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Introduction: Cavernous sinus syndrome (CSS) is a condition with varied etiology. It is characterized by ophthalmoplegia, facial sensory loss, and Horner’s syndrome. The objective of this study was to determine the clinical and radiological presentations and to identify the factors that could help in the identification of etiology. Methods: We prospectively observed all the patients presenting with CSS from October 2019 to September 2021 at a tertiary care hospital. Patients with coronavirus disease 2019 (COVID‑19)‑associated mucormycosis were excluded. All of these patients underwent detailed clinical examination, hematological, radiological, and specialized investigations based on clinical suspicion. Clinical presentations, imaging characteristics, etiology, and clinical outcomes were analyzed. 45 patients were included in our study. Results: The mean age was 44.6 ± 10.8 years with a female preponderance. The most common presentation was diplopia which was seen in all patients. The commonest cranial nerve involved was the abducens (75.9%). Infections (12 (26.6%)) constituted the commonest cause of CSS, followed by neoplastic involvement in 11 (24.4%), Tolosa–Hunt syndrome in 9 (20%) and vascular involvement in 8 (17.7%) patients. Other inflammatory causes were seen in 5 (11%) patients. Diabetes was positively associated with fungal infections. The presence of bruit was strongly associated with vascular etiology. The presence of sinusitis with bony erosions was strongly associated with fungal infections. Evidence of dilated superior ophthalmic vein with early filling in the angiographic phase was associated with carotid‑cavernous fistulas. Conclusions: CSS has variable etiology and radiological presentation. The presence of rapid progressive ophthalmoplegia with underlying diabetes with imaging evidence of sinusitis and bony erosions mandates a high degree of suspicion of fungal infections and empirical antifungal therapy needs to be considered for better outcomes. [ABSTRACT FROM AUTHOR]