How to get Outlook 2010+ to connect up externally using Outlook Anywhere (EXCH2013)?

I have a on-premise EXCH2010 / EXCH2013 deployment and I would like to allow our users to be able to access their email using their domain joined and non-domain joined (workgroup) laptop/outlook.
The clients are running Outlook 2010 and/or Outlook 2013.
The current issue is that I cannot connect, my test case is using Outlook 2013 trying to connect externally (using autodiscover). When I go and add a new profile and I select Exchange and enter my server URL (the autodiscover urL) and my user-id and click
"check name" I get nothing, just an error saying lookup failed.
I would expect for a WORKGROUP computer to get prompted for user/pass so they can get authenticated and the profile added.
Here is my OutlookAnywhere settings in my AD.
RunspaceId                         : cd27e542-1c8b-4569-b62d-cb8a19a745a4
ServerName                         : exch-server
SSLOffloading                      : False
ExternalHostname                   : webmail.mydomain.com
InternalHostname                   : 
ExternalClientAuthenticationMethod : Ntlm
InternalClientAuthenticationMethod : Ntlm
IISAuthenticationMethods           : {Ntlm}
XropUrl                            : 
ExternalClientsRequireSsl          : True
InternalClientsRequireSsl          : False
MetabasePath                       : IIS://exch-server.xand1.mydomain.com/W3SVC/1/ROOT/Rpc
Path                               : C:\Windows\System32\RpcProxy
ExtendedProtectionTokenChecking    : None
ExtendedProtectionFlags            : {}
ExtendedProtectionSPNList          : {}
AdminDisplayVersion                : Version 14.3 (Build 123.4)
Server                             : exch-server
AdminDisplayName                   : 
ExchangeVersion                    : 0.10 (14.0.100.0)
Name                               : Rpc (Default Web Site)
Identity                           : exch-server\Rpc (Default Web Site)
Guid                               : e2325c87-eb52-49cb-ab18-f02a76e07340
ObjectCategory                     : xand1.mydomain.com/Configuration/Schema/ms-Exch-Rpc-Http-Virtual-Directory
ObjectClass                        : {top, msExchVirtualDirectory, msExchRpcHttpVirtualDirectory}
OrganizationId                     : 
OriginatingServer                  : xan-dc02.xand1.mydomain.com
IsValid                            : True
ObjectState                        : Changed
RunspaceId                         : cd27e542-1c8b-4569-b62d-cb8a19a745a4
ServerName                         : exch-server01
SSLOffloading                      : True
ExternalHostname                   : webmail.mydomain.com
InternalHostname                   : webmail.mydomain.com
ExternalClientAuthenticationMethod : Ntlm
InternalClientAuthenticationMethod : Ntlm
IISAuthenticationMethods           : {Ntlm}
XropUrl                            : 
ExternalClientsRequireSsl          : True
InternalClientsRequireSsl          : True
MetabasePath                       : IIS://exch-server01.xand1.mydomain.com/W3SVC/1/ROOT/Rpc
Path                               : C:\Program Files\Microsoft\Exchange Server\V15\FrontEnd\HttpProxy\rpc
ExtendedProtectionTokenChecking    : None
ExtendedProtectionFlags            : {}
ExtendedProtectionSPNList          : {}
AdminDisplayVersion                : Version 15.0 (Build 847.32)
Server                             : exch-server01
AdminDisplayName                   : 
ExchangeVersion                    : 0.20 (15.0.0.0)
Name                               : Rpc (Default Web Site)
Identity                           : exch-server01\Rpc (Default Web Site)
Guid                               : 4f20a6e4-ed74-4d75-8e6b-43fb0687848a
ObjectCategory                     : xand1.mydomain.com/Configuration/Schema/ms-Exch-Rpc-Http-Virtual-Directory
ObjectClass                        : {top, msExchVirtualDirectory, msExchRpcHttpVirtualDirectory}
OrganizationId                     : 
OriginatingServer                  : xan-dc02.xand1.mydomain.com
IsValid                            : True
ObjectState                        : Changed
Any idea how to make it work? We use Split DNS and one DNS entry for both internal/external clients (webmail.mydomain.com).

Hi,
Please verify whether you can logon OWA successfully.
If OWA works well, it seems there is no problem when access mailbox directly.
Then I suggest configure Outlook as following blog:
Manual configuration guide for Outlook 2013 in Windows 8 (Exchange 2013)
http://support.sherweb.com/Faqs/show/manual-configuration-guide-for-outlook-2013-in-windows-8-exchange-2013
Disclaimer:
Microsoft is providing this information as a convenience to you. The sites are not controlled by Microsoft. Microsoft cannot make any representations regarding the quality, safety, or suitability of any software or information found there. Please make sure
that you completely understand the risk before retrieving any suggestions from the above link.
Thanks
Mavis
If you have feedback for TechNet Subscriber Support, contact
[email protected]
Mavis Huang
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