United States v. Darrah

23-7001-cr
United States v. Darrah
United States Court of Appeals 1
for the Second Circuit 2
3
AUGUST TERM 2024 4
No. 23-7001-cr 5
6
7
UNITED S TATES OF AMERICA, 8
Appellee, 9
10
v. 11
12
KENNETH D ARRAH, 13
Defendant-Appellant. 14
15
16
S UBMITTED: O CTOBER 15, 2024 17
D ECIDED: MARCH 28, 2025 18
19
20
Before: WALKER , J ACOBS, and MERRIAM, Circuit Judges. 21
22
Kenneth Darrah appeals from a judgment of the United States 23
District Court for the Northern District of New York (Suddaby, J.), 24
entered on August 23, 2023, convicting him, following a guilty plea, 25
of distribution of child pornography in violation of 18 U.S.C 26
§2252A(a)(2)(A), and sentencing him principally to a prison term of 27
106 months, to be followed by a 20-year term of supervised release. 28
For the reasons that follow, we affirm the district court’s judgment as 29
to its application of the five-level Guidelines increase for distribution 30
of child pornography under the newly-amended U.S.S.G. 31
§2G2.2(b)(3)(B) and (ii) as harmless error, vacate the judgment insofar 32
as it impermissibly delegates judicial authority to the Probation Office 33

-- 1 of 18 --

2
to determine how many internet-capable devices Darrah may possess 1
upon supervised release, and remand for resentencing consistent 2
with this opinion. 3
AFFIRMED in part and VACATED and REMANDED in 4
part. 5
6
J AMES P. E GAN, Assistant 7
Federal Public Defender, 8
Syracuse, NY, for Defendant- 9
Appellant. 10
11
12
RAJIT S. D OSANJH, Assistant 13
United States Attorney, for 14
Carla B. Freedman, United 15
States Attorney for the 16
Northern District of New York, 17
for the United States of America. 18

-- 2 of 18 --

3
D ENNIS J ACOBS, Circuit Judge: 1
Kenneth Darrah exchanged messages for two months with an 2
undercover law enforcement officer, or Online Covert Employee 3
(“OCE”), who was posing as the mother of a nine-year-old girl. The 4
generally revolting particulars can be elided. What matters is that, in 5
expectation of receipt of a picture of the child, Darrah transmitted to 6
the OCE an audiovisual file of child pornography through the Kik 7
Messenger application. He pled guilty to a one-count indictment, 8
charging distribution of child pornography in violation of 18 U.S.C. 9
§2252A(a)(2)(A); and he was sentenced by the United States District 10
Court for the Northern District of New York (Suddaby, J.), as relevant 11
here, to 106 months’ imprisonment and 20 years’ supervised release. 12
On appeal, Darrah challenges: (i) the procedural 13
reasonableness of a five-level increase for distribution of child 14
pornography in exchange for valuable consideration under U.S.S.G. 15
§2G2.2(b)(3)(B); (ii) the substantive reasonableness of the 106-month 16
sentence; and (iii) the imposition of a special condition of supervised 17
release limiting him to possession of a single internet-capable device 18
upon release. 19
First, we conclude that it was error to apply the five-level 20
increase for distribution of child pornography when there was no 21
evidence of an agreement to exchange anything of value as required 22
under the amended version of U.S.S.G. §2G2.2(b)(3)(B). However, the 23
district court’s error was harmless. Next, we conclude that the below- 24
Guidelines 106-month sentence was substantively reasonable. 25
Finally, we conclude that the district court erred in delegating judicial 26
authority to the Probation Office to determine how many internet- 27
capable devices Darrah could possess upon supervised release. 28
Accordingly, we affirm the judgment as to the term of 29
imprisonment; but we vacate the judgment as to its impermissible 30
delegation of judicial authority and remand for resentencing 31
consistent with this opinion. 32

