Traditional child-performance measures of theory of mind (ToM) are associated with several limitations. The Theory of Mind Inventory-2 (ToMI-2) is a new broadband caregiver-informant measure designed to tap children's ToM competence. The purposes of this pilot study were to (1) gather preliminary data to explore the scope of the ToM challenges experienced by oral and late-signing children with hearing loss (CHL) and, (2) gather pilot data to explore the criterion-related validity of the ToMI-2 for use with this population. ToMI-2 results revealed wide variation in ToM strengths and challenges both within and between individuals. ToMI-2 scores also positively correlated with scores for hearing vocabulary and a test of pragmatic language development and negatively correlated with the age of cochlear implantation. The present results are encouraging for the use of the ToMI-2 to detect ToM challenges in CHL. Clinical implications and directions for future research are discussed.