A middle-aged male Caucasian had rejected previous offers of surgery for submandibular gland removal in the past due to concerns about surgical complications. He presented with a month’s history of submandibular swelling and severe pain, which impeded his ability to eat. Prior to admission, he had been experiencing intermittent sialadenitis for several months. Cross-sectional imaging demonstrated a 16×12 mm migratory sialolith, located superficial to the right submandibular gland within a large loculated abscess. The patient underwent an incision and drainage of the abscess under general anaesthetic and the sialolith was expressed. He was discharged home with oral antibiotics and was followed up as an outpatient. This case serves to highlight a rare complication of chronic sialolithiasis.