Research on attitudes to assistive technology (AT) has shown both the positive and negative impact of these technologies on quality of life. Building on this research, we examine the sociocultural and technological frustrations with hearing loss (HL) technologies that motivate personal approaches to solving these issues. Drawing on meet-up observations and contextual interview data, we detail participants' experiences of and attitudes towards hearing AT that influences hacking hearing loss. Hearing AT is misunderstood as a solution to the impairment, influencing one-to-one interactions, cultural norms, and systematic frustrations. Participants' exasperation with the slow development of top-down solutions has led some members to design and develop their own personalised solutions. Beyond capturing a segment of the growing DIY health and wellbeing phenomenon, our findings extend beyond implications for design to present recommendations for the hearing loss industry, policy makers, and importantly, for researchers engaging with grassroots DIY health movements.