Appeal Waivers Remain Enforceable Despite Sentencing-Court Misstatements About Preserved Constitutional Challenges (United States v. Pena)

1. Introduction

In United States v. Pena (5th Cir. Mar. 26, 2026) (per curiam) (unpublished), Angel Alejandro Pena appealed after pleading guilty to violating 18 U.S.C. § 922(n), which criminalizes receiving/transporting firearms or ammunition while “under indictment” for a felony-level offense. Pena sought to attack the constitutionality of § 922(n) under the Second Amendment, but his plea agreement contained a broad appeal waiver expressly covering “any challenge to the constitutionality of the statute of conviction.”

The central issues on appeal were procedural rather than constitutional: whether Pena’s appeal waiver was knowing and voluntary, whether ineffective assistance of counsel (IAC) could defeat the waiver, and whether an alleged government breach (opposing acceptance of responsibility) made the waiver unenforceable. The Fifth Circuit dismissed the appeal based on the waiver and did not reach the Second Amendment question.

2. Summary of the Opinion

  • Appeal waiver enforced: The court held Pena’s waiver was knowing and voluntary and covered his intended Second Amendment challenge.
  • Sentencing-court misstatements did not undo waiver: The district court incorrectly told Pena at sentencing that he was “not foreclosed” from challenging § 922(n)’s constitutionality, but the Fifth Circuit held that such confusion at sentencing does not invalidate an otherwise valid waiver.
  • IAC argument rejected procedurally: Pena raised IAC only after his opening brief, so the issue was deemed waived; additionally, the claim was not ripe for direct appeal because the record was not developed.
  • No plain error on alleged plea breach: The Fifth Circuit found no “clear or obvious” error in the government’s position on acceptance of responsibility, given the plea’s “prior to sentencing” language and U.S.S.G. § 3E1.1.
  • Disposition: Government’s motion to dismiss granted; appeal dismissed.

3. Analysis

3.1. Precedents Cited

Validity and Scope of Appeal Waivers

  • United States v. Keele, 755 F.3d 752 (5th Cir. 2014): Provided the governing framework—de novo review and a two-step inquiry: (1) whether the waiver was knowing and voluntary; and (2) whether the waiver’s plain language covers the issue raised.
    In Pena, this structured approach guided the court’s threshold decision to enforce the waiver without reaching the Second Amendment merits.
  • United States v. Portillo, 18 F.3d 290 (5th Cir. 1994): Confirmed that a defendant must know of the right to appeal and that he is giving it up, but also held that judges are not required to “specifically admonish[] [the defendant] concerning the waiver of appeal” for the waiver to be knowing.
    This was central to rejecting Pena’s argument that the plea colloquy was insufficient because the magistrate judge discussed appeal rights in the sentencing context.
  • United States v. McKinney, 406 F.3d 744 (5th Cir. 2005): Supplied the frequently used formulation that a waiver is knowing and voluntary where the defendant indicates he read and understood the agreement and the agreement contains an “explicit, unambiguous waiver of appeal.”
    The court used this to anchor its conclusion that Pena’s signed, express waiver—specifically including constitutional challenges—was enforceable.
  • United States v. Higgins, 739 F.3d 733 (5th Cir. 2014): Reinforced that the Fifth Circuit will enforce a waiver “regardless of whether the district court addressed it directly” when the record shows the defendant read and understood the plea agreement and raised no questions.
    This undercut Pena’s attempt to rely on the magistrate judge’s not explicitly reviewing the waiver’s full breadth.

Effect of Sentencing-Court Statements on a Prior Waiver

  • United States v. Melancon, 972 F.2d 566 (5th Cir. 1992): Held that a waiver can remain valid despite a district court incorrectly informing the defendant at sentencing that he had appellate rights; also treated the government’s failure to correct the misstatement as not fatal.
    In Pena, this precedent did the decisive work: the panel treated the sentencing-court’s erroneous statement as not undoing the earlier knowing waiver.
  • United States v. Gonzalez, 259 F.3d 355 (5th Cir. 2001): Stated that “any confusion at [sentencing] has no effect on the validity of the waiver.”
    The court cited this as a direct answer to Pena’s reliance on the sentencing colloquy to re-open constitutional appellate review.

Ineffective Assistance of Counsel (IAC) as a Limited Escape Hatch

  • United States v. Kelly, 915 F.3d 344 (5th Cir. 2019): Two key rules: (1) IAC can defeat an appeal waiver only when the waiver itself was tainted by IAC; and (2) IAC is generally not resolved on direct appeal without a developed record, except on “rare occasions.”
    The panel used Kelly to reject IAC as both procedurally mishandled and not ripe on the existing record.
  • United States v. Pompa, 434 F.3d 800 (5th Cir. 2005): Issues not raised in the opening brief are waived.
    This allowed the court to dispose of Pena’s IAC argument because it first appeared in a later response filing.

Alleged Government Breach and Plain-Error Review

  • United States v. Kirkland, 851 F.3d 499 (5th Cir. 2017): Applied plain-error review to unpreserved claims of plea breach.
    This controlled the standard of review because Pena did not object in the district court.
  • United States v. Kelley, 40 F.4th 276 (5th Cir. 2022) (quoting United States v. Nava, 762 F.3d 451 (5th Cir. 2014)): Restated the four-part plain-error test.
    The court used this framework to emphasize Pena’s burden—particularly the requirement that any error be “clear or obvious.”
  • Puckett v. United States, 556 U.S. 129, 135, 129 S. Ct. 1423, 1429 (2009): For plain error, an issue that is “subject to reasonable dispute” is not “clear or obvious.”
    That principle was dispositive against Pena’s breach claim because the plea’s language (“prior to sentencing”) and § 3E1.1 did not plainly support his timing limitation.

