Indeed, the ContextMenu is a bit tricky to interact with especially on the framework level. Using an HTML output inspector like the Firefox Firebug add-on you may notice the element containing the menu items is actually rendered out of the HtmlForm. Additionally, the items holder element has no relation with the actual control needed for the control wrapper and WebUI Test Studio translator. This as a whole prevent us from supporting the ContextMenu on translator level excluding a few specific scenarios like the Grid Filtering menu and the built-in TreeView context menu.
I've discussed the problem with the RadMenu devs here and we should come up with a solution shortly. I will make sure it will become officially part of the WebAii Testing Framework / WebUI Test Studio v2.0 release due in December.
In the meantime there are a few possible options out of the RadControls translators.
1. You can record a test based on the span element with the help of the Desktop Mouse Actions. I've attached such a test and you can find the options available in WebUI Test Studio v2.0 recording interface on the following snapshot.
2. Additionally you can access and click on the base span element of the MenuItem via some code. See the code snippet I posted at this forum thread
I hope this helps. Please let me know if the official release of WebUI Test Studio v2.0 in December in addition to the next official release of RadControls for ASP.NET AJAX (Service Pack of Q3 2009 release) is acceptable timeframe for you. Alternatively we may prepare internal builds of both products including improved support of RadContextMenu in WebAii Testing Framework and WebUI Test Studio v2.0.
the Telerik team