A young man in his early 20s presented with extraoral swelling on left side of his face, which had been present for a period of 1 month. Intraoral examination revealed an erythematous swelling on the left side of floor of the mouth at the ductal opening of left submandibular salivary gland. On palpation, multiple firm masses were noted, and pus mixed with blood was discharged from the ductal opening. He reported a history of swelling occurring in the same region, which was associated with mild fever and subsided after taking antibiotics. Keeping the history in mind, multiple radiographical investigations were carried out, focusing on the submandibular salivary gland. These investigations revealed the presence of salivary calculi, also known as salivary stones or sialolith, in the ductal pathway, causing obstruction to the glandular parenchyma. Hence, a final diagnosis of obstructive chronic bacterial sialadenitis was made. The case was treated surgically due to the size of the salivary stones, in combination with a preoperative antibiotic course. Multiple stones were retrieved and the incision was sutured. Complete healing was noted in a span of 2 weeks. This case report highlights the effectiveness of conventional imaging modalities in early diagnosis compared with advanced imaging techniques. By using conventional imaging, the case was managed with a simple surgical procedure rather than the more invasive option of removing the entire gland, thereby preserving the patient’s quality of life. This case report underscores the importance of clinical examination and selecting appropriate investigative tools for early diagnosis, supported by a comprehensive literature review.