The case involves Isabel Rico, who absconded from supervised release for approximately 37 months before being apprehended. During that period, she was convicted of a drug offense in state court. The central dispute is whether the time she spent as a fugitive counted toward discharging her supervised release term — and, critically, whether a crime she committed after the scheduled expiration of that term could be treated as a violation of supervised release, triggering a higher sentencing guidelines range at her revocation hearing.

Adam G. Unikowsky, arguing for Rico, told the Court that the Sentencing Reform Act created a deliberate two-track scheme: parole with fugitive tolling, supervised release without it. He pointed to a 1976 statute and a 1983 implementing regulation that established fugitive tolling for parole. Congress prospectively repealed the 1976 statute when it enacted the Sentencing Reform Act in 1984 — while leaving the parole framework intact for legacy parole cases — and enacted no equivalent provision for supervised release. Unikowsky also argued that the government's position was internally contradictory: the government simultaneously contended that Rico was not serving her sentence during the abscondment period and that she violated the conditions of that same sentence during that period, warranting an increased sentence.

Joshua K. Handell, arguing for the government, countered that a supervisee cannot be discharging a term of supervised release while entirely evading supervision. He argued that the supervised release statutes require that a supervisee be both subject to release conditions and under the supervision of a probation officer, and that deliberate evasion of the latter does not discharge the former. Without fugitive tolling, he warned, supervisees could simply wait out the expiration of their terms and render the supervision component of their judgment a nullity.

Several justices pressed Handell on whether the government's theory was really tolling at all. Justice Jackson suggested the government was seeking an extension rule rather than a tolling rule — one that keeps release conditions running during the abscondment period rather than simply stopping the clock. Justice Alito observed that neither party actually wants a pure tolling rule, since under true tolling Rico would not have been subject to supervised release conditions during the abscondment period at all, which would undermine the government's case. Justice Sotomayor questioned whether the government's theory amounted to judicially extending a period of punishment beyond the statutory maximum of five years for supervised release.

Justice Gorsuch raised a separate concern: that ruling for the government would require the Court to construct a common law fugitive tolling doctrine from scratch, including resolving existing circuit splits over what conduct constitutes abscondment and when the abscondment period begins. He noted that the government had already gone to Congress to amend the warrant-extension provision in Section 3583(i) once before, and suggested that if the government needed additional tools, Congress was the appropriate venue. Handell acknowledged there is no explicit fugitive tolling provision in the Sentencing Reform Act but argued that reading supervision out of supervised release would render 18 U.S.C. 3601 and 3603 a nullity.

Justice Alito and Unikowsky agreed that, on the specific facts of this case, the practical stakes largely reduce to a guidelines question — whether conduct Rico committed after the 37-month mark is treated as a supervised release violation driving a higher guidelines range, or instead considered only through the court's discretionary sentencing authority at the revocation hearing. Unikowsky acknowledged that other cases could present higher-stakes applications of the fugitive tolling question.