The Safety Valve: Appeal Waivers After Hunter

The Supreme Court held on June 18, 2026, that a knowing and voluntary appeal waiver in a plea agreement is unenforceable when enforcing it would produce a miscarriage of justice. Hunter v. United States, No. 24-1063 (U.S. June 18, 2026). Justice Kagan wrote for eight members of the Court. Six weeks later, the Fifth Circuit applied the new standard on remand.  It enforced the waiver anyway.

Fifty-One Months on a $38,648 Plea

Hunter was indicted on ten counts of bank fraud and wire fraud in the Southern District of Texas. He pleaded to a single count of aiding and abetting wire fraud under 18 U.S.C. section 1343, involving one transaction of $38,648.77.

Justice Gorsuch’s concurrence lays out what happened next. The district court sentenced Hunter based on relevant conduct of $488,352.25 across 26 transactions, most of which was charged in counts that the government dropped or never brought at all. The advisory range on the plea amount alone was 15 to 21 months. On the relevant conduct, it was 41 to 51 months. The court imposed 51.

Hunter didn’t appeal the loss calculation. He appealed a condition of supervised release requiring him to take all mental-health medication a physician prescribed. The Fifth Circuit dismissed under its own long-standing rule that an appeal waiver has exactly two exceptions: ineffective assistance of counsel, and a sentence above the statutory maximum. United States v. Barnes, 953 F.3d 383 (5th Cir. 2020).

The government defended that dismissal with a position that warrants a moment of reflection: At argument, when asked whether a waiver would still be enforceable against a sentence that a judge merely picked out of a hat, the government said yes. Eight Justices disagreed.

When Can A Defendant Appeal Despite an Appeal Waiver?

The Court’s formulation is one sentence:

an agreement not to appeal a sentence is unenforceable when it would result in a miscarriage of justice—meaning, when it would leave in place the kind of egregious error that would bring the judicial system into disrepute.

The Court then gave three illustrations. A sentence exceeding what the statute allows. A sentence infected with blatant constitutional error—a judge weighing race, or imposing a constitutionally infirm supervised-release condition, the Court’s example being an order barring a defendant from becoming pregnant. And a sentence imposed without “some minimum of civilized procedure.”

But two limitations in the Court’s opinion will likely swallow the rule: “[S]tandard-fare errors in misapplying sentencing law cannot cancel an appeal waiver.” And: “The error must be obvious—not one a judge could reasonably make.”

They make clear that the rule the Court announced targets sentences that no functioning system would produce—a relatively narrow target, and narrower than the ordinary run of federal economic-crime sentencing ever gets.

But the decision resolves a longstanding circuit split. Eight circuits had recognized some version of a miscarriage-of-justice limit. Four had refused, including the Fifth. Those four must now recognize a limit they had previously rejected.

Six Weeks Later, the Fifth Circuit Said No

On July 29, 2026, a Fifth Circuit panel dismissed Hunter’s appeal. United States v. Hunter, No. 24-20211 (5th Cir. July 29, 2026).

The panel rejected the constitutional theory because no controlling precedent addressed the question. Washington v. Harper and Sell v. United States govern prisoners and pretrial detainees, not people on supervised release, and neither the Supreme Court nor the Fifth Circuit has ever set a standard requiring medication as a release condition. An error can’t be obvious where the law is unsettled, it reasoned.

And the panel added three practical points: the condition was modifiable, the medication would be prescribed by a physician rather than a judge, and the condition appears both in the sentencing court’s general order on supervised release and in the template posted for courts and probation offices nationwide. On that last point, the opinion is blunt—”the widespread imposition of this exact condition is strong evidence that this is not an ‘extreme case’ of the kind the Supreme Court contemplated would vitiate an appeal waiver.”

Ubiquity as a defense to egregiousness. It’s a fair reading of “obvious,” perhaps, but a condition can be common and still be wrong.

The Conveyer Belt of Plea Bargains

Justice Gorsuch, joined by Justices Sotomayor and Jackson, argued that the Court has spent fifty years accommodating coercive plea practice:  “In our times, the jury trial has given way to a conveyor belt of plea bargains.” Justice Gorsuch sets up a broad reading of the three categories, one that would reach unlawful restitution orders, benefits bans reserved for other offenses, and plain guidelines-calculation error. He also floated a question the Court didn’t decide: whether a prospective waiver of the right to appeal a sentence that doesn’t yet exist can be “knowing” at all.

Justice Thomas dissented alone, noting that Hunter received 51 months against an indictment exposing him to hundreds of years, and that the Court “cannot identify any source of law for its exception.”

Implications for Plea Bargaining

Nothing in Hunter prevents the parties from negotiating a waiver that is narrower than the floor the Court established.

The Court noted that the Justice Department’s own policy calls for an ineffective-assistance carve-out in its plea agreements. Ask for more: A carve-out for guidelines-calculation error, for restitution and forfeiture, and for conditions of supervised release.

Treat the waiver, the loss stipulation, and the relevant-conduct stipulation as one negotiation.  The Hunter court’s math illustrates why: the guidelines exposure came from transactions that he didn’t plead to, and the waiver closed the door on contesting how those transactions were counted. Actual versus intended loss under section 2B1.1 is where a white-collar sentence is primarily decided, and how courts calculate that figure deserves as much attention as the count of conviction.

Counsel in the Fifth, Sixth, Seventh, and Eleventh Circuits should also look backward, in light of Hunter’s change in those circuits, and anyone advising a client through a federal investigation should read the waiver as part of the client’s defense posture rather than as boilerplate. Appeals dismissed on some waiver grounds under the closed-list rule now rest on abrogated authority. Whether anything can be done depends on whether the mandate has already been issued and what collateral vehicle remains, but the question is worth asking on any case dismissed in those circuits before June 18.

Questions

Does an appeal waiver also waive a collateral attack under section 2255?

That depends on the agreement’s text. Many waivers cover both direct appeal and collateral review, with a carve-out for ineffective assistance of counsel. Hunter addressed the appeal waiver in front of it and did not decide how the miscarriage-of-justice limit applies to a collateral waiver, which is one of several open questions the opinion leaves for the circuits.

Does this decision reach criminal tax cases?

It applies to any federal plea agreement containing an appeal waiver, including tax cases. The criminal tax wrinkle is that tax loss and restitution are frequently the contested issues at sentencing, and a broad waiver signed before those numbers are fixed forecloses exactly the dispute the defendant is most likely to want.

This article is for general information only and is not legal advice. Reading it does not create an attorney-client relationship with Freeman Law. The law is fact-specific and subject to change, the decisions discussed above may be subject to further proceedings, and you should consult qualified counsel about your particular situation.