Medication-Compliance Clarifications and Reasonable‑Suspicion Digital‑Search Conditions on Supervised Release: The Second Circuit’s Guidance in United States v. Woods (Summary Order)

Medication-Compliance Clarifications and Reasonable‑Suspicion Digital‑Search Conditions on Supervised Release: The Second Circuit’s Guidance in United States v. Woods (Summary Order)

Court: U.S. Court of Appeals for the Second Circuit

Date: September 8, 2025

Panel: Judges Wesley, Park, and Robinson

Disposition: Affirmed

Note on precedential status: This is a Summary Order under FRAP 32.1 and Local Rule 32.1.1. It is nonprecedential, but it provides useful guidance on two recurring supervised‑release issues.

Introduction

This appeal arises from the sentencing of Tishawn C. Woods, who pleaded guilty in the Southern District of New York to: (1) conspiracy to commit Hobbs Act robbery (18 U.S.C. § 1951); (2) discharging a firearm in furtherance of a crime of violence (18 U.S.C. § 924(c)(1)(A)(iii)); and (3) brandishing a firearm in furtherance of a crime of violence (18 U.S.C. § 924(c)(1)(A)(ii)). He received a 240‑month prison term and five years of supervised release with six special conditions. On appeal, Woods challenges two of those conditions:

  • Special Condition Two: participate in an outpatient mental health treatment program approved by Probation and “continue to take any prescribed medications unless otherwise instructed by the health care provider.”
  • Special Condition Three: submit computers, electronic communication or data‑storage devices, cloud storage, or media to search upon reasonable suspicion of unlawful conduct or violation of supervision, at a reasonable time and in a reasonable manner.

The case presents two familiar supervised‑release issues: (1) when a written judgment may “clarify” an oral pronouncement without creating an impermissible variance, particularly in light of the Second Circuit’s recent decision in United States v. Maiorana; and (2) how courts evaluate digital‑device search conditions for procedural adequacy and substantive reasonableness, especially where the offense conduct involved online communications.

Summary of the Opinion

  • Affirmed the judgment in full.
  • Special Condition Two (mental health treatment + medication compliance): The written requirement to “continue to take any prescribed medications unless otherwise instructed by the health care provider” permissibly clarified the oral pronouncement that Woods must participate in outpatient mental health treatment. There was no impermissible variance because the oral sentence left the exact language to be set in the judgment, and medication compliance is a foreseeable and inherent component of outpatient mental‑health treatment. The panel found no error even under de novo review.
  • Special Condition Three (digital‑device searches on reasonable suspicion): No procedural error; the justification for the condition was self‑evident from the record—Woods organized a violent robbery spree and used Facebook Messenger to coordinate with co‑conspirators. No substantive error; the condition is tailored (reasonable suspicion, reasonable time and manner) and consistent with the reduced privacy expectations on supervised release.

