23-7001-cr United States v. Darrah
1 United States Court of Appeals 2 for the Second Circuit 3 4 AUGUST TERM 2024 5 No. 23-7001-cr 6 7 8 UNITED STATES OF AMERICA, 9 Appellee, 10 11 v. 12 13 KENNETH DARRAH, 14 Defendant-Appellant. 15 16 17 SUBMITTED: OCTOBER 15, 2024 18 DECIDED: MARCH 28, 2025 19 20 21 Before: WALKER, JACOBS, and MERRIAM, Circuit Judges. 22 23 Kenneth Darrah appeals from a judgment of the United States 24 District Court for the Northern District of New York (Suddaby, J.), 25 entered on August 23, 2023, convicting him, following a guilty plea, 26 of distribution of child pornography in violation of 18 U.S.C 27 §2252A(a)(2)(A), and sentencing him principally to a prison term of 28 106 months, to be followed by a 20-year term of supervised release. 29 For the reasons that follow, we affirm the district court’s judgment as 30 to its application of the five-level Guidelines increase for distribution 31 of child pornography under the newly-amended U.S.S.G. 32 §2G2.2(b)(3)(B) and (ii) as harmless error, vacate the judgment insofar 33 as it impermissibly delegates judicial authority to the Probation Office 1 to determine how many internet-capable devices Darrah may possess 2 upon supervised release, and remand for resentencing consistent 3 with this opinion.
4 AFFIRMED in part and VACATED and REMANDED in 5 part. 6 7 JAMES P. EGAN, Assistant 8 Federal Public Defender, 9 Syracuse, NY, for Defendant- 10 Appellant. 11 12 13 RAJIT S. DOSANJH, Assistant 14 United States Attorney, for 15 Carla B. Freedman, United 16 States Attorney for the 17 Northern District of New York, 18 for the United States of America.
2 1 DENNIS JACOBS, Circuit Judge:
2 Kenneth Darrah exchanged messages for two months with an 3 undercover law enforcement officer, or Online Covert Employee 4 (“OCE”), who was posing as the mother of a nine-year-old girl. The 5 generally revolting particulars can be elided. What matters is that, in 6 expectation of receipt of a picture of the child, Darrah transmitted to 7 the OCE an audiovisual file of child pornography through the Kik 8 Messenger application. He pled guilty to a one-count indictment, 9 charging distribution of child pornography in violation of 18 U.S.C. 10 §2252A(a)(2)(A); and he was sentenced by the United States District 11 Court for the Northern District of New York (Suddaby, J.), as relevant 12 here, to 106 months’ imprisonment and 20 years’ supervised release.
13 On appeal, Darrah challenges: (i) the procedural 14 reasonableness of a five-level increase for distribution of child 15 pornography in exchange for valuable consideration under U.S.S.G. 16 §2G2.2(b)(3)(B); (ii) the substantive reasonableness of the 106-month 17 sentence; and (iii) the imposition of a special condition of supervised 18 release limiting him to possession of a single internet-capable device 19 upon release.
20 First, we conclude that it was error to apply the five-level 21 increase for distribution of child pornography when there was no 22 evidence of an agreement to exchange anything of value as required 23 under the amended version of U.S.S.G. §2G2.2(b)(3)(B). However, the 24 district court’s error was harmless. Next, we conclude that the below- 25 Guidelines 106-month sentence was substantively reasonable. 26 Finally, we conclude that the district court erred in delegating judicial 27 authority to the Probation Office to determine how many internet- 28 capable devices Darrah could possess upon supervised release.
29 Accordingly, we affirm the judgment as to the term of 30 imprisonment; but we vacate the judgment as to its impermissible 31 delegation of judicial authority and remand for resentencing 32 consistent with this opinion.
