United States v. Thompson

23-6943
United States v. Thompson
In the
United States Court of Appeals
For the Second Circuit
August Term, 2024
No. 23-6943
UNITED S TATES OF AMERICA,
Appellee,
v.
K ENNETH THOMPSON,
Defendant-Appellant.
On Appeal from a Judgment of the United States District Court for
the Eastern District of New York.
S UBMITTED: JANUARY 16, 2025
DECIDED: JULY 10, 2025
Before: L IVINGSTON, Chief Judge, R AGGI and NARDINI, Circuit Judges.
Defendant-Appellant Kenneth Thompson was convicted,
following a guilty plea, of one count of being a felon in possession of
a firearm and ammunition in violation of 18 U.S.C. §§ 922(g)(1) and
924(a)(2). The United States District Court for the Eastern District of

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New York (Diane Gujarati, District Judge) sentenced Thompson to
thirty-seven months of imprisonment, to be followed by a two-year
term of supervised release. The court also imposed special conditions
of supervised release requiring Thompson to: (i) submit to reasonable
searches of his person, property, residence, vehicle, and electronic
devices upon reasonable suspicion that he violated a condition of his
supervision and that the areas to be searched contain evidence of that
violation; (ii) comply with any applicable sex offender registration
requirements; and (iii) undergo a mental health evaluation and, if
necessary, participate in a mental health treatment program.
Thompson now appeals. Through counsel, he argues that the
district court procedurally erred in imposing the three special
conditions because it failed to make an individualized assessment of
the need to impose them and failed to state on the record its reasons
for doing so. In a separate pro se submission, Thompson also argues
that his counsel before the district court was ineffective and that his
guilty plea was involuntary. He therefore attempts to raise several
challenges to his conviction and sentence, including that the district
court erred in its Sentencing Guidelines calculation and that 18 U.S.C.
§ 922(g)(1) violates the Second Amendment to the Constitution.
We disagree. First, we conclude that Thompson waived any
challenge to the mental health treatment condition because the record
shows he consented to its imposition. Next, we hold that the district
court made an individualized assessment of the need for the
conditions, that the court adequately explained its reasons for
imposing them, and that the court’s reasoning was amply supported
by the record. Lastly, we decline to consider Thompson’s ineffective
assistance of counsel claim, hold that the district court sufficiently
ensured that his plea was voluntary and knowing, and hold that his
remaining challenges to his conviction and sentence are barred by the
appellate waiver of his plea agreement.
We therefore AFFIRM the judgment of the district court.

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Amy Busa and Irisa Chen, Assistant United
States Attorneys, for Breon Peace, United
States Attorney for the Eastern District of
New York, Brooklyn, NY, for Appellee.
Lawrence Gerzog, New York, NY, for
Defendant-Appellant.
WILLIAM J. NARDINI, Circuit Judge:
Defendant-Appellant Kenneth Thompson was convicted,
following a guilty plea, of one count of being a felon in possession of
a firearm and ammunition in violation of 18 U.S.C. §§ 922(g)(1) and
924(a)(2). The United States District Court for the Eastern District of
New York (Diane Gujarati, District Judge) sentenced Thompson to
thirty-seven months of imprisonment, to be followed by a two-year
term of supervised release. The court also imposed three special
conditions of supervised release requiring Thompson: (i) to submit to
reasonable searches of his person, property, residence, vehicle, and
electronic devices upon reasonable suspicion that he violated a
condition of his supervision and that the areas to be searched contain
evidence of that violation; (ii) to comply with any applicable sex
offender registration requirements; and (iii) to undergo a mental
health evaluation and, if necessary, to participate in a mental health
treatment program.

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Thompson now appeals. He argues that the district court
procedurally erred in imposing the conditions because it failed to
make an individualized assessment of the need to impose them and
failed to state on the record its reasons for doing so. Thompson also
argues that his counsel before the district court was ineffective and
that his plea was involuntary. He therefore attempts to raise several
challenges to his conviction and sentence, including that the district
court erred in its Guidelines calculation and that 18 U.S.C. § 922(g)(1)
violates the Second Amendment to the Constitution.
We disagree. First, we conclude that Thompson waived any
challenge to the mental health treatment condition because the record
shows he consented to its imposition. Next, we hold that the district
court made an individualized assessment of the need for the
conditions, that the court adequately explained its reasons for
imposing them, and that the court’s reasoning was amply supported
by the record. Lastly, we decline to consider Thompson’s ineffective
assistance of counsel claim, hold that the district court sufficiently
ensured that his plea was voluntary and knowing, and hold that his
remaining challenges to his conviction and sentence are barred by the
appellate waiver of his plea agreement.
We therefore AFFIRM the judgment of the district court.
I. Background
On June 6, 2022, officers from the New York City Police
Department (NYPD) reported to a subway platform in Jackson
Heights, Queens, after a 911 caller reported that someone was

