This paper assesses five major transboundary-related problems currently troubling the Bengal region and bedeviling, in particular, the relationship between Bangladesh and India. These problems relate to settlement of the land boundary (enclaves and adverse possessions), facilitation of transboundary transit (road, rail, and waterway), curbing of transboundary illicit activity (smuggling, human trafficking, and covert support for radical Islamist groups and separatist militants), sharing of transboundary river resources, and control of transboundary migration. The paper’s focus is on the potential and capacity of the political entities sharing the Bengal region to identify, agree upon, and implement effective and sustainable solutions to these problems. It argues that such solutions, to be sustainable, would have to prioritize cross-border cooperation and mutual benefit—objectives that have thus far neither been aggressively nor consistently pursued in this region. The authors observe that the transboundary problems troubling the Bengal region vary substantially in the extent of their intractability and that some of them will persist far into the future. Nevertheless, they conclude that the present scale as well as the severity of the consequences of these problems are not permanent fixtures and will vary enormously with the political will, perseverance, and skill of those charged with determining the political destiny of this hugely important region.