3 1 BACKGROUND
2 Darrah’s Presentence Investigation Report (“PSR”) reflected a 3 base offense level of 22. The offense level was increased, inter alia, by 4 five levels because the district court determined that the child 5 pornography was distributed for valuable consideration. See U.S.S.G. 6 §2G2.2(b)(3)(B). The Probation Office determined that Darrah’s total 7 adjusted offense level was 34. Based on Darrah’s adjusted offense 8 level and criminal history category of I, Darrah’s Guidelines range 9 was 151 to 188 months. Darrah objected to the five-level increase.
10 At Darrah’s sentencing hearing, the district court likewise 11 calculated a total offense level of 34 and a criminal history category of 12 I, with a total Guidelines range of 151 to 188 months. The district court 13 imposed a below-Guidelines term of 106 months’ imprisonment and 14 recommended that Darrah participate in sex offender treatment while 15 in the custody of the Bureau of Prisons. In support of its sentence, the 16 district court referenced the nature of Darrah’s communications, in 17 which he sought explicit images and videos of a nine-year-old girl, 18 provided the OCE instructions on how to pose her, and expressed 19 interest in meeting her. The court also considered that Darrah had a 20 single prior criminal conviction, that he had no known history of 21 sexual contact with minors, and that the instant offense involved the 22 distribution of a single child pornography video. The court reinforced 23 the sentence imposed:
24 [R]egardless of any errors that may have been argued 25 with regard to defense counsel and the guideline scoring, 26 the Court would have imposed this sentence as it is 27 sufficient but not greater than necessary to meet the goals 28 of sentencing outlined in 18 USC Section 3553(a). Had the 29 guideline range not been affected by the five-level 30 enhancement, this sentence would have been still not 31 outside of that guideline range, but below. 32
4 1 App’x at 99.
2 The district court also imposed a 20-year term of supervised 3 release and ordered Darrah to comply with 13 special conditions of 4 supervised release recommended by the Probation Office. Among 5 those, Special Condition 8, a limitation on internet capable devices, as 6 recommended in the PSR, provided that upon release Darrah could 7 not possess an internet-capable device until he participated in the 8 Internet and Computer Management Program (ICMP); the 9 recommended condition did not limit how many devices Darrah 10 could then possess once he successfully completed the ICMP. At 11 sentencing, the district court imposed an additional internet 12 restriction, limiting Darrah to a single internet-capable device upon 13 release and completion of the ICMP. The district court premised this 14 limitation on Darrah’s “poor impulse control.” App’x at 103. The 15 district court further explained that the restriction was necessary “to 16 promote the defendant’s rehabilitation and protect the public from 17 further crimes of this defendant.” Id.
18 Defense counsel asked the district court to confirm that it was 19 limiting Darrah to one internet-capable device as a condition of 20 supervised release. The court explained:
21 Initially, yes, as part of that special condition for 22 supervised release, unless and until probation feels like 23 they can monitor his use beyond that and there aren’t 24 any problems. That can be adjusted, but initially the 25 special condition calls for only one internet-capable 26 device, which will be in the probation’s monitoring 27 program. 28 29 App’x at 105-06.
30 The written judgment contained the 13 special conditions 31 recommended in the PSR, but Special Condition 8 of the written 32 judgment omitted the limitation dictated at sentencing that Darrah
5 1 would be restricted to a single internet-capable device.
2 DISCUSSION
3 “We review sentencing decisions for procedural and 4 substantive reasonableness,” United States v. Eaglin, 913 F.3d 88, 94 (2d 5 Cir. 2019), applying “a deferential abuse-of-discretion standard,” 6 United States v. Cavera, 550 F.3d 180, 189 (2d Cir. 2008) (en banc) (citing 7 Gall v. United States, 552 U.S. 38, 41 (2007)). “Where we identify 8 procedural error in a sentence, but the record indicates clearly that 9 ‘the district court would have imposed the same sentence’ in any 10 event, the error may be deemed harmless, avoiding the need to vacate 11 the sentence and to remand the case for resentencing.” United States 12 v. Jass, 569 F.3d 47, 68 (2d Cir. 2009) (citing Cavera, 550 F.3d at 197); see 13 also United States v. Mandell, 752 F.3d 544, 553 (2d Cir. 2014) (“Thus, 14 any error in the district court’s calculations was harmless, since the 15 district court would have imposed the same sentence in any event.”) 16 (internal quotation marks and citation omitted).
