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Ralph Scharping
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Exchnage ./. Sophos Web Application Firewall


is there anyone here who has ever configured Sophos UTM and it's Web Application Firewall reverse proxy feature with Exchange 2010 using a single domain certificate and SRV-records as autodiscover-method?

The guide uses three different certificates and I am unable to follow as I have only one.



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Ralph Scharping

8/22/2022 - Mon

May just be the wording you have used, but it can be very difficult if you mean you only have single domain SSL that covers a single FQDN. Exchange doesn't like that and it can be a proper pain to sort. Much better to get the right kind of cert to start with.

To clarify:

Does your existing cert only cover a single host/domain?

or is it a wildcard certificate?

Or a UCC/SAN certificate?
Ralph Scharping

I do have a single domain cert covering one single name.  It works just fine in a lot of installations.  All it takes is split-brain DNS config internally and SRV-record for autodiscover externally.  No worries there.

My issue is in regard to the reverse-proxy in Sophos.  I have only one IP and I need to publish another host in addition to Exchange.  So I need Sophos Web Application Firewall to forward different names to different physical hosts.
In the guide I am following there are multiple certificates for Exchange - and so far I was certain that it's not even possible to use different certificates (not names) for Outlook Anywhere, Autodiscover and OWA/ECP, as the service HTTPS can only be bound to one certificate.

So I am asking:  Has anyone ever done this before using a single name for all exchange services?

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Ralph Scharping

Even a "right" multi domain cert would be ONE cert.  The guide uses three.
I started with Experts Exchange in 2004 and it's been a mainstay of my professional computing life since. It helped me launch a career as a programmer / Oracle data analyst
William Peck
Ralph Scharping

Well, it seems that this actually works, if you pay attention.
Sophos Proxy ignores all certificate errors on the inside.  So if you are careful not to access Exchange using https from the inside, it's fine.  You can actually get different Single-Domain-Certificates and bind them to different virtual web servers within the firewall.

It's a bit abusive, though, and a wildcard-certificate really is your better choice.