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pointing a gun at him on a subway car. As the E train pulled into the
station, the NYPD officers saw that most passengers had moved to
one end of a crowded subway car, to avoid a dispute occurring at the
other end. The police found the caller, who said that Thompson had
pulled a gun from his waistband and pointed it at him after the two
got into an argument. The officers ordered Thompson to stop, but he
fled, dropping a black plastic bag into a trash can as he ran. The
officers caught Thompson, pulled the bag out of the garbage, and
found inside a loaded Norinco .45 caliber automatic pistol and loose
rounds of ammunition.
II. District Court Proceedings
On April 18, 2023, Thompson pled guilty, pursuant to a plea
agreement, to one count of being a felon in possession of a firearm
and ammunition in violation of 18 U.S.C. §§ 922(g)(1) and 924(a)(2)
(Ramon E. Reyes, Jr., Magistrate Judge). The plea agreement included
an appellate waiver, which barred Thompson from appealing his
conviction or prison sentence if that sentence did not exceed 41
months.1
1 The full text of the appellate waiver is as follows:
The defendant agrees not to file an appeal or otherwise
challenge, by petition pursuant to 28 U.S.C. § 2255 or any other
provision, the conviction or sentence in the event that the Court
imposes a term of imprisonment of 41 months or below. This
waiver is binding without regard to the sentencing analysis used
by the Court. The defendant waives all defenses based on the
statute of limitations and venue with respect to any prosecution

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During the plea hearing, the magistrate judge confirmed with
Thompson that he read and understood the plea agreement and had
discussed it with counsel. Thompson also confirmed that he was fully
satisfied with the representation that his counsel had provided to him.
The magistrate judge then went over the terms of the plea agreement,
including the appeal waiver: “You . . . have agreed in the plea
agreement that if you are sentenced to 41 months or less, that you will
not appeal or otherwise challenge your conviction or your sentence.
Do you understand?” Gov’t App’x. at 28–29. Thompson confirmed
that he did.
On May 22, 2023, the district court (Diane Gujarati, District
Judge) accepted Thompson’s guilty plea, finding that Thompson
understood “his rights and the consequences of his plea of guilty,”
that is not time-barred on the date that this agreement is signed in
the event that (a) the defendant’s conviction is later vacated for any
reason, (b) the defendant violates this agreement, or (c) the
defendant’s plea is later withdrawn. The defendant further waives
the right to raise on appeal or on collateral review any argument
that (a) the statutes to which the defendant is pleading guilty are
unconstitutional and (b) the admitted conduct does not fall within
the scope of the statutes. Nothing in the foregoing waiver of
appellate and collateral review rights shall preclude the defendant
from raising a claim of ineffective assistance of counsel in an
appropriate forum.
Gov’t App’x at 3.

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that he “knowingly and voluntarily entered a plea of guilty,” and that
“there [was] a factual basis for the plea.” Dist. Ct. Dkt. 23.
On June 29, 2023, the U.S. Probation Office issued a Presentence
Investigation Report (PSR).2 The PSR described Thompson’s offense
conduct and detailed his criminal history, which included at least four
felonies in New York state court, including (i) a 1982 conviction for
rape in the first degree, (ii) 2000 conviction for attempted rape in the
first degree, (iii) 1982 conviction for robbery in the first degree, and
(iv) 1980 conviction for attempted burglary in the third degree. In
addition, Thompson had a 2016 conviction for forcible touching, a
misdemeanor.
The Probation Office also submitted a Sentence
Recommendation, which proposed that the court impose a sentence
of thirty-seven months of imprisonment and two years of supervised
release with the following three special conditions: (i) a search
condition authorizing a probation officer to conduct a reasonable
search of Thompson’s “person, property, house, residence, vehicle,
papers, computers, . . . other electronic communications or data
storage devices or media, or office,” upon “reasonable suspicion . . .
that the defendant has violated a condition of his supervision and that
the areas to be searched contain evidence of this violation”;
2 On July 31, 2023, the Probation Office issued an addendum amending the
PSR based on Thompson’s objections. Thompson did not object to the accuracy of
the offense conduct detailed in the PSR, but rather objected that the Probation
Office omitted facts he deemed essential to the district court’s understanding of
his case. That additional information was incorporated into the PSR via the
addendum.

