-SIZE 35882577\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-AUTH LOGIN PLAIN XOAUTH XOAUTH2 PLAIN-CLIENTTOKEN\r\n'
reply: '250-ENHANCEDSTATUSCODES\r\n'
reply: '250 CHUNKING\r\n'
reply: retcode (250); Msg: mx.google.com at your service, [86.139.211.82]
SIZE 35882577
8BITMIME
AUTH LOGIN PLAIN XOAUTH XOAUTH2 PLAIN-CLIENTTOKEN
ENHANCEDSTATUSCODES
CHUNKING
send: AUTH <censored>
reply: '535-5.7.8 Username and Password not accepted. Learn more at\r\n'
reply: '535 5.7.8
http://support.google.com/mail/bin/a...y?answer=14257 o3sm33640067wix.15 - gsmtp\r\n'
reply: retcode (535); Msg: 5.7.8 Username and Password not accepted. Learn more at
5.7.8
http://support.google.com/mail/bin/a...y?answer=14257 o3sm33640067wix.15 - gsmtp
Sending failed...
Traceback (most recent call last):
File "site-packages/calibre/gui2/email.py", line 43, in run
File "site-packages/calibre/gui2/email.py", line 124, in sendmail
File "site-packages/calibre/utils/smtp.py", line 135, in sendmail
File "site-packages/calibre/utils/smtplib.py", line 617, in login
SMTPAuthenticationError: (535, '5.7.8 Username and Password not accepted. Learn more at\n5.7.8
http://support.google.com/mail/bin/a...y?answer=14257 o3sm33640067wix.15 - gsmtp')
Job: "Email Glenn Greenwald | guardian.co.uk to
swabey@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 98, in __call__
SMTPAuthenticationError: (535, '5.7.8 Username and Password not accepted. Learn more at\n5.7.8
http://support.google.com/mail/bin/a...y?answer=14257 o3sm33640067wix.15 - gsmtp')
Called with args: (u'/var/folders/bk/lwwwww4x30n3kcyc_6_r7nwm0000gn/T/calibre_1.42.0_tmp_lFBVa9/huhIwJcaltmpfmt.mobi', u'Glenn Greenwald _ guardian.co.uk.mobi', u'swabey@kindle.com', u'News: Glenn Greenwald | guardian.co.uk', u'Attached is the Glenn Greenwald | guardian.co.uk periodical downloaded by calibre.') {u'notifications': <Queue.Queue instance at 0x1161fdd88>, u'abort': <threading._Event object at 0x1161fe6d0>, u'log': <calibre.utils.logging.GUILog object at 0x1161fe750>}