The topic of trapped cash, or cash permanently reinvested overseas to avoid tax upon repatriation, has become a hot topic in accounting, finance and policy circles over the past two years. This case study analyzes the activities of two major technology firms, Microsoft and Apple, to liberate enormous holdings of trapped cash. The case prompts a discussion of the topic of trapped cash, stakeholder considerations and tools available to manage cash balances held outside the United States. The focus is to examine the strategies available and those selected by Microsoft and Apple to meet or at least appease stakeholder demands while freeing trapped cash.