This immigration article presents a pure question of law, What is the operative date of the plea for purposes of the INA § 212 (c) waiver or the St. Cyr analysis? While the First and Second Circuit Courts of Appeal have advocated for the date of conviction, the Fifth Circuit has advocated for the date of the plea of guilty not the date of conviction. This circuit court split is thrown into further disarray, as the United States Department of Justice's regulations provide a third answer or the date that the parties reached the agreement. Following the Real ID Act's removal of jurisdictional bars over questions of law and constitutional issues, this issue is ripe for reconsideration or review by the other circuit courts. Inter alia, this article hopes to provide some guidance to the circuit courts in favor of the DOJ's regulations, instead of the First, Second, and Fifth Circuit's precedent decisions. Following Chevron, because Congress gave an expressed delegation of authority to the agency to issue regulations, the courts should uphold the regulations unless they are manifestly contrary to statute. The author argues that because the government's regulations are a reasonable interpretation of statute and of St. Cyr, a reviewing court cannot ignore the regulations and impose its own will under the pretext of de novo review. The author's thesis agrees with the regulations, insofar as the moment of perception is the triggering date of the plea for purposes of the INA § 212(c) waiver or the St. Cyr analysis. Meaning, the moment that the prosecutor perceived that he or she received a tangible benefit in anticipation of the defendant's guilty plea is the answer to the question. Because the prosecutor's perceptions and the quasi plea agreement are not necessarily documented in the criminal record, the author provides some creative suggestions to the alien on carrying the burden of proof in establishing eligibility for the INA § 212(c) waiver. The author concludes by providing a brief statutory history of the INA § 212(c) waiver and predicts that when the other circuits are given the opportunity to review this issue, they will give Chevron deference to the regulations if the appropriate evidence is contained in the administrative record on review.