Enforcement of Appellate Waivers Under Rule 11(b)(1)(N): United States v. Landa

Introduction

The Second Circuit’s summary order in United States v. Landa, No. 24-1307-cr (2d Cir. May 16, 2025), addresses the enforceability of appellate‐waiver provisions in criminal plea agreements—specifically when a defendant challenges both a conviction-based sentence and a supervised‐release violation (VOSR) sentence. Okami Landa pleaded guilty to possession of child pornography (Count Two) and admitted a VOSR specification. He agreed in writing to waive his right to appeal any sentence up to a stipulated guideline range. After receiving a total term of 130 months (120 months on Count Two and 10 months for the VOSR), Landa appealed the substantive reasonableness of his sentence. The Second Circuit dismissed the appeal, holding that he had knowingly and voluntarily waived his appellate rights, despite a Rule 11 colloquy that did not explicitly recite the VOSR appeal waiver.

Summary of the Judgment

The court first identified the appellate‐waiver language in Landa’s plea agreement, which precluded appeals “at or below” 120 months for Count Two and “within or below” 4–10 months for the VOSR specification—even if consecutive. Landa argued the district court violated Rule 11(b)(1)(N) by failing to inform him of the VOSR waiver. The Second Circuit assumed, arguendo, there was a Rule 11 error but found no prejudice under the four‐part plain‐error test: (1) any colloquy omission was not clear legal error; (2) there was no reasonable probability Landa would have refused the plea but for the omission; and (3) his signed agreement, sworn court statements, and concise acknowledgment of the terms defeated any claim of misunderstanding. Consequently, the appellate waiver was enforceable, and the appeal was dismissed.

Analysis

Precedents Cited

United States v. Arevalo, 628 F.3d 93 (2d Cir. 2010): Affirms presumption of enforceability for appellate waivers.
United States v. Gomez‐Perez, 215 F.3d 315 (2d Cir. 2000): Explains that waivers must be made knowingly, voluntarily, and competently; lists exceptions.
United States v. Lloyd, 901 F.3d 111 (2d Cir. 2018): Holds that Rule 11 errors can invalidate waivers if they undermine the plea’s knowing nature.
United States v. Torrellas, 455 F.3d 96 (2d Cir. 2006): Directs courts to consider the entire record when assessing Rule 11 errors.
United States v. Dominguez Benitez, 542 U.S. 74 (2004): Sets standard for plain‐error relief in unpreserved Rule 11 claims (reasonable probability test).
United States v. Hernandez, 242 F.3d 110 (2d Cir. 2001): Emphasizes reliability of a defendant’s sworn statements at plea.
United States v. Sanford, 841 F.3d 578 (2d Cir. 2016): Finds a waiver enforceable despite colloquy omissions when the record shows understanding.
Recent summary orders (Piccarreto, Pagliuca, Germosen): Reinforce that colloquy omissions do not invalidate waivers if the agreement and record demonstrate informed consent.
United States v. Ready, 82 F.3d 551 (2d Cir. 1996): Clarifies that a waiver will not include appeals of illegally imposed sentences, but distinguishes from the present case due to lack of ambiguity.

Legal Reasoning

The Second Circuit’s core reasoning unfolded in three steps:

Applicability of Rule 11(b)(1)(N): The court recognized the district court must “inform the defendant of, and determine that the defendant understands, the terms of any plea‐agreement provision waiving the right to appeal.” Although the court assumed a colloquy omission regarding the VOSR waiver, it did not rest on that assumption.
Plain‐Error Review: Because Landa did not object at the plea hearing, the court applied the four‐prong plain‐error framework from Dominguez Benitez:
- (1) Was there an error? Possibly yes (colloquy omitted mention of the VOSR waiver).
- (2) Was it clear or obvious? Not necessarily, given split authority on whether admissions to VOSR fall under Rule 11 at all.
- (3) Did it affect substantial rights? No—Landa’s signed plea, his sworn acknowledgments, and his counsel’s advice created no reasonable probability he would have refused the deal.
- (4) Would correction of the error seriously affect the fairness, integrity, or public reputation of judicial proceedings? No—enforcing plea agreements promotes finality and predictability.
Entire Record Consideration: Following Torrellas, the court examined Landa’s written plea, the district court’s affirmation that he reviewed and understood all terms, and his stipulated guideline ranges, concluding that any colloquy gap was harmless.

Impact

This decision reinforces a clear presumption in favor of enforcing appellate waivers when:

The waiver language is unambiguous and comprehensive.
The defendant executed the agreement knowingly and voluntarily (as evidenced by a signed plea, lawyer advice, and court questioning).
Any Rule 11 colloquy omission is minor or non‐prejudicial under plain‐error review.

Defendants will therefore face a high bar to challenge sentences under appeal waivers, including § 1038(a)(1) VOSR specifications, absent a clear demonstration of misunderstanding or coercion. Practitioners should ensure that waiver provisions are explicitly covered during the plea colloquy to avoid potential appellate disputes.

Complex Concepts Simplified

Appellate Waiver: A contractual clause in a plea agreement where the defendant agrees not to challenge the sentence on direct appeal or by collateral attack, subject to specified limits.
Rule 11(b)(1)(N): A Federal Rule of Criminal Procedure requiring the judge to inform and secure the defendant’s understanding of any appellate‐waiver provisions at the plea hearing.
Plain‐Error Review: A four‐part test for unpreserved errors on appeal: (1) error, (2) clear or obvious, (3) affecting substantial rights, and (4) affecting fairness, integrity, or public reputation of proceedings.
VOSR Specification: A violation of a supervised‐release condition that carries its own penalty upon admission or finding of violation.

Conclusion

United States v. Landa clarifies that appellate waivers in plea agreements—covering both new counts and supervised‐release violations—are presumptively enforceable so long as the defendant’s consent is knowing and voluntary. Even if a district court omits explicit mention of the waiver in a Rule 11 colloquy, courts will uphold the waiver absent a reasonable probability the defendant misunderstood or would have declined the plea. This reinforces plea‐agreement finality, underscores the importance of thorough colloquies, and signals that defendants face a steep uphill battle when seeking to evade appellate waivers.