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Migrating from Exchange 2010 to Exchange 2013 while coexisting

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Hellow everyone.

I would like some knowledge insight in my preparation for a migration of exchange 2010 to exchange 2013 with DAG in our DR Site.

First of all, what i would like to achieve. 

  1. after moving users mailbox to exh2013, i would prefer not to have any manual intervention in the users outlook profile
  2. iPhones/Android using active sync ( if possible, be reconfigure automatically )

What i have done so far.

  1. exchange 2010 upgrade to sp3 (current owa.pro.mydomain.com, it has an old cert that will expire next year owa.pro.mydomain.com )
  2. Exchange 2013 installed in Prod ( PROD2013 current webmail.mydomain.com )
  3. and DR (DR2013 current drwebmail.mydomain.com )
  4. wildcard certificate installed in both exch ( *.mydomain.com )
  5. my internal domain is mydomain.local, so i created split DNS in my DNS servers
  6. configure DAG ( 2013DAG.mydomain.local ) and give its IP - Tested and working
  7. changed its Virtual Directory to use the same address for internal and external, including autodiscover
  8. created the A records to DNS to point to its respective servers

Now the issues i am facing.

  1. When move a test user to new PROD2013, the user can use the OWA successfully, but i cant successfully use outlook 2013 or 2010, it get error The action cannot be completed. the connection to microsoft exchange is unavailable. outlook must be online or connected to complete this action.
  2. I can complete it manually, but everytime i open the outlook i get prompt for username and password

it led me to believe that is   authentication issue, here is my autodiscover details, which in my point of view it is correct.

C:\>Get-OutlookAnywhere -server PROD2013

RunspaceId                         : 6512e9c9-4e21-43eb-bc03-7a45185ae23d
ServerName                         : PROD2013
SSLOffloading                      : False
ExternalHostname                   : webmail.mydomain.com
InternalHostname                   : webmail.mydomain.com
ExternalClientAuthenticationMethod : Basic
InternalClientAuthenticationMethod : Ntlm
IISAuthenticationMethods           : {Basic, Ntlm}
XropUrl                            :
ExternalClientsRequireSsl          : True
InternalClientsRequireSsl          : True
MetabasePath                       : IIS://PROD2013.mydomain.local/W3SVC/1/ROOT/Rpc
Path                               : C:\Program Files\Microsoft\Exchange Server\V15\FrontEnd\HttpProxy\rpc
ExtendedProtectionTokenChecking    : None
ExtendedProtectionFlags            : {}
ExtendedProtectionSPNList          : {}
AdminDisplayVersion                : Version 15.0 (Build 913.22)
Server                             : PROD2013
AdminDisplayName                   :
ExchangeVersion                    : 0.20 (15.0.0.0)
Name                               : Rpc (Default Web Site)
DistinguishedName                  : CN=Rpc (Default Web
                                     Site),CN=HTTP,CN=Protocols,CN=PROD2013,CN=Servers,CN=Exchange Administrative
                                     Group (FYDIBOHF23SPDLT),CN=Administrative Groups,CN=mydomain,CN=Microsoft
                                     Exchange,CN=Services,CN=Configuration,DC=mydomain,DC=local
Identity                           : PROD2013\Rpc (Default Web Site)
Guid                               : 22368d46-0985-498d-83c3-aabf395ece3c
ObjectCategory                     : mydomain.local/Configuration/Schema/ms-Exch-Rpc-Http-Virtual-Directory
ObjectClass                        : {top, msExchVirtualDirectory, msExchRpcHttpVirtualDirectory}
WhenChanged                        : 17/06/2014 14:48:00
WhenCreated                        : 02/06/2014 12:18:00
WhenChangedUTC                     : 17/06/2014 13:48:00
WhenCreatedUTC                     : 02/06/2014 11:18:00
OrganizationId                     :
OriginatingServer                  : PRO-ADC02.mydomain.local
IsValid                            : True
ObjectState                        : Changed

If someone could give some help it will be very appreciated.

Cheers


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