[Setup] Unable to send test e-mail

Mikko Ohtamaa mikko+plone at redinnovation.com
Thu Jun 18 23:41:48 UTC 2015

On 18 June 2015 at 08:45, James Hanson <jahanso at gmail.com> wrote:

> We are getting the following message when setting up the Mail settings and
> doing the "save and send test email".
> Error Unable to send test e-mail [Errno 1] _ssl.c:504: error:1411809D:SSL
> routines:SSL_CHECK_SERVERHELLO_TLSEXT:tls invalid.
> Sending through our SMTP server works from the command line.
> Traceback at: http://pastie.org/10247132
> Plone version 4.2.1 on linux
> Not finding much help from searching.

It is related to Python 2.7, it's SSL built and what default SSL/TLS Python
uses when it negotiates the secret connection. Knowing what kind of
encryption the mail server uses might give a hint.

Here is a mixed bag of related errors:


Potential causes I come up in my mind are

- Python tries SSLv2 when SSLv3 required

- The server requires Server Name Identification (SNI) support which Python
version running Plone supports

Unfortunately I am not sure how to fix, but with more information I am sure
this is solvable.

As a work around what you can always do: Setting up a mail server on the
server (localhost) which works as a slave for the actual external mail
server. Here is an example for Ubuntu Linux and Postfix:



> James.
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> Setup at lists.plone.org
> https://lists.plone.org/mailman/listinfo/plone-setup

Mikko Ohtamaa
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