Mutual-Exchange Required for §2G2.2(b)(3)(B) Enhancement; Courts, Not Probation, Must Decide Single-Device Limits on Supervised Release

Introduction

In United States v. Darrah, No. 23-7001-cr (2d Cir. Mar. 28, 2025), the Second Circuit addressed two recurrent issues in federal child-exploitation prosecutions: (1) what proof is necessary to trigger the five-level enhancement for distributing child pornography “in exchange for” valuable consideration under U.S.S.G. §2G2.2(b)(3)(B) as amended in 2016, and (2) who decides, and on what record, whether a supervisee may be limited to a single internet-capable device as a condition of supervised release.

The panel (Walker, Jacobs, Merriam, JJ.; opinion by Judge Jacobs) held that §2G2.2(b)(3)(B) now requires proof of an actual agreement—explicit or implicit—between the defendant and the recipient of the material, and that a defendant’s unilateral hope or expectation of receiving images does not suffice. While the district court erred in applying the five-level enhancement to Kenneth Darrah absent evidence of mutual assent, that error was harmless because the court unequivocally stated it would impose the same sentence and did so below even the corrected Guidelines range. The court also vacated a special supervised-release condition that effectively delegated to Probation the decision how many internet-capable devices Darrah could possess, reaffirming that such a significant liberty restriction must be imposed by the court, supported by particularized findings, and cannot be left to Probation’s discretion.

Case Background

Kenneth Darrah pleaded guilty to one count of distributing child pornography, 18 U.S.C. §2252A(a)(2)(A), after sending an undercover law enforcement officer (an Online Covert Employee, or “OCE”) an audiovisual file via Kik Messenger. The OCE posed as the mother of a nine-year-old child. The Presentence Report (PSR) set a base offense level of 22 and recommended multiple enhancements, including the five-level increase for distribution “in exchange for” valuable consideration under §2G2.2(b)(3)(B). With adjustments, the district court calculated a total offense level of 34 and a criminal history category I, yielding a Guidelines range of 151–188 months. The court imposed a below-Guidelines sentence of 106 months’ imprisonment and 20 years’ supervised release. At sentencing, the court also added an internet restriction that, after completion of the Internet and Computer Management Program (ICMP), initially limited Darrah to use of a single internet-capable device, with the understanding that Probation could adjust that number if monitoring proved feasible.

On appeal, Darrah challenged: (i) the procedural reasonableness of applying the five-level enhancement under §2G2.2(b)(3)(B); (ii) the substantive reasonableness of the 106-month prison term; and (iii) the validity of the special supervised-release condition limiting him to one internet-capable device.

Summary of the Opinion

Guidelines enhancement (§2G2.2(b)(3)(B)): The Second Circuit adopted the Sixth Circuit’s framework in United States v. Oliver, requiring proof that the defendant agreed—explicitly or implicitly—to exchange child pornography for valuable consideration with the same recipient. Because the record showed only Darrah’s unilateral expectation and no assent (even implicit) by the OCE, applying the five-level enhancement was error. The error was harmless, however, because the district court explicitly stated it would impose the same sentence regardless, and the 106-month term was below the range that would have applied with only the two-level distribution enhancement.
Substantive reasonableness: The 106-month sentence—below the applicable Guidelines range and supported by a balanced consideration of 18 U.S.C. §3553(a) factors—was substantively reasonable.
Supervised-release condition: The district court impermissibly delegated judicial authority to Probation by allowing it to decide whether Darrah could possess more than one internet-capable device. The Second Circuit vacated the condition and remanded for resentencing consistent with United States v. Kunz, directing the court to make its own particularized findings if it chooses to impose such a restriction.

Disposition: Affirmed in part (sentence length), vacated and remanded in part (special condition concerning device limits).

Detailed Analysis

I. The §2G2.2(b)(3)(B) “exchange for valuable consideration” enhancement

A. The Amendment 801 pivot: From unilateral “expectation” to bilateral “exchange”

Before November 2016, §2G2.2(b)(3)(B) authorized a five-level enhancement for “[d]istribution for the receipt, or expectation of receipt, of a thing of value, but not for pecuniary gain.” Amendment 801 (effective Nov. 2016) removed the “expectation of receipt” language and replaced it with the current standard: “If the defendant distributed in exchange for any valuable consideration, but not for pecuniary gain, increase by 5 levels.” Application Note 1 clarifies that this means the defendant “agreed to an exchange with another person” and distributed for the specific purpose of obtaining valuable consideration from that same person (e.g., other child pornography, preferential access, or access to a child).

