The case asks what penalties apply to a defendant convicted under 18 U.S.C. § 924(c) who was sentenced before the enactment of the First Step Act but whose sentence was later vacated. Specifically, it addresses whether such a defendant is eligible for the more lenient penalties provided by the Act during resentencing. The central issue is whether a vacated prior sentence constitutes a sentence that "has... been imposed" under Section 403(b) of the First Step Act.

• A sentence that has been vacated is not a sentence that "has . . . been imposed" for purposes of § 403(b) of the First Step Act.
• Because their prior sentences were voided, they should be treated as if they had not yet been sentenced as of the Act's enactment date.
• They are therefore entitled to the retroactive application of the Act's more lenient mandatory minimum penalties rather than the pre-Act "stacked" 25-year penalties.

• The United States agreed with petitioners on the merits; however, amicus curiae argued that § 403(b) applies only to defendants for whom a sentence "had not been imposed" as of the enactment date.
• Sentencing is a historical fact, and because the petitioners had already been sentenced twice prior to the Act's enactment, they are ineligible for the more lenient penalties regardless of subsequent vacatur.
• The act of imposing a sentence occurs at a fixed point in time and is not erased by later legal invalidity.

• The Court held that under § 403(b) of the First Step Act, a sentence "has . . . been imposed" only if the sentence is extant and has not been vacated.
• The Court relied on the present-perfect tense ("has... been"), which refers to an act or condition that is now completed or continues to be true or valid (*Chicago Manual of Style* § 5.132; *Huddleston & Pullum, The Cambridge Grammar of the English Language*).
• It distinguished this from the past-perfect tense ("had been"), which would have focused on sentencing as a mere historical relic rather than a continuing state.
• The Court applied the background legal presumption that vacated court orders are void *ab initio* and lack prospective legal effect (*United States v. Ayres*).
• It noted that by operation of legal fiction, the law acts as though a vacated conviction or sentence never occurred (*Fiswick v. United States*; *North Carolina v. Pearce*).
• The Court cited *Lewis v. United States* and *Pepper v. United States* to support the "common-sense" notion that vacatur "wipes the slate clean."
• Reasoning from context, the Court found Congress intended to execute a "clean break" from the harsh "stacking" practice established in *Deal v. United States*.
• The Court concluded that requiring judges to revert to the pre-Act draconian scheme for resentenced defendants would undermine the primary purpose of § 403 and create unnecessary administrative burdens.