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(ii) compliance with sex offender registration requirements; and
(iii) participation “in a mental health treatment program, which may
include participation in a treatment program for sexual disorders.”3
Probation Sentencing Recommendation at 1.
3 The full text of the special conditions recommended by the Probation
Office is as follows:
The defendant shall submit his person, property, house,
residence, vehicle, papers, computers (as defined in 18 U.S.C.
§ 1030(e)(1)), other electronic communications or data storage
devices or media, or office, to a search conducted by a United States
probation officer. Failure to submit to a search may be grounds for
revocation of release. The defendant shall warn any other
occupants that the premises may be subject to searches pursuant to
this condition. An officer may conduct a search pursuant to this
condition only when reasonable suspicion exists that the defendant
has violated a condition of his supervision and that the areas to be
searched contain evidence of this violation. Any search must be
conducted at a reasonable time and in a reasonable manner.
The defendant shall comply with any applicable state
and/or federal sex offender registration requirements, as instructed
by the probation officer, the Bureau of Prisons, or any state offender
registration agency in the state where he resides, works, or is a
student.
The defendant shall participate in a mental health treatment
program, which may include participation in a treatment program
for sexual disorders, as approved by the U.S. Probation
Department. The defendant shall contribute to the cost of such
services rendered and/or any psychotropic medications prescribed
to the degree he is reasonably able, and shall cooperate in securing
any applicable third-party payment. The defendant shall disclose
all financial information and documents to the Probation

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In his sentencing submission, Thompson objected to the
condition requiring mental health treatment, including “for sexual
disorders,” on the grounds that it was not relevant to his current
offense and that he had no significant mental health history. Dist. Ct.
Dkt. 30 at 3.
On August 7, 2023, Thompson appeared before the district
court for sentencing. Thompson and his counsel affirmed that they
had reviewed and discussed both the PSR and the Sentence
Recommendation. Thompson again told the court that he was
satisfied with his counsel’s representation. After confirming there
were no further objections to the PSR beyond what Thompson had
included in his sentencing submission, the district court adopted the
factual information included in the PSR. In light of the seriousness of
Thompson’s crime, his criminal history, his upbringing, and his
health, the court sentenced Thompson to thirty-seven months in
prison, followed by two years of supervised release.
The court stated it was imposing three special conditions of
supervised release “[g]iven the nature and circumstances of
[Thompson’s] offense, and [his] history and characteristics.” Gov’t
App’x at 88. The court imposed the search condition and sex offender
Department to assess his ability to pay. As part of the treatment
program for sexual disorders, the defendant shall participate in
polygraph examinations and/or visual response testing to obtain
information necessary for risk management and correctional
treatment.
Probation Sentencing Recommendation at 1.

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registration condition largely as written in the Probation Officer’s
Sentence Recommendation. With respect to the mental health
treatment condition to which Thompson had initially objected, the
court indicated that it intended to impose a “more general” mental
health-related condition than the one recommended by the Probation
Office, id. at 50, and imposed the following condition, which made no
mention of sexual disorders:
The defendant shall undergo a mental health evaluation,
and if deemed necessary, participate in a mental health
treatment program as approved by the U.S. Probation
Department. The defendant shall contribute to the cost of
such services rendered and/or any psychotropic
medications prescribe[d] to the degree he is reasonably
able[,] [a]nd shall cooperate in securing any applicable
third-party payment. The defendant shall disclose all
financial information and documents to the Probation
Department to assess his ability to pay.
Id. at 89. The district court asked the parties if there were any
objections to the conditions as imposed. Both said no.
On August 7, 2023, the district court entered a written
judgment, which included the supervised release conditions as
recommended by the Probation Office, except for the mental health
condition, which was imposed as set forth on the record at the
sentencing hearing.
Thompson now appeals his conviction and sentence.

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III. Discussion
On appeal, Thompson argues that the district court
procedurally erred by failing to make an individualized assessment
when imposing the three special conditions of supervised release, and
by failing to state on the record its reasons for imposing those
conditions. Thompson also argues that his counsel before the district
court was ineffective and that his plea was involuntary. He therefore
attempts to raise several challenges to his conviction and sentence,
including that the district court erred in its Guidelines calculation and
that 18 U.S.C. § 922(g)(1) violates the Second Amendment to the
Constitution.
a. Conditions of Supervised Release
We generally “review the imposition of conditions of
supervised release for abuse of discretion.” United States v. Eaglin, 913
F.3d 88, 94 (2d Cir. 2019). When, as here, the defendant does not object
to the conditions before the district court, we review for plain error.
See United States v. Green, 618 F.3d 120, 122 (2d Cir. 2010); see also Fed.
R. Crim. P. 52(b). “Under plain error review, an appellant must
demonstrate that (1) there is an error; (2) the error is clear or obvious,
rather than subject to reasonable dispute; (3) the error affected the
appellant’s substantial rights, which in the ordinary case means it
affected the outcome of the district court proceedings; and (4) the
error seriously affects the fairness, integrity or public reputation of
judicial proceedings.” United States v. Napout, 963 F.3d 163, 183 (2d
Cir. 2020) (internal quotation marks and citation omitted). For the

