Appeal Waivers Are Not Absolute: Supreme Court Creates a Miscarriage-of-Justice Safety Valve

Hunter v. United States preserves appeal waivers in federal plea agreements—but permits review of obvious, egregious sentencing errors that could undermine confidence in the courts.

By Michael Alcocer June 22, 2026 · 9 min read

An appeal waiver can be one of the most consequential provisions in a federal plea agreement. By signing one, a defendant may surrender the right to challenge a sentence before knowing what that sentence will be.

The Supreme Court has now made clear that such waivers remain powerful—but they are not absolute.

In an 8–1 decision issued June 18, 2026, the Court held in Hunter v. United States that an agreement not to appeal a federal sentence is unenforceable when enforcement would result in a miscarriage of justice. The exception applies only to extreme cases involving an obvious and egregious error serious enough to damage public confidence in the judicial system.

The ruling establishes an important national safeguard while preserving the ordinary usefulness of appeal waivers in plea negotiations. It also clarifies the relationship among three distinct questions: whether a claim falls within the waiver, whether the waiver was validly obtained, and whether a valid waiver should nevertheless be enforced.

The cleanest way to understand Hunter is this: an appeal waiver may be valid, may cover the issue being raised, and still be unenforceable in an extraordinary case.

What Is an Appeal Waiver?

Federal defendants possess a statutory right to appeal certain sentencing errors. Under 18 U.S.C. § 3742, a defendant may ordinarily seek appellate review of a sentence imposed in violation of law, resulting from an incorrect application of the Sentencing Guidelines, exceeding the applicable guideline range in specified circumstances, or otherwise meeting the statute's requirements.

That right, however, can generally be waived as part of a plea agreement.

A typical appeal waiver states that the defendant gives up the right to appeal the conviction, the sentence, or both, subject to whatever exceptions the agreement preserves. Common negotiated exceptions may include ineffective assistance of counsel, prosecutorial misconduct, a sentence exceeding the statutory maximum, or an upward departure or variance.

The precise text matters. A claim that falls outside the waiver's language is not barred by the waiver in the first place. A claim that falls within the waiver ordinarily cannot proceed unless the waiver is invalid or another non-enforcement principle applies.

The Plea Agreement in Hunter

Munson P. Hunter III was charged with ten counts of bank and wire fraud arising from a years-long scheme that allegedly cost financial institutions approximately half a million dollars.

Under a written plea agreement, Hunter pleaded guilty to one count of aiding and abetting wire fraud. In return, the government agreed to dismiss the other nine charges and refrain from prosecuting him in the future for the conduct described in the agreement.

Hunter's agreement included a broad waiver of his right to appeal his conviction and sentence. It expressly preserved his ability to raise an ineffective-assistance-of-counsel claim. The agreement also provided that any modification had to be in writing and signed by all parties.

During the plea hearing, the district judge reviewed the waiver with Hunter and confirmed that he understood it. The court then accepted his plea as knowing and voluntary.

The Mandatory-Medication Condition

At sentencing, the probation office recommended a period of supervised release that would require Hunter to participate in mental-health treatment and take any mental-health medication prescribed by his treating physician.

Hunter objected to the medication portion of the condition. The district court nevertheless imposed a sentence of 51 months in prison followed by three years of supervised release, including the disputed medication requirement.

At the end of the hearing, the judge told Hunter that he had a right to appeal and that trial counsel would continue representing him if he chose to do so. Neither defense counsel nor the prosecutor corrected the statement.

Hunter appealed the medication condition, arguing that it infringed his constitutional liberty interest in avoiding unwanted medical treatment. The government moved to dismiss the appeal based on the waiver.

The Fifth Circuit Enforced the Waiver

The Fifth Circuit dismissed Hunter's appeal.

Under its existing precedent, an appeal waiver generally remained enforceable unless the waiver itself was tainted by ineffective assistance of counsel or the sentence exceeded the statutory maximum. The circuit did not recognize a broader exception simply because a defendant alleged that part of the sentence was unconstitutional.

The Fifth Circuit also concluded that the district court's statement about Hunter having a right to appeal did not alter the written agreement.

