Why Aren’t My Exchange Certificates Validating?

Updated 10/13: Updated the link to the blog article on configuring Squid for Exchange per the request of the author Owen Campbell. Thank you, Owen, for letting me know the location had changed!

By now you should be aware that Microsoft strongly recommends that you publish Exchange 2010/2007 client access servers (and Exchange 2003/2000 front-end servers) to the Internet through a reverse proxy like Microsoft’s Internet Security and Acceleration Server 2006 SP1 (ISA) or the still-in-beta Microsoft Forefront Threat Management Gateway (TMG). There are other reverse proxy products out there, such as the open source Squid (with some helpful guides on how to configure it for EAS, OWA, and Outlook Anywhere), but many of them can only be used to proxy the HTTP-based protocols (for example, the reverse proxy module for the Apache web server) and won’t handle the RPC component of Outlook Anywhere.

When you’re following this recommendation, you keep your Exchange CAS/HT/front-end servers in your private network and place the ISA Server (or other reverse proxy solution) in your perimeter (DMZ) network. In addition to ensuring that your reverse proxy is scrubbing incoming traffic for you, you can also gain another benefit: SSL bridging. SSL bridging is where there are two SSL connections – one between the client machine and the reverse proxy, and a separate connection (often using a different SSL certificate) between the reverse proxy and the Exchange CAS/front-end server. SSL bridging is awesome because it allows you radically reduce the number of commercial SSL certificates you need to buy. You can use Windows Certificate Services to generate and issue certificates to all of your internal Exchange servers, creating them with all of the Subject Alternate Names that you need and desire, and still have a commercial certificate deployed on your Internet-facing system (nice to avoid certificate issues when you’re dealing with home systems, public kiosks, and mobile devices, no?) that has just the public common namespaces like autodiscover.yourdomain.tld and mail.yourdomain.tld (or whatever you actually use).

In the rest of this article, I’ll be focusing on ISA because, well, I don’t know Squid that well and haven’t actually seen it in use to publish Exchange in a customer environment. Write what you know, right?

One of the most irritating experiences I’ve consistently had when using ISA to publish Exchange securely is getting the certificate configuration on ISA correct. If you all want, I can cover certificate namespaces in another post, because that’s not what I’m talking about – I actually find that relatively easy to deal with these days. No, what I find annoying about ISA and certificates is getting all of the proper root CA certificates and intermediate CA certificates in place. The process you have to go through varies on who you buy your certificates from. There are a couple, like GoDaddy, that offer inexpensive certificates that do exactly what Exchange needs for a decent price – but they require an extra bit of configuration to get everything working.

The problem you’ll see is two-fold:

  1. External clients will not be able to connect to Exchange services. This will be inconsistent; some browsers and some Outlook installations (especially those on new Windows installs or well-updated Windows installs) will work fine, while others won’t. You may have big headaches getting mobile devices to work, and the error messages will be cryptic and unhelpful.
  2. While validating your Exchange publishing rules with the Exchange Remote Connectivity Analyzer (ExRCA), you get a validation error on your certificate as shown in Figure 1.

ExRCA can't find the intermediate certificate on your ISA server
Figure 1: Missing intermediate CA certificate validation error in ExRCA

The problem is that some devices don’t have the proper certificate chain in place. Commercial certificates typically have two or three certificates in their signing chain: the root CA certificate, an intermediate CA certificate, and (optionally) an additional intermediate CA certificate. The secondary intermediate CA certificate is typically the source of the problem; it’s configured as a cross-signing certificate, which is intended to help CAs transition old certificates from one CA to another without invalidating the issued certificates. If your certificate was issued by a CA that has these in place, you have to have both intermediate CA certificates in place on your ISA server in the correct certificate stores.

By default, CAs will issue the entire certificate chain to you in a single bundle when they issue your cert. You have to import this bundle on the machine you issued the request from or else you don’t get the private key associated with the certificate. Once you’ve done that, you need to re-export the certificate, with the private key and its entire certificate chain, so that you can import it in ISA. This is important because ISA needs the private key so it can decrypt the SSL session (required for bridging), and ISA needs all the certificate signing chain so that it can hand out missing intermediate certificates to devices that don’t have them (such as Windows Mobile devices that have the root CA certificates). If the device doesn’t have the right intermediates, can’t download it itself (like Internet Explorer can), and can’t get it from ISA, you’ll get the certificate validation errors.

Here’s what you need to do to fix it:

  • Ensure that your server certificate has been exported with the private key and *all* necessary intermediate and root CA certificates.
  • Import this certificate bundle into your ISA servers. Before you do this, check the computer account’s personal certificate store and make sure any root or intermediate certificates that got accidentally imported there are deleted.
  • Using the Certificate MMC snap-in, validate that the certificate now shows as valid when browsing the certificate on your ISA server, as shown in Figure 2.

Even though the Certificates MMC snap-in shows this certificate as valid, ISA won't serve it out until the ISA Firewall Service is restarted!
Figure 2: A validated server certificate signing chain on ISA Server

  • IMPORTANT STEP: restart the ISA Firewall Service on your ISA server (if you’re using an array, you have to do this on each member; you’ll want to drain the connections before restarting, so it can take a while to complete). Even though the Certificate MMC snap-in validates the certificate, the ISA Firewall only picks up the changes to the certificate chain on startup. This is annoying and stupid and has caused me pain in the past – most recently, with 3Sharp’s own Exchange 2010 deployment (thanks to co-worker and all around swell guy Tim Robichaux for telling me how to get ISA to behave).

Also note that many of the commercial CAs specifically provide downloadable packages of their root CA and intermediate CA certificates. Some of them get really confusing – they have different CAs for different tiers or product lines, so you have to match the server certificate you have with the right CA certificates. GoDaddy’s CA certificate page can be found here.

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Husband and father; technology consultant, speaker, author, and blogger; Microsoft Exchange architect and MVP; writer, reader, Xbox player, karate student, and music lover. Seeker of balance, reveler in life, learning how to look for the uplifting.

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