The current mixed-methods study examined everyday problems among deaf and hard of hearing (DHH) adolescents across various life domains. To better understand the factors influencing levels of perceived stress, the impact of DHH adolescents’ coping and pragmatic abilities was also examined. Thirty DHH adolescents completed questionnaires about everyday stressors and coping, and 13 of these respondents were interviewed regarding their everyday problems. All participants used spoken language and attended mainstream high schools. Teachers evaluated the pragmatic skills of each participant through a communication assessment tool. The quantitative-based results showed that DHH adolescents perceived greatest stress related to the future, peers, and school, in that order. Considerably less stress was experienced with regard to parents, leisure, and romantic relationships. The qualitative data reflected the context-specific everyday stressors experienced by DHH adolescents and suggested they have been generated by problems related to having a hearing loss, experiences in social interactions, classroom environment, and academic challenges. Importantly, lower pragmatic abilities and increased level of withdrawal coping style were found to be associated with higher perceived stress. The conclusions focused on ways in which schools, teachers, and professionals can implement prevention and intervention efforts to adequately support DHH adolescents in facing everyday challenges.