This Article evaluates a conundrum and identifies a genuine risk faced by state and federal courts in interpreting and applying the Statute of Frauds to contract law disputes. The Article provides a thorough analytical dissection of the Statute of Frauds as it has been interpreted and applied by the courts in light of the inescapable tension between the Statute’s formalities, mandated by the legislature, and the judiciary’s profound goal of attaining justice and fairness in deciding each contract law dispute in which the Statute is implicated. The Article discusses in depth how the Statute has been construed by state and federal courts in the unique factual context presented by each individual case argued before these courts. It investigates how judicial application of the Statute to particular facts has invoked creativity and ingenuity on the part of the courts that has led to the formulation of two equitable, ameliorating doctrines consisting of equitable estoppel and more recently, equitable estoppel’s evolutionary progeny, promissory estoppel. The Article discusses the potential dilemma of rigid application of the Statute at the expense of fair and just decisions, faced by the courts in applying the Statute, in light of the uniqueness of the factual context of each case; however, this Article criticizes impulses to apply promissory estoppel too readily because of the risk of eviscerating the Statute entirely. The Article’s analytical examination of a plethora of recent state and federal court decisions has concluded that the application of equitable estoppel principles in deciding whether to decline enforcement of a contract, based upon the defense of the Statute of Frauds, is viable and vibrant and is serving the legal community very well, but that there may also be a clear and present danger of over exuberance in unrestrained application of promissory estoppel by state and federal courts to override the application of the Statute and thereby nullify its mandate.