This account demonstrates the key challenges faced in producing engaging educational content for information and communication technologies (ICT) deployed in rural India. The 'Stills in Sync' (SIS) project aims to enhance literacy through the revival and proliferation of popular regional folksongs with social awareness themes in rural India. This product entails the use of the Same Language Subtitling (SLS) karaoke feature that won the Worldbank Development Marketplace award in 2002 and the 'Tech Laureate' honor from the Technology Museum of Innovation in 2003. This case study highlights the struggles faced in the production process as we sought to negotiate localism with scalability. The paper is meant to stimulate discussion and further research on the process of digitalizing cultural and educational content in muliple languages for literacy gains and empowerment. I attempt to give three-dimensionality to current buzzwords in education content creation using ICT: localism, relevance and engagement.