United States v. Thompson: Clarifying the Individualized-Assessment Requirement and Affirming Broad Electronic-Search Conditions on Supervised Release

1. Introduction

In United States v. Thompson, No. 23-6943 (2d Cir. July 10, 2025), the Second Circuit reviewed—principally for plain error—the imposition of three special conditions of supervised release that followed Kenneth Thompson’s guilty plea for being a felon in possession of a firearm and ammunition, in violation of 18 U.S.C. §§ 922(g)(1) and 924(a)(2). Thompson challenged (i) a suspicion-based search condition encompassing electronic devices, (ii) a sex-offender registration condition, and (iii) a mental-health evaluation/treatment condition. He also advanced, pro se, a panoply of attacks on his conviction—including ineffective assistance, involuntariness of his plea, a Guidelines miscalculation, and a Second-Amendment challenge—all of which the court ultimately rejected or declined to reach.

The decision is most noteworthy for the guidance it furnishes on how district courts can satisfy the “individualized assessment” requirement when imposing special conditions, and for its approval of a reason-suspicion-plus-electronics search condition even where the underlying offense did not involve electronic devices. The court also confirms that a defendant’s express contemporaneous consent to a condition constitutes a true waiver, extinguishing appellate review.

2. Summary of the Judgment

Appellate holding: Judgment of the Eastern District of New York (Judge Gujarati) affirmed in all respects.
Special conditions:
- Mental-health assessment/treatment – challenge waived by defendant’s consent.
- Suspicion-based search of person, property, residence, and electronic devices – upheld; district court’s rationale was sufficiently articulated and supported.
- Sex-offender registration – upheld; condition mirrors independent state/federal obligations and is justified by defendant’s prior sex offenses.
Ineffective assistance: not considered on direct review; may be raised under 28 U.S.C. § 2255.
Plea voluntariness and other sentencing claims: barred by a valid appellate waiver; plea colloquy complied with Rule 11 and Rehaif.

3. Analysis

3.1 Precedents Cited and Their Influence

The panel relied heavily on its own recent supervised-release jurisprudence, weaving earlier decisions into an integrated framework:

United States v. Robinson, 134 F.4th 104 (2d Cir. 2025) – upheld an identical electronic-search condition; Thompson extends Robinson by approving such a condition after an individualized yet concise explanation.
United States v. Sims, 92 F.4th 115 (2d Cir. 2024) – emphasized the need for an individualized assessment; Thompson clarifies that this requirement can be satisfied succinctly when the record makes the rationale “self-evident.”
United States v. Lawrence, 139 F.4th 115 (2d Cir. 2025) and United States v. Kunz, 68 F.4th 748 (2d Cir. 2023) – establish that district courts need not deliver a point-by-point justification for every special condition. Thompson, viewed together with Lawrence and Kunz, now cements that principle.
United States v. Betts, 886 F.3d 198 (2d Cir. 2018) – set out the statutory factors for special conditions. Thompson applies Betts but demonstrates how a court may simply reference those factors on the record.
United States v. Bolin, 976 F.3d 202 (2d Cir. 2020) – delineated the heightened scrutiny required when a condition intrudes on a fundamental liberty interest. Thompson reaffirms that reasonable-suspicion-based searches do not implicate such a fundamental interest.
United States v. Spruill, 808 F.3d 585 (2d Cir. 2015) and United States v. Quinones, 511 F.3d 289 (2d Cir. 2007) – stand for the proposition that a defendant who “actively invites” or “agrees to” a condition waives any appellate challenge. Thompson applies these cases to mental-health treatment.
Rehaif v. United States, 588 U.S. 225 (2019) – informs the required plea colloquy for § 922(g) violations. The Thompson court found full compliance with Rehaif, defeating the defendant’s Rule 11 attack.