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reasons set forth below, we hold that the district court committed no
error at sentencing. Accordingly, we need not consider the remaining
three prongs of plain-error review.
“Our caselaw is clear that a district court retains wide latitude
in imposing conditions of supervised release.” United States v. Lewis,
125 F.4th 69, 75 (2d Cir. 2025) (alteration adopted) (internal quotation
marks and citation omitted). “In general, a district court may impose
special conditions of supervised release that are reasonably related to
certain statutory factors governing sentencing, involve no greater
deprivation of liberty than is reasonably necessary to implement the
statutory purposes of sentencing, and are consistent with pertinent
Sentencing Commission policy statements.” United States v. Farooq,
58 F.4th 687, 694 (2d Cir.) (internal quotation marks and citation
omitted), cert. denied, 143 S. Ct. 2677 (2023). Relevant sentencing
factors include “‘the nature and circumstances of the offense and the
history and characteristics of the defendant’; ‘the need for the
sentence imposed to afford adequate deterrence to criminal conduct’;
‘the need to protect the public from further crimes of the defendant’;
and ‘the need to provide the defendant with needed educational or
vocational training, medical care, or other correctional treatment in
the most effective manner.’” United States v. Betts, 886 F.3d 198, 202
(2d Cir. 2018) (quoting U.S.S.G. § 5D1.3(b)). When a fundamental
liberty interest is at stake, the condition is “reasonably necessary only
if the deprivation is narrowly tailored to serve a compelling
government interest.” United States v. Bolin, 976 F.3d 202, 210 (2d Cir.
2020) (internal quotation marks and citation omitted).

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Additionally, “[a] district court is required to make an
individualized assessment when determining whether to impose a
special condition of supervised release, and to state on the record the
reason for imposing it; the failure to do so is error.” Betts, 886 F.3d at
202. “In the absence of such an explanation, we may uphold the
condition imposed only if the district court’s reasoning is self-evident
in the record.” Id. (internal quotation marks and citation omitted).
When the reason for a special condition “is self-evident in the
record . . . and the condition[ ] meet[s] the purposes of supervised
release, any error . . . in this respect is harmless.” United States v. Balon,
384 F.3d 38, 41 n.1 (2d Cir. 2004).
1. Mental Health Treatment Condition
We first consider the district court’s imposition of the mental
health treatment condition. We conclude that Thompson has waived
any challenge to the condition’s imposition. At sentencing, the
district court explained that it planned to impose a more general
mental health treatment condition that (unlike the one recommended
by the Probation Office) made no mention of treatment for sexual
disorders, but before doing so, it directed defense counsel to consult
with his client. Thompson’s counsel then reported that he had spoken
with his client and that Thompson “knows the good in counseling”
and therefore “ha[d] no issue with” what the district court was
“suggesting.” Gov’t App’x at 75. A defendant who expresses
agreement with a special condition of supervised release waives any
challenge to that condition on appeal. See United States v. Spruill, 808
F.3d 585, 597 (2d Cir. 2015) (“[T]his court has recognized waiver

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where a party actively solicits or agrees to a course of action that he
later claims was error.”). Thompson’s consent to the district court’s
proposed special condition in lieu of the condition recommended by
the Probation Office “constitutes a true waiver which . . . negate[s]
even plain error review.” United States v. Quinones, 511 F.3d 289, 321
(2d Cir. 2007) (internal quotation marks and citation omitted).
Even if Thompson’s challenge to the condition had not been
waived but merely forfeited, we identify no error—much less plain
error—because the court’s remarks, in their totality, were sufficient to
satisfy “the requirement that [a] court must conduct an
individualized assessment . . . and must state on the record the reason
for imposing [a special condition].” United States v. Sims, 92 F.4th 115,
126 (2d Cir. 2024). The district court said it was ordering the special
conditions given Thompson’s personal “history and characteristics.”
Gov’t App’x at 88. Just moments earlier, the district court had
highlighted Thompson’s difficult upbringing and background,
stating that “[t]he record reflects the defendant has had struggles
during his life, including from an early age. He has suffered
abandonment and abuse, and I have considered those.” Id. at 85. The
district court went on to tailor the mental health treatment condition,
omitting the Probation Office’s recommended focus on sexual
disorder treatment and instead imposing a more general mental
health treatment program because “[t]hat [could] be very helpful to
[Thompson].” Id. at 74. We have previously stated that “[a] court
may require as a special condition of [supervised release] that a
defendant participate in a mental health program ‘[i]f the court has

