Mutual Exchange Requirement in U.S.S.G. §2G2.2(b)(3)(B) and Limits on Delegation of Supervised Release Conditions

Introduction

United States v. Darrah, 23-7001-cr (2d Cir. Mar. 28, 2025), presents two significant developments in federal sentencing law. First, it clarifies how courts must apply the five-level enhancement under U.S.S.G. §2G2.2(b)(3)(B) for distribution of child pornography “in exchange for any valuable consideration” after the 2016 amendment. Second, it reinforces the principle that a sentencing court may not delegate to probation officers the authority to impose or calibrate significant restrictions—here, on the number of internet-capable devices a supervisee may possess.

Kenneth Darrah pled guilty to one count of distributing child pornography in violation of 18 U.S.C. §2252A(a)(2)(A). At sentencing in the Northern District of New York, he received a 106-month prison term (below the 151–188-month Guidelines range) plus 20 years of supervised release. On appeal, he challenged three aspects of the sentence: the application of the five-level Guidelines enhancement; the substantive reasonableness of the 106-month term; and a special release condition limiting his internet devices. The Second Circuit’s decision affirms in part, vacates in part, and remands for resentencing on the supervised release condition.

Summary of the Judgment

The Court of Appeals reached three principal holdings:

Guidelines Enhancement (U.S.S.G. §2G2.2(b)(3)(B)). The district court erred procedurally by applying the five-level enhancement without finding a bilateral “exchange” agreement. Nonetheless, the error was harmless because the court plainly would have imposed the same below-Guidelines sentence even if the enhancement had not applied.
Substantive Reasonableness of the 106-Month Sentence. The below-Guidelines prison term was substantively reasonable. The sentencing court carefully balanced the §3553(a) factors—seriousness, deterrence, personal history, and the specific offense conduct—and imposed a sentence “sufficient but not greater than necessary.”
Delegation of Supervised Release Condition. The district court impermissibly delegated to probation the power to decide how many internet-capable devices Darrah could possess after completing the Internet and Computer Management Program. That portion of the judgment was vacated and remanded for the court to make its own on-the-record findings and impose (or decline) the limitation itself.

Analysis

1. Precedents Cited

Sentencing Guideline Amendment 801 (2016). Revised §2G2.2(b)(3)(B) to require distribution “in exchange for any valuable consideration,” removing the former “expectation of receipt” language.
Oliver (6th Cir., 2019). Held that the amended §2G2.2(b)(3)(B) demands proof of a bilateral agreement: the defendant must knowingly distribute child pornography pursuant to an explicit or implicit pact to receive something of value.
Morehouse (4th Cir., 2022) and Randall (9th Cir., 2022). Applied Oliver’s framework to interpret the “exchange” requirement.
Stinson v. United States (1993). Established that Guidelines commentary is binding unless it conflicts with statute or is plainly erroneous.
Feldman (2d Cir., 2011) and Jass (2d Cir., 2009). Explained when a procedural error in Guidelines calculation is harmless if the court would have imposed the same sentence anyway.
Dorvee (2d Cir., 2010). Warned against uncritical application of §2G2.2 enhancements that push sentences to or beyond statutory maxima.
Kunz (2d Cir., 2023). Held that imposing a one-device internet restriction—or delegating its scope to probation—requires particularized, on-the-record judicial findings.

2. Legal Reasoning

A. Interpreting “In Exchange For Any Valuable Consideration.”
The 2016 amendment substituted “in exchange for” for the prior “expectation of receipt” phrasing. Under the plain meaning, an “exchange” refers to a mutual understanding—an agreement—between two parties about each other’s rights and duties. Application Note 1 confirms: the defendant must have “agreed to an exchange” under which he distributed child pornography “for the specific purpose of obtaining something of valuable consideration.”

