TLS connection on Mail server

Posted on 2016-09-13
Last Modified: 2016-09-14
For mail server to establish TLS, do I need to install a certfiicate on the server ?

Question by:AXISHK

Expert Comment

by:Ned Ramsay
ID: 41797190
Unfortunately yes.
You can use an Internal Windows CA but only if you have one setup in active directory.

Author Comment

ID: 41797195
Can i generate a self certficate in the server for this purpose ?

LVL 14

Expert Comment

by:Todd Nelson
ID: 41797262
Yes, you need a certificate for TLS.  If you are using for something like Office 365 it cannot be a self signed certificate.

Author Comment

ID: 41797266
We own our Exchange 2010. If I use the self certificate, will TLS be established with other side ?

Why are Office 365 signatures so complicated?

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Assisted Solution

by:Ned Ramsay
Ned Ramsay earned 200 total points
ID: 41797287
It will work for connecting through TLS from your client workstations/phones etc.

TLS to another mail server no. The receiving mailserver has no way of knowing if it is genuine if you dont have a recognized CA cert.

I had to do something like this recently to encrypt legal data between two companies.

Author Comment

ID: 41797299
can Exchange use other connection for mail transmission in case TLS can't be established ?

Can you share how to setup the TLS on the Exchange ?

LVL 63

Accepted Solution

Simon Butler (Sembee) earned 300 total points
ID: 41798832
Exchange does Opportunist TLS - so it will fall back to plain SMTP if TLS cannot be done. There is nothing to setup to do that.
You only need to change the configuration if you want to use Mutual TLS (basically use TLS or drop the connection).

Do you not have a trusted SSL certificate on Exchange already? It is pretty much mandatory for Exchange to have a trusted SSL certificate if you have external clients. The self signed certificates are not supported for use with Outlook Anywhere and ActiveSync.

When you can get a suitable certificate for less than $60, trying to get a self signed certificate to work is a false economy.

Author Closing Comment

ID: 41799017

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