We evaluated the association between radiographically-assessed extension and density of root canal fillings and post-operative apical radiolucencies (AR) using data from 288 participants in the Veterans Affairs Dental Longitudinal Study. Study subjects were not VA patients; all received their medical and dental care in the private sector. Generalized Estimating Equations were used to account for multiple teeth within subjects and to control for covariates of interest. Defective root filling density was associated with increased odds of post-operative AR among teeth with no pre-operative AR (Odds Ratio=3.0, 95%CI=1.3-7.1), though pre-operative AR was the strongest risk factor for postoperative AR (Odds Ratio=29.2, 95%CI=13.6-63.0 among teeth with ideal density). Compared to well-extended root fillings, neither over-nor under-extended root fillings separately were related to post-operative AR, but when those two categories were collapsed into one "poorly-extended" category, poor extension was related to post-operative AR (Odds Ratio=1.8, 95%CI=1.1-3.2).