Cannot connect to Outlook Anywhere (Outlook 2007 RPC over HTTP)

While am a sure there are a ton of reasons Outlook Anywhere will not work, here are the two huge issues we ran into when getting this working.

1) Wild Card Certificates (special handling)

If you are using a wild card certificate, you will need to run the following connect on whatever CAS server you are using:

Set-OutlookProvider -Identity EXPR -CertPrincipalName msstd:*.contoso.com

You can also check what the current settings are by using:

Note: *.contoso.com is replaced with your wildcard certificate name.

Get-OutlookProvider

by changing that setting it will update autodiscovery to set that into the outlook client configuration as shown here:

For more details about wildcards and Outlook Anywhere go here: http://technet.microsoft.com/en-us/library/cc535023.aspx

2) Issues with IIS and Certificate Settings

Everyone who is trying to get Outlook Anywhere working should triple check that on the root of the IIS site is set to ignore client certificates.

To do that first go to the properties of the IIS website that has your RPC proxy (the root of the website)


Then click the directory Security Tab, and click Edit on Secure communications

Make sure “Ignore Client Certificates” is selected.

You can change all of the sub folders but you must make sure it is set to ignore on the root site.

So there you have it, those were to two issues we had and were able to resolve.

I would like to thank Jason B (one of my Network Administrators) who did the research to discover the second issue.

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About Eric

My name is Eric Weintraub. I am an IT Professional with over 12 years of real world experience. I currently work as a Senior IT Manager for a large software company that develops products for Information Technology workers. Professionally, I love what I do and it shows in my work. Personally, I enjoy technology as a whole. Enterprise Technology, Social Media, and Mobile technologies are all things I follow. I also love to play golf, go snowboarding, cook, love to eat, and read. Also big on photography, check out my recent photography at http://www.ericweintraubphotography.com and also Flickr: http://www.flickr.com/photos/ericweintraub/. As much as I don’t have a lot of free time, I always come across things that I believe could help others. I just wanted to be able to share what I find with others. Thanks for reading the blog, please setup a RSS feed and keep in touch! Eric Weintraub

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