Are We Grading Properly? Understanding Failure Modes in Medical Benchmarks

Medical evaluation is shifting from static option-based questioning to realistic clinical scenarios with open-ended output modes. Grading these at scale naively, however, is expensive, and rubric-based evaluation has become the dominant scalable alternative. We ask what happens when the rubrics themselves are not airtight, and whether such flaws can be detected and corrected. We apply RIFT, a global rubric failure taxonomy, to two clinical benchmarks (HealthBench Professional and LiveMedBench), and find failure modes are meaningful: on HealthBench Professional an LLM judge flags 29.6\% of criteria as non-atomic and 65.4\% as misaligned/rigid. Then, we show that these flaws are meaningful and not simply cosmetic. As an example, rewriting bundled criteria of the form "at least one of / all of the following" as equally weighted children and regrading identical responses shifts scores by up to 15.9 percentage points on affected conversations, with disjunctive bundles inflating scores and conjunctive bundles deflating them. We also find that RIFT generally under-detects bundling on clinical rubrics, flagging 3.3\% of LiveMedBench criteria as non-atomic where surface-form analysis finds structure in 25.8\%.