PSR Notice and “Self‑Evident” Rationales Sustain Discretionary Supervised‑Release Conditions on Plain‑Error Review: Commentary on United States v. Oliva (2d Cir. 2025)

Introduction

In United States v. Oliva, the Second Circuit affirmed a judgment of conviction and a suite of supervised-release conditions imposed following a guilty plea to a conspiracy charge under 18 U.S.C. § 371 involving heroin, fentanyl, and cocaine base. The panel—Judges Kearse, Raggi, and Maria Araújo Kahn—considered whether the district court erred in imposing two “standard” conditions and three “special” conditions of supervised release without individualized on-the-record explanations. Because the defendant did not object below, the court reviewed for plain error and found none, concluding that the justifications for each challenged condition were either adequately noticed through the Presentence Report (PSR) and/or self-evident from the record.

Although issued as a summary order without precedential effect, the decision is instructive in several respects: it underscores the strength of a PSR as notice of proposed discretionary conditions; it reiterates that “self‑evident” record-based rationales can cure the absence of a tailored oral explanation for both standard and special conditions; it reaffirms the permissibility of a reasonable-suspicion search condition—explicitly reaching digital devices and cloud storage—when the offense conduct relied on phones and social media; it recognizes that a sustained marijuana-use history can support a drug-treatment condition; and it treats a GED requirement as reasonable and, in any event, modifiable if later shown to be unattainable.

The parties: Defendant-Appellant Adelmir Oliva was represented by Donna R. Newman; the government by AUSA Adam S. Hobson, for the U.S. Attorney for the Southern District of New York. The district judge was Sidney H. Stein. The Second Circuit affirmed in full.

Summary of the Opinion

The court held that:

Standard Conditions 5 (residence approval and advance notice of changes) and 6 (probation visits and seizure of items in plain view) were properly imposed. The PSR listed them; the district court confirmed counsel and the defendant reviewed the PSR; and the rationales—housing instability, firearms possession, and ongoing drug-trafficking history—were self-evident from the record.
The special outpatient drug-treatment condition was supported by the defendant’s own admission of daily marijuana use until arrest, which is sufficient under U.S.S.G. § 5D1.3(d)(4) to justify treatment. His apparent abstinence while incarcerated did not make the condition improper because risk increases upon reentry.
The reasonable-suspicion search condition authorizing searches of person, residence, vehicles, papers, electronic devices, and cloud storage was justified by the offense context—multi-year drug distribution using phones, social-media boasting about dealing and cash, and multiple firearm possessions—and thus reasonably related to deterrence, public protection, and the nature of the offense.
The GED condition was upheld. The challenge was speculative and unripe; the record suggested capability and motivation; and § 3583(e) allows modification if compliance later proves impossible.

Because the defendant did not object at sentencing, the court applied plain-error review (not the “relaxed” variant), given that the PSR gave adequate notice. It affirmed across the board.

Analysis

Precedents Cited and Their Roles

United States v. Kunz, 68 F.4th 748 (2d Cir. 2023): Reiterates the district court’s wide latitude in imposing supervised-release conditions and the usual abuse-of-discretion review.
United States v. Dupes, 513 F.3d 338 (2d Cir. 2008): Establishes that unpreserved challenges to conditions are reviewed for plain error.
United States v. Matta, 777 F.3d 116 (2d Cir. 2015): Discusses a “less stringent” plain-error approach in the absence of notice; the panel explains it does not apply here because the PSR provided adequate notice of the challenged conditions.
U.S.S.G. § 5D1.3(b) and 18 U.S.C. §§ 3553(a), 3583(d): Provide the statutory and Guidelines framework for imposing conditions—requiring reasonable relation to specified sentencing factors, no greater deprivation than necessary, and consistency with policy statements.
United States v. Bolin, 976 F.3d 202 (2d Cir. 2020), and United States v. Brown, 402 F.3d 133 (2d Cir. 2005): Clarify that a discretionary condition need only be reasonably related to one (or more) of the four § 5D1.3(b)(1) factors, despite the Guidelines’ conjunctive phrasing.
United States v. Sims, 92 F.4th 115 (2d Cir. 2024), and United States v. Thomas, 299 F.3d 150 (2d Cir. 2002): Recognize that standard conditions are “presumed suitable” but still discretionary and subject to the “no greater deprivation” constraint.
United States v. Thompson, 143 F.4th 169 (2d Cir. 2025), United States v. Betts, 886 F.3d 198 (2d Cir. 2018), and United States v. Balon, 384 F.3d 38 (2d Cir. 2004): Require an individualized assessment and on-the-record explanation for special conditions, but permit affirmance when the rationale is “self-evident in the record,” rendering any omission harmless.
United States v. Maiorana, 2025 WL 2471027 (2d Cir. Aug. 28, 2025) (en banc): Encourages listing all proposed discretionary conditions in the PSR to ensure notice and meaningful opportunity to object, minimizing appeals like this one.
United States v. Akinrosotu, 637 F.3d 165 (2d Cir. 2011): Finds challenges unripe where the asserted harms are hypothetical; supports rejecting speculative attacks on the GED condition.