The Second Circuit had not previously interpreted the amended provision. In Darrah, it expressly “agree[d] with and adopt[ed]” the Sixth Circuit’s test in United States v. Oliver, 919 F.3d 393 (6th Cir. 2019), which requires the government to prove:

(1) an explicit or implicit agreement to an exchange with another person;
(2) the defendant knowingly distributed child pornography to that person;
(3) for the specific purpose of obtaining valuable consideration;
(4) from that same person.

Critically, “the distribution must be part of that explicit or implicit agreement,” meaning the defendant understands or believes that his distribution fulfills his obligation under the exchange. The Second Circuit emphasized that, unlike the pre-2016 guideline’s “expectation of receipt,” the amended text requires a bilateral exchange; a defendant’s unilateral “personal belief or expectation” is not enough.

The court grounded this interpretation in the guideline’s plain language and its commentary (which is authoritative under Stinson v. United States), and in the ordinary meaning of “agreement” as a manifestation of mutual assent. It also endorsed the consensus that the government need not prove actual receipt of consideration; proof of an agreement to exchange suffices. See fn. 1 (aligning with Oliver and decisions from the Ninth and Fifth Circuits).

B. Application to Darrah: No assent, no exchange

The record showed that Darrah sent the OCE an unsolicited child pornography video and, in return, sought images of the purported child. But the OCE’s responses were noncommittal: she “mighttt” have pictures, was “nervous with new ppl,” and she “can try and take a pic for u later tho if you tell me what u want in it.” The panel concluded that such tentative language did not amount to assent—explicit or implicit—to furnish child pornography in exchange for Darrah’s distribution. The PSR itself framed the basis for the enhancement in terms of Darrah’s “expectation” of receiving material or access, which is no longer sufficient under the amended guideline.

The government’s alternative theory—that Darrah furnished his video as “proof of trustworthiness” as part of an implicit exchange—failed for the same reason: the OCE never expressed assent to exchange contraband upon proof of trustworthiness. Evidence of Darrah’s “specific purpose” to obtain valuable consideration is relevant but cannot substitute for proof of mutual assent; reading the guideline otherwise would render the exchange requirement superfluous.

Result: The district court committed procedural error by applying the five-level enhancement based solely on Darrah’s unilateral expectation rather than an actual exchange agreement.

C. Harmless error: Why the misapplication did not require resentencing

A procedural error in calculating the Guidelines does not mandate remand if the record makes clear the district court would have imposed the same sentence regardless. See United States v. Jass; United States v. Mandell. While appellate courts are wary of “simple incantations,” the Second Circuit found the harmlessness showing here robust:

The district court explicitly and unambiguously stated it would impose the same 106-month sentence even if the five-level enhancement did not apply.
The court dealt with a single enhancement, identified it specifically, and explained that the sentence remained “sufficient but not greater than necessary” under §3553(a).
With the two-level distribution enhancement (§2G2.2(b)(3)(F)) instead of the five-level increase, Darrah’s range would have been 108–135 months. The imposed 106-month sentence would still be below that corrected range.
Consistent with Molina-Martinez v. United States, the record affirmatively shows the court deemed the sentence appropriate independent of the Guidelines range.

Accordingly, the error was harmless and the prison term was affirmed.

II. Substantive reasonableness of the 106-month sentence

Reviewing for abuse of discretion, the court rejected Darrah’s challenge to the length of his sentence. Although United States v. Dorvee cautions that §2G2.2 “must be applied with great care,” the circumstances here differed from Dorvee:

Darrah’s Guidelines range (151–188 months) did not exceed the 240-month statutory maximum; Dorvee’s range did, “a signal that something misfired.”
The district court reviewed the PSR, considered both aggravating and mitigating factors (including a risk assessment indicating low risk to reoffend), and explained the §3553(a) rationale—seriousness, deterrence, protection of the public, and just punishment—for a below-Guidelines sentence.

Given the “particularly deferential” standard and the general principle that below-Guidelines sentences are “difficult to find unreasonable,” the 106-month sentence fell well within the permissible range.

III. Supervised release: Single-device limit and impermissible delegation

A. The rule: Courts must impose, justify, and retain control over significant liberty restrictions

Special conditions of supervised release must be:

Reasonably related to the relevant §3553(a) factors;
No greater deprivation of liberty than reasonably necessary; and
Consistent with Sentencing Commission policy statements. 18 U.S.C. §3583(d).

They require an individualized assessment and on-the-record justification. Building on United States v. Kunz, the panel reiterated that limiting a supervisee to “just one internet-connected device” is a significant liberty restriction that must be imposed by the court and supported by particularized findings. It also reiterated Kunz’s companion rule: any special condition that grants Probation discretion to decide whether to impose such a single-device restriction is an impermissible delegation of judicial authority.

