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As per subject which one overrides other?

executionTimeout in web.config or Connection Time-out property in iis7 website properties?

+1  A: 

If the connection times out, it could be caught and a response still served. If the executionTimeout is hit, it has to be handled differently(most likely in the Application_Error method). If neither are handled, both would cause a bad response.

Yuriy Faktorovich
thanks, on upload wich one would timeout for large files? my guess is execution
nLL
Most likely. You could make sure that happens by allowing the upload and then storing in a different process/thread to speed up the response. Or see if you can change the executionTimeout value for that specific request.
Yuriy Faktorovich