-- 3 of 18 --

4
BACKGROUND 1
Darrah’s Presentence Investigation Report (“PSR”) reflected a 2
base offense level of 22. The offense level was increased, inter alia, by 3
five levels because the district court determined that the child 4
pornography was distributed for valuable consideration. See U.S.S.G. 5
§2G2.2(b)(3)(B). The Probation Office determined that Darrah’s total 6
adjusted offense level was 34. Based on Darrah’s adjusted offense 7
level and criminal history category of I, Darrah’s Guidelines range 8
was 151 to 188 months. Darrah objected to the five-level increase. 9
At Darrah’s sentencing hearing, the district court likewise 10
calculated a total offense level of 34 and a criminal history category of 11
I, with a total Guidelines range of 151 to 188 months. The district court 12
imposed a below-Guidelines term of 106 months’ imprisonment and 13
recommended that Darrah participate in sex offender treatment while 14
in the custody of the Bureau of Prisons. In support of its sentence, the 15
district court referenced the nature of Darrah’s communications, in 16
which he sought explicit images and videos of a nine-year-old girl, 17
provided the OCE instructions on how to pose her, and expressed 18
interest in meeting her. The court also considered that Darrah had a 19
single prior criminal conviction, that he had no known history of 20
sexual contact with minors, and that the instant offense involved the 21
distribution of a single child pornography video. The court reinforced 22
the sentence imposed: 23
[R]egardless of any errors that may have been argued 24
with regard to defense counsel and the guideline scoring, 25
the Court would have imposed this sentence as it is 26
sufficient but not greater than necessary to meet the goals 27
of sentencing outlined in 18 USC Section 3553(a). Had the 28
guideline range not been affected by the five-level 29
enhancement, this sentence would have been still not 30
outside of that guideline range, but below. 31
32

-- 4 of 18 --

5
App’x at 99. 1
The district court also imposed a 20-year term of supervised 2
release and ordered Darrah to comply with 13 special conditions of 3
supervised release recommended by the Probation Office. Among 4
those, Special Condition 8, a limitation on internet capable devices, as 5
recommended in the PSR, provided that upon release Darrah could 6
not possess an internet-capable device until he participated in the 7
Internet and Computer Management Program (ICMP); the 8
recommended condition did not limit how many devices Darrah 9
could then possess once he successfully completed the ICMP. At 10
sentencing, the district court imposed an additional internet 11
restriction, limiting Darrah to a single internet-capable device upon 12
release and completion of the ICMP. The district court premised this 13
limitation on Darrah’s “poor impulse control.” App’x at 103. The 14
district court further explained that the restriction was necessary “to 15
promote the defendant’s rehabilitation and protect the public from 16
further crimes of this defendant.” Id. 17
Defense counsel asked the district court to confirm that it was 18
limiting Darrah to one internet-capable device as a condition of 19
supervised release. The court explained: 20
Initially, yes, as part of that special condition for 21
supervised release, unless and until probation feels like 22
they can monitor his use beyond that and there aren’t 23
any problems. That can be adjusted, but initially the 24
special condition calls for only one internet-capable 25
device, which will be in the probation’s monitoring 26
program. 27
28
App’x at 105-06. 29
The written judgment contained the 13 special conditions 30
recommended in the PSR, but Special Condition 8 of the written 31
judgment omitted the limitation dictated at sentencing that Darrah 32

