The initial release of the LINQ-to-SQL designer support in VS 2008 doesn't have a good way of keeping changes in the database schema synchronized with the dbml (designer) data. I've really only found two products so far that claim to do this for you.
Huagati DBML Tools
http://www.huagati.com/dbmltools/
Database Restyle by Perpetuum Software
http://www.perpetuumsoft.com/Product.aspx?lang=en&pid=55
I have not personally tried either of these yet.
Just some random development ramblings mostly related to the Microsoft .NET platform.
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If you want to try out the first one you can download it and get a trial license from http://www.huagati.com/dbmltools/
I haven't tried the second one but from the description it sounds like it is for updating the database rather than updating the L2S designer.
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