[ww-bugs] Bug 3407: Failed to open the mailer: IO::Socket::SSL->start_SSL failed: SSL connect attempt failed with unknown error error:14090086:SSL routines:SSL3_GET_SERVER_CERTIFICATE:certificate verify failed

Tue Sep 1 09:38:24 EDT 2015

http://bugs.webwork.maa.org/show_bug.cgi?id=3407

--- Comment #5 from Mike Gage <gage at math.rochester.edu>  2015-09-01 09:38:24 ---
and one more early comment

Hi Mike,

Short answer: if we know what OS and version the server is running, and if
it was recently upgraded, that would provide some sense of whether the
issue is the server upgrade.

The error 

Failed to open the mailer: IO::Socket::SSL->start_SSL failed: SSL
connect attempt failed with unknown error error:14090086:SSL
routines:SSL3_GET_SERVER_CERTIFICATE:certificate verify failed

does seem to suggest that the webwork server is trying to connect to the
SMTP server through SSL, and that the webwork servers SSL certificate
isn't being recognized.  It seems that this negotiation (whether to use
SSL, and if so what certificates are valid) occurs outside of webwork,
which is consistent with your hypothesis.

We did run into trouble at some point years ago when the University
required authentication to use their smtp server to send mail.  That was
resolved by getting our server on the list of servers allowed to send mail
through their mail relay server without authentication.

Gavin

On Thu, Feb 21, 2013 at 08:31:26AM -0500, Michael Gage wrote:
Hi,

We're getting a lot of messages about problems setting up the email facility. I
have some suspicion that 
the configuration of the sendmail applications are changing -- possibly related
to 
increased security needs?

We may need IT type help to deal with these.   The extraneous reply-to entries
inserted at interlochen are another example.

Any ideas about how to handle this?

Take care,

Mike

Begin forwarded message:

From: Ben Walter <benwalt at gmail.com>
Subject: Re: email on webwork 2.5
Date: February 21, 2013 6:07:17 AM EST
To: Michael Gage <gage at math.rochester.edu>

... I still haven't been able to figure out what is causing this error, or why
it doesn't happen on my other installation.  Any insight would be appreciated.

Ben

On Thu, Feb 21, 2013 at 10:47 AM, Ben Walter <benwalt at gmail.com> wrote:
Follow-up..... Email is working on my Turkish webwork server.... it looks like
whatever is wrong is my fault.  I'll compare the two installations and see if I
get get things fixed on my own. :)

Ben

On Thu, Feb 21, 2013 at 10:22 AM, Ben Walter <benwalt at gmail.com> wrote:
Hi Michael --

I've been trying to get a new webwork server up and running 2.5 for our
students this semester.  I've managed to get everything going well, except for
one thing.... the server can't send email.

When I try to send email using the "feedback to the instructor" button, I get
an error: 

Failed to open the mailer: IO::Socket::SSL->start_SSL failed: SSL connect
attempt failed with unknown error error:14090086:SSL
routines:SSL3_GET_SERVER_CERTIFICATE:certificate verify failed

Sending email using the instructor function doesn't work either. Though that
fails silently.

This may be related to METU using self-signed certificates for its systems (or
to the webwork server using a self-signed certificate). Chrome also complains
about the certificate whenever I login to the METU system/webwork.  

Looking online it appears that I should be able to tell Socket to not check
certificates.... but I can't figure out where to modify the webwork code. 
Could you help out please?

(Incidentally, this problem never happened with the 2.4 installation. I'm not
sure if it is due to a change in 2.5 code, or to me switching the server to
https in the new installation.)

Ben

-- 
P Gavin LaRose, PhD | glarose at umich.edu | 734.764.6454    ...you have to
Program Manager, Instructional Tech.    | respect someone who can spell
Mathematics Dept.,  Univ. of Michigan   | Tuesday, even if they can't
http://www.math.lsa.umich.edu/~glarose/ | spell it right.   -Milne

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