B. Application to Darrah and the remedy

At sentencing, the court announced an initial one-device limit, predicated largely on Darrah’s “poor impulse control,” the role of internet devices in his offense, and his possession of multiple phones at arrest; it simultaneously stated that Probation could adjust the restriction “unless and until probation feels like they can monitor his use beyond that and there aren’t any problems.” That formulation vested Probation with discretion to decide whether Darrah should remain limited to a single device.

Even though Darrah did not raise impermissible delegation, the Second Circuit exercised its authority to notice obvious errors in criminal cases in the public interest, vacating the condition under Silber. The court remanded with instructions: the district court must itself decide, based on particularized findings, whether to impose a single-device restriction and, if so, must not delegate to Probation the authority to decide whether or when such a restriction applies. The court explicitly left open what findings might justify a single-device limit in an appropriate case.

Precedents and Authorities Cited and Their Influence

Sentencing Review and Harmless Error

Gall v. United States; United States v. Cavera: Established the abuse-of-discretion framework for procedural and substantive reasonableness review.
United States v. Jass; United States v. Mandell: Articulated harmless-error principles for Guidelines miscalculations where the sentencing judge states it would impose the same sentence.
United States v. Feldman: Warned against “simple incantation” harmlessness; Darrah distinguished Feldman because the district court here specifically identified a single enhancement and gave a non-perfunctory §3553(a) rationale.
Molina-Martinez v. United States: Confirmed no reasonable probability of prejudice if the record shows the district court deemed the sentence appropriate irrespective of the guideline range.

Interpretation of §2G2.2(b)(3)(B)

United States v. Oliver (6th Cir.); United States v. Morehouse (4th Cir.); United States v. Randall (9th Cir.): Provided the agreement-based standard; the Second Circuit adopted Oliver’s test in full and aligned with Randall on no actual receipt requirement.
United States v. Fucito (5th Cir.): Cited approvingly in footnote for the proposition that actual receipt is not required.
Stinson v. United States: Established that guideline commentary interpreting a guideline is authoritative unless inconsistent with the guideline or law; supported reliance on Application Note 1 to §2G2.2.
United States v. Maria; Black’s Law Dictionary definition of “Agreement”; Krumme v. WestPoint Stevens Inc.: Emphasized common-meaning and mutual-assent concepts, reinforcing the bilateral nature of “exchange.”
TRW, Inc. v. Andrews; Lamie v. U.S. Trustee: Canon against superfluity and plain-meaning enforcement; used to reject the government’s attempt to equate “specific purpose” with an exchange, which would nullify the agreement element.

Supervised Release Conditions and Delegation

United States v. Kunz: Core authority confirming that a one-device limitation is a significant liberty restriction requiring court-imposed, particularized findings, and that giving Probation discretion to decide whether to impose such a restriction is an impermissible delegation.
United States v. Matta: Underpins the rule that conditions impacting significant liberty interests require on-the-record findings showing no greater deprivation than necessary.
United States v. Eaglin; United States v. Betts: Mandate individualized assessment and reasons for special conditions.
Silber v. United States; United States v. Armetta: Permit appellate correction of obvious errors sua sponte in criminal cases.
18 U.S.C. §3583(d): Statutory criteria for special conditions; frames the court’s analysis.

Substantive Reasonableness Context

United States v. Dorvee: Cautionary note on §2G2.2’s propensity to escalate ranges; distinguished in Darrah because the range did not exceed the statutory maximum and the court gave a balanced §3553(a) analysis.
United States v. Spoor; United States v. Ingram; United States v. Perez-Frias; United States v. Broxmeyer: Articulate the deferential substantive reasonableness standard and emphasize that below-Guidelines sentences are rarely unreasonable.

Key Legal Reasoning

The post-2016 text and commentary to §2G2.2(b)(3)(B) create a bilateral “exchange” requirement; evidence must show mutual assent to trade child pornography (or comparable valuable consideration), not merely a defendant’s unilateral aim to receive something in return.
Assent can be explicit or implicit, and may be inferred from context, words, or conduct. But equivocal, tentative, or noncommittal statements by the recipient (“might,” “can try”) do not suffice to establish even an implicit agreement.
Absent an exchange agreement, applying the five-level enhancement is procedural error. Nevertheless, where the district court makes an explicit and supported statement that it would impose the same sentence, and the sentence sits below the corrected range, the error is harmless.
Conditions that meaningfully curtail liberty—such as limiting a person to one internet-capable device—must be imposed by the court, supported by individualized findings, and may not be delegated to Probation to decide whether or when to impose or relax. Probation may administer monitoring programs and manage logistics but may not wield the power to determine the existence or scope of a core liberty restriction.