17 I
18 Darrah challenges as procedural error the application of the 19 five-level increase under §2G2.2(b)(3)(B). “A district court commits 20 procedural error where it fails to calculate the Guidelines range. . . , 21 makes a mistake in its Guidelines calculation, or treats the Guidelines 22 as mandatory.” Cavera, 550 F.3d at 190.
23 Prior to November 2016, an individual convicted of 24 distributing child pornography in violation of 18 U.S.C. §2252A(a)(2) 25 faced a five-level increase under §2G2.2(b)(3)(B) if the offense 26 involved “[d]istribution for the receipt, or expectation of receipt, of a 27 thing of value, but not for pecuniary gain.” U.S.S.G. §2G2.2(b)(3)(B) 28 (2015) (emphasis added). In November 2016, the Sentencing 29 Commission promulgated amendment 801, which created the current 30 (and here, controlling) text of §2G2.2(b)(3)(B) and the accompanying 31 commentary. The guideline now omits “expectation of receipt”: “If
6 1 the defendant distributed in exchange for any valuable consideration, 2 but not for pecuniary gain, increase by 5 levels.” U.S.S.G. 3 §2G2.2(b)(3)(B). The updated application note to this guideline 4 explains that the phrase “[t]he defendant distributed in exchange for 5 any valuable consideration”:
6 means the defendant agreed to an exchange with another 7 person under which the defendant knowingly 8 distributed to that other person for the specific purpose 9 of obtaining something of valuable consideration from 10 that other person, such as other child pornographic 11 material, preferential access to child pornographic 12 material, or access to a child. 13 14 U.S.S.G. §2G2.2 cmt. n.1.
15 We have not been presented with the need to interpret the 16 amended version of this offense-level increase. The prevailing test, 17 and the test applied by both parties in their respective briefs, is the 18 Sixth Circuit’s test in United States v. Oliver, 919 F.3d 393 (6th Cir. 19 2019). See also United States v. Morehouse, 34 F.4 381, 391 (4th Cir. 2022); 20 United States v. Randall, 34 F.4th 867, 872 (9th Cir. 2022). There, the 21 Sixth Circuit held that application of Section 2G2.2(b)(3)(B) requires 22 the government to show the defendant: “(1) agreed—either explicitly 23 or implicitly—to an exchange with another person under which (2) 24 the defendant knowingly distributed child pornography to that other 25 person (3) for the specific purpose of obtaining something of valuable 26 consideration (4) from that same other person.” Id. at 403. Moreover, 27 “[t]he distribution must be part of that explicit or implicit agreement, 28 i.e., the defendant understands or believes—even if incorrectly—that 29 his distribution is in pursuance of his obligation under the 30 agreement.” Id. The court explained: “[u]nlike the previous 31 ‘expectation of receipt’ language, which imposes a forward-looking 32 requirement and includes a unilateral understanding by the 33 defendant that, were he to distribute the child pornography, he would
7 1 reasonably anticipate receiving something of value in return, the new 2 enhancement uses the phrase ‘in exchange for.’” Id. at 401. No longer 3 can a district court rely solely on the defendant’s “personal belief or 4 expectation” or “unilateral purpose or belief.” Id. at 401, 405. Now a 5 court must find an agreement. To do so, “a court must examine the 6 purpose (or reasonably inferred purpose) of both parties, including 7 the context of their discussions and circumstantial evidence such as 8 their actions or comments.” Id. (emphasis in original).
