>By 'send a new update' do you mean you use the publish option from VS?
>If so do you mean that the actual 'Publish' doesn't work or that clients don't see the updated version ?

Whenever I send a new DLL in the Bin directory, such as MyWebSite.dll, sometimes, the IIS does not respond. This is an issue I have addressed before here. You might find some related threads about it. Basically, randomly, sometimes, I have to force a IISRESET /RESTART so it would start answering back.