How do owners of family firm portfolios restructure poorly performing firms? To answer this question, we conducted an in-depth qualitative case-study analysis of six poorly performing family portfolio firms, on the basis of 39 interviews, 117 pieces of archival data, and observations we gathered over 2 years. Drawing upon the socioemotional wealth (SEW) perspective and escalation-of-commitment literature, we suggest that family firm owners initially show refraining behaviors toward restructuring their poorly performing portfolio firms. Subsequently, they exhibit escalating behaviors by first investing and then reshuffling assets, to safeguard firm-level SEW. Yet, when retaining these poorly performing firms threatens the existence of the remaining portfolio and, thus, portfolio-level SEW, family firm owners exhibit de-escalating behaviors by divesting. Preferably, they attempt a sale and, when a sale is no longer an option, a liquidation. We developed a model that contributes to a more granular theoretical understanding of the family firm’s restructuring behavior, in the context of portfolio entrepreneurship.