Childcare instability can negatively affect family well-being. Yet not all childcare changes are bad for families. This qualitative study (N = 85) examines work, family, provider, and subsidy-related factors contributing to childcare changes among families with low incomes. We focus on the desirability—the extent to which parents wanted to leave their provider—and the planned nature of childcare changes—the extent to which parents anticipated the change and had time to plan. We find that although nearly all desired changes were planned, undesired changes were both planned and unplanned. Planning was important but not enough for finding care that aligned with family needs, and undesired changes, especially sudden changes, were often driven by the loss of a childcare subsidy, sometimes accompanied by a job loss. We discuss how these findings can help researchers and policymakers understand the implications of complex childcare trajectories for family well-being and early care and education policy. (author abstract)