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After moving to Office 365 Outlook sometimes gets server unavailable error for some functions RRS feed

  • Question

  • We moved to Office 365 earlier this year. We have less than 100 mailboxes, so we opted to created new mailboxes instead of migrating from the Exchange 2003 server we were running. In was in the nick-of-time because the Exchange 2003 server crashed the same weeked we moved to Office 365. It is a hardware issue and is offline.

    When we were connecting users to their new mailbox we had some issues. If they were on the LAN we had to manually configure it, because Outlook wanted to only find the old Exchange 2003 server even though it was offline and removed from the DNS servers. I'm sure it has to do with metadata that needs to be cleaned up. If they were a remote user it had no problem finding the Office 365 Exchange and connected seamlessly.

    Everyone is able to send and receive email, but some of the functions in Outlook don't work. For example, if a user tries to Automatic Replies (Out of Office) it returns the error "Your automatic reply settings cannot be displayed because the server is currently unavailable. Try again later." To work around we have the users setup Automatic Replies through the web app of Office 365. This doesn't happen to remote users.

    We've noticed this behavior in Lync as well. We're able to use Lync on the LAN, but it doesn't update the status from a user's calendar like when they have a meeting scheduled. It does update the status for users not on the LAN.

    I'm thinking this has to do with the footprints left over from not being able to disassociate AD users as mail-enabled with the old Exchange 2003 box and then bringing Exchange 2003 offline cleanly. Is there any way to clean this up? Or maybe I'm thinking down the wrong line. Has any seen this behavior?


    Tim

    Thursday, July 19, 2012 8:49 PM

Answers

  • You are correct in that this is caused by metadata held over from the old environment.

    The issues you are describing perfectly describe AutoDiscover failing.  If you have to manually configure Outlook to point to O365, it means that AutoDiscover is not functioning properly (you will need to set the DNS record internally for this).  OOF (Out of Office), the Offline Address Book, and Free/Busy are all features of AutoDiscover that will fail if AutoDiscover is failing.

    I would recommend checking the AutoDiscover registry keys in Windows, the internal DNS record for AutoDiscover, as well as any cached DNS records in your routers/firewalls/proxies/intermediary hardware and force a purge or update of all DNS caches.

    Have a great day,

    Dan


    http://insecurityinc.info

    • Proposed as answer by Daniel Trautman Friday, July 20, 2012 6:12 PM
    • Marked as answer by TimPrattBP Monday, July 23, 2012 2:51 PM
    Friday, July 20, 2012 6:12 PM

All replies

  • You are correct in that this is caused by metadata held over from the old environment.

    The issues you are describing perfectly describe AutoDiscover failing.  If you have to manually configure Outlook to point to O365, it means that AutoDiscover is not functioning properly (you will need to set the DNS record internally for this).  OOF (Out of Office), the Offline Address Book, and Free/Busy are all features of AutoDiscover that will fail if AutoDiscover is failing.

    I would recommend checking the AutoDiscover registry keys in Windows, the internal DNS record for AutoDiscover, as well as any cached DNS records in your routers/firewalls/proxies/intermediary hardware and force a purge or update of all DNS caches.

    Have a great day,

    Dan


    http://insecurityinc.info

    • Proposed as answer by Daniel Trautman Friday, July 20, 2012 6:12 PM
    • Marked as answer by TimPrattBP Monday, July 23, 2012 2:51 PM
    Friday, July 20, 2012 6:12 PM
  • That's what I was affraid of. I've added the CNAME for the AutoDiscover and MX record to our internal DNS servers. I flushed the DNS on a workstation and tried it, but still it behaves the same. I searched the Registry for AutoDiscover and there are several entried with CLSID numbers. I have no idea which would be correct. I have an upgrade to our ERP system tomorrow, but after that I'll get back into this to see what else I can clean up. Thanks for your suggestions. I'll update this on Monday.

    Tim

    Friday, July 20, 2012 7:32 PM
  • After updating the local DNS servers with CNAME for the autodisover and MX record pointing to our mail online it started working. It took some time for it to update everyone, but eventually it has. Thanks for your help.


    Tim

    Monday, July 23, 2012 2:55 PM