An ill-defined association exists between diabetes mellitus (insulin resistance) and primary hyperparathyroidism. This article explores this phenomenon while providing an explanation for such a relationship and reviewing the evidence regarding the response to insulin sensitivity following a parathyroidectomy. Primary hyperparathyroidism may increase the risk of developing insulin resistance; peculiarly, this is not present in all patients. It is likely that both intracellular hypercalcemia and hypophosphatemia alter the insulin receptor expression and response; the contribution of parathyroid hormone is less clear. Following parathyroidectomy, patients may demonstrate improvement in their insulin sensitivity, while others have no response or a detrimental effect. A varied phenotype exists among patients, and furthermore, it is unclear why certain patients demonstrate improvement in insulin sensitivity following a parathyroidectomy, whereas others fail to do so. While this review provides a broad overview of the general endocrine community, it is imperative to note that clinical applicability is limited until further studies address these remaining uncertainties. Due to the lack of understanding regarding this endocrinological enigma, the presence of insulin resistance, at this present time, should not be a criterion for a parathyroidectomy.