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My company is in the process of migrating from Exchange 2010 to Exchange 2013 -- currently the environment is mixed, OWA is up and running, and AutoConfig is working properly.

For our Exchange 2007 -> 2010 upgrade I was able to pre-build the Exchange account profile using the Office Customization Tool to define an Exchange account (as well as some fake-POP accounts that we use for alternate SMTP sending) into a dynamic profile that was created when Outlook was first run.

When trying to do this same procedure for 2013, I am unable to open Outlook using the new default profile. Depending on how I tweak the settings I am greeted with various error messages that range from "The Exchange server might be down for maintenance," or "you must connect with the current profile before opening the OST," to "Cannot open the default set of folders", and once I was given a network password authorization box that would not accept any account/password combo that it was given.

If I create a new profile and allow it auto-configure, it does so successfully and Outlook will start up without any problems.

I suspect that the problem is how Ex2013 uses unique (per-mailbox) addressing to describe the 'Server' field in the mail profile -- The TechNet documentation states that the 'Server' entry in OCT should point to an Exchange server, and that it will be corrected when the profile first connects, however that does not appear to be happening. The 2010 CAS is providing proxy services between the two Exchange server environments, so it might be possible that the authorization is not being forwarded through there as well.

I have scoured the internet for a use case that was successful in deploying an Ex2013 account using the OCT, but I cannot find anything useful that helps me understand my situation.

Allowing the current user profiles to upgrade is not an option, as we are building new VMs that will not carry over the profile information; first-run autoconfigure is also not an option because we need the fake-POP accounts to be added ahead of time to the profiles.

Do we know if the 2013 OCT is able to preconfigure Exchange accounts? If not that is a huge step backwards in my opinion, as this feature is paramount to our upgrade path. Any thoughts would be helpful, I am happy to provide more information upon request.

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You need to use Exchange 2013 CAS and not 2010 CAS. As soon as you deployed first Exchange 2013 CAS in the organization, all the connection must be made to it, as it will broker the access to the legacy environment (Exchange 2010).

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If your environment is like ours, Outlook will auto configure itself properly if you do not customize it with the Office Customization Tool. There is a 5 step wizard where you mostly just click next until you are done. If that is the case, you want to reset the Outlook customization done by the OCT. You can do this by deleting the file c:\program files\Microsoft Office\custom15.prf or custom14.prf. That will restore the 5 step wizard that works.

We employed computer side group policy preferences to delete the file when the computers boot up.

To suppress the wizard and let Outlook open without asking questions, we set a user side group policy. This requires the ADMX templates for Office 2010/2013 to be downloaded and added to your GP console. User->Admin Templates->Outlook 2013->Account Settings->Exchange->Automatically configure based on Active Directory Primary SMTP address.

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