9 We agree with and adopt the Sixth Circuit’s interpretation of 10 the amended U.S.S.G. §2G2.2(b)(3)(B). 1 When interpreting the 11 Sentencing Guidelines, we give “the words used their common 12 meaning, absent a clearly expressed manifestation of contrary intent.” 13 United States v. Maria, 186 F.3d 65, 70 (2d Cir. 1999) (internal quotation 14 marks and citation omitted). As explained in Application Note 1 of 15 U.S.S.G. §2G2.2, the amended language to the Guidelines requires an 16 agreement “to an exchange with another person.” 2 Whereas the 17 “expectation of receipt” language considered unilateral expectation 18 to receive something of value in return, the present requirement of an 19 “exchange” considers whether a mutual understanding arose 20 between two or more persons regarding their respective rights and 21 duties. See Agreement, Black’s Law Dictionary (12th ed. 2024) (“A 22 mutual understanding between two or more persons about their 23 relative rights and duties regarding past or future performances; a 24 manifestation of mutual assent by two or more persons.”); see also 25 Krumme v. WestPoint Stevens Inc., 143 F.3d 71, 83 (2d Cir. 1998)
1 We share the Sixth Circuit’s view that §2G2.2(b)(3)(B) contains no requirement of actual receipt. Accord Oliver, 919 F.3d at 403–04; Randall, 34 F.4th at 872; United States v. Fucito, No. 23-20260, 2025 WL 517874, at *4 (5th Cir. Feb. 18, 2025). 2 Guidelines commentary “that interprets or explains a guideline is
authoritative unless it violates the Constitution or a federal statute, or is inconsistent with, or a plainly erroneous reading of, that guideline.” Stinson v. United States, 508 U.S. 36, 38 (1993).
8 1 (“Under New York Law, an acceptance must comply with the terms 2 of the offer and be clear, unambiguous, and unequivocal.”) (internal 3 quotation marks and citation omitted).
4 Under the plain meaning of the Sentencing Guidelines, and its 5 commentary, the district court erred in applying Section 6 2G2.2(b)(3)(B) by relying solely on Darrah’s unilateral expectations 7 absent any assenting language or conduct from the OCE—even 8 assuming that a government agent can effectively create such an 9 agreement. Based on the record, the OCE never expressed assent, 10 explicitly or implicitly, to send videos of her notional daughter, either 11 explicitly or implicitly. In response to Darrah’s request for pictures of 12 her daughter, the OCE responded that she “mighttt” have pictures of 13 her daughter, but that she was “nervous with new ppl.” PSR at 7, ¶10. 14 Similarly, after Darrah sent the OCE an unsolicited video of child 15 pornography, the OCE responded “I can try and take a pic for u later 16 tho if you tell me what u want in it.” Id. at 8, ¶12 (emphasis added). 17 This noncommittal language does not create even an implicit 18 agreement to an exchange.
19 At sentencing, and over Darrah’s objection, the district court 20 applied the five-level distribution increase because “the evidence 21 supports that application for the reasons detailed by the probation 22 officer in the Presentence Investigation Report and the addendum.” 23 App’x at 96. The district court added: “It is clear by the standard that 24 the Court has to consider that this defendant exchanged the one video 25 with the related conduct along with that video being exchanged, not 26 only with the expectation, but certainly understanding and seeking to 27 receive, asking [] subsequently for images/videos, what he could 28 receive from what he thought was the mother of a 9-year-old child.” 29 Id. at 96-97. But Darrah’s understanding and what he sought amount 30 to no more than hope and unilateral expectation.
31 Similarly, the Presentence Report explicitly relied upon by the 32 district court erroneously applied the increase based on Darrah’s 33 expectations rather than on any “exchange.” The PSR explained that
9 1 “Darrah shared a child pornography video with the undercover agent 2 over Kik with the expectation of receiving child pornography, and/or 3 gaining access to the undercover agent’s child, or inducing her to 4 produce and send child pornography depicting the child, in return.” 5 PSR at 13, ¶33 (emphasis added). The PSR adduces no evidence that 6 the OCE ever agreed to such an exchange. The district court’s reliance 7 on Darrah’s unilateral words, actions, and expectations does not 8 satisfy the requirement that both parties need enter into an 9 agreement.
