Wellbeing has predominantly been measured using self-report. However, methodological issues have led to an increased interest in informant-report. Māori literature suggests wellbeing measures should involve the self and others, providing a holistic view of Māori experience. Given the potential for differing impressions, and the implications of this for Māori, self-report versus other-report approaches to assessing wellbeing is an important area of exploration. This study administered the Hua Oranga wellbeing measure to 60 Māori male offenders and 11 officers at Waikeria Prison, to investigate the relationship between self-reported and informant-reported wellbeing. Data were analysed via correlation coefficients and a generalised linear model. Results indicated significant differences between stakeholders, with offenders reporting higher wellbeing, and greater change in wellbeing over time, than informants. This study may inform future assessments of Māori offenders’ wellbeing, in terms of the complexities, issues and implications that exist in the differing methods of measurement.