Rather than having a button on the web page, it would probably be easier to have a COM Add-in or compiled .exe on their laptop that would automate MapPoint.. the program could pull directly from an xml file or database on the web server.

One reason I mention this is because there might be some different security settings with IE or whatever browser that would prevent the button on the web page from launching a process running locally. It might work on one machine but then require some troubleshooting on the next machine. I would recommend taking the web site button out of the equation.

Eric

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