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Best practices with https certificates

I have Exchange, web servers, and other applications like Jabber all published through the WAF.  On each application, I have to configure an SSL certificate, then export it, and import it into Sophos to use on the Virtual Webserver.  There are two certificates for every application.  It's a tedious, slow process to configure each site, and maintain them as they come up for renewal.

My question is, is there a better way, or is this the only way to do it?  It seems like in a perfect world Sophos would have the certificate on it, then would pass authentication in the backend to the webservers and exchange servers, with no cert needed on the backend.  But I haven't seen any docs or talk about this, or if it would break finicky applications like Exchange.  I can't go playing around with it much or I'll kick active users off.

So, what do you all do?



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  • I do use their SAN certs for my several servers, and I tried to use one for everything.

    I did not work, and I cannot remember the reason.

    You are right, it seems like it should.  I may revisit this sometime.

  • I am using it for one cert supporting two host names.  It works fine.  When you request the cert, you just list multiple domains.  Unlike a true wildcard, you have to request a new certificate if you add to the list of SANS.  However, when WAF, you really don't HAVE to use lots of different host names.  Just use site path routing.