Clarifying “Exchange” Under Amended U.S.S.G. §2G2.2(b)(3)(B) and Supervisory Device Restrictions

Introduction

The Second Circuit’s decision in United States v. Darrah, No. 23-7001-cr (2d Cir. Mar. 28, 2025), addresses two critical issues: how to interpret the Sentencing Guidelines enhancement for distribution of child pornography “in exchange for any valuable consideration” under the revised U.S.S.G. §2G2.2(b)(3)(B), and the proper allocation of judicial authority when imposing special conditions of supervised release restricting internet-capable devices. Defendant Kenneth Darrah, having pled guilty to distribution of child pornography, challenged (1) the five-level Guidelines increase for distribution in exchange for valuable consideration, (2) the substantive reasonableness of his 106-month sentence, and (3) a special release condition limiting his possession of internet-capable devices. The Court affirmed in part, vacated in part, and remanded for resentencing on the device-restriction issue.

Summary of the Judgment

The Second Circuit held that:

The district court erred in applying a five-level enhancement under U.S.S.G. §2G2.2(b)(3)(B) based solely on Darrah’s unilateral expectation of receiving child pornography. Post-2016 amendment, the enhancement requires evidence of a bilateral agreement to exchange the defendant’s distribution for valuable consideration, which was absent here. That error was deemed harmless because the below-Guidelines 106-month sentence would have remained unchanged under the correct two-level rather than five-level increase.
The 106-month term of imprisonment was substantively reasonable. It fell below the correctly calculated Guidelines range (151–188 months), reflected the §3553(a) factors, and balanced aggravating and mitigating circumstances.
The district court impermissibly delegated judicial authority to the Probation Office by allowing it to determine how many internet-capable devices Darrah could possess after completing a treatment program. The condition was vacated and remanded for resentencing with particularized, on-the-record findings if a single-device restriction is to be imposed.

Analysis

Precedents Cited

United States v. Cavera, 550 F.3d 180 (2d Cir. 2008) (en banc) – Articulates the deferential review standard for procedural and substantive reasonableness of sentences.
Gall v. United States, 552 U.S. 38 (2007) – Confirms that sentencing courts may vary from the Guidelines range based on §3553(a).
United States v. Jass, 569 F.3d 47 (2d Cir. 2009) – Explains harmless error analysis in sentencing.
United States v. Oliver, 919 F.3d 393 (6th Cir. 2019) – Provides the controlling four-part test for “exchange” under amended §2G2.2(b)(3)(B).
United States v. Dorvee, 616 F.3d 174 (2d Cir. 2010) – Warns against applying §2G2.2 enhancements mechanically, emphasizing careful consideration of §3553(a).
United States v. Matta, 777 F.3d 116 (2d Cir. 2015) – Requires particularized on-the-record findings for significant liberty-depriving supervised release conditions.
United States v. Kunz, 68 F.4th 748 (2d Cir. 2023) – Holds that delegating to Probation the authority to restrict a supervisee to a single internet device is an impermissible delegation of judicial power.

Legal Reasoning

1. Interpreting “Exchange for Valuable Consideration.” Amendment 801 (Nov. 2016) revised §2G2.2(b)(3)(B), replacing “expectation of receipt” with “in exchange for any valuable consideration.” The Court adopted the Sixth Circuit’s four-part Oliver test:

The defendant agreed—explicitly or implicitly—to an exchange;
He knowingly distributed child pornography to another person;
He did so for the specific purpose of obtaining something of value;
He understood the distribution to fulfill his obligation under that agreement.

In Darrah’s case, no evidence showed the undercover officer assenting to any exchange. Unilateral hope or expectation does not satisfy the “exchange” requirement. Therefore, the five-level enhancement was procedurally erroneous.

2. Harmless Error Analysis. Under Jass and Feldman, procedural errors in Guidelines calculations may be harmless if the district court clearly states it would impose the same sentence absent the error. Here, the court expressly affirmed that the 106-month sentence would have stood even with a reduced two-level enhancement (yielding a 108–135 month range). Because 106 months lies below both the correctly and incorrectly calculated ranges, the error was harmless.

3. Substantive Reasonableness. The 106-month below-Guidelines sentence was reviewed for abuse of discretion under Gall/Cavera. The Court found it well within the broad range of reasonable outcomes, given Darrah’s criminal history, offense conduct, lack of prior sexual offenses, and mitigation (risk assessment indicating low recidivism). Unlike in Dorvee, the Guidelines range here did not exceed statutory maxima, and the district court balanced §3553(a) factors correctly.

4. Delegation of Judicial Authority on Supervised Release Condition. The district court imposed a special condition limiting Darrah to one internet-capable device—initially—and then allowed Probation to expand that limit at its discretion. Under Matta and Kunz, significant restraints on liberty (like device restrictions) must be justified by particularized, on-the-record findings and cannot be delegated to Probation. The Second Circuit therefore vacated this condition and remanded for proper judicial findings if the restriction is to be reimposed.

Impact

This decision clarifies two important points for future sentencing:

Amended U.S.S.G. §2G2.2(b)(3)(B) enhancements require bilateral agreement evidence, not merely the defendant’s unilateral expectation. Sentencers must identify explicit or implicit assent by the recipient before applying the five-level increase.
District courts must themselves articulate particularized findings on the record before imposing or maintaining significant supervised release conditions—such as single-device internet restrictions—and may not delegate that decision to Probation.

Practitioners should scrutinize plea allocutions, discovery, and PSRs for proof of mutual assent when advocating against or for the §2G2.2(b)(3)(B) enhancement. Supervised-release conditions requiring technology restrictions will demand specific factual findings as to necessity and proportionality.

Complex Concepts Simplified

“In Exchange for Valuable Consideration”: The defendant and another person must both understand they are swapping something—the defendant sends child pornography and, in return, expects something of value (e.g., other pornographic material, access to a child). It is no longer enough that the defendant simply hopes to get something back.
Harmless Error: If a court makes a procedural mistake but clearly states it would have imposed the same sentence anyway, the error does not require a new sentencing.
Abuse of Discretion: Appellate courts will overturn a sentence only if it lies outside the broad range of reasonable outcomes or involves a clear legal mistake.
Delegation of Judicial Authority: A court cannot shift its responsibility to set significant conditions of supervision to Probation. Any major restriction must be imposed and justified by the judge.
Particularized On-the-Record Findings: When a supervised-release condition significantly limits liberty, the judge must explain on the record why it is necessary and no more restrictive than required.

Conclusion

United States v. Darrah establishes two new precedents in the Second Circuit’s sentencing jurisprudence. First, it enshrines the requirement that §2G2.2(b)(3)(B) enhancements depend on an actual agreement between parties, not mere expectation. Second, it reaffirms that district courts must personally impose and justify significant supervised-release conditions—especially those restricting technology—without delegating that power to Probation. Together, these holdings promote precision in Guidelines application and safeguard defendants’ liberty interests during supervised release. Future cases will look to Darrah for guidance on proving “exchange” and structuring enforceable, lawful release conditions.