That approach placed the Fifth Circuit on the stricter side of a disagreement among the federal appellate courts. Most circuits had already recognized some form of a miscarriage-of-justice limitation, while the Fifth Circuit and several others relied on narrower, specifically defined exceptions.

What the Supreme Court Held

Justice Elena Kagan wrote the majority opinion, joined by Chief Justice John Roberts and Justices Samuel Alito, Sonia Sotomayor, Neil Gorsuch, Brett Kavanaugh, Amy Coney Barrett, and Ketanji Brown Jackson.

The Court adopted the majority approach among the federal courts of appeals:

A federal appeal waiver cannot be enforced when enforcement would result in a miscarriage of justice.

The Court emphasized that this is a high bar. It does not allow defendants to avoid their waivers merely by identifying an arguable sentencing mistake.

Instead, the alleged error must be obvious, egregious, and of a type that would seriously damage the judiciary's reputation for following the law. Ordinary disagreements over guideline calculations, sentencing factors, or routine legal issues generally remain covered by a valid waiver.

The Court explained that appeal waivers implicate more than the contractual interests of prosecutors and defendants. Courts approve plea agreements, impose sentences, and ultimately decide whether to enforce waivers. An appellate court therefore cannot disclaim responsibility when enforcing a waiver would preserve a plainly intolerable judicial result.

Three Questions Courts Should Ask After Hunter

The decision is best understood as establishing a three-stage analysis.

1. Does the claim fall within the scope of the waiver?

The court first examines the agreement's language.

A waiver of the right to challenge a sentence may cover guideline calculations, the length of imprisonment, restitution, forfeiture, supervised-release conditions, or collateral review—but only to the extent the agreement actually says so.

When an issue is outside the waiver's scope, the defendant does not need to invalidate the waiver. The waiver simply does not apply to that issue.

2. Was the waiver validly obtained?

Even a broadly written waiver is valid only if the defendant entered it knowingly and voluntarily.

A defendant may challenge the waiver by alleging, for example:

• Ineffective assistance of counsel in negotiating or explaining it.
• Coercion, fraud, or material misrepresentation.
• Mental incompetence at the time of the plea.
• An inadequate understanding of the rights being surrendered.
• A government breach of the plea agreement.

These arguments concern the waiver's validity.

3. Would enforcing a valid waiver produce a miscarriage of justice?

This is the additional inquiry recognized in Hunter.

Even when the claim falls within the waiver and the defendant knowingly and voluntarily accepted it, an appellate court must consider whether enforcement would preserve an extreme and obvious injustice that threatens the integrity of the judiciary.

That inquiry concerns enforceability, not validity.

What Errors May Meet the New Standard?

The Supreme Court declined to create an exhaustive list. Extreme cases are difficult to predict, and the standard will necessarily develop through future appellate decisions.

The majority nevertheless offered three principal categories for guidance.

A Sentence the Law Does Not Authorize

The clearest example is a punishment exceeding what the governing statute permits.

If a statute authorizes no more than one year of imprisonment, an appeal waiver cannot require an appellate court to preserve a life sentence. The same general concern may arise when a court imposes a form of punishment that the law does not authorize for the offense of conviction.

The focus is not simply that the judge made an error. The problem is that the judiciary would knowingly leave in place a punishment it had no lawful authority to impose.

A Blatant Constitutional Violation

The Court also identified sentences infected by obvious constitutional error.

Examples include a sentence based on race or religion, or a supervised-release condition that directly violates an established constitutional right. The majority referred to an actual case involving a supervised-release condition prohibiting a defendant from becoming pregnant.

A constitutional label alone will not satisfy the standard. The constitutional violation must be sufficiently clear and serious to meet Hunter's demanding institutional test.

A Sentence Imposed Without Basic Judicial Procedure

A waiver may also be unenforceable when the sentence was imposed without a minimum level of legitimate judicial process.

This could include a court refusing to hold a required hearing or abandoning basic sentencing procedures so completely that the resulting punishment cannot credibly be described as a lawful judicial sentence.

The examples are not exclusive. Their purpose is to illustrate the exceptional nature of the required error.

The Court's Memorable Orangutan Hypothetical

One of the opinion's most unusual details involved an orangutan.

