Outlook prompting users for credentials? Outlook users disconnected from their mailboxes? These are a couple of common issues and they can be frustrating to the user. Enter the Outlook Connectivity Guided Walkthrough (GWT).
Outlook connectivity issues with Exchange server can be a very frustrating for both the user and the administrator. Unfortunately, connectivity issues aren't uncommon and will likely occur at some point in time whether your mailboxes are hosted on-premises, in Office 365, or a combination of both, i.e. Hybrid setup. Earlier this year we released a guided walkthrough for Outlook connectivity issues in Office 365.
Read more at source: http://blogs.technet.com/b/exchange/archive/2013/11/15/outlook-connectivity-guided-walkthrough-exchange-on-premises.aspx