10 The government argues, however, that Darrah’s “specific 11 expectation or purpose” of receiving child pornography was 12 sufficient to imply an agreement. Gov’t Br. at 36. Darrah’s purpose 13 certainly has bearing on whether an (implicit) agreement existed and 14 whether Darrah’s distribution was pursuant thereto. It is not, on its 15 own, sufficient to infer an agreement. See Oliver, 919 F.3d at 404-05. If 16 Darrah’s “specific purpose” were alone sufficient to create an 17 agreement, it would be superfluous to also require that he “agreed to 18 an exchange with another person.” See TRW, Inc. v. Andrews, 534 U.S. 19 19, 31 (2001) (“[N]o clause, sentence, or word” of a statute should be 20 read as “superfluous, void, or insignificant.”) (citation omitted); see 21 also Lamie v. U.S. Trustee, 540 U.S. 526, 534, (2004) (“[W]hen the 22 statute’s language is plain, the sole function of the courts . . . is to 23 enforce it according to its terms.”) (internal quotation marks and 24 citations omitted). Some evidence of mutuality is required, and there 25 was none here.
26 The government also argues that Darrah and the OCE made an 27 implicit agreement: that Darrah furnish proof of his trustworthiness 28 in exchange for child pornography. But the government recognizes 29 that Darrah merely “believed” that his obligation was to establish 30 trustworthiness, and its argument otherwise asserts the unsupported 31 proposition that the OCE agreed to send Darrah child pornography 32 when, as explained, the OCE never expressed assent to send the 33 anticipated videos of her notional daughter.
10 1 Because the district court relied solely on Darrah’s unilateral 2 purpose when it applied the five-level increase, it committed 3 procedural error.
4 We next consider whether that error was harmless. “Where we 5 identify procedural error in a sentence, but the record indicates 6 clearly that the district court would have imposed the same sentence 7 in any event, the error may be deemed harmless, avoiding the need 8 to vacate the sentence and to remand the case for resentencing.” 9 United States v. Jass, 569 F.3d 47, 68 (2d Cir. 2009) (internal quotation 10 marks and citation omitted); see also United States v. Mandell, 752 F.3d 11 544, 553 (2d Cir. 2014) (“[A]ny error in the district court’s calculations 12 was harmless, since the district court would have imposed the same 13 sentence in any event.”) (internal quotation marks and citation 14 omitted). Although criminal sentences should not be “exempted from 15 procedural review” through the use of a “simple incantation,” such 16 as that the district court would have imposed the same sentence 17 regardless of any errors in calculating the Guidelines range, such a 18 statement may still support a finding of harmlessness where, as here, 19 the error “dealt with a single enhancement, specifically identified by 20 the district court . . . and imposed with the explicit and unambiguous 21 declaration that the enhancement did not affect the ultimate 22 sentence.” United States v. Feldman, 647 F.3d 450, 459-60 (2d Cir. 2011).
23 Darrah does not dispute that the district court indicated that it 24 would have imposed the same sentence irrespective of the five-level 25 distribution increase. Instead, Darrah, citing to Feldman, contends that 26 the error was not harmless because (i) the sentence was “anchored” 27 by the district court’s “unquestioned adherence to the guideline 28 provisions of U.S.S.G. §2G2.2,” and (ii) the district court did not 29 provide “any explanation[] beyond an empty reference to the 30 parsimony clause of 18 U.S.C. §3553(a), for how the district court 31 might have arrived at the 106-month sentence.” Darrah’s arguments 32 are refuted by the case law and the record.
33 Feldman concluded that there was no “unambiguous
11 1 declaration that the district court would impose the same sentence,” 2 because “[t]he district court referred, without specificity, to ‘some’ of 3 the [four challenged] enhancements, without stating which 4 enhancement—or which combination of enhancements—would not 5 affect Feldman’s sentence.” 647 F.3d at 459 (quotation marks omitted). 6 Here, the district court considered the §3553(a) sentencing factors; 7 held that the sentence was still “sufficient but not greater than 8 necessary to meet the goals of sentencing;” and explained why the 9 same sentence would have been justified, even if the Guidelines range 10 was reduced. App’x at 97. The district court specifically stated: “Had 11 the guideline range not been affected by the five-level enhancement,” 12 the 106-month sentence it concluded was appropriate still would 13 have been below the resulting Guidelines range. Id. at 99.