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reason to believe that the defendant is in need of psychological or
psychiatric treatment.’” See United States v. Peterson, 248 F.3d 79, 84
(2d Cir. 2001) (third alteration in original) (quoting U.S.S.G.
§ 5B1.3(d)(5)).
Indeed, the record makes clear that the district court was
presented with, and considered, an ample basis for imposing the
mental health treatment condition. Thompson admitted he was
diagnosed with anxiety as a young adult and was prescribed an
antidepressant while serving a sentence for a previous conviction. He
also stated at his plea hearing that he “was at a psych ward for the
state . . . for stress and anxieties.” Gov’t App’x at 13. At sentencing,
in arguing for a downward departure, defense counsel emphasized
Thompson’s “pretty horrible childhood,” stating that “it’s difficult to
imagine a tougher start in life,” id. at 65–66, and urged the court to
consider the emotional and physical abuse Thompson had suffered at
a young age. As noted above, when the court gave Thompson the
opportunity to discuss the mental health treatment condition, defense
counsel stated that “after speaking with Mr. Thompson . . . [h]e knows
the good in counseling, and to what you’re suggesting, he has no issue
with [it].” Id. at 75. Thompson’s own admissions on the record of his
struggles with mental health and his acknowledgment of the benefit
of treatment fully support the district court’s imposition of the
condition. See United States v. Arguedas, 134 F.4th 54, 70 (2d Cir. 2025)
(finding that the reasoning for a mental health treatment condition
was “self-evident in the record” given the defendant’s “history of . . .
struggles with mental health”). Thus, based on Thompson’s

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statements to the Probation Office, at his plea hearing, and at
sentencing, the condition is reasonably related to his history and
characteristics.
2. Search Condition
We next consider the district court’s imposition of the search
condition. As stated above, the court said it was imposing all three
special conditions of supervised release given “the nature and
circumstances of [Thompson’s] offense, and [his] history and
characteristics.” Gov’t App’x at 88. In this case, the court’s remark
adequately demonstrated the district court’s individualized
assessment of the need for the search condition, and explained its
basis for imposing it. As we have previously explained, “[t]he court
[is] under no obligation . . . to pick through every condition and
explain, point-by-point, how each was responsive to the offending
conduct.” United States v. Kunz, 68 F.4th 748, 760 (2d Cir. 2023). “The
specific obligation to state on the record the reason for imposing a
special condition is merely a subset of the broader requirement to
state in open court the reasons for the particular sentence . . . [a]nd
that requirement leaves the appropriateness of brevity or length to the
judge’s own professional judgment.” United States v. Lawrence,
139 F.4th 115, 124 (2d Cir. 2025) (internal quotation marks and
citations omitted); see also United States v. Jenkins, 854 F.3d 181, 194 (2d
Cir. 2017) (“[A] district court is under no obligation to provide
elaborate reasons for the sentence it imposes.”). Just as we have held
that a district court typically need not separately articulate its reasons
for imposing a term of supervised release when it has already

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generally stated its reasons for imposing a term of imprisonment, see
United States v. Williams, 998 F.3d 538, 541–42 (2d Cir. 2021), a district
court generally need not articulate separate reasons for imposing
every single special condition where it has already explained the
overall reasons for its sentencing decision. We therefore conclude
that the district court demonstrated its individualized assessment of
the search condition when it stated that, in imposing these special
conditions, it was taking into account the nature and circumstances of
Thompson’s offense, as well as his history and characteristics—all of
which were laid out in detail in the PSR and sentencing submissions.
See Lawrence, 139 F.4th at 124 n.8 (explaining district court’s reliance
on PSR’s “case-specific reasons” may provide “precisely the type of
individualized assessment our precedent requires”) (internal
quotation marks and citation omitted).
The court’s reliance on these factors was amply supported by
the record here, given Thompson’s history of recidivism and the
nature of his past crimes. The court pointed out that Thompson has
a “serious[,] long and varied criminal history,” which includes
“convictions for rape, attempted rape, forcible touching, robbery and
burglary.” Gov’t App’x at 84. The court noted that despite his prior
“sentences, some lengthy,” Thompson remained undeterred from
committing further crimes, including two crimes that he had
committed more recently. Id. at 84–85. The record also reflects that
Thompson’s attempted rape offense was committed while he was on
parole supervision for his conviction of first-degree rape, casting
additional doubt on his ability to conduct himself in good faith while

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on supervised release. “Under these circumstances, the special search
condition . . . is necessary for ensuring the effectiveness of
supervision.” United States v. Robinson, 134 F.4th 104, 112 (2d Cir.
2025). “[I]t operates as an important means for enforcing the court’s
other conditions and enabling the detection of evidence of supervised
release violations.” Id. For these reasons, we find that the condition
is reasonably related to Thompson’s history and characteristics and
the need for deterrence, and it meets the purposes of supervised
release.
Thompson argues that the breadth of the search condition
imposed here, which includes searches of electronic devices, “cannot
possibly be viewed as in compliance with this Court’s precedents.”
Appellant Br. at 14–15. We disagree. We recently upheld an identical
search condition containing an electronic search provision in United
State v. Robinson. See 134 F.4th at 108, 112. In that case, we held that
despite the district court’s failure to conduct an individualized
assessment when imposing the condition,4 the need for the condition
was self-evident in the record given the defendant’s “criminal history”
and “extensive history of recidivism.” Id. at 111. The imposition of
an identical electronic search provision in this case is therefore
4 In Robinson, we held there were insufficient indicia of an individualized
assessment where the district court said merely that “the special condition of
search is obviously indicated here.” 134 F.4th at 108. In the present case, by
contrast, the district court pointed to several of the § 3553(a) factors as the basis for
imposing the special conditions in question, such as the nature and circumstances
of the offense, as well as Thompson’s history and characteristics. And in context,
as we explain in the text, it was clear which aspects of the record the district court
was referring to, such as Thompson’s recidivism and criminal history.

