Harmless-Deficiency Doctrine for Anders Briefs in Appeal-Waiver Cases

Introduction

This commentary examines the Second Circuit’s decision in United States v. Arguedas, 22-1355-cr (2d Cir. Apr. 9, 2025), which clarifies when a deficient Anders brief may nonetheless support counsel’s motion to withdraw. Alexander Arguedas pled guilty to racketeering, narcotics, and firearms charges in the Southern District of New York and waived his right to appeal most aspects of his sentence. His appellate counsel filed an Anders brief that rigorously addressed the plea and appeal waiver but omitted discussion of the supervised-release conditions, which fell outside the waiver. The Court of Appeals held that such omissions can be harmless in appropriate circumstances and set out a two-part test for harmlessness.

Key parties:

• Plaintiff/Appellee: United States of America
• Defendant-Appellant: Alexander Arguedas
• Circuit Judges: Jacobs, Nardini, Menashi
• District Judge below: Jesse M. Furman

Main issues:

• Validity and scope of an appeal waiver in a plea agreement
• Sufficiency of an Anders brief when it omits aspects of the sentence not covered by the waiver
• Establishing a harmless-deficiency standard for Anders briefs in appeal-waiver cases

Summary of the Judgment

Arguedas pled guilty to: (1) racketeering conspiracy (18 U.S.C. § 1962(d)); (2) narcotics conspiracy (21 U.S.C. §§ 846, 841(b)(1)(A)); and (3) using and carrying firearms in furtherance of a narcotics conspiracy (18 U.S.C. § 924(c)(1)(A)(i)). He received a below-Guidelines term of 390 months’ imprisonment, five years of supervised release, and a $300 special assessment. His plea agreement contained a broad appeal waiver covering any sentence at or below the Guidelines range, supervised-release terms up to the statutory maximum, fines up to $10 million, and assessments up to $300.

On appeal, counsel filed an Anders brief arguing that the plea was valid, the waiver enforceable, and no non-frivolous issues existed as to imprisonment. Counsel neglected to discuss the conditions of supervised release, which fell outside the waiver. The government moved to dismiss under the waiver or, alternatively, for summary affirmance.

The Second Circuit held that:

1. A deficient Anders brief is not automatically fatal if the deficiency is harmless.
2. Where counsel omits discussion of sentencing components not covered by the waiver, the omission is harmless if the court can determine from the record that no non-frivolous issues exist regarding those components.
3. If issues might exist, counsel may cure the deficiency by certifying that the defendant knowingly declined to appeal those components after discussing the risks and benefits.

Applying this framework, the Court found no non-frivolous issues as to the mandatory and standard conditions of release or five of the seven special conditions (substance abuse treatment, mental-health treatment, search condition, non-association with gang members, district supervision). But two special conditions—financial disclosure and restrictions on new credit—could raise non-frivolous arguments because no fine, forfeiture, or restitution order had been imposed. The Court therefore deferred decision and ordered supplemental briefing.

Analysis

1. Precedents Cited

• Anders v. California, 386 U.S. 738 (1967): Established counsel’s duty to file a brief identifying any arguable issues when seeking withdrawal.
• Reyes-Arzate, 91 F.4th 616 (2d Cir. 2024): Held that in appeal-waiver cases, an Anders brief must address plea validity, waiver scope, and any non-waived issues (e.g., supervised-release conditions).
• Garza v. Idaho, 586 U.S. 237 (2019): Emphasized that valid appeal waivers do not bar all appellate claims—only those within the waiver’s scope.
• United States v. Burden, 860 F.3d 45 (2d Cir. 2017): Confirmed that a silent waiver does not foreclose challenges to non-waived aspects of the sentence.
• United States v. Burnett, 989 F.2d 100 (2d Cir. 1993); Zuluaga, 981 F.2d 74 (2d Cir. 1992); Whitley, 503 F.3d 74 (2d Cir. 2007); Urena, 23 F.3d 707 (2d Cir. 1994): Illustrate Anders briefs so deficient they amounted to constructive denial of counsel.

