A 51-year-old female presented with discomfort associated with the upper left posterior quadrant. Discomfort consisted of sinus pressure on the left side and a constant dull ache. Radiolucent areas were present at the apex of tooth #13 & #15. A bridge was present from tooth #12 to #15. Tooth #13 had an old silver point root canal and a post. Tooth #15 had an incomplete root canal and a post in the palatal canal. In addition, a separated file was present in the bone beyond the apex of the palatal root. Treatment consisted of surgical removal of the separated file and an apicoectomy/retrograde on all roots.