-- 5 of 18 --

6
would be restricted to a single internet-capable device. 1
DISCUSSION 2
“We review sentencing decisions for procedural and 3
substantive reasonableness,” United States v. Eaglin, 913 F.3d 88, 94 (2d 4
Cir. 2019), applying “a deferential abuse-of-discretion standard,” 5
United States v. Cavera, 550 F.3d 180, 189 (2d Cir. 2008) (en banc) (citing 6
Gall v. United States, 552 U.S. 38, 41 (2007)). “Where we identify 7
procedural error in a sentence, but the record indicates clearly that 8
‘the district court would have imposed the same sentence’ in any 9
event, the error may be deemed harmless, avoiding the need to vacate 10
the sentence and to remand the case for resentencing.” United States 11
v. Jass, 569 F.3d 47, 68 (2d Cir. 2009) (citing Cavera, 550 F.3d at 197); see 12
also United States v. Mandell, 752 F.3d 544, 553 (2d Cir. 2014) (“Thus, 13
any error in the district court’s calculations was harmless, since the 14
district court would have imposed the same sentence in any event.”) 15
(internal quotation marks and citation omitted). 16
I 17
Darrah challenges as procedural error the application of the 18
five-level increase under §2G2.2(b)(3)(B). “A district court commits 19
procedural error where it fails to calculate the Guidelines range. . . , 20
makes a mistake in its Guidelines calculation, or treats the Guidelines 21
as mandatory.” Cavera, 550 F.3d at 190. 22
Prior to November 2016, an individual convicted of 23
distributing child pornography in violation of 18 U.S.C. §2252A(a)(2) 24
faced a five-level increase under §2G2.2(b)(3)(B) if the offense 25
involved “[d]istribution for the receipt, or expectation of receipt, of a 26
thing of value, but not for pecuniary gain.” U.S.S.G. §2G2.2(b)(3)(B) 27
(2015) (emphasis added). In November 2016, the Sentencing 28
Commission promulgated amendment 801, which created the current 29
(and here, controlling) text of §2G2.2(b)(3)(B) and the accompanying 30
commentary. The guideline now omits “expectation of receipt”: “If 31

-- 6 of 18 --

7
the defendant distributed in exchange for any valuable consideration, 1
but not for pecuniary gain, increase by 5 levels.” U.S.S.G. 2
§2G2.2(b)(3)(B). The updated application note to this guideline 3
explains that the phrase “[t]he defendant distributed in exchange for 4
any valuable consideration”: 5
means the defendant agreed to an exchange with another 6
person under which the defendant knowingly 7
distributed to that other person for the specific purpose 8
of obtaining something of valuable consideration from 9
that other person, such as other child pornographic 10
material, preferential access to child pornographic 11
material, or access to a child. 12
13
U.S.S.G. §2G2.2 cmt. n.1. 14
We have not been presented with the need to interpret the 15
amended version of this offense-level increase. The prevailing test, 16
and the test applied by both parties in their respective briefs, is the 17
Sixth Circuit’s test in United States v. Oliver, 919 F.3d 393 (6th Cir. 18
2019). See also United States v. Morehouse, 34 F.4 381, 391 (4th Cir. 2022); 19
United States v. Randall, 34 F.4th 867, 872 (9th Cir. 2022). There, the 20
Sixth Circuit held that application of Section 2G2.2(b)(3)(B) requires 21
the government to show the defendant: “(1) agreed—either explicitly 22
or implicitly—to an exchange with another person under which (2) 23
the defendant knowingly distributed child pornography to that other 24
person (3) for the specific purpose of obtaining something of valuable 25
consideration (4) from that same other person.” Id. at 403. Moreover, 26
“[t]he distribution must be part of that explicit or implicit agreement, 27
i.e., the defendant understands or believes—even if incorrectly—that 28
his distribution is in pursuance of his obligation under the 29
agreement.” Id. The court explained: “[u]nlike the previous 30
‘expectation of receipt’ language, which imposes a forward-looking 31
requirement and includes a unilateral understanding by the 32
defendant that, were he to distribute the child pornography, he would 33