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entirely appropriate for similar reasons. Additionally, in Robinson we
stated that “the justification for [the] electronic search portion of the
condition would be even more apparent if [the defendant’s]
[underlying or prior] convictions involved sex offenses.” Id. at 112
(referencing U.S.S.G. § 5D1.3(d)(7)(C) (recommending electronic
search conditions for those convicted of sex offenses)). Given
Thompson’s history of sex offenses, we find that in this case the
electronic search provision is especially justified.
Thompson also argues that the search condition implicates
significant liberty interests that the district court failed to consider.
We conclude that this argument, too, is without merit. This Court has
held that “[a] search condition that requires reasonable suspicion
does not implicate . . . a fundamental [liberty] interest” that would
“require narrow tailoring.” Lawrence, 139 F.4th at 125 (internal
quotation marks and citation omitted). Moreover, under the
circumstances of this case, the search condition “involve[s] no greater
deprivation of liberty than is reasonably necessary to implement the
statutory purposes of sentencing.” Lewis, 125 F.4th at 77 (internal
quotation marks and citation omitted). We have made clear that “[a]n
offender on supervised release has a diminished expectation of
privacy that is inherent in the very term ‘supervised release.’” Balon,
384 F.3d at 44 (internal quotation marks and citation omitted). “As
we have repeatedly explained in affirming [similar] search conditions,
th[e]se conditions do not constitute a greater deprivation than
reasonably necessary because they require reasonable suspicion.”
United States v. Oliveras, 96 F.4th 298, 315 (2d Cir. 2024). That the

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search condition here includes an electronic search provision does not
change our analysis. We know of no reason why a limited search
condition would implicate a greater liberty interest because it reaches
a supervisee’s electronic devices in addition to his home and person.
We therefore find that the condition was properly imposed.
We take this opportunity to emphasize again that a district
court can reasonably conclude that such search conditions are
“necessary for ensuring the effectiveness of supervision,” Robinson,
134 F.4th at 112, and that “both electronic and non-electronic search
conditions are often crucial” for doing so, even where the record does
not indicate electronic devices were misused in the underlying crime
of conviction or criminal history, id. at 112 n.4. As we have previously
observed, district courts exercise their discretion to “impose terms of
supervised release in nearly every federal sentence, despite being
required to do so only in certain limited circumstances.” Sims, 92
F.4th at 119–20. This demonstrates a clear consensus amongst the
district courts—who are on the front lines working with released
defendants—that supervised release is essential for “assist[ing]
individuals in their transition to community life.” United States v.
Johnson, 529 U.S. 53, 59 (2000). The courts have an “overwhelming
interest” in monitoring those on supervised release to “reduc[e]
recidivism and thereby promot[e] reintegration and positive
citizenship” among supervisees. Samson v. California, 547 U.S. 843, 853
(2006). We have therefore recognized that in overseeing individuals
on supervised release, probation officers must be given “considerable
investigative leeway,” United States v. Reyes, 283 F.3d 446, 457 (2d Cir.

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2002), because in bringing a supervisee’s offending conduct to the
attention of the court, they act as the “eyes and ears” of the judge, id.
at 455. A search condition, like the one imposed here, can be an
important tool for probation officers to carry out that mandate. To
strike such a condition here would improperly intrude upon the
district court’s broad discretion to determine how best to monitor
Thompson’s adherence to conditions of release and therefore impair
the court’s ability to enforce those conditions.
We also emphasize again the limited nature of the search
condition here. The condition requires that the Probation Office have
(i) reasonable suspicion that Thompson has violated a condition of his
supervised release; and (ii) reasonable suspicion that evidence of that
violation is to be found in one of the specified areas. Both the
justification for the search and the limitation on the search parameters
directly relate to the district court’s need to ensure adequate
supervision of a releasee—the Probation Office can search only those
areas reasonably suspected to be implicated in a possible violation of
the court-imposed conditions of supervised release. See Robinson, 134
F.4th at 113–14 (holding that an identical condition requiring
reasonable suspicion was constitutional given the limitations of the
condition). To constrain the district court to further limit a search
condition to the contours of a defendant’s prior misconduct—and
parse through whether those violations entailed the discovery of
particular evidence in, say, his home versus his phone versus his car
or other property—is unnecessary, given that the search condition as
written already requires reasonable suspicion that evidence of a

