Can You Still Challenge a Guilty Plea After Signing a Waiver?

Update (October 2026): In June 2026, the Supreme Court held that an appeal waiver cannot be enforced when enforcing it "would result in a miscarriage of justice." The Court said this is a high bar. It covers only obvious, serious errors that would bring the courts into disrepute, not ordinary sentencing mistakes. Hunter v. United States, 608 U.S. 713 (2026).

Signing a plea deal with a waiver does not always end your chance to challenge the guilty plea. Courts recognize several exceptions, and if the government breaks the deal, the waiver no longer protects it. There is a real risk to weigh, though: if you win and are convicted again, you can sometimes end up with more time. This final column in the series, based on the book WinningCites: Attacking the Guilty Plea, walks through each of these points.

This article originally appeared in the November 2020 issue of Criminal Legal News. It is reprinted with permission. Copyright, 2020 Criminal Legal News. It is based on the book WinningCites: Attacking the Guilty Plea.

Waivers in Plea Agreements

A waiver is a promise in your plea deal to give up a right, such as the right to appeal. Over 67 percent of plea agreements in 2015 had waivers. They are usually standard language the government puts in every deal, and defense lawyers rarely negotiate them. Waivers are so common that defendants often accept them as a necessary evil of pleading guilty.

But you cannot give up a right you were never told about. In United States v. Chua, 349 F. Supp. 3d 214 (E.D.N.Y. 2018), Judge Jack Weinstein criticized a "blanket" waiver that barred any challenge to the plea or sentence without listing the rights being given up. He rewrote the waiver to spell out each right the defendant was and was not waiving.

In a 28 U.S.C. § 2255 case (a motion asking the sentencing court to throw out a federal conviction or sentence), a waiver is an "affirmative defense." That means the government has to raise it, or the defense is lost. A § 2255 case is a civil proceeding, and Federal Rule of Civil Procedure 8(c)(1) requires affirmative defenses to be raised.

A judge cannot raise the waiver on the government's behalf. But the judge can, and usually does, ask the government whether it plans to rely on it. See Burgess v. United States, 874 F.3d 1292 (11th Cir. 2017) (vacating a § 2255 denial where the district court invoked the waiver on its own).

Courts read plea agreements like contracts. Santobello v. New York, 404 U.S. 257 (1971). Under contract law, anything unclear in the deal is read against the side that wrote it, which is the government.

Collateral Attack Waivers vs. Appeal Waivers

A collateral attack is a challenge filed after the appeal is over, such as a § 2255 motion (for federal prisoners) or a § 2254 petition (for state prisoners). Because plea deals are read against the government, some courts have held that a waiver of your right to "appeal" does not also waive a collateral attack. See Hunter v. United States, 160 F.3d 1109 (6th Cir. 1998).

Courts apply the same rules to both kinds of waivers, so the exceptions below apply to both.

Exception: The Waiver Was Not Knowing and Voluntary

Your guilty plea must be knowing and voluntary, and so must any waiver in your plea deal. United States v. Ruiz, 536 U.S. 622 (2002). That means you understood "the relevant circumstances and likely consequences."

Ineffective assistance of counsel (IAC), meaning your lawyer's work fell below basic standards, can make a waiver invalid if it happened while negotiating the deal. Hurlow v. United States, 726 F.3d 958 (7th Cir. 2013); Padilla v. Kentucky, 559 U.S. 356 (2010) (plea bargaining is a critical phase that requires effective counsel).

A more disputed question is whether a waiver is invalid when prosecutors hid evidence that helps the defense. In Chua, Judge Weinstein noted the Second Circuit had not decided whether such serious government misconduct could cancel a collateral attack or appeal waiver. Pointing to how many cases end in guilty pleas, he concluded the right to challenge a conviction is not waived when the government withholds evidence. "This right is retained as part of the 'voluntary and knowing' exception," he wrote. Courts are split, and the Supreme Court has not decided it. See Friedman v. Rehal, 618 F.3d 142 (2d Cir. 2010).

A waiver is also not knowing and voluntary if you were not told the nature of the charge. Frederick v. Warden, 308 F.3d 192 (2d Cir. 2002) (a defendant must have "real notice of the true nature of the charge").

Exception: A Change in the Law

Some courts allow a challenge, despite a waiver, when a later change in the law makes the conviction or sentence invalid. This includes major court decisions that apply retroactively, as well as changes in the law made by lawmakers. For example, the Supreme Court struck down the residual clause of the Armed Career Criminal Act in Johnson v. United States, 576 U.S. 591 (2015), and made that ruling retroactive in Welch v. United States, 578 U.S. 120 (2016).

The Fourth Circuit held a collateral attack waiver did not bar a Johnson challenge, because the court never had power to impose an illegal sentence. United States v. Cornette, 932 F.3d 204 (4th Cir. 2019). The Fifth Circuit disagreed and enforced the waiver. United States v. Barnes, 953 F.3d 383 (5th Cir. 2020). The same reasoning could apply to waivers of challenges to a guilty plea.