During oral argument, the justices considered whether a waiver would have to be enforced if a judge allowed an orangutan to select the defendant's sentence from a hat. The majority used the hypothetical to demonstrate why automatic enforcement could not be the correct rule.

The example was intentionally absurd, but its doctrinal point was serious: courts cannot use a private agreement to legitimize something that no reasonable observer would recognize as lawful adjudication.

The judiciary remains responsible for the judgments it approves and preserves.

What Will Usually Not Meet the Standard?

The Court was equally clear about the other side of the rule.

A routine mistake in applying the Sentencing Guidelines will generally not overcome an appeal waiver. Neither will an ordinary disagreement about:

• The appropriate guideline enhancement.
• The weight assigned to a sentencing factor.
• Whether a variance was warranted.
• The factual basis for a routine supervised-release condition.
• The substantive reasonableness of an otherwise lawful sentence.

These issues may be appealable when no waiver exists. But Hunter does not convert every potentially reversible error into a miscarriage of justice.

The distinction is between an error that may be legally wrong and an error so extreme that enforcing the waiver would implicate the legitimacy of the judicial system itself.

The Judge's Statement Did Not Modify the Agreement

Hunter also argued that the district court effectively restored his right to appeal when it told him at sentencing that he could do so.

The Supreme Court rejected that argument.

The plea agreement required modifications to be in writing and signed by the parties. The judge's oral statement did not satisfy that provision. More fundamentally, the court explained that modifying the agreement required mutual assent between Hunter and the government. A judge's mistaken advisement, followed by silence from the lawyers, did not demonstrate that the parties intended to rewrite their bargain.

The prosecutor also did not waive or forfeit the government's enforcement right by remaining silent at sentencing. The proper time to decide whether to enforce an appeal waiver ordinarily arises after the defendant files an appeal and the government can evaluate the claim being raised.

This part of the decision has an important practical consequence: a routine sentencing advisement about appellate rights will not necessarily override a valid written waiver.

When Is an Appeal Waiver Knowing and Voluntary?

Federal Rule of Criminal Procedure 11 requires the judge to address the defendant personally in open court before accepting a guilty plea.

Rule 11(b)(1)(N) specifically requires the court to inform the defendant of, and determine that the defendant understands, any plea-agreement provision waiving the right to appeal or collaterally attack the sentence.

Courts ordinarily examine the total record, including:

• Whether the waiver is written clearly.
• Whether its scope and exceptions were explained.
• Whether the defendant discussed it with counsel.
• Whether the judge addressed it during the plea colloquy.
• Whether the defendant appeared competent and understood the proceeding.
• Whether the plea resulted from threats, improper promises, or coercion.
• Whether the defendant knew the sentence had not yet been determined.

Statements made under oath during a plea hearing carry considerable weight. A defendant who repeatedly confirms understanding will usually face a substantial evidentiary obstacle when later claiming otherwise.

Those statements are not necessarily conclusive in every case. A defendant may still present evidence that counsel materially misrepresented the waiver, that the defendant was incompetent, or that some other defect prevented an informed and voluntary decision. But a later assertion of misunderstanding ordinarily must be supported by credible evidence from the plea process.

Ineffective Assistance in Plea Negotiations

Hunter also reaffirmed that an appeal waiver produced by ineffective assistance of counsel is not knowing and voluntary and therefore is not enforceable.

The controlling framework comes from Strickland v. Washington. A defendant must establish both:

1. Deficient performance: Counsel's representation fell below an objective standard of professional reasonableness.
2. Prejudice: There is a reasonable probability that counsel's error changed the outcome of the plea process.

Courts evaluate counsel's conduct from the circumstances existing at the time, not with hindsight. Reasonable strategic judgments receive substantial deference. A bad outcome, unsuccessful prediction, or later regret does not independently establish deficient performance.

Examples of Potentially Deficient Plea Advice

Ineffective assistance during plea negotiations may include:

• Failing to communicate a formal and favorable plea offer.
• Allowing a time-sensitive offer to expire without consulting the client.
• Advising the defendant to reject an offer based on materially incorrect law.
• Grossly misrepresenting mandatory sentencing exposure.
• Failing to conduct a reasonable investigation before advising whether to plead.
• Misrepresenting which appellate or collateral claims will survive the waiver.
• Failing to explain that an agreement waives both direct appeal and review under 28 U.S.C. § 2255.
• Giving incorrect advice about a clear and automatic immigration consequence.

