Disclaimer: I am actively involved in the development of Rubberduck.
An interface IAssertthat implements both Rubberduck.AssertClass, and Rubberduck.PermissiveAssertClass, includes an optional parameter messagefor each individual member:

Just add a different and descriptive message for each statement:
Assert.AreEqual expected, actual, "oops, didn't expect this"
Assert.IsTrue result, "truth is an illusion"
In the test explorer window, a custom message will be displayed in the "Message" column only if the approval is not completed:
