For the first problem, I'll need some more info in order to properly diagnose the issue. What exactly happens when you execute the code? Is there an error displayed or it passes without error and without clicking the button?
As for the second problem, I you add and start the DialogMonitor after you click the button to start the upload. those lines must be before that the upload button is clicked or the dialog will not be properly handled, which is exactly the issue you are experiencing. Here is a working sample:
var x =
Element e2 = Find.ById(
Element e3 = Find.ById(
Please also check out this documentation
article on "Handling FileUpload Dialogs" .
Hope to here from you soon!
the Telerik team