-- 7 of 18 --

8
reasonably anticipate receiving something of value in return, the new 1
enhancement uses the phrase ‘in exchange for.’” Id. at 401. No longer 2
can a district court rely solely on the defendant’s “personal belief or 3
expectation” or “unilateral purpose or belief.” Id. at 401, 405. Now a 4
court must find an agreement. To do so, “a court must examine the 5
purpose (or reasonably inferred purpose) of both parties, including 6
the context of their discussions and circumstantial evidence such as 7
their actions or comments.” Id. (emphasis in original). 8
We agree with and adopt the Sixth Circuit’s interpretation of 9
the amended U.S.S.G. §2G2.2(b)(3)(B). 1 When interpreting the 10
Sentencing Guidelines, we give “the words used their common 11
meaning, absent a clearly expressed manifestation of contrary intent.” 12
United States v. Maria, 186 F.3d 65, 70 (2d Cir. 1999) (internal quotation 13
marks and citation omitted). As explained in Application Note 1 of 14
U.S.S.G. §2G2.2, the amended language to the Guidelines requires an 15
agreement “to an exchange with another person.” 2 Whereas the 16
“expectation of receipt” language considered unilateral expectation 17
to receive something of value in return, the present requirement of an 18
“exchange” considers whether a mutual understanding arose 19
between two or more persons regarding their respective rights and 20
duties. See Agreement, Black’s Law Dictionary (12th ed. 2024) (“A 21
mutual understanding between two or more persons about their 22
relative rights and duties regarding past or future performances; a 23
manifestation of mutual assent by two or more persons.”); see also 24
Krumme v. WestPoint Stevens Inc., 143 F.3d 71, 83 (2d Cir. 1998) 25
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 of 18 --

9
(“Under New York Law, an acceptance must comply with the terms 1
of the offer and be clear, unambiguous, and unequivocal.”) (internal 2
quotation marks and citation omitted). 3
Under the plain meaning of the Sentencing Guidelines, and its 4
commentary, the district court erred in applying Section 5
2G2.2(b)(3)(B) by relying solely on Darrah’s unilateral expectations 6
absent any assenting language or conduct from the OCE—even 7
assuming that a government agent can effectively create such an 8
agreement. Based on the record, the OCE never expressed assent, 9
explicitly or implicitly, to send videos of her notional daughter, either 10
explicitly or implicitly. In response to Darrah’s request for pictures of 11
her daughter, the OCE responded that she “mighttt” have pictures of 12
her daughter, but that she was “nervous with new ppl.” PSR at 7, ¶10. 13
Similarly, after Darrah sent the OCE an unsolicited video of child 14
pornography, the OCE responded “I can try and take a pic for u later 15
tho if you tell me what u want in it.” Id. at 8, ¶12 (emphasis added). 16
This noncommittal language does not create even an implicit 17
agreement to an exchange. 18
At sentencing, and over Darrah’s objection, the district court 19
applied the five-level distribution increase because “the evidence 20
supports that application for the reasons detailed by the probation 21
officer in the Presentence Investigation Report and the addendum.” 22
App’x at 96. The district court added: “It is clear by the standard that 23
the Court has to consider that this defendant exchanged the one video 24
with the related conduct along with that video being exchanged, not 25
only with the expectation, but certainly understanding and seeking to 26
receive, asking [] subsequently for images/videos, what he could 27
receive from what he thought was the mother of a 9-year-old child.” 28
Id. at 96-97. But Darrah’s understanding and what he sought amount 29
to no more than hope and unilateral expectation. 30
Similarly, the Presentence Report explicitly relied upon by the 31
district court erroneously applied the increase based on Darrah’s 32
expectations rather than on any “exchange.” The PSR explained that 33

