We are having an issue trying to set the Out Of Office Assistant through Outlook 2007.

It works fine through OWA but all of the users cannot set it through Outlook. They get:

your out of office settings cannot be displayed because the server is unavailable

We have run through: https://www.testexchangeconnectivity.com/

and we get this error: Certificate name validation error

More info:

Host name xxxxxxxxxxxx.com does not match any name found on the server certificate
CN=*.securedwebspace.com, OU=Domain Control Validated - RapidSSL(R), OU=See www.rapidssl.com/resources/cps (c)09, OU=GT93715821, O=*.securedwebspace.com, C=GB 

Any ideas on how we can fix this? (Everything else seems to work fine - Its just the Out of Office through Outlook)

Server is SBS 2008 with Exchange 2007 installed.


  • Are your Outlook clients connecting using Outlook Anywhere? – nabrond Jan 27 '10 at 12:17
  • No just Outlook on the LAN – Adam Chetnik Jan 27 '10 at 12:26
  • Do you have a third-party SSL cert assigned to your SBS? Or are you using a self-signed? If it's third-party, did you assign it within the SBS 2008 wizard or did you assign it manually via Exchange's shell? – tcv Jan 27 '10 at 14:31
  • self-signed no 3rd party – Adam Chetnik Jan 27 '10 at 15:04
  • No interest in getting a cert? – tcv Jan 27 '10 at 21:37

I feel a little conflicted about my answer. Basically the short of it is this: I don't know the SBS-approved way to fix your problem. I was sort of hoping someone else would come along with the SBS-approved way. I've resolved this issue in plain-vanilla E2007 setups, but not SBS 2008. ::shrugs::

The problem in your Exchange setup not being complete with relation to internal and external URLs. Basically, Exchange 2007 uses FQDNs, whether they're internal or external, unlike earlier versions which could use NETBIOS names. Somewhere, you don't have a URL or another quite set up and your Outlook clients don't know where to go for OOO.

So, what I'd do is this. Go to this site: http://www.amset.info/exchange/singlenamessl.asp -- Read it through. Since you have a self-signed cert, you have a single name cert, so this page's information is relevant.

Why not get a third-party cert? They just ain't expensive anymore and Exchange 2007 really wants one. ;-)

I'll try to help you as you go along.


"Ain't expensive". Why do I have to pay at all. This is just another money generating exercise. These throw away lines just get me very angry. Why should everybody have to pay "again" for Microsoft's shortcomings. It's just demanding money with menaces.

  • I wouldn't say this is a shortcoming. Your options are to either buy a cert that will work with all devices and browsers, or use a self-signed and manually install it. To some places with only a handful of devices and browsers, they may not care about self-signed. Are you going to argue that spending a few hundred $ a year to secure your site, have all of its features working for hundreds or thousands of browsers and devices is "demanding money with menaces"? – DanBig Oct 20 '10 at 12:17

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