Software modernization is an essential process in today’s dynamic landscape of technology. It involves replacing, reusing, re-developing, or migrating the software to meet the continuously evolving demands. For an organization to stay competitive, it has to ensure that it adapts at the rate at which technological evolutions are introduced. The need for modernization becomes evident when the system becomes outdated, maintenance is costly, and updating the system is a challenging endeavor. Key factors driving modernization include technological obsolescence, increased risks and costs, and the need for improved performance and security. Legacy systems, technical debt, and resistance to change pose significant hurdles in modernization efforts. However, with the right strategies and stakeholder engagement, these challenges can be overcome, leading to a successful modernization process. If not handled properly, outdated systems can lead to increased risk and costs, adversely affecting performance and security and lacking flexibility and maintainability. Previous research has extensively explored various aspects of software modernization and it has highlighted the importance of technological updates and stakeholder engagement in ensuring successful modernization. However, there is a gap in understanding the comprehensive impact of stakeholder perspectives on the modernization process. While existing literature emphasizes the technical challenges, it often overlooks the nuanced role of diverse stakeholder opinions in shaping modernization strategies. This gap underscores the necessity of our research, which aims to bridge this understanding and provide a holistic view of the modernization process within the context of stakeholder engagement. This paper employed a systematic mapping study to gather and analyze different stakeholders involved in the process. Furthermore, it is quintessential to understand the interests and goals associated with internal (leadership, technical, and business) and external (users, experts, and regulatory bodies) stakeholders. However, with such diverse stakeholders, numerous challenges were identified and gathered into categories based on their shared characteristics. Moreover, different modernization strategies and stakeholder engagement strategies were classified and mapped to their corresponding set of challenges. Interviews were conducted with different stakeholders to evaluate the results. Their feedback ensured that the identified challenges would significantly impact the modernization process. Secondly, the diverse set of participants, which we carefully selected to represent a wide range of perspectives, also reflected the difference in interests and goals that validated the research concerns. With these results, we were able to gather different validated sets of challenges and their corresponding strategies. By addressing the critical role of stakeholders, this research positively impacts the field of software modernization, ensuring more efficient and successful outcomes.