-- 9 of 18 --

10
“Darrah shared a child pornography video with the undercover agent 1
over Kik with the expectation of receiving child pornography, and/or 2
gaining access to the undercover agent’s child, or inducing her to 3
produce and send child pornography depicting the child, in return.” 4
PSR at 13, ¶33 (emphasis added). The PSR adduces no evidence that 5
the OCE ever agreed to such an exchange. The district court’s reliance 6
on Darrah’s unilateral words, actions, and expectations does not 7
satisfy the requirement that both parties need enter into an 8
agreement. 9
The government argues, however, that Darrah’s “specific 10
expectation or purpose” of receiving child pornography was 11
sufficient to imply an agreement. Gov’t Br. at 36. Darrah’s purpose 12
certainly has bearing on whether an (implicit) agreement existed and 13
whether Darrah’s distribution was pursuant thereto. It is not, on its 14
own, sufficient to infer an agreement. See Oliver, 919 F.3d at 404-05. If 15
Darrah’s “specific purpose” were alone sufficient to create an 16
agreement, it would be superfluous to also require that he “agreed to 17
an exchange with another person.” See TRW, Inc. v. Andrews, 534 U.S. 18
19, 31 (2001) (“[N]o clause, sentence, or word” of a statute should be 19
read as “superfluous, void, or insignificant.”) (citation omitted); see 20
also Lamie v. U.S. Trustee, 540 U.S. 526, 534, (2004) (“[W]hen the 21
statute’s language is plain, the sole function of the courts . . . is to 22
enforce it according to its terms.”) (internal quotation marks and 23
citations omitted). Some evidence of mutuality is required, and there 24
was none here. 25
The government also argues that Darrah and the OCE made an 26
implicit agreement: that Darrah furnish proof of his trustworthiness 27
in exchange for child pornography. But the government recognizes 28
that Darrah merely “believed” that his obligation was to establish 29
trustworthiness, and its argument otherwise asserts the unsupported 30
proposition that the OCE agreed to send Darrah child pornography 31
when, as explained, the OCE never expressed assent to send the 32
anticipated videos of her notional daughter. 33

-- 10 of 18 --

11
Because the district court relied solely on Darrah’s unilateral 1
purpose when it applied the five-level increase, it committed 2
procedural error. 3
We next consider whether that error was harmless. “Where we 4
identify procedural error in a sentence, but the record indicates 5
clearly that the district court would have imposed the same sentence 6
in any event, the error may be deemed harmless, avoiding the need 7
to vacate the sentence and to remand the case for resentencing.” 8
United States v. Jass, 569 F.3d 47, 68 (2d Cir. 2009) (internal quotation 9
marks and citation omitted); see also United States v. Mandell, 752 F.3d 10
544, 553 (2d Cir. 2014) (“[A]ny error in the district court’s calculations 11
was harmless, since the district court would have imposed the same 12
sentence in any event.”) (internal quotation marks and citation 13
omitted). Although criminal sentences should not be “exempted from 14
procedural review” through the use of a “simple incantation,” such 15
as that the district court would have imposed the same sentence 16
regardless of any errors in calculating the Guidelines range, such a 17
statement may still support a finding of harmlessness where, as here, 18
the error “dealt with a single enhancement, specifically identified by 19
the district court . . . and imposed with the explicit and unambiguous 20
declaration that the enhancement did not affect the ultimate 21
sentence.” United States v. Feldman, 647 F.3d 450, 459-60 (2d Cir. 2011). 22
Darrah does not dispute that the district court indicated that it 23
would have imposed the same sentence irrespective of the five-level 24
distribution increase. Instead, Darrah, citing to Feldman, contends that 25
the error was not harmless because (i) the sentence was “anchored” 26
by the district court’s “unquestioned adherence to the guideline 27
provisions of U.S.S.G. §2G2.2,” and (ii) the district court did not 28
provide “any explanation[] beyond an empty reference to the 29
parsimony clause of 18 U.S.C. §3553(a), for how the district court 30
might have arrived at the 106-month sentence.” Darrah’s arguments 31
are refuted by the case law and the record. 32
Feldman concluded that there was no “unambiguous 33

