Precedents Cited and Their Influence

• Appeal Waivers and Scope: United States v. Burden holds that an appeal waiver silent on supervised release conditions does not foreclose challenges to those conditions. The panel relied on Burden to find Schloss’s appeal permissible notwithstanding his plea agreement.
• Standards of Review for Conditions:
  • United States v. Oliveras: Generally, supervised release conditions are reviewed for abuse of discretion.
  • United States v. Boles: Pure issues of law in such challenges are reviewed de novo.
  • United States v. Matta: If the defendant had prior notice and an opportunity to object but did not, review is for plain error—critical here because the PSR advised of the conditions months before sentencing.
  • United States v. Moore: Articulates the four-part plain-error test, including whether the error seriously affects the fairness, integrity, or public reputation of judicial proceedings.
• Duty to Explain Special Conditions:
  • United States v. Betts: Sentencing courts must make individualized assessments and state reasons on the record for special conditions—failure to do so is error.
  • United States v. Sims and United States v. Kunz: Reinforce Betts’s requirement in recent terms and recognize that courts may sometimes affirm where the rationale is self-evident or by construing conditions to mitigate concerns.
  • United States v. Bleau: A failure to explain can be plain error where the necessity is not obvious from the record.
  • United States v. Young and Kunz: Appellate courts may construe ambiguous conditions in a manner that renders them reasonable when no contemporaneous objection was made.
• Constitutional Interests Implicated:
  • Fourth Amendment/Privacy: California v. Carney recognizes the fundamental nature of freedom from unreasonable searches and seizures—implicated by the search condition.
  • Medical Autonomy: Sell v. United States and Washington v. Glucksberg confirm the constitutionally protected interest in avoiding unwanted medical treatment—implicated by the medication-compliance requirement in the mental health condition.
  • Associational and Family Liberty: United States v. Myers and United States v. Reeves recognize fundamental associational rights and the right to maintain intimate personal relationships—implicated by the gang-association restriction; United States v. Jacques cautions that constitutional concerns arise if a condition interferes with family relations.
  • Vagueness/Knowledge Limits: United States v. Green “assumes” constitutionally required limitations to association bans (knowledge requirement; exclusion of incidental contacts)—used here to save the gang-related restrictions.
• Recent 2025 Decisions Applied:
  • United States v. Robinson: Upheld an electronics search condition on a record of recidivism and dishonesty; used here to support Condition 1 where the defendant used electronic communications in the trafficking conspiracy.
  • United States v. Arguedas: Approved a gang-association restriction, where the defendant admitted association and the record linked the association to the offense; applied to uphold Condition 4 due to Schloss’s Blixky involvement.
  • United States v. Roberson (summary order): Notes post-release rights to seek modification of conditions—a safety valve referenced to mitigate due process concerns regarding medication compliance.

The Court’s Legal Reasoning

The Second Circuit proceeded in three steps. First, it confirmed that the appeal waiver did not bar a challenge to special conditions because the waiver did not address them (Burden). Second, it determined that plain-error review governed because Schloss received the PSR and sentencing recommendation—each flagging the conditions—months before sentencing and lodged no objection (Matta). Third, it applied the plain-error standard, acknowledging error (failure to state reasons as Betts requires) but concluding that the error did not warrant reversal given the record and permissible limiting constructions.

Under Betts, Sims, and Kunz, the district court’s failure to make an individualized assessment and to state reasons was error. Nevertheless, the Court could affirm if:

• the rationale is self-evident on the record and the condition is reasonably related to the § 3553(a) objectives and § 3583(d) criteria; or
• the condition can be construed in a reasonable, constitutionally sound manner that neutralizes vagueness or overbreadth concerns (Young; Kunz).

The panel then addressed each condition:

1. Condition 1 (Searches of property/electronics without a warrant):

   The Court analogized to Robinson and found that Schloss’s use of electronic communications to further the firearms conspiracy, coupled with his criminal history and dishonesty, made the need for monitoring and search of electronic media self-evident. While acknowledging the serious Fourth Amendment interests, the Court concluded that, on this record, any explanatory omission did not “seriously affect the fairness, integrity or public reputation of judicial proceedings.” It therefore affirmed.

