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We have DNS servers on win2003 and recently migrated to Office 365 using cutover migration. When we try to make a new profile in Outlook, it's picking up the user from the AD and associating the user with our old Exchange server and not the Office 365 exchange server in the cloud. If we change the DNS to the gateway, it resolves fine. But then, we won't have access to our local resources anymore.

When I make a new profile in Outlook, it automatically fills out the Domain assigned username. This happens when the DNS is set to our internal DNS. When I set it to the gateway, it will allow us to type the user name and password and it will connect to Office 365's email servers from the internet.

We do have the CNAME record at our registrar for autodiscover purposes. What can I change in my DNS server that will allow me to connect to cloud based office 365 servers? I tried "Forwarders" and it didn't worked.

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up vote 3 down vote accepted

It sounds like you've got Exchange 2007 or 2010 running internally. If that's the case then it sounds like you're running into Exchange Autodiscover. The easiest way to get around it is to set the MSExchangeAutodiscoverAppPool application pool in IIS to not start Automatically. Once you do that and stop the app pool you should be OK.

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Thanks! That worked! – fmysky Jan 10 '12 at 20:56
Glad to help... – joeqwerty Jan 11 '12 at 0:47
Joeqwerty, Can I change the URL of the Autodiscover like this to achieve the above? Will that work? – fmysky Jan 11 '12 at 23:22
I'm talking about URL redirection as shown in the image – fmysky Jan 11 '12 at 23:23
I've never tried it. The reason I suggested "disabling" the application pool is because that doesn't require any configuration changes. If you need to use Autodiscover in the future you just need to "reenable" the application pool. Any other method (such as a redirect) requires a configuration change and with that you risk "borking" the configuration. – joeqwerty Jan 12 '12 at 0:59

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