The district court applied the enhancement based solely on Darrah’s unilateral expectation to receive further material or contact with a minor. Under Oliver and the binding commentary, expectation alone is insufficient. The court must find evidence—direct or circumstantial—of an explicit or implicit agreement by both sides that the defendant’s act of distribution would be reciprocated. Here, the undercover agent never assented, even implicitly, to send videos of her fictitious child. The Fifth Circuit has reached the same conclusion.

B. Harmless-Error Analysis.
Although the district court procedurally erred, it made a clear, unambiguous statement that it would have imposed the same 106-month sentence even without the enhancement. Darrah’s effective Guidelines range absent the five-level bump (but with a two-level distribution increase) would have been 108–135 months—still above 106. Under Jass, Feldman, and Molina-Martinez, this declaration renders the procedural error harmless.

C. Substantive Reasonableness.
Sentencing courts enjoy wide discretion. The 106-month term is well below the 151–188-month range and stands far below the statutory maximum (240 months). The court considered (i) the gravamen of Darrah’s conduct—soliciting explicit imagery of a nine-year-old; (ii) his criminal history (Category I); (iii) lack of direct prior sexual contact with minors; (iv) mental health and treatment needs; and (v) Dr. Bashkoff’s low-risk assessment. Under Dorvee’s caution and “sufficient but not greater than necessary” parsimony mandate (§3553(a)), the below-Guidelines sentence is firmly within the broad range of reasonable outcomes.

D. Delegation of Supervised Release Conditions.
The district court imposed a special condition restricting Darrah to a single internet-capable device upon release and completion of the Bureau of Prisons’ Internet and Computer Management Program (ICMP). At sentencing, the judge explained the finding of poor impulse control and public-protection goals, then stated probation could “adjust” the limit later. This delegation conflicts with Kunz: a court may not grant probation open-ended discretion to impose or modify such a significant liberty restriction. The court must make its own particularized, on-the-record findings whenever it imposes a one-device internet restriction. Accordingly, that portion of the judgment is vacated and remanded for fresh findings and an express judicial determination.

3. Impact

Uniform Application of §2G2.2(b)(3)(B). Circuits must require proof of a bilateral agreement—explicit or implicit—before applying the five-level enhancement. Mere “hope” or unilateral expectation is insufficient.
Harmless-Error Doctrine in Sentencing. District courts should make explicit statements when a sentence would remain unchanged, ensuring harmless-error review on appeal.
Guardrails on Supervised Release Conditions. Judges retain full responsibility for imposing significant restrictions on liberty, including internet access limits. Delegation to probation officers without particularized findings will be reversed.
Sentencing Practice and Training. Judges and practitioners must be vigilant when applying amended Guidelines and crafting special conditions, ensuring all statutory and constitutional requirements are scrupulously met.

Complex Concepts Simplified

“Harmless Error.” An appellate court need not undo a sentence if the lower court clearly indicated it would have imposed the same sentence, even without the error.
“Exchange” vs. “Expectation.” Post-2016, to enhance a sentence under §2G2.2(b)(3)(B), there must be evidence that both parties agreed to swap something—child pornography for some other benefit—not merely that the defendant hoped for something in return.
“Particularized On-the-Record Findings.” When imposing a condition that significantly limits freedom (e.g., restricting all but one internet device), the sentencing judge must explain on the record why this precise restriction is needed to serve statutory goals.
“Delegation of Judicial Authority.” Judges cannot pass off core decisions—like how many devices a felon may own—to probation officers. Judicial sentencing authority is non-delegable.

Conclusion

United States v. Darrah establishes two enduring precedents. First, courts must require a genuine mutual agreement—beyond a defendant’s lone expectations—before applying the five-level child pornography distribution enhancement under amended U.S.S.G. §2G2.2(b)(3)(B). Second, sentencing courts may not delegate significant supervised-release restrictions, such as limiting internet-capable devices, to probation without making their own detailed, on-the-record findings. These rulings will shape the uniform and constitutionally sound application of child pornography sentencing standards and safeguard the separation of judicial and probationary functions.