14 Unlike the sentencing court in Feldman, the district court here 15 “dealt with a single enhancement, specifically identified by the 16 district court . . . and imposed with the explicit and unambiguous 17 declaration that the enhancement did not affect the ultimate 18 sentence.” 647 F.3d at 459. Darrah does not dispute that had the 19 district court instead imposed the otherwise applicable two-level 20 distribution increase pursuant to §2G2.2(b)(3)(F), Darrah’s Guidelines 21 range would have been 108 to 135 months—still higher than the 22 below-Guidelines 106-month sentence imposed.
23 Darrah characterizes the district court’s pronouncement that it 24 would have imposed the same sentence as a “simple incantation,” 25 Gov’t Br. 23 (quoting Feldman, 647 F.3d at 460), but the district court’s 26 statement was not perfunctory. The district court reviewed the 27 parties’ sentencing submissions ; considered Darrah’s objection under 28 Oliver to the application of the single, five-level-increase; explained its 29 reasons for applying the increase and separately for the imposed 30 sentence; and considered the §3553(a) sentencing factors. The record 31 confirms the district court’s recitation that the same sentence would 32 have been imposed regardless of the increase, such that the error here 33 was harmless. See Jass, 569 F.3d at 68; see also Molina-Martinez v. United
12 1 States, 578 U.S. 189, 200-01 (2016) (“[A] reasonable probability of 2 prejudice does not exist” where the record shows that “the district 3 court thought the sentence it chose was appropriate irrespective of the 4 Guidelines range.”).
5 II
6 “A defendant challenging the substantive reasonableness of his 7 or her sentence bears a heavy burden because our review of a sentence 8 for substantive reasonableness is particularly deferential.” United 9 States v. Spoor, 904 F.3d 141, 156 (2d Cir. 2018) (internal quotation 10 marks and citation omitted). The analysis amounts to “a ‘deferential 11 abuse-of-discretion standard.’” Cavera, 550 F.3d at 189 (quoting Gall, 12 552 U.S. at 41).
13 This Court sets aside “only those sentences that are so 14 shockingly high, shockingly low, or otherwise unsupportable as a 15 matter of law that allowing them to stand would damage the 16 administration of justice.” United States v. Muzio, 966 F.3d 61, 64 (2d 17 Cir. 2020) (quoting United States v. Broxmeyer, 699 F.3d 265, 289 (2d 18 Cir. 2012)). In the context of child pornography sentencing, we bear 19 in mind that the Guidelines must be “applied with great care” to 20 prevent the imposition of unreasonable sentences inconsistent with 21 what 18 U.S.C. §3553(a) requires. United States v. Dorvee, 616 F.3d 174, 22 184 (2d Cir. 2010).
23 Darrah argues that that the district court committed 24 substantive error in sentencing Darrah to a below-Guidelines term of 25 imprisonment of 106 months. He principally relies on our decision in 26 Dorvee to support his argument that the sentence was greater than 27 necessary to serve the purposes of sentencing. This argument is 28 without merit.
29 Dorvee observed that U.S.S.G. §2G2.2, the Guideline at issue 30 here, can, “unless applied with great care, [] lead to unreasonable 31 sentences that are inconsistent with what §3553 requires” because the
13 1 offense-level increases in that guideline “routinely result in 2 Guidelines projections near or exceeding the statutory maximum, 3 even in run-of-the-mill cases.” 616 F.3d at 184, 186. The various child 4 pornography offense-level increases applied in Dorvee resulted in a 5 Guidelines range that, at the low end, was twenty-two months longer 6 than the statutory maximum, id. at 180, a signal that something 7 misfired.
