Outlook client can’t connect to Exchange 2016 – continually prompts for login credentials

Problem

I came across this issue while working on an Exchange Hybrid deployment.  During the testing phase, I successfully migrated mailboxes from Exchange 2010 to Exchange Online.  However, when I migrated a mailbox from Exchange 2010 to Exchange 2016, my Outlook client could not connect to its mailbox and would continually prompt for login credentials read more

External Outlook Anywhere “Cant login” / “Trying to Connect” via IIS ARR & MSExchange 2013

Recently I worked on an Exchange 2007 to Exchange 2013 on premise migration.  We had cut over the client access services from Exchange 2007 to 2013.  Client Access was published externally via IIS ARR.  I used this post by my good friend (and Lync Guru) Yoav Barzilay  to configure IIS ARR.  Although the post is for Lync, it is a great guide that will also apply to Exchange. read more