It is worth noting that the "Get Latest on Checkout" feature requires server support to function. In other words, you must connect to a TFS 2008 (or later) server for Get Latest on Checkout to work. There has been some confusion in the forums because the Get Latest on Checkout option appears to be configurable...

In the course of working on the improved offline experience for Orcas, we discovered that going online with Get Latest On Checkout turned on was rather painful. Specifically, you would never get a chance to generate a version conflict. This, in turn, meant you would not be offered an opportunity to merge...

At the end of November my crew wrapped up our work on the Get Latest on Checkout feature and checked it into the Orcas sourcebase. This feature is obviously targetted at users who are more comfortable with the Visual SourceSafe model of exclusive locking combined with Get Latest on Checkout. Note that...