-- 11 of 18 --

12
declaration that the district court would impose the same sentence,” 1
because “[t]he district court referred, without specificity, to ‘some’ of 2
the [four challenged] enhancements, without stating which 3
enhancement—or which combination of enhancements—would not 4
affect Feldman’s sentence.” 647 F.3d at 459 (quotation marks omitted). 5
Here, the district court considered the §3553(a) sentencing factors; 6
held that the sentence was still “sufficient but not greater than 7
necessary to meet the goals of sentencing;” and explained why the 8
same sentence would have been justified, even if the Guidelines range 9
was reduced. App’x at 97. The district court specifically stated: “Had 10
the guideline range not been affected by the five-level enhancement,” 11
the 106-month sentence it concluded was appropriate still would 12
have been below the resulting Guidelines range. Id. at 99. 13
Unlike the sentencing court in Feldman, the district court here 14
“dealt with a single enhancement, specifically identified by the 15
district court . . . and imposed with the explicit and unambiguous 16
declaration that the enhancement did not affect the ultimate 17
sentence.” 647 F.3d at 459. Darrah does not dispute that had the 18
district court instead imposed the otherwise applicable two-level 19
distribution increase pursuant to §2G2.2(b)(3)(F), Darrah’s Guidelines 20
range would have been 108 to 135 months—still higher than the 21
below-Guidelines 106-month sentence imposed. 22
Darrah characterizes the district court’s pronouncement that it 23
would have imposed the same sentence as a “simple incantation,” 24
Gov’t Br. 23 (quoting Feldman, 647 F.3d at 460), but the district court’s 25
statement was not perfunctory. The district court reviewed the 26
parties’ sentencing submissions ; considered Darrah’s objection under 27
Oliver to the application of the single, five-level-increase; explained its 28
reasons for applying the increase and separately for the imposed 29
sentence; and considered the §3553(a) sentencing factors. The record 30
confirms the district court’s recitation that the same sentence would 31
have been imposed regardless of the increase, such that the error here 32
was harmless. See Jass, 569 F.3d at 68; see also Molina-Martinez v. United 33

-- 12 of 18 --

13
States, 578 U.S. 189, 200-01 (2016) (“[A] reasonable probability of 1
prejudice does not exist” where the record shows that “the district 2
court thought the sentence it chose was appropriate irrespective of the 3
Guidelines range.”). 4
II 5
“A defendant challenging the substantive reasonableness of his 6
or her sentence bears a heavy burden because our review of a sentence 7
for substantive reasonableness is particularly deferential.” United 8
States v. Spoor, 904 F.3d 141, 156 (2d Cir. 2018) (internal quotation 9
marks and citation omitted). The analysis amounts to “a ‘deferential 10
abuse-of-discretion standard.’” Cavera, 550 F.3d at 189 (quoting Gall, 11
552 U.S. at 41). 12
This Court sets aside “only those sentences that are so 13
shockingly high, shockingly low, or otherwise unsupportable as a 14
matter of law that allowing them to stand would damage the 15
administration of justice.” United States v. Muzio, 966 F.3d 61, 64 (2d 16
Cir. 2020) (quoting United States v. Broxmeyer, 699 F.3d 265, 289 (2d 17
Cir. 2012)). In the context of child pornography sentencing, we bear 18
in mind that the Guidelines must be “applied with great care” to 19
prevent the imposition of unreasonable sentences inconsistent with 20
what 18 U.S.C. §3553(a) requires. United States v. Dorvee, 616 F.3d 174, 21
184 (2d Cir. 2010). 22
Darrah argues that that the district court committed 23
substantive error in sentencing Darrah to a below-Guidelines term of 24
imprisonment of 106 months. He principally relies on our decision in 25
Dorvee to support his argument that the sentence was greater than 26
necessary to serve the purposes of sentencing. This argument is 27
without merit. 28
Dorvee observed that U.S.S.G. §2G2.2, the Guideline at issue 29
here, can, “unless applied with great care, [] lead to unreasonable 30
sentences that are inconsistent with what §3553 requires” because the 31

