BackgroundAnterior triangle masses pose an important clinical dilemma. It is very difficult to distinguish the potential pathologies pre operatively by clinical and radiological assessment.Case reportThe first case highlights the management of a bilateral chemodectoma, the second case is a presentation of castleman's disease and the third is that of metastatic tonsillar adenocarcinoma. All three cases had a similar presentation and radiological appearance pre-operatively.ConclusionAnterior triangle masses span the clinical spectrum of pathologies from chemodectoma to castleman's disease to carcinoma. Expert vascular and radiological management is required for optimum patient care and should take place in a tertiary referral centre. Duplex US, CTA and MRA are important pre operative assessment tools to ensure that adequate information regarding the relationship of the lesion to the carotid artery is available to the operating surgeon who should have vascular expertise as deliberate practice volume has been repeatedly shown to result in improved patient outcome.