One of the things that are causing a lot of headache using ADFS with ADFS-proxy in combination with Office 365, is the fact that you have to type in your username twice when logging on to the portal or to the webmail externally. One way to avoid this is just go to the webmail directly using the address http://outlook.com/domain.com, but it might not be the easiest address to remember for your end users.
Luckily enough, this has been sorted out when using the Web Application Proxy in Windows Server 2012 R2. The Web Application Proxy in Server 2012 R2 replaces the ADFS proxy in earlier versions of Windows Server, and have been expanded with functionality to publish other resources in a secure manner as well.
Earlier, this would have been the place where you were putting in your username once again. Not this time though, your username have now been passed along to the Web Application Proxy and you can continue by just typing in your password!
Never thought I could be impressed by such a small feature…
I think we’ll see lots of customers upgrading their ADFS infrastructure due to this! 🙂