Hi guys, so before i begin, here's my current configuration:

• A Server 2003 Domain controller
• A single Exchange 2010 SP3 Server (previously migrated from 2003, however 2003 had to be decommissioned using ADSIEdit, and deleting the server object)
• a new Exchange 2013 SP1 Server configured identical to the 2010, interms of the virtual directory paths, certificates etc...

So here is whats happening, clients are connecting fine to 2010, i migrated a mailbox to 2013, and EVERYTHING works internally,  except for Outlook, externally i'm passing all tests like, Outlook anywhere, OWA, Activesync etc.. no certificate pop ups, no cert trust problems. Outlook just refuses to connect internally, just shows up as disconected.

Whats i've tried and noticed:

• Manually edited the host file to point autodiscover.domain.com and mail.domain.com directly to Exchange 2013, ping tests passing.
• Did autodiscover test setting from outlook, and its saying it cant determine my settings
• Manually edited host file on a 2010 mailbox and noticed that outlook was still connecting through mapi instead of proxying through 2013.
• Internal DNS has the correct records.
• Outlook has the correct http proxy settings, with the correct login, also everything is set to ntlm between both servers.
• OWA proxing works, 2010 users can login using the 2013 login page.
• Created a new 2013 mailbox and still nothing, if i do a new profile it errors telling Exchange needs to be online, then a popup with the name of the server instead of a guid
• After a mailbox move says its complete, and i login to OWA, i'm presented with the old 2010 OWA, but mail flow works and appears to be originating from the 2013 server, but it took almost 15 minutes for me to get the 2013 OWA on login.
• Even adsi entries for the user has the homedb  the 2013 server listed.
• I also ran every Test-OutlookConnectivty test from HERE and all passed
• And they don't use any proxying

This one is real head scratcher, so any has any ideas because i'm out :(

Thanks in advance, looking forward to your replies.

• Edited by jumbi Friday, January 23, 2015 5:32 PM

Hi

What authentication methods do you have setup on Exchange 2013?

Clientauth set to Ntlm and IISAuth has both ntlm and basic on both 2010 and 2013.

Would very high latency cause this to happen? we've noticed really high pings coming from this machine, 100, 200 even 500ms.

Hi,

Please check the following settings in Exchange 2013:

Get-ClientAccessServer | FL Identity,AutodiscoverServiceInternalUri

In Exchange server, please make sure all Exchange services are started and running. Restart IIS service by running IISReset from a Command Prompt window. Please reboot your Exchange 2013 to have a try.

In client side, please provide the detailed results in Log tab about your autodiscover service testing by running Test E-mail AutoConfiguration. Additionally, here is a KB that may be helpful to you:

http://support2.microsoft.com/kb/2931385

Regards,

Tried it, heres a look at my autodiscover directory for both servers

RunspaceId                      : f6168437-95d7-4430-b685-da91cb9daa31
Name                            : Autodiscover (Default Web Site)
InternalAuthenticationMethods   : {Basic, Ntlm, WindowsIntegrated, WSSecurity}
ExternalAuthenticationMethods   : {Basic, Ntlm, WindowsIntegrated, WSSecurity}
LiveIdSpNegoAuthentication      : False
WSSecurityAuthentication        : True
LiveIdBasicAuthentication       : False
BasicAuthentication             : True
DigestAuthentication            : False
WindowsAuthentication           : True
MetabasePath                    : IIS://mail2010.internaldomain.com/W3SVC/1/ROOT/Autodiscover
Path                            : C:\Program Files\Microsoft\Exchange Server\V14\ClientAccess\Autodiscover
ExtendedProtectionTokenChecking : None
ExtendedProtectionFlags         : {}
ExtendedProtectionSPNList       : {}
Server                          : mail2010
InternalUrl                     : https://autodiscover.publicname.com/autodiscover/autodiscover.xml
ExternalUrl                     : https://autodiscover.publicname.com/autodiscover/autodiscover.xml
AdminDisplayName                : 
ExchangeVersion                 : 0.10 (14.0.100.0)
DistinguishedName               : CN=Autodiscover (Default Web Site),CN=HTTP,CN=Protocols,CN=mail2010,CN=Servers,
                                  CN=Exchange Administrative Group (FYDIBOHF23SPDLT),CN=Administrative Groups,CN=Paramo
                                  unt Transport,CN=Microsoft Exchange,CN=Services,CN=Configuration,DC=PTT,DC=COM
Identity                        : mail2010\Autodiscover (Default Web Site)
Guid                            : ad93f6ad-ad7f-479f-9dba-239abf98b371
ObjectCategory                  : internaldomain.com/Configuration/Schema/ms-Exch-Auto-Discover-Virtual-Directory
ObjectClass                     : {top, msExchVirtualDirectory, msExchAutoDiscoverVirtualDirectory}
WhenChanged                     : 19/01/2015 12:13:42 PM
WhenCreated                     : 19/01/2015 12:00:04 PM
WhenChangedUTC                  : 19/01/2015 04:13:42 PM
WhenCreatedUTC                  : 19/01/2015 04:00:04 PM
OrganizationId                  : 
OriginatingServer               : dc.internaldomain.com
IsValid                         : True

