Apologies for the late reply, but we dug a little deeper and found the problem.
Turns out that the detach function was throwing a null pointer exception. Our program was being shutdown by the updater quicker than Telerik could run the detach function. As I understand it, unhandled exceptions are considered a failure which is why the next test kicked off automatically. We simply removed the detach function and everything started working as expected. I'm assuming that the detach function was used before we implemented the mock application that gets fed in in place of our actual application. The test runner locks onto the mock application instead of our fed in one. This is why we can now manipulate the fed in one without needing to execute the detach function anymore.