3.2. Legal Reasoning

A. The waiver’s text controlled

The plea agreement did not merely waive “sentencing” appeals; it broadly waived appeal of “the conviction or sentence on any ground,” including “any challenge to the constitutionality of the statute of conviction.” This specificity mattered: Pena’s intended Second Amendment claim fell squarely within the waiver’s express terms. The panel therefore treated the appeal as a straightforward contract-like enforcement question: once the waiver was found knowing and voluntary, the court would not reach the constitutional merits.

B. The plea colloquy record supported knowingness

The court emphasized Pena’s sworn rearraignment statements that he read, discussed, understood, and agreed to the plea agreement, and that nothing in the proceeding confused him. Under Portillo and Higgins, the absence of an explicit judicial admonition about every contour of the waiver does not defeat knowingness when the written waiver is explicit and the defendant affirms understanding.

C. Sentencing misstatements did not vitiate the waiver

Even though the district court incorrectly told Pena at sentencing that he could still challenge § 922(n)’s constitutionality, the Fifth Circuit treated the waiver as fixed at the time of the plea. Citing Melancon and Gonzalez, the panel held that sentencing-stage “confusion” does not retroactively invalidate a previously knowing and voluntary waiver—nor does the government’s failure to object to the judge’s misstatement.

D. IAC could not be used (here) to escape the waiver

The panel identified two independent procedural barriers: (1) the IAC claim was forfeited under Pompa because it was not raised in the opening brief; and (2) even if properly raised, Kelly disfavors direct-appeal resolution without an evidentiary record. In effect, the court signaled that the proper vehicle would typically be post-conviction litigation where counsel’s advice and motivations can be developed.

E. No plain error on the alleged plea breach

Pena argued the government breached by opposing acceptance of responsibility based on pre-plea misconduct. The court read the plea’s condition as extending to conduct “prior to sentencing,” and noted U.S.S.G. § 3E1.1 does not contain Pena’s proposed temporal limitation. Because the issue was reasonably disputable, it could not be “clear or obvious” error under Puckett. That failure at prong two ended the plain-error inquiry.

3.3. Impact

  • Reinforcement of waiver finality: Pena reinforces a Fifth Circuit line that once a defendant knowingly signs a broad waiver, later courtroom statements at sentencing do not “restore” appellate rights—even for constitutional challenges explicitly waived.
  • Strategic consequences for constitutional litigation: Defendants who want to preserve constitutional attacks on statutes of conviction (including Second Amendment challenges) must negotiate explicit carve-outs; otherwise, the waiver may foreclose appellate review entirely.
  • Government’s silence at sentencing is not necessarily a forfeiture: By relying on Melancon, the opinion signals that prosecutors are not required, as a matter of waiver enforceability, to correct a judge’s mistaken advisement at sentencing—though doing so may still be prudent to avoid disputes.
  • Channeling IAC claims away from direct appeal: The decision underscores the Fifth Circuit’s preference that most IAC arguments proceed through a record-developing forum rather than on direct appeal.
  • Second Amendment question left open: The court’s dismissal means the panel created no new merits precedent on § 922(n) under the Second Amendment; the procedural holding may, however, reduce the number of vehicles reaching the merits when defendants sign broad waivers.

4. Complex Concepts Simplified

  • Appeal waiver: A plea-agreement term where a defendant gives up some (often most) rights to appeal. Courts generally enforce these if the defendant knowingly and voluntarily agreed.
  • Knowing and voluntary: The defendant understood what rights existed and that he was giving them up, and did so without coercion. In the Fifth Circuit, a clear written waiver plus the defendant’s confirmation that he read and understood the plea agreement usually suffices.
  • Plain-error review: A demanding appellate standard applied when an issue wasn’t preserved in the trial court. The appellant must show an obvious legal mistake that mattered and seriously affected the proceedings’ fairness.
  • Acceptance of responsibility (U.S.S.G. § 3E1.1): A Sentencing Guidelines reduction for defendants who clearly demonstrate acceptance of responsibility. Courts may consider post-charge conduct and give the sentencing judge “great deference” in evaluating whether the defendant qualifies.
  • Ineffective assistance of counsel (IAC): A claim that defense counsel performed deficiently and prejudiced the defendant. Appellate courts often require a fuller factual record (typically developed outside direct appeal) to assess counsel’s advice and strategy.

5. Conclusion

United States v. Pena is a procedural enforcement decision: the Fifth Circuit dismissed a Second Amendment-based appeal because the defendant’s plea agreement explicitly waived any challenge to the constitutionality of the statute of conviction, and the waiver was deemed knowing and voluntary. The opinion’s most practical contribution is its reaffirmation that sentencing-stage misstatements suggesting an appeal remains available do not unwind a previously valid appeal waiver, and that unpreserved breach claims and undeveloped IAC claims will not easily reopen appellate review. In the broader legal landscape, Pena underscores that the path to merits review of contested criminal statutes may depend as much on plea drafting and waiver carve-outs as on constitutional doctrine.