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I am working on an add-in for Microsoft Expression Web. We would like to check for an update each time that the users activate the add-in. Note that the add-in consists of a number of main assembly plus a number of supporting .NET assemblies.

I am currently researching the possibility of using the "smart client" technology. That technology is looking a little awkward at this point but the day is young.

I have also thought of creating a "front end" application that takes care of updating the add-in assemblies before activating Expression Web.

Are there any other approaches that I should be looking at?