RunspaceId                      : f6168437-95d7-4430-b685-da91cb9daa31
Name                            : Autodiscover (Exchange Back End)
InternalAuthenticationMethods   : {Ntlm, WindowsIntegrated, WSSecurity}
ExternalAuthenticationMethods   : {Ntlm, WindowsIntegrated, WSSecurity}
LiveIdSpNegoAuthentication      : False
WSSecurityAuthentication        : True
LiveIdBasicAuthentication       : False
BasicAuthentication             : False
DigestAuthentication            : False
WindowsAuthentication           : True
MetabasePath                    : IIS://mail2013.internaldomain.com/W3SVC/2/ROOT/Autodiscover
Path                            : c:\Program Files\Microsoft\Exchange Server\V15\ClientAccess\Autodiscover
ExtendedProtectionTokenChecking : None
ExtendedProtectionFlags         : {}
ExtendedProtectionSPNList       : {}
Server                          : mail2013
InternalUrl                     : 
ExternalUrl                     : 
AdminDisplayName                : 
ExchangeVersion                 : 0.10 (14.0.100.0)
DistinguishedName               : CN=Autodiscover (Exchange Back End),CN=HTTP,CN=Protocols,CN=mail2013,CN=Servers,CN=
                                  Exchange Administrative Group (FYDIBOHF23SPDLT),CN=Administrative Groups,CN=Paramount
                                   Transport,CN=Microsoft Exchange,CN=Services,CN=Configuration,DC=PTT,DC=COM
Identity                        : mail2013\Autodiscover (Exchange Back End)
Guid                            : 84d854de-300e-4ae1-b230-fecbb4be82f4
ObjectCategory                  : internaldomain.com/Configuration/Schema/ms-Exch-Auto-Discover-Virtual-Directory
ObjectClass                     : {top, msExchVirtualDirectory, msExchAutoDiscoverVirtualDirectory}
WhenChanged                     : 27/01/2015 03:11:05 PM
WhenCreated                     : 27/01/2015 03:11:05 PM
WhenChangedUTC                  : 27/01/2015 07:11:05 PM
WhenCreatedUTC                  : 27/01/2015 07:11:05 PM
OrganizationId                  : 
OriginatingServer               : dc.internaldomain.com
IsValid                         : True

RunspaceId                      : f6168437-95d7-4430-b685-da91cb9daa31
Name                            : Autodiscover (Default Web Site)
InternalAuthenticationMethods   : {Basic, Ntlm, WindowsIntegrated, WSSecurity}
ExternalAuthenticationMethods   : {Basic, Ntlm, WindowsIntegrated, WSSecurity}
LiveIdSpNegoAuthentication      : False
WSSecurityAuthentication        : True
LiveIdBasicAuthentication       : False
BasicAuthentication             : True
DigestAuthentication            : False
WindowsAuthentication           : True
MetabasePath                    : IIS://mail2013.internaldomain.com/W3SVC/1/ROOT/Autodiscover
Path                            : c:\Program Files\Microsoft\Exchange Server\V15\FrontEnd\HttpProxy\Autodiscover
ExtendedProtectionTokenChecking : None
ExtendedProtectionFlags         : {}
ExtendedProtectionSPNList       : {}
Server                          : mail2013
InternalUrl                     : https://autodiscover.publicname.com/autodiscover/autodiscover.xml
ExternalUrl                     : https://autodiscover.publicname.com/autodiscover/autodiscover.xml
AdminDisplayName                : 
ExchangeVersion                 : 0.10 (14.0.100.0)
DistinguishedName               : CN=Autodiscover (Default Web Site),CN=HTTP,CN=Protocols,CN=mail2013,CN=Servers,CN=E
                                  xchange Administrative Group (FYDIBOHF23SPDLT),CN=Administrative Groups,CN=Paramount 
                                  Transport,CN=Microsoft Exchange,CN=Services,CN=Configuration,DC=PTT,DC=COM
Identity                        : mail2013\Autodiscover (Default Web Site)
Guid                            : ddc04d36-830c-4b08-8ef0-9620693ed79c
ObjectCategory                  : internaldomain.com/Configuration/Schema/ms-Exch-Auto-Discover-Virtual-Directory
ObjectClass                     : {top, msExchVirtualDirectory, msExchAutoDiscoverVirtualDirectory}
WhenChanged                     : 27/01/2015 03:53:53 PM
WhenCreated                     : 27/01/2015 03:20:46 PM
WhenChangedUTC                  : 27/01/2015 07:53:53 PM
WhenCreatedUTC                  : 27/01/2015 07:20:46 PM
OrganizationId                  : 
OriginatingServer               : dc.internaldomain.com
IsValid                         : True

More output.