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current violation will be found in one of those areas. To conclude
otherwise would undermine the core purposes of supervised
release—“rehabilitation and protecting society from future criminal
violations.” United States v. Knights, 534 U.S. 112, 113 (2001) (emphasis
added).
3. Sex Offender Registration Condition
Finally, with respect to the sex offender registration condition,
we conclude for the same reasons stated above that the district court
made an individualized assessment in imposing the condition and
that this condition, too, is supported by the record. District courts
have broad discretion to impose certain conditions of supervised
release related to a defendant’s sexual behavior even when the
present conviction does not involve a sexual offense. See United States
v. Dupes, 513 F.3d 338, 343–44 (2d Cir. 2008) (upholding conditions
requiring the defendant to, inter alia, attend sex offender treatment
and register as a sex offender where his conviction was for securities
fraud). Here, Thompson had multiple prior convictions for sex
offenses, including rape, attempted rape, and forcible touching.
Thompson does not dispute that the law already requires him to
register as a sex offender on the New York State Sex Offender Registry.
The condition therefore simply requires Thompson to comply with
legal obligations to which he is already subject. It is hardly a
revolutionary proposition to require a supervisee to obey the law.
The condition was therefore entirely appropriate.

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Accordingly, we affirm the district court’s imposition of the
special conditions of supervised release.
b. Ineffective Assistance of Counsel
Thompson contends for the first time on appeal that his trial
counsel was constitutionally ineffective and that his conviction
should therefore be vacated. He argues pro se that trial counsel failed
to raise certain stronger issues over weaker ones, failed to appeal the
denial of his bail application, waived a preliminary hearing, and
failed to object to certain portions of the PSR, even though he twice
confirmed at his plea hearing that he was fully satisfied with his
counsel’s representation.
When an ineffective assistance of counsel claim is raised on
direct appeal, the Court may: (1) decline to hear the claim and permit
the appellant to raise the issue under 28 U.S.C. § 2255; (2) remand to
the district court for necessary factfinding; or (3) decide the claim on
the record before it. United States v. Adams, 768 F.3d 219, 226 (2d Cir.
2014). In general, we have preferred the first option when “there has
been no opportunity to fully develop the factual predicate for the
ineffective assistance of counsel claim.” United States v. Ortiz, 100
F.4th 112, 118 (2d Cir. 2024) (internal quotation marks omitted). Such
claims often cannot “be assessed . . . without [the] benefit of [further]
district court findings” and therefore are “not amenable to
adjudication” on appeal. United States v. Laurent, 33 F.4th 63, 96–97
(2d Cir. 2022).

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Because Thompson did not raise his ineffective assistance claim
in the district court, and did not submit to this Court the transcript of
the proceeding denying his application for bail, “there is no[t a
sufficient] record that would permit [it] to be assessed on this appeal.”
Id. at 97. His arguments are based primarily on his attorney’s strategic
decisions, such as the decision to waive preliminary hearings or
advance certain arguments. But the record tells us nothing about why
counsel made those choices, much less why they could be considered
deficient or prejudicial in any way. We therefore decline to adjudicate
the claim on this appeal. Thompson is free to raise the claim in the
district court—which is “best suited to developing the facts necessary
to determining the adequacy of representation”—through a motion
under 28 U.S.C. § 2255. Massaro v. United States, 538 U.S. 500, 505
(2003).
c. Appellate Waiver
Thompson raises additional pro se challenges to his sentence
and conviction, including that the district court erred in its Guidelines
calculation and that § 922(g)(1) violates the Second Amendment. The
valid appeal waiver in this case, see supra n.1, requires that we dismiss
these challenges.
“This Court has repeatedly held that a knowing and voluntary
waiver of the right to appeal a sentence is presumptively enforceable.”
United States v. Ojeda, 946 F.3d 622, 629 (2d Cir. 2020). “[T]he
exceptions to this rule occupy a very circumscribed area of our
jurisprudence.” United States v. Borden, 16 F.4th 351, 354–55 (2d Cir.

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2021) (internal quotation marks and citation omitted). In certain cases,
“a defendant may have a valid claim that the waiver of appellate
rights is unenforceable, such as [1] when the waiver was not made
knowingly, voluntarily, and competently, [2] when the sentence was
imposed based on constitutionally impermissible factors, such as
ethnic, racial or other prohibited biases, [3] when the government
breached the plea agreement, or [4] when the sentencing court failed
to enunciate any rationale for the defendant’s sentence, thus
amounting to an abdication of judicial responsibility subject to
mandamus.” United States v. Gomez-Perez, 215 F.3d 315, 319 (2d Cir.
2000) (alteration adopted) (internal quotation marks and citations
omitted).
Thompson argues that his plea was unknowing because the
district court failed to inform him that to prosecute under § 922(g)(1)
and § 924(a)(2), the government would have to prove not only that
Thompson knew he possessed a firearm, but also that he knew he was
a felon at the time he committed the offense. See Rehaif v. United States,
588 U.S. 225, 237 (2019). Federal Rule of Criminal Procedure
11(b)(1)(G) requires the district court to “inform the defendant of,”
and ensure “that the defendant understands, . . . the nature of each
charge to which the defendant is pleading.” A district court’s failure
“to comply with the important strictures of Rule 11” may render an
appellate waiver unenforceable. United States v. Lloyd, 901 F.3d 111,
118 (2d Cir. 2018). Where, as here, a defendant alleges a violation of
Rule 11 but did not object to the violation at the time of the plea, this
Court reviews the alleged violation for plain error under Rule 52(b).

