Mixed-criticality systems integrate components of different criticality. Different criticality levels require different levels of confidence in the correct behavior of a component. One aspect of correctness is timing. Confidence in worst-case execution time (WCET) estimates depends on the process by which they have been obtained. A somewhat naive view is that static WCET analyses determines safe bounds in which we can have absolute confidence, while measurement-based approaches are inherently unreliable. In this paper, we refine this view by exploring sources of doubt in the correctness of both static and measurement-based WCET analysis.