Providing adequate and affordable housing to the growing population in urban areas is a major challenge for urban planning and sustainability in South Asia, especially in India. Urban development authorities are striving to control the growth of informal settlements over the peri-urban spaces and accommodate the increasing population by managing urban housing projects. These authorities have resorted to traditional land acquisition policy to acquire land for urban development works, especially housing projects for the lower-and middle-income population. The present chapter, being qualitative research, investigates the issues and challenges of the land acquisition process for urban housing projects in a rapidly expanding city in western Uttar Pradesh in North India. Taking the case of the Aligarh City Master Plan, the study examines the ground realities of the practicing land acquisition policy, which more or less replicates the Land Acquisition Act of 1894. Finally, it has adopted a multi-stakeholder analysis approach to explore the issues and challenges of the land acquisition process by gathering information through in-depth interviews and focused group discussions with different stakeholders. The findings expose the gaps between housing demand and the government supply mechanisms. Aligarh Development Authority (ADA) planned and developed only 5216 housing plots over the last four decades, extending over six major and seven minor housing projects, but failed to acquire the required land and build adequate housing plots due to the lengthy and complex land acquisition process. The multi-stakeholder analysis reveals that issues like the lengthy acquisition process, the delayed land transfer, ownership disputes, the unwillingness of landowners, and the competing real estate market pose serious questions about the viability and applicability of the current land acquisition policy.