Objectives: We sought to compare the decision-making process between women with Medicaid and private insurance undergoing postpartum sterilization. To prevent involuntary sterilizations, regulations require that Medicaid-insured women wait 30 days between signing a consent form and undergoing this surgery. This waiting period has been associated with unfulfilled requests for postpartum sterilization procedures, and in turn, increased risk of unintended pregnancy. In light of this policy’s potential benefits and harms, we explored how the waiting period affects women’s decision-making. Methods: We completed semi-structured qualitative interviews with 25 women (15 with Medicaid insurance, 10 with private insurance) who underwent postpartum sterilization at an urban tertiary care hospital. We used an iterative consensus coding process with multiple coders to identify themes in the data. Results: Decision-making timeline, influences, and process were similar between women insured through Medicaid and women with private insurance. Some women were certain of their desire for sterilization upon discovering their pregnancies, and nearly all had considered the option before their third trimester. All respondents, regardless of insurance, experienced similar levels of counseling from a health care provider. Many participants recognized at least one potential benefit of the mandated 30-day waiting period; however, women who experienced this waiting period reported that they did not personally derive benefit from it. Conclusions: The mandated 30-day waiting period did not appear to dictate when women considered and finalized their decision to undergo sterilization. Women who experienced the waiting period did not cite personal benefits. The utility of the mandated waiting period should be further evaluated.