Scanty data are available on the progression risk in patients with persistent thyroid cancer (TC) before pregnancy. We aimed to evaluate this topic in our series and to review available literature data. This was a retrospective study performed in a tertiary care Italian TC center. We included 8 patients with persistent papillary TC who became pregnant after initial treatments (mean time interval of 62 months). Seven patients had the structural disease (lung and/or neck node metastases), while one patient had biochemical persistence. During a mean follow-up of 97 months, none of the patients showed disease progression either during pregnancy or during a follow-up of at least 12 months after delivery, and no additional treatments were needed. A sequential biochemical evaluation showed that thyroglobulin levels can significantly increase during pregnancy, returning to preconception levels after delivery. In conclusion, our data confirm that pregnancy is not associated with disease progression in patients with stable local and/or distant persistence before conception. Thus, pregnancy should not be contraindicated in metastatic women, although a precise clinical characterization, including the disease stage at diagnosis, the ATA risk class, and the dynamic risk stratification, should be conducted before conception.