3.2 Legal Reasoning

Waiver of the mental-health condition. The court invoked the doctrine of “true waiver”: once Thompson expressly endorsed the modified condition during sentencing, any later challenge was extinguished. This approach treats contemporaneous consent as deliberative, eclipsing even plain-error review.
“Individualized assessment” satisfied by concise reference to § 3553(a) factors. The court held that a sentencing judge may fulfill Betts/Sims by a brief statement—here, noting “the nature and circumstances of the offense and [the defendant’s] history and characteristics”—provided the record renders those factors self-evident. Critical supporting facts (Thompson’s violent and sexual criminal history, recidivism, prior mental-health issues) were detailed in the PSR and explicitly acknowledged by the judge.
Reasonable-suspicion electronic-search condition does not unduly burden liberty interests. Building on Robinson, the panel characterized supervised release as a phase of “diminished expectation of privacy.” Because the condition required (i) reasonable suspicion of a violation and (ii) nexus between evidence and the area to be searched, it entailed no “greater deprivation of liberty than reasonably necessary” and therefore survived challenge without narrow-tailoring analysis under Bolin.
Sex-offender registration condition justified by past sexual offenses. The court applied Dupes to reaffirm that registration and treatment conditions tied to sexual conduct may be imposed even when the new offense is non-sexual, so long as the defendant’s history signals a continuing public-safety concern.
Plea-agreement waiver enforced. After confirming that the plea colloquy covered every element, including Rehaif’s knowledge-of-status requirement, the court enforced Thompson’s agreement not to appeal if the custodial sentence did not exceed 41 months. No recognized exception (e.g., breach, bias, miscarriage of justice) applied.

3.3 Likely Impact of the Decision

Simplified Sentencing Colloquies & Orders. District judges in the Second Circuit may feel more confident that a short, on-the-record reference to § 3553(a) factors is adequate for imposing multiple special conditions, so long as the PSR and allocution ground those factors.
Electronic-device searches mainstreamed. Thompson, in conjunction with Robinson, may prompt probation offices to seek electronic-search language as a matter of course, particularly for recidivists—even where no digital component exists in the offense of conviction.
True waiver doctrine strengthened. By labeling contemporaneous consent as “true waiver” immune from plain-error review, Thompson discourages defendants from strategically acceding to a condition below and challenging it later.
Second-Amendment challenges under § 922(g)(1) further limited. Though dicta, the panel’s citation to its own Zherka v. Bondi decision signals that Bruen-based facial attacks on § 922(g)(1) will not succeed in this Circuit.
Procedural economy on ineffective-assistance claims. By again remitting such claims to § 2255, the court reinforces the principle that fact-finding belongs in the district court, thereby streamlining direct appeals.

4. Complex Concepts Simplified

Supervised Release: A court-imposed period of monitoring after imprisonment, designed to aid reintegration while protecting the public. Violation may lead to re-incarceration.
Special Condition: An extra requirement (beyond the standard set) that the sentencing judge deems necessary under 18 U.S.C. § 3583(d) and Sentencing Guideline § 5D1.3.
Individualized Assessment: The obligation that a judge tailor each special condition to the specific defendant and explain why it is appropriate. Thompson clarifies that concise remarks referencing § 3553(a) factors suffice when the rationale is apparent from the record.
Reasonable Suspicion: A lower evidentiary threshold than probable cause; it exists when specific, articulable facts give rise to a belief that a supervisee is violating conditions.
True Waiver vs. Forfeiture:
- Waiver – the intentional relinquishment of a known right; appellate review is extinguished.
- Forfeiture – the mere failure to object; may still be reviewed for plain error.
Thompson shows that explicit courtroom consent is “true waiver.”
Appellate Waiver: A plea-agreement clause in which a defendant agrees not to challenge conviction/sentence if certain conditions (e.g., maximum term) are met. Generally enforceable unless the plea is involuntary or a miscarriage of justice occurs.

5. Conclusion

United States v. Thompson delivers a multi-faceted contribution to federal sentencing practice. It concretizes how little may be required—when the record is robust—for a court to satisfy the individualized-assessment mandate; it confirms that suspicion-based searches of digital media may be imposed without tying the condition to prior electronic misuse; and it reinforces the potency of explicit waivers, whether embedded in a plea agreement or voiced in open court. For practitioners, the message is two-fold: defendants must raise objections contemporaneously or risk losing them entirely, and judges retain broad—but not unbounded—discretion to craft conditions that further the rehabilitative and protective aims of supervised release. In the broader doctrinal landscape, Thompson tightens the Second Circuit’s alignment with a national trend favoring pragmatic, supervision-enhancing conditions while streamlining appellate scrutiny.