Get-ClientAccessServer | fl

RunspaceId                           : ea617092-768a-4813-bcfa-32968b0ab49a
Name                                 : mail2010
Fqdn                                 : mail2010.internaldomain.com
ClientAccessArray                    : 
OutlookAnywhereEnabled               : True
AutoDiscoverServiceCN                : mail2010
AutoDiscoverServiceClassName         : ms-Exchange-AutoDiscover-Service
AutoDiscoverServiceInternalUri       : https://mail.publicdomain.com/autodiscover/autodiscover.xml
AutoDiscoverServiceGuid              : 77378f46-2c66-4aa9-a6a6-3e7a48b19596
AutoDiscoverSiteScope                : {Default-First-Site-Name}
AlternateServiceAccountConfiguration : 
IsOutOfService                       : False
WorkloadManagementPolicy             : 
Identity                             : mail2010
IsValid                              : True
ExchangeVersion                      : 0.1 (8.0.535.0)
DistinguishedName                    : CN=mail2010,CN=Servers,CN=Exchange Administrative Group 
                                       (FYDIBOHF23SPDLT),CN=Administrative Groups,CN=Paramount Transport,CN=Microsoft 
                                       Exchange,CN=Services,CN=Configuration,DC=PTT,DC=COM
Guid                                 : 9ee27a7e-ac27-4333-b9b9-28145b0bc681
ObjectCategory                       : internaldomain.com/Configuration/Schema/ms-Exch-Exchange-Server
ObjectClass                          : {top, server, msExchExchangeServer}
WhenChanged                          : 19/01/2015 12:24:04 PM
WhenCreated                          : 19/01/2015 11:43:09 AM
WhenChangedUTC                       : 19/01/2015 04:24:04 PM
WhenCreatedUTC                       : 19/01/2015 03:43:09 PM
OrganizationId                       : 
OriginatingServer                    : dc.internaldomain.com
ObjectState                          : Unchanged

RunspaceId                           : ea617092-768a-4813-bcfa-32968b0ab49a
Name                                 : mail2013
Fqdn                                 : mail2013.internaldomain.com
ClientAccessArray                    : 
OutlookAnywhereEnabled               : True
AutoDiscoverServiceCN                : mail2013
AutoDiscoverServiceClassName         : ms-Exchange-AutoDiscover-Service
AutoDiscoverServiceInternalUri       : https://mail.publicdomain.com/autodiscover/autodiscover.xml
AutoDiscoverServiceGuid              : 77378f46-2c66-4aa9-a6a6-3e7a48b19596
AutoDiscoverSiteScope                : {Default-First-Site-Name}
AlternateServiceAccountConfiguration : 
IsOutOfService                       : False
WorkloadManagementPolicy             : DefaultWorkloadManagementPolicy_15.0.825.0
Identity                             : mail2013
IsValid                              : True
ExchangeVersion                      : 0.1 (8.0.535.0)
DistinguishedName                    : CN=mail2013,CN=Servers,CN=Exchange Administrative Group 
                                       (FYDIBOHF23SPDLT),CN=Administrative Groups,CN=Paramount Transport,CN=Microsoft 
                                       Exchange,CN=Services,CN=Configuration,DC=PTT,DC=COM
Guid                                 : aeaec1a2-4988-4ee5-8fea-8839c2e473d5
ObjectCategory                       : internaldomain.com/Configuration/Schema/ms-Exch-Exchange-Server
ObjectClass                          : {top, server, msExchExchangeServer}
WhenChanged                          : 27/01/2015 04:24:41 PM
WhenCreated                          : 22/01/2015 04:04:34 PM
WhenChangedUTC                       : 27/01/2015 08:24:41 PM
WhenCreatedUTC                       : 22/01/2015 08:04:34 PM
OrganizationId                       : 
OriginatingServer                    : dc.internaldomain.com
ObjectState                          : Unchanged

Also when i do a test autodiscover, it says unable to determine settings, if i do it while the mailbox is on 2010 it detects the settings. i also observed when i hit reconnect i can see it trying to connect to the 2013 then it switches to the 2010 and says established, not sure how it established considering the mailbox is on 2013.

So i did some monitoring on TMG and it turns out all my https traffic was still being sent to exchange 2010 even though i was using a modded host file, so i changed the address in DNS, so now my traffic is going to 2013. that said, i'm getting a new error when trying to setup the migrated user s profile. Before, it said the name of the my 2013 server and the mailbox name, but the traffic was indeed going to 2010. Now that traffic is going to the right server, it still wont get the settings, but atleast the mailbox info looks like it supposed to.

So turns out the windows 7 client though updated to SP1 still needed updates, i had to edit a registry setting to set disable mapithttp.

• Marked as answer by jumbi Saturday, January 31, 2015 3:46 AM