In Missouri v. Frye, the Supreme Court held that counsel has a duty to communicate formal plea offers that may be favorable. In Lafler v. Cooper, deficient legal advice caused the defendant to reject a favorable offer and receive a substantially harsher result after trial.

The Constitution does not guarantee a favorable plea agreement, a particular sentence, or a perfect prediction. It requires competent advice sufficient to allow the defendant to make an informed decision.

Proving Prejudice

The required prejudice showing depends on what allegedly went wrong.

When deficient advice caused a defendant to accept a guilty plea, Hill v. Lockhart generally requires proof of a reasonable probability that, with competent advice, the defendant would have rejected the plea and proceeded to trial.

When counsel caused the loss or rejection of a more favorable offer, Frye and Lafler generally require proof of a reasonable probability that:

• The defendant would have accepted the offer.
• The prosecution would not have withdrawn it.
• The court would have accepted its terms.
• The result would have been more favorable than the conviction or sentence ultimately imposed.

A defendant's later statement that an offer would have been accepted is relevant but not automatically sufficient. Courts look for contemporaneous support, such as prior communications, the sentencing disparity, the defendant's conduct during negotiations, available defenses, and whether later testimony conflicts with statements previously made in court.

A Separate Rule When Counsel Fails to File an Appeal

Ineffective assistance in negotiating a waiver is distinct from ineffective assistance after sentencing.

In Garza v. Idaho, the Supreme Court held that counsel performs deficiently by disregarding a defendant's express instruction to file a notice of appeal. The usual presumption of prejudice applies even when the defendant signed an appeal waiver.

That is because an appeal waiver does not necessarily waive every possible appellate claim. Filing a notice of appeal is also a ministerial act that preserves the defendant's ability to determine which issues, if any, remain reviewable.

Counsel therefore should not refuse to file a requested notice of appeal merely because the plea agreement contains a waiver.

An Error Outside the Waiver Is Different From an Unenforceable Waiver

This distinction is especially important.

Suppose an agreement waives challenges to imprisonment but expressly preserves an appeal of restitution. A restitution challenge would proceed because it falls outside the waiver's scope. The defendant would not need to prove ineffective assistance or a miscarriage of justice.

By contrast, when a sentencing issue clearly falls within the waiver, the court asks whether the waiver was knowing and voluntary and whether enforcing it would violate Hunter's miscarriage-of-justice limitation.

The proper analysis is therefore not that every unlawful sentence invalidates an appeal waiver. Many statutory appellate rights may be waived. The question is first what the defendant agreed to waive and then whether the agreement may lawfully be enforced in the circumstances presented.

Government Breach Remains a Separate Issue

A government breach of the plea agreement presents another distinct basis for relief.

Plea agreements involve reciprocal promises. The government generally cannot obtain the benefits of a defendant's plea and waiver while refusing to provide the concessions it promised in return.

A breach claim should not be confused with Hunter's miscarriage-of-justice inquiry. A defendant alleging breach is arguing that the government failed to honor the agreement—not necessarily that the sentencing judge committed the type of extreme error addressed in Hunter.

Similarly, a generic allegation of prosecutorial misconduct does not automatically survive every waiver. Whether it does depends on the agreement's language, the nature of the alleged misconduct, and the governing law.

The Separate Opinions Reveal a Continuing Debate

Although eight justices agreed on the result, the separate opinions show substantial disagreement over what Hunter may mean in future cases.

Justice Gorsuch, joined by Justices Sotomayor and Jackson, described the ruling as an important first step toward limiting the excesses of appeal waivers. He questioned whether defendants can truly make a knowing prospective waiver of challenges to sentences that have not yet been imposed and suggested that future cases may present deeper questions about the validity of such waivers.

Justice Kavanaugh, joined by Justices Alito and Barrett, emphasized that the majority's standard is exceptionally demanding. He cautioned that Justice Gorsuch's discussion could be read as adopting a lower threshold than the controlling opinion permits.

