This is a case of a 70-year-old male who presented with a mass in his right testicle. He was treated with antibiotics for epididymitis while undergoing serial ultrasounds for one year due to testicular swelling and pain. His fourth ultrasound revealed a mild hydrocele with a large paratesticular mass of undescribed size, superior to the right testicle, thought to be an inguinal hernia. Preoperative CT scan demonstrated a large fat-containing inguinal hernia extending into the scrotal sac. An inguinal hernia repair was complicated by fatty tissue surrounding the testicle requiring a right orchiectomy. Pathology review of the tissue demonstrated well-differentiated liposarcoma with a small focus of dedifferentiation grade 2 tumor. Tumor was identified at the inked margins indicating an incomplete resection. It was decided that no further surgical intervention was needed and the patient would undergo surveillance for local tumor recurrence. Six-month follow-up MRI scan was negative for any recurrence of disease. A liposarcoma presenting as a paratesticular mass with spermatic cord involvement is rare, and imaging studies may fail to distinguish a liposarcoma from normal adipose tissue.