Exchange 2010 SSL Offloading

One of the deployments I’ve been working on recently involved using F5 BigIP hardware load balancers to do SSL offloading for a two-node Exchange 2010 design. To give some background here usually you would just pass through port 443 (I’m skipping over the RPC Client Access piece since it’s not relevant here) from your load balancer straight to the Exchange servers, letting the servers handle the SSL encryption like in this diagram:


The benefit of that approach is it’s simple and a very common deployment method. On the flip side, you can benefit from offloading SSL encryption to the BigIPs and gain some more advanced forms of load balancing. In this case the improved load balancing was the goal along with some internal policies forcing this approach. What happens with SSL offloading is the HTTPS traffic ends at the BigIPs which turn around and pass port 80 clear-text traffic back to the Exchange servers so they have a bit less CPU work to do. That strategy looks more like this:


The problem with this configuration is Exchange is really designed to operate with SSL in mind and you have to go out of your way to allow it to operate in clear-text. What you’ll need to configure on each CAS server is:

The issue I ran into is after following all of these steps Autodiscover was still not functional through the load balancing. I could enter https://<CAS Array FQDN>/Autodiscover/Autodiscover.xml into a browser and reach the XML file with no problem, but running the Autodiscover test within Outlook would return a 404 error. Every other service was working just fine:


This threw me for awhile and after a bit of searching I ran across KB 980048 where it’s noted that Autodiscover cannot be used on port 80 with an HTTP POST request, which is what Outlook uses. My attempts at accessing the XML directly succeeded because I was only trying to download the file. Supposedly this is going to be fixed in Service Pack 1.

While the KB provides no immediate solution what I found that works is to use the same methodology Technet recommends for the Exchange Web Services web.config file. Go into your /Autodiscover folder and edit the web.config to replace all instances of httpsTransport with httpTransport (a simple search and replace should work). Be sure to save a copy before you make modifications, restart your server after making the change and you should be able to offload SSL for Autodiscover successfully. Since as far as I know this is undocumented today you can try this at your own risk, but it appears to be working.


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Hi there. My name is Tom Pacyk and this is my small home on the web. I love the intersection of design, technology, and communication, which is a combination that led me to a career in sales and marketing roles at places like Zoom and ServiceNow. They're a bit old now, but I also had the opportunity to publish a couple of books along the way.

Portland, Oregon is home for me, my wife Beth, and our three kids, but I'm actually a Midwestern transplant—I grew up in the Chicago suburbs and went to school at Purdue and Illinois. When I find some free time I'm probably going to concerts, rooting for the Portland Timbers, or working on my Sunshine Burn Photography project.