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United States v. Cook, 722 F.3d 477, 481 (2d Cir. 2013). “In assessing the
likely effect of a Rule 11 error, we are to examine the entire record.”
United States v. Torrellas, 455 F.3d 96, 103 (2d Cir. 2006).
We find that the district court met its obligations under Rule 11
and sufficiently informed Thompson of the elements of his crime. The
magistrate judge explicitly stated to Thompson at his plea hearing
that in addition to proving that he “knowingly possessed the firearm
and ammunition as charged in the indictment,” “the government
would [also] have to prove that [Thompson was] convicted in any
court of a crime punishable by imprisonment for a term exceeding
one year and that [he] knew [he] had been convicted of such a crime.”
Gov’t App’x at 17 (emphasis added). The magistrate judge then asked
Thompson if he understood its explanation of the elements of the
crime and the government’s burden of proof, to which Thompson
confirmed that he did. Moreover, the magistrate judge confirmed
Thompson “fully discussed [with counsel] the charge in the
indictment,” id. at 16, which states that Thompson was charged with
possessing a firearm and ammunition while “knowing that he had
previously been convicted . . . of one or more crimes” constituting a
felony, App’x at 10 (emphasis added). The record therefore reflects
that the district court ensured Thompson understood the elements of
the crime and entered into the guilty plea knowingly and voluntarily.

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We conclude that the plea agreement therefore bars
Thompson’s remaining challenges to his sentence and conviction.5
His constitutional claim and challenge to the district court’s
Guidelines calculation are explicitly barred by the language of the
appellate waiver, which states that Thompson “agrees not to file an
appeal or otherwise challenge . . . [his] conviction or sentence”
including by raising “any argument that . . . the statutes to which [he]
is pleading guilty are unconstitutional.” Gov’t App’x at 3; see also Cook
v. United States, 84 F.4th 118, 125 (2d Cir. 2023) (holding that a valid
waiver precludes a post-conviction claim that a defendant’s
conviction was predicated on an unconstitutional statute). Though
we have left open the question of whether a defendant can challenge
the constitutionality of his conviction on appeal notwithstanding a
waiver in the rare circumstance when there has been a “complete
miscarriage of justice,” Cook. 84 F.4th at 125 n.4 (internal quotation
marks and citation omitted), there has been no miscarriage of justice
here. Thompson argued before the district court that § 922(g)(1) was
unconstitutional pursuant to New York State Rifle & Pistol Association
v. Bruen, 597 U.S. 1 (2022). But the Supreme Court issued its decision
in Bruen on June 23, 2022, almost a year before Thompson pled guilty
to the instant offense and the district court accepted his plea.
Thompson thus had an adequate opportunity to plead not guilty or
5 To the extent Thompson attempts to argue that the district court lacked
jurisdiction because he is a “sovereign citizen” or because his case was improperly
removed from state court to federal court, any such arguments are meritless.
Thompson has been charged with a crime under federal law, 18 U.S.C. § 922(g)(1),
and federal district courts “have original jurisdiction, exclusive of the courts of the
States, of all offenses against the laws of the United States,” 18 U.S.C. § 3231.

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withdraw his guilty plea before the court based on a challenge under
Bruen. And in any case, his argument would be foreclosed by our
Court’s recent decision in Zherka v. Bondi, 140 F.4th 68 (2d Cir. 2025),
which rejected an identical argument and upheld the constitutionality
of § 922(g)(1). The claims are therefore barred.
IV. Conclusion
In sum, we hold as follows:
1. Thompson’s consent to the mental health treatment
condition waives any challenge to that condition on appeal.
2. The district court’s explanation that it was imposing the
special conditions given the nature and circumstances of
Thompson’s offense, as well as his history and
characteristics, manifested both an individualized
assessment of the need for each condition and a statement
of its reasons for their imposition. The district court
therefore did not procedurally err in imposing the
conditions.
3. The district court’s reasons for imposing the conditions
were amply supported by the record.
4. The district court was not required to justify the inclusion of
a particular place or thing under the defendant’s custody or
control in the search condition, where the condition requires
reasonable suspicion that the defendant has violated a
condition of his supervised release and that evidence of a
violation would be found there.

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5. We decline to consider Thompson’s claim of ineffective
assistance of counsel, which is raised for the first time on
appeal.
6. The district court ensured that Thompson’s plea was
voluntary and knowing, and consequently his remaining
challenges to his conviction and sentence are barred by the
appellate waiver in his plea agreement.
Accordingly, we AFFIRM the district court’s judgment.

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