Attachment theory suggests that an “enduring sense of joy” in caregiver-child interactions is vital to children’s mental health, yet attachment insecurity may undermine parents’ experiences of joy. We considered the role of compassion in the link between attachment insecurity and parents’ well-being. In Study 1 (N=270), we investigated the associations between attachment avoidance, compassionate caregiving goals, and parents’ behaviors and emotions in a 9-day daily diary study. Attachment avoidance was associated with less compassionate caregiving goals, which predicted parents’ perceptions of their child’s behaviors and daily well-being. In Study 2, parents (N=605) were randomly assigned to: 1) write a gratitude letter to someone who made them feel secure (attachment-oriented gratitude), 2) write a gratitude letter to someone who was kind to them (general gratitude), or 3) write about their daily activities. Attachment-oriented gratitude led to the greatest compassion and to improvements in feelings of connectedness only among participants high in attachment avoidance or anxiety, which predicted improved perceptions of child’s behavior, parental overcontrol, meaning in life, positive emotion, and negative emotion five days later. Thus, gratitude may help close the happiness gap for insecurely attached parents.