Email problem -TLS

AustinTim · 02-08-2011, 03:26 PM

I had everything working fine for almost three weeks and early this morning i started getting errors sending emails through our corp server...

anyone have any ideas as to what's going on?

calibre, version 0.7.44
ERROR: Failed to email book: <b>Failed</b>: Email IEEE Spectrum to xxx@free.kindle.com

Email IEEE Spectrum to xxxx@free.kindle.com
connect: (u'torsmtp.amd.com', 587)
connect: (587, u'torsmtp.amd.com')
reply: '220 storexhtp02.amd.com Microsoft ESMTP MAIL Service ready at Tue, 8 Feb 2011 15:19:05 -0500\r\n'
reply: retcode (220); Msg: storexhtp02.amd.com Microsoft ESMTP MAIL Service ready at Tue, 8 Feb 2011 15:19:05 -0500
connect: storexhtp02.amd.com Microsoft ESMTP MAIL Service ready at Tue, 8 Feb 2011 15:19:05 -0500
send: 'ehlo StecklerLab22.amd.com\r\n'
reply: '250-storexhtp02.amd.com Hello [10.236.113.154]\r\n'
reply: '250-SIZE 41943040\r\n'
reply: '250-PIPELINING\r\n'
reply: '250-DSN\r\n'
reply: '250-ENHANCEDSTATUSCODES\r\n'
reply: '250-AUTH GSSAPI NTLM\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-BINARYMIME\r\n'
reply: '250 CHUNKING\r\n'
reply: retcode (250); Msg: storexhtp02.amd.com Hello [10.236.113.154]
SIZE 41943040
PIPELINING
DSN
ENHANCEDSTATUSCODES
AUTH GSSAPI NTLM
8BITMIME
BINARYMIME
CHUNKING

Sending failed...
Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 117, in run
File "site-packages\calibre\gui2\email.py", line 171, in sendmail
File "site-packages\calibre\utils\smtp.py", line 105, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 632, in starttls
SMTPException: STARTTLS extension not supported by server.

Retrying in 1 seconds...
connect: (u'torsmtp.amd.com', 587)
connect: (587, u'torsmtp.amd.com')
reply: '220 storexhtp02.amd.com Microsoft ESMTP MAIL Service ready at Tue, 8 Feb 2011 15:19:07 -0500\r\n'
reply: retcode (220); Msg: storexhtp02.amd.com Microsoft ESMTP MAIL Service ready at Tue, 8 Feb 2011 15:19:07 -0500
connect: storexhtp02.amd.com Microsoft ESMTP MAIL Service ready at Tue, 8 Feb 2011 15:19:07 -0500
send: 'ehlo StecklerLab22.amd.com\r\n'
reply: '250-storexhtp02.amd.com Hello [10.236.113.154]\r\n'
reply: '250-SIZE 41943040\r\n'
reply: '250-PIPELINING\r\n'
reply: '250-DSN\r\n'
reply: '250-ENHANCEDSTATUSCODES\r\n'
reply: '250-AUTH GSSAPI NTLM\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-BINARYMIME\r\n'
reply: '250 CHUNKING\r\n'
reply: retcode (250); Msg: storexhtp02.amd.com Hello [10.236.113.154]
SIZE 41943040
PIPELINING
DSN
ENHANCEDSTATUSCODES
AUTH GSSAPI NTLM
8BITMIME
BINARYMIME
CHUNKING

Sending failed...
Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 117, in run
File "site-packages\calibre\gui2\email.py", line 171, in sendmail
File "site-packages\calibre\utils\smtp.py", line 105, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 632, in starttls
SMTPException: STARTTLS extension not supported by server.

kovidgoyal · 02-08-2011, 03:30 PM

You mail server is not responding to the STARTTLS request. You need to contact your mail server admin and ask them if they dropped TLS support.

AustinTim · 02-08-2011, 03:57 PM

yea, like i know who that is in a company this size...
I'm hoping that it'll just magically re-appear...
i narrowed it down to stopping working between 4:30AM and 5:30AM this morning...
hopefully someone else in the company uses it for something work related.

AustinTim · 02-08-2011, 03:58 PM

any chance you can make it so that Calibre can use a proxy? that way I can use gmail instead of our internal servers...

kovidgoyal · 02-08-2011, 03:58 PM

There are no proxies for mail servers.

Manichean · 02-08-2011, 04:21 PM

Also, proxies for Mail protocols would be an insane security risk.

