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The increasing use of media and technologies for enhancing teaching and learning is an important current trend to overcome the challenges of schooling and teacher training in the changing world. Many countries in the Global South are trying to adopt technologies in their school and teacher training systems to achieve the UN Millennium Development Goals. Though some recent research shows impacts of using technologies for enhancing teaching and learning in technology-poor contexts, no research actually addresses the challenges and difficulties associated with using the technologies in those specific contexts. This article presents interview data derived from secondary schools teachers in Bangladesh, in a context beset with many difficulties associated with technology use. In a pilot project, Apple iPods were introduced in 2009 to explore the challenges and consequences of using technology in schools. The data reveal the implications for the teachers’ professional development when they used the iPod as a multimedia player to access educational resources made available to support teaching and learning. This article has also thrown some light on current debates about using technologies for enhancing teaching and learning in technology-poor contexts.