I would ctr-right-click on the outlook systray icon to get a copy of the connection status screen on both computers to compare. I suspect he's got his office Outlook set to sync to Exchange on a defined schedule, say, once every 10 minutes.
Then, he does a bunch of mailbox cleanup right before leaving for the day, and closes Outlook before it syncs.
MAPI over HTTP provides the ability for Messaging API (MAPI) clients and servers to communicate across a HTTP connection without using remote procedure calls (RPCs).
Ever since its debut back in 1996, Exchange and its clients have used RPCs.
Not sure of the best way of explaining this but I'll give it my best: We're running Exchange Server 2010 and the mail clients are Outlook 2007.
One of my users, when at the office and connected to Exchange over the LAN, will read some mail, delete others, etc. When that user goes home he will check his mail (also with Outlook 2007), this time connected via Outlook Anywhere.
If you are currently using Outlook 2007 or an earlier version then just click on File – if there is a checkmark next to Work Offline, then uncheck it, and that should solve it.
The external host name you choose should ideally be one that is already included in the Exchange certificate configured on the Client Access server.The age and relative lack of recent development in the RPC mechanism is reflected in much of its documentation, such as the "How RPC Works" article, which is based on Windows Server 2003 and last updated in March 2003.Today, more and more of our communications flow over the Internet.Thanks to SSL encryption Outlook Anywhere is also inherently more secure than other protocols that have non-encrypted options that companies often deploy.Outlook Anywhere is a service provided by the Client Access server role that allows Outlook clients to make a secure connection over SSL/HTTPS to the mailbox from remote locations.Then of course there are those times when that solves absolutely nothing.