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Adenocarcinoma in situ (AIS) of the endocervix is typically confined to the cervix, but may be extensive. We report 2 cases of extensive AIS—one with intraendometrial spread—that recurred after cone biopsy and were associated with ovarian metastases. In both cases, primary and metastatic tumors were positive for human papillomavirus 16. Both patients are currently disease-free and one has had no recurrence after a follow-up period of 145 months. Extensive, recurring AIS is a rare variant that may be unique for its risk of coincident ovarian involvement. However, ovarian spread, albeit rare, does not invariably result in an adverse outcome.