Thanks for making the post. In regard to your case above, I created a test method that returns custom request object from the mocked context and finally asserts it.
Accordingly, I have a target method:
Then wrote the test method in the following way:
Mock.Arrange(() => HttpContext.Current.Request).Returns(request);
Mock.Assert(() => HttpContext.Current.Request);
Since, Request is a nested property it additionally illustrates the nested mocking capabilities of JustMock that can save you additional lines.
Here to mention that to mock HttpContext and its members you need to add additional MockedClassAttribute on top your test class as like mocking mscorlib types.
Finally, I attached the test project to also let you have a look and please do feel free to write back for any issues.
the Telerik team