Analysis

A. Precedents and Authorities Cited

  • Standards of Review
    • United States v. MacMillen, 544 F.3d 71 (2d Cir. 2008): District courts have “wide latitude” to impose supervised‑release conditions.
    • United States v. Green, 618 F.3d 120 (2d Cir. 2010) and United States v. Marcus, 560 U.S. 258 (2010): Plain‑error review where no objection below; four‑part test for plain error.
    • United States v. Washington, 904 F.3d 204 (2d Cir. 2018); United States v. Rosado, 109 F.4th 120 (2d Cir. 2024): De novo review where defendant lacked notice of an added sentencing term introduced only in the written judgment.
  • Oral Pronouncement vs. Written Judgment
    • United States v. A‑Abras Inc., 185 F.3d 26 (2d Cir. 1999): Unambiguous oral pronouncement controls over conflicting written judgment.
    • United States v. Rosado, 109 F.4th at 124–25: Written judgments may clarify an ambiguous oral sentence but may not impose new, burdensome punishments or create substantive discrepancies.
    • United States v. Truscello, 168 F.3d 61 (2d Cir. 1999), overruled on other grounds by United States v. Maiorana, No. 22‑1115‑CR, 2025 WL 2471027 (2d Cir. Aug. 28, 2025): Historically allowed clarifying additions in the written judgment where “necessary” to effect supervision. The panel explains that Maiorana narrows but does not erase the general “clarification” principle: a written judgment may clarify an oral sentence, but not to add discretionary supervised‑release conditions that were never orally imposed.
    • United States v. Washington, 904 F.3d at 208: A written, post‑sentencing addition of a polygraph‑testing requirement to a sex‑offender treatment condition was impermissible because polygraph testing is burdensome and not a necessary or invariable part of treatment.
  • Substantive and Procedural Requirements for Special Conditions
    • United States v. Betts, 886 F.3d 198 (2d Cir. 2018); U.S.S.G. § 5D1.3(b): Special conditions must relate to offense characteristics, deterrence, protection of the public, or correctional treatment, and impose no greater deprivation of liberty than reasonably necessary.
    • United States v. Kunz, 68 F.4th 748 (2d Cir. 2023): The sentencing court must make an individualized assessment and state reasons; lack of detailed findings can be excused where the rationale is self‑evident from the record.
  • Digital‑Search Conditions
    • United States v. Lewis, 125 F.4th 69 (2d Cir. 2025): Courts routinely uphold digital‑search conditions where the offense involved computers or other electronic devices.
    • United States v. Washington, No. 22‑688‑CR, 2024 WL 2232464 (2d Cir. May 17, 2024) (summary order): Upheld where a co‑defendant used social media; the record supported the condition.
    • United States v. Robinson, 134 F.4th 104 (2d Cir. 2025): Similar conditions sustained even where the underlying conviction did not involve devices, if the record supports the need.
    • United States v. Lawrence, 139 F.4th 115 (2d Cir. 2025): Supports the tailoring of search conditions.
    • United States v. Oliveras, 96 F.4th 298 (2d Cir. 2024); Mont v. United States, 587 U.S. 514 (2019): Supervised release entails conditional liberty and diminished privacy expectations.
    • United States v. Sims, 92 F.4th 115 (2d Cir. 2024): Confirms the sentencing court’s broad discretion to craft special conditions.

B. The Court’s Legal Reasoning

1) Special Condition Two: Medication compliance within an outpatient mental‑health treatment condition

Issue: Did the written judgment impermissibly add a new, burdensome requirement (medication compliance) that was not part of the oral sentence?

Key facts: Defense counsel affirmatively requested mental‑health evaluation and treatment; Woods personally asked for “any program possible,” specifically including mental‑health services. The judge orally imposed outpatient mental‑health treatment, explicitly stating that the “exact language” would be set out in the written judgment and would be consistent with the judge’s standard language. The written judgment then added the now‑challenged clause: “continue to take any prescribed medications unless otherwise instructed by the health care provider.”

Holding and rationale: The panel found no error even under de novo review. Under the oral‑vs‑written framework (A‑Abras; Rosado), a written judgment can clarify an ambiguous oral sentence but cannot add a new, burdensome condition or create a substantive discrepancy. In light of Maiorana’s narrowing of earlier practice, the court was careful to characterize this clause not as the addition of a discretionary condition but as a foreseeable and intrinsic component of the already‑imposed outpatient mental‑health treatment. Because outpatient treatment commonly includes medication when medically indicated, requiring Woods to follow a provider‑prescribed regimen (and to discontinue only upon provider instruction) is a clarification of what “participation” in that treatment entails, not a new and independently burdensome punishment. This stands in contrast to Washington (2018), where polygraph testing was deemed burdensome and not an “invariable” part of treatment.

Notable doctrinal alignment post‑Maiorana: The panel emphasizes that Maiorana does not abolish the general clarification principle; it limits it. District courts may still use the written judgment to articulate the mechanics of an orally imposed condition—so long as they do not add a new discretionary condition or materially heighten the burden. Medication compliance tied to a clinician’s judgment was placed on the safe side of that line.

2) Special Condition Three: Reasonable‑suspicion searches of digital devices

Procedural challenge: Woods argued the district court failed to justify the condition, especially because his crimes involved physical force rather than the use of electronic devices. The panel disagreed, finding the rationale “self‑evident” from the record. The district court stated that Woods committed four gunpoint robberies, including a home invasion, over two weeks, and that he communicated with co‑conspirators via Facebook Messenger to orchestrate the “violent crime spree.” Under Kunz and Betts, while individualized findings are ordinarily expected, reasons can be inferred where the record makes them obvious. That standard was met here.

