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Objective Traditional audiological assessments, such as the audiogram, often fail to capture the complexity of real-world hearing experiences. This study aims to determine whether hearing assessments that incorporate key real-world factors: the presence of visual information, the focus of assessment, the interactive nature of communication, and the naturalness of the environment, provide a more accurate and ecologically valid reflection of individuals' everyday hearing challenges compared to traditional clinical measures. Methods In this within-subjects correlational study, adults with normal hearing or mild to moderate hearing loss completed a single 2–3-h session. Assessments included audiometry, self-report questionnaires, and speech-in-babble tasks in both auditory-only and audiovisual formats. For participants with a familiar partner, additional conversation and podcast listening tasks were conducted in both quiet and noisy environments. Objective and subjective outcomes were analyzed across assessment type, modality, environment, and noise condition. Results Speech intelligibility and listening comprehension tasks in noise, especially those with audiovisual cues, were most sensitive to hearing difficulties. Real-time self-reports of speech understanding and listening effort, collected during tasks, strongly correlated with objective performance and audiogram results, while retrospective self-reports were less predictive. Measures of vocal effort in noise reflected perceived listening effort but did not reliably indicate hearing loss. Conclusion Assessments designed to better approximate real-world listening conditions, such as audiovisual intelligibility tasks, listening comprehension, and real-time self-report, provide a more sensitive and individualized evaluation of hearing ability than traditional clinical tests alone. Structuring assessments around real-world factors can support more effective and personalized interventions.