Cryptorchidism is a condition in which one or both testicles fail to descend to its normal position in the scrotum. The testicle may reside in the retroperineum, in the internal inguinal ring, in the inguinal canal, or even at the external ring. The exact cause is unknown but several risk factors have been linked to this condition such as premature birth, low birth weight, family history, Down syndrome, alcohol use, and cigarette smoking. Undescended testis occurs in approximately 30% of preterm infants and 1-3% of term infants. Diagnosis is made during examination at birth or shortly thereafter, and timely recognition and management of this condition prevents adverse consequences. The goal of treatment is to relocate the undescended testicle to its proper location in the scrotum. Treatment before 1 year of age lowers the risk of complications such as infertility, testicular cancer, inguinal hernia, and testicular torsion. Treatment can be hormonal, surgical or a combination of both. Hormones such as hCG can sometimes induce descent of the testicle; however, surgery is the preferred option. Orchiopexy is the surgical procedure to free an undescended testicle and implant it in the scrotum. Phimosis is the inability to retract the foreskin covering the glans of the penis. It may appear as a tight ring of the foreskin around the tip of the penis preventing full retraction. Phimosis can be physiologic or pathologic. Physiologic phimosis is seen in children born with tight foreskin at birth and separation occurs naturally overtime while pathologic phimosis is caused by scarring, infection or inflammation. A tight foreskin can interfere with the passage of urine as seen as ballooning of the foreskin during urination. This can lead to inflammation of the penis called balanitis or inflammation of the penis and foreskin called balanoposthitis. Physiologic phimosis does not require intervention and will resolve with daily gentle retraction while pathologic phimosis is treated with topical steroid cream or circumcision. Here we present the case of a young male with an undescended right testicle and phimosis. The right testicle was located in the right inguinal area and was brought down into the scrotum. Circumcision was also done to resolve the phimosis.