Intrauterine devices have been gaining popularity for the past 2 decades. Current data report that >10% of women who use contraception are using an intrauterine device. With <1% failure rates, the intrauterine device is one of the most effective forms of long-acting reversible contraception, yet evidence shows that fear of pain during intrauterine device placement deters women from choosing an intrauterine device as their contraceptive method. The objective of this analysis was to estimate the association between anticipated pain with intrauterine device placement and experienced pain. We also assessed other factors associated with increased discomfort during intrauterine device placement. We hypothesized that patients with higher levels of anticipated pain would report a higher level of discomfort during placement. We performed a secondary analysis of the Contraceptive CHOICE Project. There were 9256 patients enrolled in Contraceptive CHOICE Project from the St. Louis region from 2007-2011; data for 1149 subjects who came for their first placement of either the original 52-mg levonorgestrel intrauterine system or the copper intrauterine device were analyzed in this study. Patients were asked to report their anticipated pain before intrauterine device placement and experienced pain during placement on a 10-point visual analog scale. We assessed the association of anticipated pain, patient demographics, reproductive characteristics, and intrauterine device type with experienced pain with intrauterine device placement. The mean age of Contraceptive CHOICE Project participants in this subanalysis was 26 years. Of these 1149 study subjects, 44% were black, and 53% were of low socioeconomic status. The median expected pain score was 5 for both the levonorgestrel intrauterine system and the copper intrauterine device; the median experienced pain score was 5 for the levonorgestrel intrauterine system and 4 for the copper intrauterine device. After we controlled for parity, history of dysmenorrhea, and type of intrauterine device, higher anticipated pain was associated with increased experienced pain (adjusted relative risk for 1 unit increase in anticipated pain, 1.19; 95% confidence interval, 1.14-1.25). Nulliparity, history of dysmenorrhea, and the hormonal intrauterine device (compared with copper) also were associated with increased pain with intrauterine device placement. High levels of anticipated pain correlated with high levels of experienced pain during intrauterine device placement. Nulliparity and a history of dysmenorrhea were also associated with greater discomfort during placement. This information may help guide and treat patients as they consider intrauterine device placement. Future research should focus on interventions to reduce preprocedural anxiety and anticipated pain to potentially decrease discomfort with intrauterine device placement.