Out of Office Assistant available via OWA, but not Outlook Anywhere


  • I'm setting up a Windows 2008 SBS Server in our medical office. At the moment, I've joined only one client computer to the domain. Other users connect to the Server via Remote Web Workplace. The client joined to the domain is my laptop (a MacBook Pro running Win 7 Ultimate RC (build 7100).

    When I'm not physically on our office LAN, I'm able to connect to the Exchange Server either through Outlook Anywhere or OWA. With Outlook Web Access, the Out of Office Assistant functions normally, but I cannot use the Out of Office Assistant if I'm connected using Outlook Anywhere (a message eventually appears stating that the server is unavailable, although at the very moment I'm connected to the Exchange Server.

    My original installation was created just 3 weeks ago, and I'm still in testing before rolliing this out for my partners and staff to use for messaging, calendaring, and SharePoint access to our patient-related documents. I've done all the updates that appear in the SBS console using WSUS.

    I did have to "downgrade" from the default 128 bit security settings in the Win7 RC OS on my laptop in order to enable Outlook Anywhere connectivity to my Exchange Server; once I did that (based on recommendations I read on a support forum elsewhere), I've had no problems with connecting or keeping messages in my local cache. I did not have to change the default network connectivity security settings to obtain Outlook Anywhere Access from a Win XP SP3 client, but the Out of Office Assistant doesn't work for that client, either.

    We have an IT consultant available, but we don't have an IT budget (after all, SBS is touted as something that can be set up and managed by reasonably intelligent end-users).

    My command-line skills are exceedingly rudimentary, but with some hand-holding I'm pretty confident I could run tests to make certain autodiscovery is turned on and working, and if I'm unable to do that myself, I could bring in our consultant to run the tests. However, his SBS experience is all with 2003, and he's unfamiliar with the things that are new in SBS 2008.

    I've read other threads here that discuss somewhat similar problems, but they're several months old. I've done all recommended updates on the Server, including Update Rollup 9 for the Exchange Server 2007 and update Rollup 3 for the SBS Server, and of course all the security updates.

    I'd be very grateful for suggestions.

    Thanks so much,
    Jim Robertson
    Wednesday, September 16, 2009 1:01 PM


  • So you're not running "the world's most advanced operating system" on the the most elegant computers on the planet ... But in media res: Your problem is most likely related to Autodiscover not working from the Internet. Out of Office depends on the Availability service, which depends on Autodiscover.

    With a default installation of SBS 2008 a SAN certificate with three entries is created, for instance:


    These names were chosen at install time. Your's will of course differ, and these aren't mine either. With the examples above you need a CNAME for hosle.net referring to remote.hosle.net.

    Autodiscover will attempt these queries in this order:

    https://hosle.net/Autodiscover/Autodiscover.xml (here you are covered with your certificate)
    https://autodiscover.hosle.net/Autodiscover/Autodiscover.xml (here you would need to either generate a self-signed certificate or buy a commercial one.

    There are two additional queries, but we concentrate on the first two. 
    Then do a test from the Internet:


    • Marked as answer by Allen Song Friday, September 25, 2009 9:48 AM
    Wednesday, September 16, 2009 9:02 PM