8 The Guidelines range calculated in this case, 151–188 months, 9 was well short of the statutory maximum, 240 months, and does not 10 otherwise bespeak error. See 18 U.S.C. § 2252A(b)(1). Before imposing 11 the sentence, the district court adopted the PSR’s “factual information 12 and guideline applications.” App’x at 96. The PSR detailed Darrah’s 13 background, including his family history, physical and mental health, 14 and history of alcohol abuse. Included in the PSR was a note that 15 defense counsel had provided a risk assessment report, prepared by 16 Dr. Jacqueline Bashkoff, which determined that Darrah presented a 17 “low risk to re-offend” and a “low risk to society.” PSR at 17, ¶59.
18 The district court found that 106 months’ imprisonment was 19 “sufficient but not greater than necessary” to comply with the 20 purposes of §3553(a), “including the need for the sentence to reflect 21 the seriousness of the offense, promote respect for the law and 22 provide just punishment for the offense, afford adequate deterrence 23 to criminal conduct, and protect the public from future crimes of this 24 defendant.” App’x at 97.
25 This Court will “set aside a district court’s substantive 26 determination only in exceptional cases where the trial court’s 27 decision cannot be located within the range of permissible decisions.” 28 United States v. Ingram, 721 F.3d 35, 37 (2d Cir. 2013) (quoting Cavera, 29 550 F.3d at 189). “In the overwhelming majority of cases, a Guidelines 30 sentence will fall comfortably within the broad range of sentences that 31 would be reasonable in the particular circumstances.” United States v. 32 Perez-Frias, 636 F.3d 39, 43 (2d Cir. 2011) (quotation marks and citation 33 omitted). “It is therefore difficult to find that a below-Guidelines
14 1 sentence is unreasonable.” Id. The district court’s imposition of a 2 below-Guidelines 106-month sentence, after having balanced 3 Darrah’s aggravating and mitigating factors, is substantively 4 reasonable and not an abuse of the court’s considerable discretion.
5 III
6 This Court reviews the imposition of a special condition of 7 supervised release for abuse of discretion. United States v. Johnson, 446 8 F.3d 272, 277 (2d Cir. 2006). An abuse of discretion includes the 9 district court’s “erroneous view of the law” or a “clearly erroneous 10 assessment of the evidence.” United States v. Doe, 79 F.3d 1309, 1320 11 (2d Cir. 1996) (quoting Cooter & Gell v. Hartmarx Corp., 496 U.S. 384, 12 405 (1990)).
13 The district court “retains wide latitude in imposing conditions 14 of supervised release.” United States v. MacMillen, 544 F.3d 71, 74 (2d 15 Cir. 2008). Courts “must ‘make an individualized assessment when 16 determining whether to impose a special condition of supervised 17 release, and . . . state on the record the reason for imposing it,’” and 18 the explanation “must be adequately supported by the record.” 19 United States v. Eaglin, 913 F.3d 88, 94 (2d Cir. 2019) (quoting United 20 States v. Betts, 886 F.3d 198, 202 (2d Cir. 2018)). The “failure to do so is 21 error.” Betts, 886 F.3d at 202.
22 A sentencing court may order a defendant to follow special 23 conditions of supervision that the court “considers to be appropriate,” 24 so long as such conditions (1) are “reasonably related to specified 25 factors set forth in §3553(a)(1),” namely, the nature and circumstances 26 of the offense and the history and characteristics of the defendant, and 27 the need for deterrence, protection of the public, medical care, or 28 effective correctional treatment; (2) involve “no greater deprivation of 29 liberty than is reasonably necessary” to serve the specified factors; 30 and (3) are “consistent with any pertinent policy statements issued by 31 the Sentencing Commission pursuant to 28 U.S.C. 994(a).” 18 U.S.C. 32 §3583(d).
