Even the best laid plans can fail, and robot plans executed in real world domains tend to do so often. The ability of a robot to reliably monitor the execution of plans and detect failures is essential to its performance and its autonomy. In this paper, we propose a technique to increase the reliability of monitoring symbolic robot plans. We use semantic domain knowledge to derive implicit expectations of the execution of actions in the plan, and then match these expectations against observations. We present two realizations of this approach: a crisp one, which assumes deterministic actions and reliable sensing, and uses a standard knowledge representation system (LOOM); and a probabilistic one, which takes into account uncertainty in action effects, in sensing, and in world states. We perform an extensive validation of these realizations through experiments performed both in simulation and on real robots.