Substantive challenge: The condition was also attacked as an unreasonable burden on liberty. The panel rejected that claim. Citing Oliveras and Mont, the court underscored the reduced privacy expectations during supervised release. The condition is materially tailored: it authorizes searches only upon reasonable suspicion and only at a reasonable time and in a reasonable manner. That tailoring, combined with a direct nexus to the offense conduct (use of social media to coordinate crimes), places the condition well within the permissible bounds recognized in Lewis, Robinson, Washington (2024), and Lawrence.

C. Impact and Practical Significance

Although nonprecedential, Woods offers practical guidance in three areas:

  1. Clarifying oral sentences in written judgments post‑Maiorana.
    • District courts may still use written judgments to “spell out” the mechanics of an orally imposed condition where the oral pronouncement is genuinely ambiguous and the written language does not add a new discretionary condition or meaningfully heighten the burden.
    • Medication‑compliance language that defers to a clinician’s judgment is treated as a permissible clarification of an outpatient mental‑health treatment condition, particularly where the defendant requested treatment.
    • By contrast, adding inherently burdensome modalities not invariable to treatment (e.g., polygraph testing) remains impermissible absent oral notice and imposition at sentencing.
  2. Digital‑device search conditions remain viable where the record shows an electronic nexus.
    • Use of social media or messaging apps to plan or coordinate crimes readily supports a supervised‑release search condition that is limited by reasonable suspicion and reasonable time/manner safeguards.
    • Even where the offense did not directly involve electronics, a well‑supported record can justify such a condition; however, the closer the nexus, the stronger the justification.
  3. Sentencing practice pointers.
    • For judges: State reasons for special conditions on the record. While “self‑evident” rationales may suffice on appeal, specific findings reduce litigation risk and clarify expectations.
    • For probation and the government: Supply proposed “standard language” for special conditions in advance. If the court references future “standard language,” ensure it truly clarifies rather than expands the orally imposed condition, mindful of Maiorana.
    • For defense counsel: Object contemporaneously to contested conditions and to any open‑ended references to “standard language” if scope is disputed. If treatment is requested, be explicit about any limits (e.g., medication issues) at sentencing to avoid later “clarification” disputes.

Complex Concepts Simplified

  • Summary Order: A nonprecedential appellate disposition. It may be cited (FRAP 32.1; Local Rule 32.1.1) but does not bind future panels.
  • Supervised Release: A post‑incarceration supervisory period with conditions. It is part of the sentence and carries a reduced expectation of privacy relative to ordinary citizens.
  • Special Conditions: Tailored terms of supervised release aimed at offense characteristics, deterrence, public protection, or treatment. They must be no more restrictive than reasonably necessary (U.S.S.G. § 5D1.3(b)).
  • Oral Pronouncement vs. Written Judgment: The sentence pronounced in open court controls. A written judgment may clarify ambiguities but may not add new, burdensome conditions that were never imposed orally or create substantive discrepancies.
  • Plain Error vs. De Novo:
    • Plain error applies where no objection was made below. The error must be clear or obvious and affect substantial rights and the fairness/integrity of proceedings.
    • De novo may apply where the defendant lacked notice that the written judgment would include a contested term that was not mentioned at sentencing. In Woods, the panel did not choose between the two standards for the medication issue because there was no error even under de novo review.
  • Reasonable Suspicion: A specific, articulable basis to believe a violation or unlawful conduct has occurred. It is a lower threshold than probable cause and commonly used to cabin supervised‑release search conditions.
  • Medication‑Compliance Condition: When tied to outpatient mental‑health treatment and keyed to a licensed provider’s prescriptions and instructions, courts treat it as part of treatment participation rather than as a separate, discretionary punitive condition. This is distinct from court‑mandated “forced medication,” which would implicate different due process considerations not at issue here.

Conclusion

United States v. Woods reinforces two pragmatic lessons for supervised‑release practice in the Second Circuit. First, when a sentencing judge orally orders outpatient mental‑health treatment and signals that standard clarifying language will follow in the written judgment, a medication‑compliance clause that defers to the treating provider is a permissible clarification, not an impermissible addition—particularly after Rosado and with Maiorana’s narrowing principle in mind. Second, digital‑device search conditions limited by reasonable suspicion, time, and manner are substantively reasonable where the record shows that electronic communications (e.g., social media messaging) facilitated the underlying criminal conduct. While nonprecedential, the order provides a careful, updated roadmap for drafting, pronouncing, and reviewing supervised‑release conditions that will be persuasive in future cases.

Case Details

Year: 2025
Court: Court of Appeals for the Second Circuit

Comments