In the evaluation of painful penile swelling, the first step is to determine whether the patient is circumcised or not through a review of the medical record or discussion with the patient’s family. In an uncircumcised male, the critical next step is to assess for an entrapped and retracted foreskin (paraphimosis). Visualization of the glans penis and the urethral meatus as in this case demonstrates that the foreskin is retracted. Additionally, visualization of the glans penis and urethral meatus makes a scarred and unretractable foreskin (pathologic paraphimosis) unlikely to be the primary diagnosis. The differential diagnosis also includes hair tourniquet syndrome, chigger bites, and inflammation of the glans and foreskin (balanitis and balanoposthitis).