Hello!
Post enabling Outlook anywhere in the exchange server, please confirm if the exchange proxy settings (outlook anywhere) settings in outlook or will automatically populate on its own.
Environment
Exchange 2013 (Migration from Exchange 2007).
Outlook 2007 SP3
Outlook 2010 SP3
Outlook 2013
Outlook 2016
Authnetication methods to select- Basic, NTLM and Negotiate
Cheers
Priya