Legal Reasoning

The court’s analysis turns on three interlocking principles: (1) preserved vs. unpreserved error; (2) the sufficiency of PSR-based notice and “self-evident” rationales; and (3) the substantive limits on supervised-release conditions.

1) Standard of review: plain error, not “relaxed” plain error

Because Oliva never objected to these conditions in the district court, the Second Circuit applied plain-error review. It rejected his request for the “less stringent” form of plain-error review recognized in Matta, reasoning that the PSR here provided ample notice of the standard conditions and the first two special conditions. In short, where the PSR specifically lists a proposed discretionary condition and the district court verifies that the defendant and counsel reviewed it and had the opportunity to object, ordinary plain-error review applies.

2) PSR as notice and “self-evident” rationales

The panel repeatedly invoked two related doctrines that lower the risk of remand despite sparse oral explanation.

PSR notice: Echoing the en banc guidance in Maiorana, the court emphasized that including discretionary conditions in the PSR provides effective notice and an opportunity to object, a practice that “efficiently” avoids most appellate challenges for lack of individualized explanation at sentencing.
Self‑evident record support: Under Thompson, Betts, and Balon, failure to recite an individualized rationale for a special condition is error, but harmless where the justification is obvious from the record. Oliva’s case offered abundant, offense-specific facts—drug trafficking by phone, social-media posts about dealing and cash, multiple firearm possessions, and housing instability—that made the rationales for the conditions “self-evident.”

3) Substantive constraints: relation to sentencing purposes and no greater deprivation

The court re-stated the governing constraints from § 5D1.3(b) and § 3583(d): discretionary conditions must be reasonably related to one or more of four sentencing factors (nature of offense and defendant’s characteristics; deterrence; public protection; and provision of training, medical care, or correctional treatment) and must not involve a greater deprivation of liberty than reasonably necessary.

Applying these standards:

Standard Conditions 5 and 6: Residence approval and unannounced probation visits with seizure of items in plain view are “presumed suitable” standard conditions. Given Oliva’s housing instability, firearms history, and gang-based trafficking activity tied to a particular neighborhood, the monitoring function of these conditions reasonably serves deterrence, public protection, and reentry support, without exceeding what is necessary.
Drug-treatment condition: U.S.S.G. § 5D1.3(d)(4) specifically endorses treatment where the court “has reason to believe that the defendant is an abuser” of controlled substances. Oliva’s admission of daily marijuana use until arrest supplied that reason. The court reasonably rejected the suggestion that incarceration-based sobriety eliminates the need for treatment upon reentry.
Reasonable-suspicion search condition (including devices and cloud storage): The offense conduct—multi-year drug trafficking coordinated by phone, social-media posts advertising contraband and cash, and repeated firearm possession—creates a strong nexus between supervision searches and the aims of deterrence and public protection. The reasonable-suspicion limitation cabined the intrusion to instances where there is articulable indication of a violation, satisfying the “no greater deprivation” requirement.
GED condition: The court found the challenge speculative. The record supported capability and motivation (statements of educational goals, completion of several prison courses, prior school performance). Even if compliance later proves unfeasible, § 3583(e) permits modification. That availability, coupled with current evidence of feasibility, defeats any present claim that the condition is overbroad or unattainable.

