Since Ma Ying-jeou assumed the presidency, Taiwan’s relations with Mainland China have been profoundly transformed. This article uses the perspective of a grand strategy to interpret and explain Taiwan’s new approach to cross-Strait relations. It suggests that Ma’s government has adopted a grand strategy of accommodation that uses assurances, confidence building, and economic integration to enhance Taiwan’s security. This new grand strategy has both ideational and materialist roots. The article also assesses the preliminary results of Taiwan’s new security approach and its future sustainability.