-- 13 of 18 --

14
offense-level increases in that guideline “routinely result in 1
Guidelines projections near or exceeding the statutory maximum, 2
even in run-of-the-mill cases.” 616 F.3d at 184, 186. The various child 3
pornography offense-level increases applied in Dorvee resulted in a 4
Guidelines range that, at the low end, was twenty-two months longer 5
than the statutory maximum, id. at 180, a signal that something 6
misfired. 7
The Guidelines range calculated in this case, 151–188 months, 8
was well short of the statutory maximum, 240 months, and does not 9
otherwise bespeak error. See 18 U.S.C. § 2252A(b)(1). Before imposing 10
the sentence, the district court adopted the PSR’s “factual information 11
and guideline applications.” App’x at 96. The PSR detailed Darrah’s 12
background, including his family history, physical and mental health, 13
and history of alcohol abuse. Included in the PSR was a note that 14
defense counsel had provided a risk assessment report, prepared by 15
Dr. Jacqueline Bashkoff, which determined that Darrah presented a 16
“low risk to re-offend” and a “low risk to society.” PSR at 17, ¶59. 17
The district court found that 106 months’ imprisonment was 18
“sufficient but not greater than necessary” to comply with the 19
purposes of §3553(a), “including the need for the sentence to reflect 20
the seriousness of the offense, promote respect for the law and 21
provide just punishment for the offense, afford adequate deterrence 22
to criminal conduct, and protect the public from future crimes of this 23
defendant.” App’x at 97. 24
This Court will “set aside a district court’s substantive 25
determination only in exceptional cases where the trial court’s 26
decision cannot be located within the range of permissible decisions.” 27
United States v. Ingram, 721 F.3d 35, 37 (2d Cir. 2013) (quoting Cavera, 28
550 F.3d at 189). “In the overwhelming majority of cases, a Guidelines 29
sentence will fall comfortably within the broad range of sentences that 30
would be reasonable in the particular circumstances.” United States v. 31
Perez-Frias, 636 F.3d 39, 43 (2d Cir. 2011) (quotation marks and citation 32
omitted). “It is therefore difficult to find that a below-Guidelines 33

-- 14 of 18 --

15
sentence is unreasonable.” Id. The district court’s imposition of a 1
below-Guidelines 106-month sentence, after having balanced 2
Darrah’s aggravating and mitigating factors, is substantively 3
reasonable and not an abuse of the court’s considerable discretion. 4
III 5
This Court reviews the imposition of a special condition of 6
supervised release for abuse of discretion. United States v. Johnson, 446 7
F.3d 272, 277 (2d Cir. 2006). An abuse of discretion includes the 8
district court’s “erroneous view of the law” or a “clearly erroneous 9
assessment of the evidence.” United States v. Doe, 79 F.3d 1309, 1320 10
(2d Cir. 1996) (quoting Cooter & Gell v. Hartmarx Corp., 496 U.S. 384, 11
405 (1990)). 12
The district court “retains wide latitude in imposing conditions 13
of supervised release.” United States v. MacMillen, 544 F.3d 71, 74 (2d 14
Cir. 2008). Courts “must ‘make an individualized assessment when 15
determining whether to impose a special condition of supervised 16
release, and . . . state on the record the reason for imposing it,’” and 17
the explanation “must be adequately supported by the record.” 18
United States v. Eaglin, 913 F.3d 88, 94 (2d Cir. 2019) (quoting United 19
States v. Betts, 886 F.3d 198, 202 (2d Cir. 2018)). The “failure to do so is 20
error.” Betts, 886 F.3d at 202. 21
A sentencing court may order a defendant to follow special 22
conditions of supervision that the court “considers to be appropriate,” 23
so long as such conditions (1) are “reasonably related to specified 24
factors set forth in §3553(a)(1),” namely, the nature and circumstances 25
of the offense and the history and characteristics of the defendant, and 26
the need for deterrence, protection of the public, medical care, or 27
effective correctional treatment; (2) involve “no greater deprivation of 28
liberty than is reasonably necessary” to serve the specified factors; 29
and (3) are “consistent with any pertinent policy statements issued by 30
the Sentencing Commission pursuant to 28 U.S.C. 994(a).” 18 U.S.C. 31
§3583(d). 32

