Despite the growing interest in jailbreak methods 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. We conduct a systematic measurement study based on 37 jailbreak studies since 2022, focusing on both the methods and the evaluation systems they employ. We find that existing evaluation systems lack case-specific criteria, resulting in misleading conclusions about their effectiveness and safety implications. This paper advocates a shift to a more nuanced, case-by-case evaluation paradigm. We introduce GuidedBench, a novel benchmark comprising a curated harmful question dataset, detailed case-by-case evaluation guidelines and an evaluation system integrated with these guidelines -- GuidedEval. Experiments demonstrate that GuidedBench offers more accurate measurements of jailbreak performance, enabling meaningful comparisons across methods and uncovering new insights overlooked in previous evaluations. GuidedEval reduces inter-evaluator variance by at least 76.03\%. Furthermore, we observe that incorporating guidelines can enhance the effectiveness of jailbreak methods themselves, offering new insights into both attack strategies and evaluation paradigms.