Chapter 5 examines how the Mascarenhas family navigated the upheavals of late eighteenth- and nineteenth-century Europe. Focusing on the houses of Óbidos/Sabugal/Palma and Fronteira, it highlights contrasting survival strategies amid revolution, Napoleonic wars, and liberal–absolutist conflicts. The Mascarenhas family and their allies, epitomized to some extent in the Óbidos/Sabugal/Palma house by D. Manuel de Assis, appeared to be relatively ‘sympathetic’ to the French invaders. In the colonies, Dom Francisco, Dom Manuel’s brother, thrived in Brazil’s colonial administration, leading economic reforms and aligning with liberal causes. Meanwhile, the Fronteira branch gained prominence, also by siding with Liberal forces, adapting and calculating their political chances during Portugal’s civil wars and the subsequent unstable period. In this way, they were able to sustain their wealth and heritage through the nineteenth, and into the twentieth century, even though the Second Estate had been forced gradually to abdicate its privileges and power.