Outlook will not connect to on premise exchange. User is remote.

OK.  I have a exchange 2013 on premise.   I have a user that is remote and their mailbox stopped working.  Wierd error when trying to load.  So I am trying to build a new profile, but it will not let me connect.  I tested all the autodiscover stuff.  Also tried to manually create the profile and it never will accept the user/pw.     Internally everything works perfectly.   Any help is appreciated!
Tim PhillipsAsked:
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Valentina PerezExchange ServersCommented:
Hi,

When try to recreate the Outlook profile...what error you have?

Did you change something in Exchange?


Regards
Valentina
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Tim PhillipsAuthor Commented:
I did update to the latest CU about 3 weeks ago and this user was remote the whole time.  But maybe that caused it.   The end user client is 2016 outlook.   Basically it just doesnt except the password.  I type in the same user/pass that works in OWA but no luck on client
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Valentina PerezExchange ServersCommented:
Hi Tim,

Try to connect the user with "Domain\user" and password for example: contoso\user. Or try with the email address: user@contoso.com

When you try to connect the old profile. Which error do you have?

Regards
Valentina
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Riaz Alexander AnsaryEnterprise Infrastructure Systems EngineerCommented:
Please run a test here for outlook connectivity and share the result https://testconnectivity.microsoft.com/ 

make sure outlookanywhere external and internal hosts are setup correctly and are the same across all your exchange servers
you can test that by

Get-OutlookAnywhere -Identity "ExchangeServerName\RPC (Default Web Site)"

and look for following attributes

ExternalHostname                   : mail.yourdomain.com - or whatever your Uris are setup across
InternalHostname                   : mail.yourdomain.com - or whatever your Uris are setup across
ExternalClientAuthenticationMethod : Ntlm
InternalClientAuthenticationMethod : Ntlm
IISAuthenticationMethods           : {Basic, Ntlm, Negotiate}
XropUrl                            :
ExternalClientsRequireSsl          : True
InternalClientsRequireSsl          : True
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Valentina PerezExchange ServersCommented:
Issue seems to be solved..no more replies from the author
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