If you¹re familiar with email, you know you can add ³Send mail as²
identities and when you setup a second identity, you have the option of
using Gmail¹s SMTP server or the SMTP server for the domain to which the
³send as² identity belongs. My problem is I can¹t get it to work.  The error
I get is: 

      Authentication failed. Please check your username/password.
     [Server response: Remote server does not support TLS code(500) ]

TLS is enabled on port 25 of our server and it has a regular Thawte
certificate behind it.  Tests with Thunderbird using PLAIN authentication
(SASL method) work perfectly.  From our point of view, all we really want to
protect in any SMTP transaction are the user credentials (uid/passwd) and
what we are doing is currently sufficient.  Google, on the other hand is
doing something different or expecting something different and I have no
idea what.  If you are successfully using a similar setup with Gmail, could
you please pass on your wisdom.

Thanks,
Rob



Rob Tanner
UNIX Services Manager
Linfield College, McMinnville Oregon




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