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We've configured Outlook 2010 to use Outlook Anywhere and it works fine against SBS 2011 Std. However, on start-up, it complains about a mismatched certificate.

After a bit of sniffing with Fiddler2, we've learned that, in spite of being given a URL of for Outlook Anywhere (for which we have a proper cert), Outlook is still going off to during the autodiscover phase — hence the invalid cert warning.

Why is Outlook using a different URL for autodiscover, and how can we change it to use the correct one?

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From memory, you need to assign each individual certificate for each service, which can be done in the management console, or via powershell. – Mark Henderson Sep 22 '11 at 1:10
@Mark: Thank you for the suggestion. However, the certificate being delivered is the one I want (we don't have one for It's the URL that's incorrect. Or have I misunderstood your advice? – Marcelo Cantos Sep 22 '11 at 2:33
Sorry, I mis-understood your question. Now that I re-read it, the autodiscover URL is wrong. You'll need to set that up in the powershell interface, but I can't remember the commands. – Mark Henderson Sep 22 '11 at 2:50
@Mark: Thank you. Your advice set me on the right track (see my answer), and it's working beautifully now. – Marcelo Cantos Sep 22 '11 at 4:31

Thanks to the pointers provided by Mark Henderson, I finally nailed this one. I had to change two objects in EMS:

Set-WebServicesVirtualDirectory -identity "ourserver\ews (Default Web Site)" `
    -InternalUrl `

Set-ClientAccessServer -identity ourserver `

I also came across advice to set the following:

Set-AutodiscoverVirtualDirectory -identity "ourserver\Autodiscover (Default Web Site)" `
    -InternalUrl `

But this didn't seem to be necessary in our case (though I changed it afterwards anyway).

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