Cosmetic rhinoplasty and maxillary sinus surgery are rare causes of lacrimal obstruction. The lacrimal sac is quite vulnerable to damage by the lateral osteotomy of the rhinoplasty. While obstruction from such damage usually resolves in three months, these three cases illustrate the risk of perisitent obstruction, particularly in complicated cases. The nasoantral window in the Caldwell-Luc may damage the distal lacrimal opening if it is placed too high, or made too large. Occasionally, the duct will extend more anterior and inferior and be quite vulnerable to damage by the nasal antrostomy.