Outlook(autodiscover) problem after Exchange 2016 to Exchange 2019 migration

Question

Hi,

We have migrated exchange 2016 to 2019. Moved all mailboxes (arbitration, public folder, etc. everything). We dismounted all the databases and now shut down the 2016 server. Unfortunately outlook is trying to connect with the old server. If I do a connectivity test on outlook sometime mapi is showing new server url and sometime old server url. The problem is the same with connection status in outlook, sometime showing new server url and sometime old server url.

Thanks in advance!

Answer 1

So set the 2016 server to the 2019 URLs and be done with it :)

They exist in AD, so the clients will continue to use them.

If you removed the 2016 server, then that would solve it as well.

P.S. Now that I see whats going on, I can see the issue!

Answer 2

And all the virtual directories and autodiscover settings on the new server are pointing to the new 2019 server?
and you are positive all the mailboxes have been moved?

https://learn.microsoft.com/en-us/exchange/plan-and-deploy/post-installation-tasks/configure-mail-flow-and-client-access?view=exchserver-2019#step-5-configure-internal-urls

Example:

Set-ClientAccessService -Identity <server> -AutoDiscoverServiceInternalUri https://mail.mydomain.com/autodiscover/autodiscover.xml

Set-OwaVirtualDirectory -Identity "<server>\OWA (Default Web Site)" -ExternalUrl https://mail.mydomain.com/owa -InternalUrl https://mail.mydomain.com/owa

Set-EcpVirtualDirectory -Identity "<server>\ECP (Default Web Site)" -ExternalUrl https://mail.mydomain.com/ecp -InternalUrl https://mail.mydomain.com/ecp

Set-WebServicesVirtualDirectory -Identity "<server>\EWS (Default Web Site)" -ExternalUrl https://mail.mydomain.com/EWS/Exchange.asmx -InternalUrl https://mail.mydomain.com/EWS/Exchange.asmx

Set-ActiveSyncVirtualDirectory -Identity "<server>\Microsoft-Server-ActiveSync (Default Web Site)" -ExternalUrl https://mail.mydomain.com/Microsoft-Server-ActiveSync -InternalUrl https://mail.mydomain.com/Microsoft-Server-ActiveSync

Set-OabVirtualDirectory -Identity "<server>\OAB (Default Web Site)" -ExternalUrl https://mail.mydomain.com/OAB -InternalUrl https://mail.mydomain.com/OAB

Set-MapiVirtualDirectory -Identity "<server>\mapi (Default Web Site)" -ExternalUrl https://mail.mydomain.com/mapi -InternalUrl https://mail.mydomain.com/mapi

Set-ClientAccessServer -Identity <server> –AutoDiscoverServiceInternalUri https://mail.mydomain.com/Autodiscover/Autodiscover.xml

Set-OutlookAnywhere -Identity "<server>\RPC (Default Web Site)" -ExternalHostname mail.mydomain.com -InternalHostname mail.mydomain.com -ExternalClientsRequireSsl $true -InternalClientsRequireSsl $true -DefaultAuthenticationMethod NTLM

Answer 3

Every details are below.

owa.mydomain.com -> XCH19 (exists both private DNS and public DNS)
autodiscover.mydomain.com -> XCH19 (exists both private DNS and public DNS)

oldowa.mydomain.com -> EXCH16 (only exists in internal DNS, just using this instead of exch16.internal.local because of the certificate)

External connections:
HTTPS: Internet - (NAT) - XCH19
SMTP: Internet - (NAT) - Spam filter - XCH19
EXCH16 not accessible from internet.

Internal connections:
There is no loadbalancer or anything else in front of Exchange servers. Clients connecting directly.

EXCH16 URLs:

Server : EXCH16
Name : Microsoft-Server-ActiveSync (Default Web Site)
InternalUrl : https://oldowa.mydomain.com/Microsoft-Server-ActiveSync
ExternalUrl :

Server : EXCH16
Name : Autodiscover (Default Web Site)
InternalUrl :
ExternalUrl :

Server : EXCH16
Name : ecp (Default Web Site)
InternalUrl : https://oldowa.mydomain.com/ecp
ExternalUrl :

Server : EXCH16
Name : mapi (Default Web Site)
InternalUrl : https://oldowa.mydomain.com/mapi
ExternalUrl :

Server : EXCH16
Name : OAB (Default Web Site)
InternalUrl : https://oldowa.mydomain.com/OAB
ExternalUrl :

Server : EXCH16
Name : owa (Default Web Site)
InternalUrl : https://oldowa.mydomain.com/owa
ExternalUrl :

Server : EXCH16
Name : PowerShell (Default Web Site)
InternalUrl : http://exch16.internal.local/powershell
ExternalUrl :

Server : EXCH16
Name : EWS (Default Web Site)
InternalUrl : https://oldowa.mydomain.com/EWS/Exchange.asmx
ExternalUrl :

Name : EXCH16
AutoDiscoverServiceInternalUri :

Server : EXCH16
ExternalHostname :
InternalHostname : oldowa.mydomain.com
ExternalClientsRequireSsl : False
InternalClientsRequireSsl : True
ExternalClientAuthenticationMethod : Ntlm
InternalClientAuthenticationMethod : Ntlm

XCH19 URLs:

Server : XCH19
Name : Microsoft-Server-ActiveSync (Default Web Site)
InternalUrl : https://owa.mydomain.com/Microsoft-Server-ActiveSync
ExternalUrl : https://owa.mydomain.com/Microsoft-Server-ActiveSync

Server : XCH19
Name : Autodiscover (Default Web Site)
InternalUrl : https://autodiscover.mydomain.com/Autodiscover/Autodiscover.xml
ExternalUrl : https://autodiscover.mydomain.com/Autodiscover/Autodiscover.xml

Server : XCH19
Name : ecp (Default Web Site)
InternalUrl : https://owa.mydomain.com/ecp
ExternalUrl : https://owa.mydomain.com/ecp

Server : XCH19
Name : mapi (Default Web Site)
InternalUrl : https://owa.mydomain.com/mapi
ExternalUrl : https://owa.mydomain.com/mapi

Server : XCH19
Name : OAB (Default Web Site)
InternalUrl : https://owa.mydomain.com/OAB
ExternalUrl : https://owa.mydomain.com/OAB

Server : XCH19
Name : owa (Default Web Site)
InternalUrl : https://owa.mydomain.com/owa
ExternalUrl : https://owa.mydomain.com/owa

Server : XCH19
Name : PowerShell (Default Web Site)
InternalUrl : http://xch19.internal.local/powershell
ExternalUrl :

Server : XCH19
Name : EWS (Default Web Site)
InternalUrl : https://owa.mydomain.com/EWS/Exchange.asmx
ExternalUrl : https://owa.mydomain.com/EWS/Exchange.asmx

Name : XCH19
AutoDiscoverServiceInternalUri : https://autodiscover.mydomain.com/Autodiscover/Autodiscover.xml

Server : XCH19
ExternalHostname : owa.mydomain.com
InternalHostname : owa.mydomain.com
ExternalClientsRequireSsl : True
InternalClientsRequireSsl : True
ExternalClientAuthenticationMethod : Negotiate
InternalClientAuthenticationMethod : Ntlm