Clarifying Probation’s Authority Over Internet Restrictions in Supervised Release:
A Comprehensive Commentary on United States v. Keleher (2d Cir. 2025)

1. Introduction

On 16 June 2025 the United States Court of Appeals for the Second Circuit issued a summary order in United States v. Keleher, No. 24-2193-cr, affirming the District Court’s judgment that imposed a 30-year prison term and a lifetime of supervised release on Skyler Keleher following his guilty plea to two counts of sexually exploiting a child (18 U.S.C. § 2251(a)). The appeal focused narrowly on special conditions of supervised release governing Keleher’s future use of the internet.

The decision provides fresh guidance—albeit in a non-precedential form—on a recurring problem in federal sentencing: how far a district court may delegate to the Probation Office the day-to-day regulation of a defendant’s online activity without running afoul of the constitutional and statutory limits on delegating judicial authority.

Although issued as a “Summary Order,” the ruling helps crystallize principles scattered among earlier Second Circuit precedents and is likely to influence both counsel and courts crafting or challenging internet-related conditions of supervised release.

2. Summary of the Judgment

• Holding: The Second Circuit affirmed the lifetime term of supervised release and the two challenged special conditions, finding no abuse of discretion by the District Court.
• Key Findings:
  • The District Court made an individualized assessment tied to Keleher’s offense conduct, which involved real-time live-streaming of abuse via Facebook Live.
  • The conditions—requiring enrollment in the Internet and Computer Management Program (ICMP) and allowing Probation to tailor internet access—were “reasonably related” to § 3553(a) factors and proportional to the risk.
  • The delegation to Probation was permissible because the ICMP provides an objective framework that constrains Probation’s discretion and avoids arbitrary use of delegated authority.
  • Apparent inconsistencies between permissive “may” and mandatory “must” language in the two conditions were harmonized; read together, the court unequivocally mandated internet restrictions, leaving only details to Probation.
  • The conditions were not unconstitutionally vague, and Keleher retains the ability to seek court review should Probation overstep its authority in the future (18 U.S.C. § 3583(e)(2)).

3. Analysis

3.1 Precedents Cited and Their Influence

The panel wove together a line of Second Circuit cases that collectively define the outer limits of probationary delegation and the permissible scope of internet restrictions:

• United States v. Birkedahl, 973 F.3d 49 (2d Cir. 2020) – Restated the abuse-of-discretion standard and clarified that any error of law is per se abuse. Provided the lens through which the appellate court evaluated the District Court’s decision.
• United States v. Betts, 886 F.3d 198 (2d Cir. 2018) – Requires an individualized assessment and record-based explanation when imposing restrictive conditions. Keleher’s sentencing judge expressly cited and complied with this requirement.
• United States v. Matta, 777 F.3d 116 (2d Cir. 2015) – Distinguished permissible delegation of “minor details” from impermissible delegation of decisions affecting the “nature or extent of the liberty interest itself.” Matta framed Keleher’s delegation argument.
• United States v. Eaglin, 913 F.3d 88 (2d Cir. 2019) – Warned against “untailored internet bans.” By tethering Keleher’s restrictions to the ICMP and to a risk-needs assessment, the District Court avoided the Eaglin pitfall.
• United States v. Kunz, 68 F.4th 748 (2d Cir. 2023) – Approved probation-controlled restrictions where an objective program guided discretion. Kunz supplied the template the panel used to uphold the ICMP delegation.
• United States v. Degroate, 940 F.3d 167 (2d Cir. 2019) – Held that a court must “unambiguously authorize” restrictions; details can be delegated. Used to rebut Keleher’s “may vs. must” critique.
• United States v. Villafane-Lozada, 973 F.3d 147 (2d Cir. 2020) – Emphasized the defendant’s recourse to the sentencing court if Probation oversteps. The panel cited it to dismiss Keleher’s due-process concerns.
• United States v. Lewis, 125 F.4th 69 (2d Cir. 2025) – (A brand-new decision) Reaffirmed the District Court’s “wide latitude” in fashioning conditions related to § 3553(a) factors, lending immediate precedential heft to Keleher.

3.2 The Court’s Legal Reasoning

1. Standard of Review: Abuse of discretion, with de novo review for legal questions.
2. Individualized Nexus: The panel agreed the District Court established a concrete connection between the offense (live-streaming molestation) and the need to monitor future internet activity.
3. Delegation Analysis: Applying Matta and Kunz, the court held that:
   • The ICMP constitutes a rule-based framework, limiting Probation’s discretion.
   • The District Court itself imposed the fundamental restriction: Keleher must enroll in the ICMP to obtain any internet-capable device.
   • Probation’s subsequent decisions about time limits, specific websites, or apps are “minor details” akin to the location of a halfway house or drug-testing schedule.
4. Linguistic Harmonization: The ostensibly permissive “may” in Special Condition 6 was read in tandem with the mandatory “must” in Condition 7, yielding a single, unequivocal mandate.
5. Due Process & Vagueness: Because the ICMP supplies ascertainable standards and the defendant can seek modification under § 3583(e)(2), the conditions are neither vague nor procedurally defective.

3.3 Potential Impact on Future Cases

Although summary orders are formally non-precedential, district courts and practitioners routinely consult them for guidance, especially where the Second Circuit harmonizes several precedents. Keleher contributes three practical lessons:

1. Delegation will survive if the district judge (a) explicitly mandates program participation and (b) confines Probation’s discretion within an existing, published supervision program such as the ICMP.
2. Defense counsel challenging internet-related conditions must show either the absence of an individualized nexus or that the program grants unbounded discretion—in practice a difficult burden.
3. Judges must be meticulous in the record: briefly identifying the defendant’s internet-based misconduct and explicitly referencing § 3553(a) factors will generally suffice.

4. Complex Concepts Simplified

• Supervised Release: A period of court-ordered monitoring that follows imprisonment. Violation of its conditions can lead to additional prison time.
• Special Condition: A tailored rule—beyond the generic “standard conditions”—imposed to address a specific risk posed by the defendant.
• Delegation Doctrine (in Sentencing): While a judge may outsource administrative details (e.g., scheduling), she cannot outsource decisions that fundamentally alter the amount or nature of the defendant’s liberty.
• Abuse of Discretion: A deferential appellate standard. The District Court’s decision will be reversed only if it was arbitrary, irrational, or based on an incorrect legal premise.
• ICMP (Internet and Computer Management Program): A structured set of rules used by U.S. Probation to monitor and limit offenders’ electronic activity. Typically includes device inspections, monitoring software, and time/ content restrictions.

5. Conclusion

United States v. Keleher fortifies the Second Circuit’s emerging framework for internet-related supervised release conditions. By synthesizing earlier rulings, the panel clarified that:

Practitioners should heed the decision’s twin messages: courts must articulate individualized reasons, and defendants must prepare to meet a high bar when challenging technologically focused special conditions. Even as a non-precedential order, Keleher is poised to serve as a persuasive authority in the continuing evolution of digital-age sentencing.