The use of long-acting reversible contraception is on the rise across the United States and has contributed to a decrease in teen pregnancies. With the increased use of long-acting reversible contraception, physicians may encounter difficult insertions and removals of intrauterine devices (IUDs) and the contraceptive implant. Uterine structure (e.g., extreme anteversion or retroversion, uterine tone during the postpartum period and breastfeeding) can pose challenges during IUD insertion. Special consideration is also needed for IUD insertions in patients who are transgender or gender nonconforming, such as psychosocial support and management of vaginal atrophy. Missing IUD strings may complicate removal, possibly requiring ultrasonography and use of instruments such as thread retrievers, IUD hooks, and alligator forceps. Regarding implant removal, those that are barely palpable (e.g., because of an overly deep insertion or excessive patient weight gain), removal may require ultrasonography, use of vas clamps and skin hooks, and extra dissection.