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unrealone1Flag for United Kingdom of Great Britain and Northern Ireland

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Issues with Office 365 on premise outlook

Hi Experts, we have a client that we have migrated from sbs2003 to server 2012, approximately 7 users. We installed office 365 and although we can access mail through owa, we cannot seem to configure outlook 2016. Its almost as if the app cannot even reach autodiscover. Its strange as this new server is a fresh build. We have check all the dns records and they see to be fine. #any pointers where on the server 2012 that information might be?#
thanks.
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Vasil Michev (MVP)
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So the mailboxes are still on-prem, right? I assume by "installed O365" you mean the desktop version of Office, not the cloud service.

Run the Test E-mail autoconfiguration test is Outlook (hold the CTRL key, right-click on Outlook's icon in the tray, select the Test E-mail blabla option, enter email address and password, clear the two Guessmart checkboxes and run the test. If prompted for credentials make sure to enter the Username/password, not email address). Post the sanitized results of the test here so we can take a look.
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Hi, no apologies, the mailboxes are all on Office 365 exchange. outlook is installed on computers onsite. When trying to automatically configure outlook, the attached error comes up. the server address should be in theory outlook.office.com but that box is grayed out. It doesn't even look like the computers are querying the autodiscover record which is fully propagated as I can ping it and it resolves.

It seems to me that the computers aren't even querying DNS, they are getting the settings from elsewhere. Brand new DC, on a brand new domain, all computers on new domain and old DC on old domain isn't online anymore. Numerous ipconfig /flushdns have occured and still no joy. Have also tested credentials on OWA and that all works so it's not that.

Is there something else that outlook does before querying autodiscover.domain.com?
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Have you done the following?

The administrator completes post-migration tasks in Office 365 (assigns licenses to users and creates an Autodiscover Domain Name System (DNS) record), and optionally decommissions the on-premises Exchange servers.

Source: https://support.office.com/en-us/article/Cutover-migration-to-Office-365-9496e93c-1e59-41a8-9bb3-6e8df0cd81b4
Hi,
yes done all that thanks
Post back for the result for the test below.

https://testconnectivity.microsoft.com/
In a domain environment, Outlook will first hit the Exchange SCP, plus it might reuse the old autodiscover XML files. An easy way to confirm this is to try configuring one of the profiles outside of the domain network, say on a home PC. Or you can simply use the reg keys detailed in this article to "instruct" Outlook to only look for the CNAME record: http://support.microsoft.com/kb/2212902

You can block all other lookups, all you need working for O365 is the CNAME (HTTP Redirect) method.
Good Day,

typically DNS will direct the requests to an external DNS Server (8.8.8.8 / 4.2.2.2) depending on how your Domain Controller is configured. Autodiscover.domain.com is usually presented from your DNS records on your hosting site. I know when we configure clients with office 365, we make DNS entries on their name servers (GoDaddy / Network Solutions/ ect...) that point their autodiscover to outlook.com.

Log into portal.office.com and go to domains  and run the DNS test and see if it comes back as correct.
Hi all, the cpanel for the hosting is imap. When we use those settings and configure desktop outlook it works. When we enter O365 credentials it doesn't. It may be an issue with the hosting company as that is where the lookup is stopping. Still investigating and will keep you posted.
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Vasil Michev (MVP)
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Hi All,

Thanks for suggestions, and very much Vasil hit the nail on the head. It was settings to do with mailflow in cpanel. Despite having mx records and such, the email routing section was stuck on "local". Changed to remote and it all works fine now. Thanks all for suggetsions.

LOOK OUT FOR BLOOMING CPANEL!!