Despite the growing interest in jailbreaks as an effective red-teaming tool for building safe and responsible large language models (LLMs), flawed evaluation system designs have led to significant discrepancies in their effectiveness assessments. With a systematic measurement study based on 37 jailbreak studies since 2022, we find that existing evaluation systems lack case-specific criteria, resulting in misleading conclusions about their effectiveness and safety implications. In this paper, we introduce GuidedBench, a novel benchmark comprising a curated harmful question dataset and GuidedEval, an evaluation system integrated with detailed case-by-case evaluation guidelines. Experiments demonstrate that GuidedBench offers more accurate evaluations of jailbreak performance, enabling meaningful comparisons across methods. GuidedEval reduces inter-evaluator variance by at least 76.03%, ensuring reliable and reproducible evaluations. We reveal why existing jailbreak benchmarks fail to evaluate accurately and suggest better evaluation practices.