The Fourth Circuit has also said that not every change in law cancels a waiver. "A plea agreement, like any contract, allocates risk. And the probability of a favorable change in law occurring after a plea is one of the normal risks that accompanies a guilty plea." United States v. Archie, 771 F.3d 217 (4th Cir. 2014).

That risk cuts both ways. In one case, a defendant won a challenge based on a retroactive Supreme Court decision. The government then tried to bring back charges it had dropped under the plea deal. The court refused, citing Archie. Diri v. United States, 2019 U.S. Dist. LEXIS 175043 (W.D.N.C. 2019).

Exception: Impermissible Factors

A guilty plea or waiver does not bar some constitutional challenges. Menna v. New York, 423 U.S. 61 (1975) (double jeopardy); Blackledge v. Perry, 417 U.S. 21 (1974) (prosecutorial vindictiveness). Courts also agree that race can never play a part in a conviction or sentence, waiver or not. See United States v. Marin, 961 F.2d 493 (4th Cir. 1992).

Exception: Miscarriage of Justice

Many courts will not enforce a waiver that would cause a "miscarriage of justice." The Supreme Court adopted this rule for appeal waivers in Hunter (2026), described in the update above.

The Tenth Circuit has listed four situations: (1) the court relied on an impermissible factor like race, (2) IAC in negotiating the waiver, (3) a sentence above the legal maximum, or (4) the waiver is otherwise unlawful. United States v. Viera, 674 F.3d 1214 (10th Cir. 2012).

The Seventh Circuit has said due process is likely violated if prosecutors know a defendant is factually innocent and hide it before a guilty plea. McCann v. Mangialardi, 337 F.3d 782 (7th Cir. 2003).

A Broken Plea Deal Voids the Waiver

If the government breaks (breaches) your plea agreement, the waiver no longer protects the government. In Santobello, the Supreme Court said the trial court could order "specific performance," meaning the court enforces the deal as promised, or let the defendant withdraw the guilty plea. This is where contract law comes in. Specific performance simply gives the harmed party the benefit it was supposed to get under the deal.

Santobello also held that the government's breach violates due process. That matters because there is no constitutional right to a plea deal. Once you accept one, though, it carries constitutional protection, and habeas corpus cases (post-conviction challenges to unlawful custody) are about constitutional violations.

If you breach the deal, the government has the same options. If the deal is canceled, you start over as if you never pleaded guilty. See Ricketts v. Adamson, 483 U.S. 1 (1987) (upholding a death sentence after the defendant broke his deal by refusing to testify and was convicted of more serious charges).

Successfully withdrawing your guilty plea is not a breach of the plea deal. United States v. Newbert, 504 F.3d 180 (1st Cir. 2007).

Can You Get More Time After Winning?

Yes, but not always. In North Carolina v. Pearce, 395 U.S. 711 (1969), the Supreme Court said a longer sentence given as a "penalty" for winning a challenge is unconstitutional. But Pearce involved a new sentence after an appeal and retrial, not a guilty plea.

In Alabama v. Smith, 490 U.S. 794 (1989), the defendant got 30 years after pleading guilty. He later had the plea thrown out, went to trial, lost, and got life plus 150 years. The judge said he had been "too lenient" the first time.

Was this vindictive? Perhaps, but the Supreme Court upheld the longer sentence. It reasoned that a trial can bring out facts a judge never hears at a guilty plea, and those facts can fairly affect the sentence.

In United States v. Rodriguez, 602 F.3d 346 (5th Cir. 2010), the defendant won a resentencing because the government broke his plea deal. A different judge then gave him a longer sentence. The Fifth Circuit affirmed, finding no presumption of vindictiveness and no proof of actual vindictiveness. The Supreme Court reached a similar result for a new sentence set by a jury in Chaffin v. Stynchcombe, 412 U.S. 17 (1973), noting the jury had "no personal stake" in the earlier conviction.

These cases suggest a harsher sentence after a successful challenge can be allowed when it rests on new facts or comes from a new decision-maker.

Conclusion

Plea agreements almost always contain waivers, but a waiver does not always block a challenge to a guilty plea. Know what your waiver covers and which exceptions might apply, and weigh the risk of a longer sentence before asking to undo the plea.

A few practical steps help:

• Get the paperwork. Gather the written plea agreement, the transcript of the plea hearing (where the judge questioned you about the deal), the judgment, and the case docket number. The waiver's exact wording matters.
• Mind the deadlines. A direct appeal generally must be noticed within 14 days after the judgment is entered. FRAP 4(b)(1)(A). A § 2255 motion generally must be filed within one year, usually counted from the date the conviction became final. 28 U.S.C. § 2255(f).

Editor's note: This is the fifth column in a series on attacking the guilty plea.

About the author: Dale Chappell is a staff writer for Criminal Legal News and Prison Legal News. For over a decade, he has helped prisoners challenge their wrongful convictions and sentences, with dozens being released from prison (per the original author bio). He is a member of the National Lawyers Guild and was a firefighter for 20 years before becoming a prisoner advocate. He wrote two books with attorney Brandon Sample: WinningCites: Section 2255, A Handbook for Prisoners and Lawyers and WinningCites: Attacking the Guilty Plea.

Facing a federal sentence? Book a consultation to talk it through with Brandon Sample.