-- 15 of 18 --

16
As we explained in United States v. Kunz, “a restriction limiting 1
a supervisee to just one internet-connected device would pose a 2
significant burden on his liberty, and therefore would need to be 3
imposed by the court and justified by particularized on-the-record 4
findings.” 68 F.4th 748, 767 (2d Cir. 2023) (citing United States v. Matta, 5
777 F.3d 116, 123 (2d Cir. 2015) (“[A]ny condition that affects a 6
significant liberty interest . . . must be imposed by the district court 7
and supported by particularized findings that it does not constitute a 8
greater deprivation of liberty than reasonably necessary to 9
accomplish the goals of sentencing.”)). For the “same reason,” we 10
explained, “any special condition granting Probation discretion to 11
decide whether or not to restrict a supervisee to a single internet- 12
connected device would constitute an impermissible delegation of the 13
court’s judicial authority.” Kunz, 68 F.4th at 767. 14
On appeal, Darrah argues that Special Condition 8’s restriction 15
to a single internet-capable device was not justified by particularized 16
on-the-record findings. We agree that Special Condition 8 merits 17
vacatur, but for another reason. Although Darrah did not raise the 18
issue, we conclude that the district court erroneously delegated 19
judicial authority to the Probation Office to determine how many 20
internet-capable devices Darrah may use upon supervised release.3 21
We thus vacate the condition as imposed and remand to the district 22
court directing it to determine for itself whether this limitation should 23
be imposed based on appropriate on-the-record findings and, if not, 24
to modify or vacate the condition. 25
At sentencing, the court explained its basis for Special 26
Condition 8, initially limiting Darrah to a single internet-capable 27
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 of 18 --

17
device. Specifically, Special Condition 8 was found to be necessary “to 1
promote [Darrah]’s rehabilitation and protect the public,” App’x at 2
103, because, at the time of his arrest, Darrah “was found in 3
possession of multiple cellular phones,” App’x at 102, and had used 4
an internet-capable device to commit his offense. The court explained 5
its belief that Darrah’s “poor impulse control,” as demonstrated by 6
his offense conduct, was facilitated by his access to the internet. App’x 7
at 103. The court further emphasized that the condition would be 8
imposed as an initial step, to promote Darrah’s effective adjustment 9
to supervised release.4 10
However, Special Condition 8, as recommended in the PSR, did 11
not specify how many internet-capable devices Darrah could possess. 12
It only stated that upon release, Darrah could not possess an internet- 13
capable device until he participated in the Internet and Computer 14
Management Program (ICMP). Special Condition 8 did not specify 15
how many devices Darrah could possess once he successfully 16
completed the ICMP. The court’s explanation expressly “include[ed] 17
a restriction to one internet-capable device.” App’x at 103. When 18
defense counsel sought to confirm that the district court was 19
imposing a single-device limitation, not described in the text of 20
Special Condition 8, 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
4 We make no specific holding on what findings may warrant the
application of a single-internet-connected-device restriction.

-- 17 of 18 --

18
This delegation seems to confer discretion on the Probation 1
Office to restrict Darrah to a single internet-capable device, even if 2
only initially. As a “special condition granting Probation discretion to 3
decide whether or not to restrict a supervisee to a single internet- 4
connected device,” it is “an impermissible delegation of the court’s 5
judicial authority.” Kunz, 68 F.4th at 767. 6
CONCLUSION 7
For the foregoing reasons, we affirm the district court’s 8
application of the five-level distribution increase as harmless error 9
and vacate the judgment as to the imposition of Special Condition 8 10
and remand for resentencing to conform the sentence with our 11
opinion in Kunz, 68 F.4th 748. 12

-- 18 of 18 --