15 1 As we explained in United States v. Kunz, “a restriction limiting 2 a supervisee to just one internet-connected device would pose a 3 significant burden on his liberty, and therefore would need to be 4 imposed by the court and justified by particularized on-the-record 5 findings.” 68 F.4th 748, 767 (2d Cir. 2023) (citing United States v. Matta, 6 777 F.3d 116, 123 (2d Cir. 2015) (“[A]ny condition that affects a 7 significant liberty interest . . . must be imposed by the district court 8 and supported by particularized findings that it does not constitute a 9 greater deprivation of liberty than reasonably necessary to 10 accomplish the goals of sentencing.”)). For the “same reason,” we 11 explained, “any special condition granting Probation discretion to 12 decide whether or not to restrict a supervisee to a single internet- 13 connected device would constitute an impermissible delegation of the 14 court’s judicial authority.” Kunz, 68 F.4th at 767.
15 On appeal, Darrah argues that Special Condition 8’s restriction 16 to a single internet-capable device was not justified by particularized 17 on-the-record findings. We agree that Special Condition 8 merits 18 vacatur, but for another reason. Although Darrah did not raise the 19 issue, we conclude that the district court erroneously delegated 20 judicial authority to the Probation Office to determine how many 21 internet-capable devices Darrah may use upon supervised release. 3 22 We thus vacate the condition as imposed and remand to the district 23 court directing it to determine for itself whether this limitation should 24 be imposed based on appropriate on-the-record findings and, if not, 25 to modify or vacate the condition.
26 At sentencing, the court explained its basis for Special 27 Condition 8, initially limiting Darrah to a single internet-capable
3 See Silber v. United States, 370 U.S. 717, 718 (1962) (“In exceptional circumstances, especially in criminal cases, appellate courts, in the public interest, may, of their own motion, notice errors to which no exception has been taken, if the errors are obvious. . . .” (quoting United States v. Armetta, 378 F.2d 658, 662 (2d Cir. 1967)).
16 1 device. Specifically, Special Condition 8 was found to be necessary “to 2 promote [Darrah]’s rehabilitation and protect the public,” App’x at 3 103, because, at the time of his arrest, Darrah “was found in 4 possession of multiple cellular phones,” App’x at 102, and had used 5 an internet-capable device to commit his offense. The court explained 6 its belief that Darrah’s “poor impulse control,” as demonstrated by 7 his offense conduct, was facilitated by his access to the internet. App’x 8 at 103. The court further emphasized that the condition would be 9 imposed as an initial step, to promote Darrah’s effective adjustment 10 to supervised release. 4
11 However, Special Condition 8, as recommended in the PSR, did 12 not specify how many internet-capable devices Darrah could possess. 13 It only stated that upon release, Darrah could not possess an internet- 14 capable device until he participated in the Internet and Computer 15 Management Program (ICMP). Special Condition 8 did not specify 16 how many devices Darrah could possess once he successfully 17 completed the ICMP. The court’s explanation expressly “include[ed] 18 a restriction to one internet-capable device.” App’x at 103. When 19 defense counsel sought to confirm that the district court was 20 imposing a single-device limitation, not described in the text of 21 Special Condition 8, the court explained:
22 Initially, yes, as part of that special condition for 23 supervised release, unless and until probation feels like 24 they can monitor his use beyond that and there aren’t 25 any problems. That can be adjusted, but initially the 26 special condition calls for only one internet-capable 27 device, which will be in the probation’s monitoring 28 program. 29 30 App’x at 105-06.
4 We make no specific holding on what findings may warrant the application of a single-internet-connected-device restriction.
17 1 This delegation seems to confer discretion on the Probation 2 Office to restrict Darrah to a single internet-capable device, even if 3 only initially. As a “special condition granting Probation discretion to 4 decide whether or not to restrict a supervisee to a single internet- 5 connected device,” it is “an impermissible delegation of the court’s 6 judicial authority.” Kunz, 68 F.4th at 767.
7 CONCLUSION
8 For the foregoing reasons, we affirm the district court’s 9 application of the five-level distribution increase as harmless error 10 and vacate the judgment as to the imposition of Special Condition 8 11 and remand for resentencing to conform the sentence with our 12 opinion in Kunz, 68 F.4th 748.