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Exchange 2007 to Exchange 2013 migration Outlook auto setup problem

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Hello,

In a test environment, I am doing a test run of migrating to Exchange 2013 from Exchange 2007 using virtual machines. I have restored our live server to a virtual machine (using StorageCraft ShadowProtect).

Background info:

Virtual machine - SBS 2008 with Exchange 2007 SP3 Rollup 21 (also the AD domain server)

Virtual machine - 2012R2 with Exchange 2013 CU 14 (purely just Exchange 2013 roles, no DNS role etc.)

 

I have been following the “Exchange Server Deployment Assistant” guide:

https://technet.microsoft.com/en-us/exdeploy2013/Checklist?state=3215-W-FwBEAgAAQBCIAMFHAQDAFAgAAAAAwAMAAAA%7e

DNS information:

Internal domain uses domain1.local

Email addresses are domain2.co.uk

All virtual directory links for internal and external are set to use:

remote.domain2.co.uk

autodiscover.domain2.co.uk

legacy.domain2.co.uk

internal.domain2.co.uk

I have a forward lookup zone setup for DNS for domain2.co.uk with the above pointing to their server IP’s. OWA works fine, you go to the Exchange 2013 landing page and if your account is in Exchange 2007 you get redirected to legacy.domain2.co.uk and are signed in etc.

I haven’t setup any SSL certificates, though I am only interested in making internal email work, so do I need to care? In live with Exchange 2007, when you first open Outlook and run through the auto account setup, you get an SSL error but can just ignore it and everything is fine (again I don’t want to use public facing email, just internal).

 

 

The problem with Outlook and an Exchange 2013 based account:

As mentioned I am not using SSL certificates, do you need an SSL certificate for Exchange 2013 on internal only connections with Outlook clients regardless?

Either way: when running Outlook 2013 for the first-time, account settings are pulled in automatically, even the GUID is filled in where you normally get the server name which is how it should work with Exchange 2013, but still get the below two errors:

  • “The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action.”
  • “There is a problem with the proxy server's security certificate.

The name on the security certificate is invalid or does not match the name of the target site remote.domain2.co.uk.

Outlook is unable to connect to the proxy server. (Error Code 10)”

If I use the registry editor to add the “DS Server” on the Outlook machine to point to the SBS 2008 server FQDN, then I don’t get the “Exchange is unavailable” error and can continue to login (see: https://support.microsoft.com/en-gb/kb/319206). I don’t see this as an acceptable solution because it means I set something up wrong along the way?

Also, I can navigate successfully (choosing to ignore the certificate warning) to https://autodiscover.domain.co.uk/Autodiscover/Autodiscover.xml

Doesn’t this mean autodiscover should work? i.e. Outlook auto account setup

Aside: I’m having another problem, one with a Public Folder script – I haven’t posted here, but subject is “Exchange 2007 to Exchange 2013 Public Folder migration script problem”

Any help/direction would be very much appreciated. Please let me know if I have missed any key details that you need.

Thanks,

Graham



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