Autodiscover for Microsoft Exchange

Let’s say you have a hosted exchange account somewhere and you’re using mail forwarding rather than MX records to push your email to their servers. And you’re getting errors like these in Outlook’s Sync Issues folder:

16:59:02 Synchronizer Version 12.0.4518
16:59:02 Synchronizing Mailbox ‘YOURNAME’
16:59:02 Done
16:59:07 Microsoft Exchange offline address book
16:59:07 Not downloading Offline address book files. A server (URL) could not be located.
16:59:07 0X8004010F

Every hour, on the hour.

What is this? Outlook 2007 has a feature called “Autodiscover” that it uses to obtain various settings. But in order for it to work, you need “autodiscover.yourdomain.com” to point to the exchange server. Since you’re using hosted exchange, “autodiscover.yourdomain.com” probably *does not* resolve to your hosted Exchange server (it may point nowhere, or if you have a wildcard DNS host like TZO it may just point to your web server).

At any rate, in order to make this all better, you have to go into DNS for your domain (that might be at your registrar, or it might be in WHM/Cpanel, or you might just have to email your web hosting provider if they manage your DNS for you). Now add either a CNAME or an A record…that choice depends what you want and how the hosted exchange company wants you to do it.

For example, Sherweb, a hosted exchange provider, is pretty clear about wanting you to add an A record, and they give you the IP address to point it to. So you add a record:

autodiscover 14400 IN A xx.xx.xx.xx (I don’t recall the IP offhand, Sherweb has it posted)

But other providers aren’t as obvious. For example, when you sign up with Mailstreet with a “dummy” domain name (so they won’t be authoritative for your real domain and there’s no risk of that ever happening), they will create an autodiscover entry for your dummy domain. (Dummy domains take the form of “YOURDOMAIN.mymailstreet.com”.) So in this case you create a CNAME that points to the dummy domain, and it’ll work as well:

autodiscover 14400 IN CNAME autodiscover.YOURDOMAIN.mymailstreet.com. (Last period required)

Then wait for awhile for “propagation” (I know it’s the wrong term, but it’s pervasive). Control-click on your outlook system tray icon and choose “Test Email AutoConfiguration”. Before you do this you can ping autodiscover.yourdomain.com and make sure you get the correct response. Then uncheck Guessmart options and hit “Test” after entering your Exchange email and password. The https protocols will fail, but the http protocol will work eventually, and you should be all set.

Thanks to Sherweb for their very clear explanation (along the lines of “you must set an A record…”) that was ever so helpful in tracking this down.