02-08-2011, 03:26 PM	#1
AustinTim Member Posts: 19 Karma: 10 Join Date: Feb 2011 Device: kindle 3	Email problem -TLS I had everything working fine for almost three weeks and early this morning i started getting errors sending emails through our corp server... anyone have any ideas as to what's going on? calibre, version 0.7.44 ERROR: Failed to email book: <b>Failed</b>: Email IEEE Spectrum to xxx@free.kindle.com Email IEEE Spectrum to xxxx@free.kindle.com connect: (u'torsmtp.amd.com', 587) connect: (587, u'torsmtp.amd.com') reply: '220 storexhtp02.amd.com Microsoft ESMTP MAIL Service ready at Tue, 8 Feb 2011 15:19:05 -0500\r\n' reply: retcode (220); Msg: storexhtp02.amd.com Microsoft ESMTP MAIL Service ready at Tue, 8 Feb 2011 15:19:05 -0500 connect: storexhtp02.amd.com Microsoft ESMTP MAIL Service ready at Tue, 8 Feb 2011 15:19:05 -0500 send: 'ehlo StecklerLab22.amd.com\r\n' reply: '250-storexhtp02.amd.com Hello [10.236.113.154]\r\n' reply: '250-SIZE 41943040\r\n' reply: '250-PIPELINING\r\n' reply: '250-DSN\r\n' reply: '250-ENHANCEDSTATUSCODES\r\n' reply: '250-AUTH GSSAPI NTLM\r\n' reply: '250-8BITMIME\r\n' reply: '250-BINARYMIME\r\n' reply: '250 CHUNKING\r\n' reply: retcode (250); Msg: storexhtp02.amd.com Hello [10.236.113.154] SIZE 41943040 PIPELINING DSN ENHANCEDSTATUSCODES AUTH GSSAPI NTLM 8BITMIME BINARYMIME CHUNKING Sending failed... Traceback (most recent call last): File "site-packages\calibre\gui2\email.py", line 117, in run File "site-packages\calibre\gui2\email.py", line 171, in sendmail File "site-packages\calibre\utils\smtp.py", line 105, in sendmail File "site-packages\calibre\utils\smtplib.py", line 632, in starttls SMTPException: STARTTLS extension not supported by server. Retrying in 1 seconds... connect: (u'torsmtp.amd.com', 587) connect: (587, u'torsmtp.amd.com') reply: '220 storexhtp02.amd.com Microsoft ESMTP MAIL Service ready at Tue, 8 Feb 2011 15:19:07 -0500\r\n' reply: retcode (220); Msg: storexhtp02.amd.com Microsoft ESMTP MAIL Service ready at Tue, 8 Feb 2011 15:19:07 -0500 connect: storexhtp02.amd.com Microsoft ESMTP MAIL Service ready at Tue, 8 Feb 2011 15:19:07 -0500 send: 'ehlo StecklerLab22.amd.com\r\n' reply: '250-storexhtp02.amd.com Hello [10.236.113.154]\r\n' reply: '250-SIZE 41943040\r\n' reply: '250-PIPELINING\r\n' reply: '250-DSN\r\n' reply: '250-ENHANCEDSTATUSCODES\r\n' reply: '250-AUTH GSSAPI NTLM\r\n' reply: '250-8BITMIME\r\n' reply: '250-BINARYMIME\r\n' reply: '250 CHUNKING\r\n' reply: retcode (250); Msg: storexhtp02.amd.com Hello [10.236.113.154] SIZE 41943040 PIPELINING DSN ENHANCEDSTATUSCODES AUTH GSSAPI NTLM 8BITMIME BINARYMIME CHUNKING Sending failed... Traceback (most recent call last): File "site-packages\calibre\gui2\email.py", line 117, in run File "site-packages\calibre\gui2\email.py", line 171, in sendmail File "site-packages\calibre\utils\smtp.py", line 105, in sendmail File "site-packages\calibre\utils\smtplib.py", line 632, in starttls SMTPException: STARTTLS extension not supported by server.

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02-08-2011, 03:30 PM	#2
kovidgoyal creator of calibre Posts: 45,222 Karma: 27110894 Join Date: Oct 2006 Location: Mumbai, India Device: Various	You mail server is not responding to the STARTTLS request. You need to contact your mail server admin and ask them if they dropped TLS support.

02-08-2011, 03:57 PM	#3
AustinTim Member Posts: 19 Karma: 10 Join Date: Feb 2011 Device: kindle 3	yea, like i know who that is in a company this size... I'm hoping that it'll just magically re-appear... i narrowed it down to stopping working between 4:30AM and 5:30AM this morning... hopefully someone else in the company uses it for something work related.

02-08-2011, 03:58 PM	#4
AustinTim Member Posts: 19 Karma: 10 Join Date: Feb 2011 Device: kindle 3	any chance you can make it so that Calibre can use a proxy? that way I can use gmail instead of our internal servers...

02-08-2011, 04:21 PM	#6
Manichean Wizard Posts: 3,130 Karma: 91256 Join Date: Feb 2008 Location: Germany Device: Cybook Gen3	Also, proxies for Mail protocols would be an insane security risk.

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