Impact

While nonprecedential, Oliva consolidates several practical lessons that will shape supervised-release litigation in the Second Circuit:

PSR as the central notice vehicle: Expect district courts and probation to continue listing all discretionary conditions in the PSR. Defense counsel must vigilantly review and object in writing and at sentencing to preserve claims and to trigger a more searching review than plain error.
“Self‑evident” rationales will rescue sparse records: Where the offense facts unmistakably justify a condition (e.g., drug trafficking via phones supports device/cloud searches; a sustained marijuana-use history supports treatment), the Second Circuit is inclined to affirm despite brief oral findings.
Digital search conditions remain viable with reasonable suspicion: For technology-enabled offenses, conditions authorizing RS-based searches of devices and cloud storage will likely be sustained when appropriately tethered to the offense conduct and coupled with a reasonable-suspicion threshold.
Treatment conditions for cannabis use: Admissions of regular marijuana use can suffice to justify treatment requirements, even if the defendant abstained during incarceration. Reentry risk matters.
Educational conditions and ripeness: Challenges premised on speculative noncompliance (e.g., “I might not be able to obtain a GED”) are unlikely to succeed. The modification mechanism under § 3583(e) is an important safety valve.
Preservation strategy for defense: If the court does not articulate individualized reasons, request them; if the PSR lists a condition, object specifically and explain why the record does not justify it or why it imposes a greater-than-necessary deprivation. Absent that, plain-error review and “self-evident” rationales will often be outcome-determinative.

Complex Concepts Simplified

Supervised release vs. probation: Supervised release follows imprisonment; probation is an alternative to it. Both can include “standard” (commonly recommended) and “special” (case-specific) conditions.
Standard vs. special conditions: Standard conditions are recommended by the Guidelines and often apply generically (e.g., reporting to probation, residence approval). Special conditions are tailored to the individual case (e.g., drug treatment, device searches, education requirements).
Plain-error review: On appeal, if no objection was made below, the appellant must show an error that is clear, affects substantial rights, and seriously affects the fairness, integrity, or public reputation of judicial proceedings. This is a demanding standard.
“Relaxed” plain error (Matta): A more forgiving variant that sometimes applies when the defendant lacked notice and opportunity to object. It does not apply when the PSR provided notice of the proposed conditions.
“Self‑evident” rationale: Even though courts should explain special conditions on the record, an appellate court may affirm when the justification is obvious from the established facts—making any omission harmless.
Reasonable suspicion: A lower threshold than probable cause; requires specific, articulable facts suggesting a violation. Search conditions limited by reasonable suspicion are significantly less intrusive than suspicionless searches.
“No greater deprivation than necessary”: A mandatory limiting principle. Conditions must be calibrated to the goals of sentencing and not sweep more broadly than needed.
Modification under § 3583(e): If circumstances change or a condition proves unworkable, the district court can modify, reduce, or enlarge conditions during supervision. This mechanism mitigates concerns about speculative or future impossibility.

Conclusion

United States v. Oliva reinforces a pragmatic appellate approach to supervised-release conditions in the Second Circuit. When the PSR lists discretionary conditions and the district judge verifies that the defendant reviewed it, ordinary plain-error review applies to unpreserved challenges. Under that lens, conditions will be affirmed where their rationales are “self‑evident” from the record and where they are reasonably related to the offense, deterrence, public protection, or the defendant’s rehabilitative needs, without imposing a greater deprivation than necessary.

The order underscores four durable takeaways: phone- and social-media-based trafficking supports reasonable-suspicion search conditions that extend to devices and cloud accounts; a sustained marijuana-use history can justify an outpatient drug-treatment condition; “standard” residence and visit conditions remain robust tools of supervision, particularly amid housing instability and firearm involvement; and educational conditions like a GED requirement will be upheld when feasible and in light of the ready availability of later modification.

While nonprecedential, Oliva harmonizes with recent published Second Circuit guidance and provides a clear operational message: comprehensive PSR notice, coupled with a record that ties conditions to concrete offense and personal-history facts, will typically sustain supervised-release conditions on appeal—even where sentencing courts provide minimal oral explanations.