Emailing newspaper from Calibre failing

[JustinD]

Recently my email has started to fail.
The log is below. I am not sure whether its something to do with my PC config or something that I need to adjust in Calibre. Appreciate any insight as the log doesn't give me any insight (due to my own failings).

thanks,
Justin

calibre, version 0.9.24 (win32, isfrozen: True)
Failed to email book: Failed: Email New York Times to xxxxxx@kindle.com

Starting job: Email New York Times to xxxxxx@kindle.com
connect: (u'smtp.gmail.com', 587)
connect: (587, u'smtp.gmail.com')
reply: '220 mx.google.com ESMTP hw16sm15932476pab.19 - gsmtp\r\n'
reply: retcode (220); Msg: mx.google.com ESMTP hw16sm15932476pab.19 - gsmtp
connect: mx.google.com ESMTP hw16sm15932476pab.19 - gsmtp
send: 'ehlo [192.168.1.3]\r\n'
reply: '250-mx.google.com at your service, [60.225.134.148]\r\n'
reply: '250-SIZE 35882577\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-STARTTLS\r\n'
reply: '250 ENHANCEDSTATUSCODES\r\n'
reply: retcode (250); Msg: mx.google.com at your service, [60.225.134.148]
SIZE 35882577
8BITMIME
STARTTLS
ENHANCEDSTATUSCODES
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 [192.168.1.3]\r\n'
reply: '250-mx.google.com at your service, [60.225.134.148]\r\n'
reply: '250-SIZE 35882577\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-AUTH LOGIN PLAIN XOAUTH XOAUTH2\r\n'
reply: '250 ENHANCEDSTATUSCODES\r\n'
reply: retcode (250); Msg: mx.google.com at your service, [60.225.134.148]
SIZE 35882577
8BITMIME
AUTH LOGIN PLAIN XOAUTH XOAUTH2
ENHANCEDSTATUSCODES
send: AUTH <censored>
reply: '235 2.7.0 Accepted\r\n'
reply: retcode (235); Msg: 2.7.0 Accepted
send: u'mail FROM:<xxxxx@xxxxxx.com> size=16070535\r\n'
reply: '250 2.1.0 OK hw16sm15932476pab.19 - gsmtp\r\n'
reply: retcode (250); Msg: 2.1.0 OK hw16sm15932476pab.19 - gsmtp
send: u'rcpt TO:<xxxxxxx@kindle.com>\r\n'
reply: '250 2.1.5 OK hw16sm15932476pab.19 - gsmtp\r\n'
reply: retcode (250); Msg: 2.1.5 OK hw16sm15932476pab.19 - gsmtp
send: 'data\r\n'
reply: '354 Go ahead hw16sm15932476pab.19 - gsmtp\r\n'
reply: retcode (354); Msg: Go ahead hw16sm15932476pab.19 - gsmtp
data: (354, 'Go ahead hw16sm15932476pab.19 - gsmtp')
send: 'Content-Type: multipart/mixed; boundary="===============0322680621=="\r\nMIME-Version: 1.0\r\nSubje...
Sending timed out
Job: "Email New York Times to xxxxx@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 84, in __call__
Exception: Sending email u'E-book: New York Times' to u'xxxxxx@kindle.com' timed out, aborting

Called with args: (u'C:\\Users\\justin\\AppData\\Local\\Temp\\calibr e_k7zgul\\xu3vekcaltmpfmt.mobi', u'New York Times - calibre.mobi', u'xxxxxxx@kindle.com', u'E-book: New York Times', u'Attached, you will find the e-book\n\nNew York Times\n\tby calibre\n\nin the MOBI format.') {u'notifications': <Queue.Queue instance at 0x0490D4B8>, u'abort': <threading._Event object at 0x08DF1ED0>, u'log': <calibre.utils.logging.GUILog object at 0x08DF1C50>}

[kovidgoyal]

Either the file you are trying to email is too large or something on your computer is blocking calibre, most probably an antivirus program.

[JustinD]

thanks. I haven't worked it out yet. My pc uses Microsoft Security Essentials but it doesnt have anything in its log. Also, its not the firewall since it works 75-80% of the time. It also seems to have greater sucess post reboot. Not sure what thats about.