it seems to me that the problem might be that the Dialog is not triggered in Chrome. Try this:
Find the step that is supposed to trigger the Upload Dialog (it's probably a Click step). From its Properties windows set it to SimulateRealClick=true (screenshot 1). Re-run the test and see whether it works correctly now.
You can also try upgrading to the latest internal build (829). You can download it from your Telerik account.
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