2. Legal Reasoning

The Court’s reasoning unfolds in two steps:

Step 1: Identify the Deficiency

Counsel’s Anders brief thoroughly addressed plea validity, the appeal waiver, and the term of imprisonment but omitted any analysis of the mandatory, standard, and special conditions of supervised release, which were outside the waiver. Under Reyes-Arzate, that omission rendered the Anders brief incomplete.

Step 2: Apply Harmless-Deficiency Test

Rather than treat any omission as fatal, the Court adopts a harmless-deficiency approach analogous to harmless-error review:

1. Record-Based Harmlessness: If the record indisputably shows no non-frivolous arguments exist on the omitted issues, the deficiency is harmless.
2. Cure by Client Authorization: If arguable issues could exist, counsel may remedy the omission by certifying that, after discussing risks and benefits, the client chose not to pursue those issues.

Applying this test, the Court concluded five of the seven special conditions and all mandatory/standard conditions presented no non-frivolous challenge:

• Substance abuse and mental-health treatment conditions reflected the defendant’s history and the § 3553(a) factors.
• The search condition was justified by Arguedas’s violent history and use of electronic devices to document crimes.
• The no-association/gang-avoidance condition related directly to his racketeering conduct.
• Supervision by district of residence is a routine administrative condition.

But financial disclosure and new-credit restrictions (Special Conditions #2 & #3) typically accompany fines, forfeiture, or restitution orders. Here none of those financial penalties was imposed, so non-frivolous issues may exist as to whether those conditions were authorized and reasonably related to the sentencing factors. The Court therefore deferred ruling and ordered supplemental briefing under the new framework.

3. Impact on Future Cases

This decision establishes a middle ground that preserves the Anders procedure while ensuring defendants in appeal-waiver cases receive full appellate advocacy on non-waived issues. Future implications include:

• District Courts & Defenders: Must counsel clients whether to pursue challenges to non-waived sentencing components and document that election.
• Appellate Briefing: Anders briefs in appeal-waiver cases will be evaluated for harmless omissions, reducing unnecessary remands while protecting the right to appeal non-waived issues.
• Clarified Standards: Harmless-deficiency review ensures that only genuine gaps in Anders advocacy require correction, not every minor omission.
• Sentencing Practice: Emphasizes precision in imposing special conditions—courts will be mindful to link each condition to a sentencing factor or statutory/listed obligation.

Complex Concepts Simplified

Several technical concepts arise in this case:

• Anders Brief: A limited appellate brief filed by counsel who believes an appeal to be frivolous. It must identify any arguable issues and provide the client an opportunity to file pro se arguments.
• Appeal Waiver: A contractual provision in a plea agreement where the defendant gives up the right to challenge specified aspects of the conviction and sentence.
• Harmless-Deficiency Test: An innovation parallel to harmless-error review. Counsel’s omission is deemed harmless if no non-frivolous argument exists on the omitted issue, or if the client affirmatively declines to pursue it.
• Supervised-Release Conditions: Post-imprisonment restrictions and requirements. “Mandatory” and “standard” conditions apply in every case; “special” conditions are added when reasonably related to the offense or defendant’s history, under 18 U.S.C. § 3583(d) and U.S.S.G. § 5D1.3.

Conclusion

United States v. Arguedas refines the interplay between plea-agreement appeal waivers and Anders procedure by introducing a harmless-deficiency doctrine. It strikes a balance between ensuring diligent appellate advocacy and avoiding empty procedural remands where the record establishes no non-frivolous challenges. Criminal defense counsel, district judges, and appellate panels must now apply this two-pronged test when Anders briefs in appeal-waiver contexts omit discussion of non-waived sentencing components, ensuring defendants retain meaningful appellate rights on those issues.