Urban radio broadcasting in Nigeria operates within a deeply contradictory reality: radio remains the most accessible mass medium with 77.7% of Nigerians tuning in weekly, yet many stations struggle for survival amid escalating operational costs, regulatory pressures, and the imperative of digital transformation. This study examined the challenges and opportunities confronting urban radio stations in selected Local Government Areas of Oyo State. Adopting a qualitative multiple case study design, the research employed in-depth interviews with twelve key operational personnel from four strategically selected stations: Ajayi Crowther University 88.5 FM, Dynasty 89.9 FM, Oyomesi 97.5 FM, and Oke-Ogun 96.3 FM. Thematic analysis revealed three primary thematic areas: financial constraints, regulatory challenges, and digital opportunities. Financial precarity emerged as the most pervasive challenge, driven by excessive power costs, expensive imported equipment maintenance, and inconsistent advertising revenue. Regulatory challenges, particularly the financial burden of National Broadcasting Commission licensing and compliance, coupled with the fear of sanctions, have institutionalised self-censorship and constrained editorial independence. Despite these obstacles, digital platforms offer transformative opportunities, enabling stations to reach younger audiences, expand geographic coverage, and enhance real-time audience interaction. The researcher concludes that sustainable growth requires diversified revenue models, strategic digital investment, and regulatory reforms to reduce compliance burdens.