Impact and Practical Implications

A. Charging and Sentencing Under §2G2.2(b)(3)(B)

Higher evidentiary bar for the five-level enhancement in the Second Circuit. Prosecutors must now prove an actual exchange agreement with the recipient. Evidence likely to satisfy the standard includes:
- Explicit trades (“I’ll send you X if you send me Y”);
- Group or chatroom rules requiring reciprocity, if the defendant’s distribution occurs pursuant to those rules and is linked to the reciprocation;
- Recipient assent confirming terms, timing, or conditions of the trade;
- Demonstrated quid pro quo patterns in the same chat or relationship.
What will not suffice: A defendant’s “specific purpose,” unilateral belief, or mere hope; noncommittal recipient statements; generalized trust-building absent assent.
No actual receipt required: The government need not show the defendant actually received images or access—only that he distributed pursuant to an exchange agreement.
Sting operations: OCEs should be trained to avoid muddy, noncommittal phrasing if the government intends to rely on §2G2.2(b)(3)(B); explicit reciprocation (consistent with law-enforcement constraints) is often required to support the enhancement.
Plea negotiations and advocacy: Defense counsel have a stronger basis to resist the five-level enhancement where chats lack recipient assent; the two-level distribution enhancement (§2G2.2(b)(3)(F)) may be more appropriate in many cases.

B. Sentencing Practice and Harmless Error

Alternate sentencing statements matter: District courts that explicitly state an unchanged sentencing decision under a corrected Guidelines scenario—and explain their §3553(a) reasoning—can avoid unnecessary remands if a calculation error is found on appeal.
Dorvee remains a caution, not a bar: §2G2.2 must be applied with care, but well-reasoned below-Guidelines sentences supported by individualized findings are unlikely to be disturbed.

C. Supervised Release Conditions Involving Technology

No delegation of core liberty limits: Courts cannot cede to Probation the authority to determine whether a person is restricted to a single device, even “initially” or “unless and until” Probation deems otherwise. Any later changes must be made by the court (typically via modification procedures under §3583(e)(2)).
Particularized findings required: If a court imposes a one-device limit, it must explain why that restriction is reasonably necessary in the individual case and constitutes no greater deprivation than needed. Generalized concerns about “impulse control” or offense characteristics may not suffice without more.
Permissible roles for Probation: Administering monitoring programs (e.g., ICMP), specifying brand or configuration details, setting schedules for inspections, and other ministerial tasks remain within Probation’s wheelhouse—so long as the court decides the existence and scope of the liberty restriction.

Complex Concepts Simplified

“Valuable consideration” (non-pecuniary): In this context, it means things like other child pornography, preferential access to such material, or access to a child—not money. It captures quid pro quo trades in kind.
“Exchange” vs. “expectation”: Exchange requires mutual assent—a meeting of the minds that “I give you this because you will give me that.” Expectation is one-sided—“I hope to get something if I share this.” The 2016 amendment moved the guideline from expectation-based to exchange-based.
Implicit agreement: An agreement can be inferred from words and conduct without a formal statement, but there must still be evidence of assent by both sides. Tentative or hedged statements by the recipient are not enough.
Harmless error: Even if a judge miscalculates the Guidelines, the appellate court will not resentence if the record shows the judge would have chosen the same sentence anyway for the same reasons—and the sentence is lawful.
Impermissible delegation: Judges may not hand off to Probation the decision whether a supervisee is subject to a core liberty restriction (like a one-device limit). Probation can manage the logistics but not decide whether the restriction applies.

Conclusion

Darrah establishes two important guideposts in the Second Circuit. First, for the five-level enhancement under §2G2.2(b)(3)(B), the government must prove a bilateral exchange agreement—explicit or implicit—with the recipient; a defendant’s unilateral wish or “specific purpose” to obtain contraband will not do. The Second Circuit’s adoption of Oliver cements a higher bar than the pre-2016 “expectation” standard and aligns the Circuit with the emerging consensus that actual receipt is not required but mutual assent is. Second, the decision reinforces that courts—not Probation—must decide whether to impose a single-device limit on supervised release, and must justify that significant liberty restriction with individualized, on-the-record findings; delegating that choice to Probation is error.

On the facts presented, the Guidelines error was harmless because the sentencing judge clearly and credibly stated the same sentence would apply regardless, and the imposed 106-month term lay below the corrected range. The supervised-release condition did not fare as well: because it impermissibly empowered Probation to determine whether the one-device limit would continue, the panel vacated and remanded for the district court to make its own findings and decision consistent with Kunz. Together, these holdings will sharpen charging, negotiation, and sentencing practices in child-exploitation cases and clarify the limits of judicial delegation in technology-related supervision.