Cloud-based accounting systems are reshaping how small and medium enterprises (SMEs) manage financial information, yet stakeholder readiness and implementation issues remain underexplored in the Mumbai context. This study examines stakeholders’ awareness, perceptions and implementation challenges related to cloud-based accounting systems in Mumbai’s SMEs, situated within the broader education–enterprise interface. Using a descriptive research design and structured questionnaire, the study captures insights from owners, finance professionals and accounting practitioners regarding perceived benefits, risks, skills gaps and support needs. The findings are expected to highlight mismatches between technological possibilities and stakeholder preparedness, particularly in areas of digital literacy, data security concerns, vendor dependence and change management. The paper also discusses implications for commerce education, professional training and policy support to strengthen cloud-readiness among SME stakeholders and to create a more robust bridge between academic curricula and enterprise practice.