2. Condition 3 (Mental health treatment, including compliance with prescribed medications):

   The panel recognized due process and bodily integrity interests. It noted record evidence of significant mental-health history (residential treatment for depression and anxiety; ongoing psychiatric visits) but no express history of medication noncompliance or evidence of incapacity to make treatment decisions. As written, the condition was “arguably overbroad.” To avoid constitutional difficulties, the Court reasonably construed the clause to require compliance only with medications prescribed by the providers within the ordered outpatient mental health program. The Court also highlighted the defendant’s ability to seek modification if a future prescription is objectionable (Roberson). Under this limiting construction, the condition was adequately supported and could be affirmed under plain-error review.

3. Condition 4 (No association with gang members/associates; no frequenting gang “turf”):

   The record supported a gang-association restriction: Schloss’s active involvement with the Blixky gang, prison disciplinary history tied to gang activity, and conduct involving firearms with Blixky members. However, the Court flagged overbreadth and vagueness problems in the text: no definition of “associate,” “gang,” or “turf,” and no safe harbors for incidental contacts or necessary family/obligatory presence.

   Drawing on Green and Jacques, the Court read into the condition the constitutionally required limits: it only prohibits knowing association with persons the probationer knows to be gang members or associates; incidental contacts are excluded; and “frequenting turf” is limited to knowingly and repeatedly entering areas that the defendant knows are actively controlled by the gang, leaving room for incidental or necessary presence (including familial or legal obligations). With these limits and the strong record nexus, the Court affirmed under plain-error review.

Finally, the panel included an important practice admonition: government counsel repeatedly described the conditions as “standard” at oral argument. The Court corrected that characterization. Special conditions demand individualized assessment and reasons; routine, across-the-board imposition contravenes Second Circuit law (Oliveras; Betts; Sims).

Impact and Practical Consequences

Even as a summary order, Schloss offers concrete guidance:

• For district courts: You must articulate on the record individualized reasons for each special condition and tie them to the § 3553(a) factors and § 3583(d) criteria (reasonable relation, no greater deprivation than necessary, consistency with policy statements). The panel explicitly noted that giving this explanation “would take no more than a few minutes in most cases.”
• For prosecutors and probation: Avoid labeling non‑USSG “standard” conditions as “standard.” Craft proposed special conditions with built-in knowledge requirements, incidental‑contact exclusions, and clear tailoring to the defendant’s conduct and risk factors. Provide definitional clarity (e.g., “associate,” “turf”) and tie proposals to the record.
• For defense counsel: Object to questionable conditions at sentencing and request on‑the‑record justifications; propose narrower language. Silence will trigger plain‑error review, under which appellate courts may salvage conditions via narrowing constructions. If a condition is imposed, consider later modification under 18 U.S.C. § 3583(e)(2) if factual developments warrant.
• For future litigation: The Court’s readiness to read in “constitutionally required limitations” will likely continue, especially where counsel failed to object. But where the record does not make the need self‑evident (Bleau), unexplained conditions remain vulnerable. Parties should expect closer scrutiny of electronics searches, medication compliance, and gang‑association limits, particularly their tailoring and knowledge elements.
• Substantive direction in key domains:
  • Electronics/Cloud Search Conditions: Strong evidentiary linkage to offense conduct (use of electronic communications) and recidivism/dishonesty will support such conditions even absent an on‑the‑record explanation, particularly on plain‑error review.
  • Mental‑Health Medication Compliance: Courts will limit compliance mandates to medications prescribed within the ordered program, with modification rights preserved, to avoid forced-medication concerns.
  • Gang‑Association Restrictions: Knowledge elements and incidental‑contact carve‑outs are not mere niceties; they are constitutionally grounded limitations that courts will read in to save otherwise broad text. Drafters should include them expressly.