Justice Barrett separately grounded the decision in longstanding principles under which courts may decline to enforce waivers that would severely discredit judicial proceedings.

Justice Thomas dissented. He argued that Hunter knowingly and voluntarily received substantial benefits from his plea agreement and should have been held to the bargain. He also maintained that the majority had not identified a sufficient constitutional, statutory, or rule-based source for creating the new exception.

These separate writings are likely to influence how lower courts define the boundary between an ordinary sentencing error and an institutional miscarriage of justice.

What the Decision Means for Defense Lawyers

For defense counsel, Hunter makes careful drafting and documentation more important—not less.

Counsel should identify precisely:

• Which convictions and sentences the waiver covers.
• Whether it covers restitution, forfeiture, supervised release, and collateral review.
• Whether the agreement preserves ineffective-assistance or prosecutorial-misconduct claims.
• Whether it allows an appeal from an upward departure or variance.
• Whether a conditional plea is available to preserve review of a specified pretrial ruling.
• What remedies the government may seek if the defendant files an appeal contrary to the agreement.

Counsel should also document the advice given about sentencing uncertainty, the difference between direct appeal and collateral review, and the practical consequences of the waiver.

After sentencing, counsel must preserve objections to contested conditions and comply with an express instruction to file a notice of appeal, even when counsel expects the government to invoke the waiver.

What the Decision Means for Prosecutors

The ruling preserves appeal waivers as valuable plea-bargaining tools.

Prosecutors may continue seeking broad waivers, and courts will continue enforcing them in ordinary cases. But the government can no longer argue that every knowing and voluntary waiver must be enforced regardless of the nature of the sentence.

Clear drafting will be critical. Prosecutors should avoid relying on vague or overbroad language and should specify any agreed exceptions.

The opinion may also encourage prosecutors to evaluate whether seeking enforcement is appropriate when an appeal identifies an unmistakably unlawful or unconstitutional condition. The government retains discretion not to invoke a waiver in a particular case.

What the Decision Means for Sentencing Judges

Judges have two important responsibilities.

First, Rule 11 requires a meaningful inquiry into whether the defendant understands the waiver. A mechanical reference to the written agreement may not always be sufficient. The court should explain the waiver's practical significance and confirm that the defendant understands that the sentence may differ from counsel's prediction.

Second, judges should make individualized findings before imposing unusually intrusive conditions of supervised release—particularly conditions affecting medical treatment, bodily autonomy, family relationships, religious exercise, or speech.

A contradictory statement at the conclusion of sentencing may not modify the plea agreement, but it can create unnecessary confusion and litigation. Sentencing advisements should accurately acknowledge any applicable waiver.

What Hunter Did Not Decide

The decision is significant, but its limits are equally important.

The Supreme Court did not hold that:

• Hunter's medication condition was unconstitutional.
• Hunter is automatically entitled to appellate relief.
• Every constitutional claim survives an appeal waiver.
• Every Guidelines error constitutes a miscarriage of justice.
• Appeal waivers are generally invalid.
• The same rule necessarily governs all collateral-attack waivers.
• State courts must apply identical rules to waivers in state plea agreements.

The Court vacated the Fifth Circuit's judgment and returned the case for further proceedings. The Fifth Circuit must now decide whether enforcing Hunter's waiver against his particular medication challenge would produce a miscarriage of justice.

It may conclude that the condition satisfies the demanding standard—or it may still dismiss the appeal.

The Broader Importance of Hunter

Appeal waivers require defendants to bargain before they know exactly what sentence a judge will impose. They promote finality and may help defendants obtain meaningful concessions, but they also reduce appellate oversight of federal sentencing.

Hunter attempts to preserve both interests.

The decision leaves appeal waivers intact in the overwhelming majority of cases. Defendants cannot escape them merely by identifying an arguable error or repackaging an ordinary sentencing dispute as a constitutional claim.

At the same time, appellate courts are no longer required to use those waivers to preserve an obvious and extraordinary injustice.

That is the central principle of Hunter: an appeal waiver is a strong and generally enforceable bargain, but it is not a license for judicial lawlessness.

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This article is intended for general legal education and commentary. It does not constitute legal advice and does not create an attorney-client relationship.