25-599
United States v. Stuart
United States Court of Appeals
For the Second Circuit
August Term 2025
Argued: February 27, 2026
Decided: September 3, 2026
No. 25-599
UNITED STATES OF AMERICA,
Appellee,
v.
JESSICA STUART,
Defendant-Appellant.
Appeal from the United States District Court
for the District of Connecticut
No. 03:21-cr-00083
Sarala V. Nagala, Judge.
Before: LOHIER, Chief Judge, JACOBS and SACK, Circuit Judges.
Defendant-Appellant Jessica Stuart appeals from a judgment entered in the United States District Court for the District of Connecticut (Nagala, J.), sentencing her for a violation of supervised release and imposing a new special condition of supervised release. That condition authorizes the Probation Office “to notify third parties, to whom [Stuart] may present a risk including employers and potential employers, of [Stuart’s] criminal history and past criminal conduct.” App’x 164. On appeal, Stuart contends that the district court improperly delegated its authority to the Probation Office by vesting it with sole discretion to determine who qualifies as a third party to whom Stuart presents a risk. AFFIRMED.
JOHN J. STICKNEY, Assistant Federal Defender, for Terence
S. Ward, Federal Defender, District of Connecticut,
Hartford, CT, for Defendant-Appellant.
DAVID T. HUANG (Elena Lalli Coronado, on the brief),
Assistant United States Attorneys, for David X. Sullivan,
United States Attorney for the District of Connecticut,
New Haven, CT, for the United States of America.
DENNIS JACOBS, Circuit Judge:
Inevitably there is play in the joints as one distinguishes
between [1] the permissible implementation by the Probation Office
of a judicially imposed condition and [2] the impermissible
imposition of a condition by the Probation Office itself.
2
Defendant-Appellant Jessica Stuart appeals from a judgment
entered in the United States District Court for the District of
Connecticut (Nagala, J.), sentencing her on violations of supervised
release and imposing a new special condition of supervised release.
That condition authorizes the Probation Office “to notify third
parties, to whom [Stuart] may present a risk including employers and
potential employers, of [Stuart’s] criminal history and past criminal
conduct.” App’x 164 (emphasis added). 1 The issue is whether the
district court thus improperly delegated its authority to the
Probation Office by vesting it with (as Stuart contends) “sole
discretion in determining who qualifies as” a third party to whom
Stuart presents a risk. Appellant’s Br. 13.
1The condition further provides as follows: “The probation officer is authorized to obtain employment information from any employer, including job application and payment records. You must execute any releases necessary for your employer to release this information to Probation.” Stuart does not challenge this portion of the condition. Appellant’s Reply Br. 1–2.
3
We AFFIRM. The district court sufficiently cabined the
discretion of the Probation Office to prevent it from exercising
authority reserved to the judiciary or wielding authority arbitrarily.
Although the condition as written is expansive, it is
permissible nevertheless because Stuart’s conduct presents variable
risks. A judge is not in the position to gauge these risks in real time
and therefore must delegate to the Probation Office supervision and
execution of the sentence. The court took account of Stuart’s
offenses, their number and variety, and the means used to commit
them. More particular instructions to the Probation Office cannot
easily be formulated, and if formulated, could be evaded by a
person who, like Stuart, acts opportunistically.
The account of offenses that follows is offered to illustrate the
point.
4
I
A. The Underlying Offense and Initial Sentence
This case began in spring 2019, when Stuart obtained
employment under false pretenses. She held herself out as a BoardCertified Behavioral Analyst (“BCBA”) and purported to render
applied behavioral analysis (“ABA”) services to children diagnosed
with autism spectrum disorder, and to their families. Stuart, who
was not a BCBA, impersonated a real one, whose name and
credentials she appropriated.
Stuart collected at least $143,000 in pay from the service
provider that employed her, and caused her employer to submit
$369,439.96 in fraudulent claims to Medicaid, which requires that
treatments be given by licensed practitioners.
When questioned in November 2020 by investigating agents
of the Federal Bureau of Investigation and Department of Health
and Human Services Office of the Inspector General, Stuart admitted
5
that she was not a BCBA and had impersonated a real one. She
pleaded guilty in June 2021 to one count of health care fraud in
violation of 18 U.S.C. § 1347 and one count of using false
identification in connection with another crime in violation of 18
U.S.C. § 1028(a)(7), (b)(1)(D), and (c)(3)(A). Addressing Stuart at
sentencing in October 2021, Judge Meyer, to whom the case was
then assigned, located Stuart’s criminal conduct within a broader
“pattern” of apparent “fundamental dishonesty.” Gov’t App’x 68–
69.
Stuart had previously been convicted of other crimes,
including issuing a bad rent check in 2018 for nearly $2,500.
In 2019, Stuart moved temporarily into the home of an 89-year-old woman, whose dogs Stuart was previously hired to walk.
The woman’s daughter, who lived on the premises, noticed that
jewelry and cash were missing, that unauthorized transactions were
charged to a bank card which had also gone missing, and that $15
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checks for dog-walking had been doctored to pay Stuart
considerably larger amounts. The daughter told police that, though
Stuart had claimed to work at a nearby school, a school
administrator told her that the (fortunate) school had decided not to
hire her because of her questionable professional background.
Stuart was thereafter convicted of forgery and larceny.
Separate conduct in 2019 led to yet another larceny conviction.
Another roommate of Stuart’s, who also shared an address with her
mother, reported to police that her mother’s property started
disappearing after Stuart helped clean her mother’s bedroom. The
roommate also reported finding her purse in Stuart’s car, along with
jewelry belonging to the roommate and her mother.
The court sentenced Stuart to 27 months’ incarceration and
three years’ supervised release.
B. Supervised Release Violations
Stuart was released from prison and began her term of
supervised release on December 1, 2023. Within a year, the
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government petitioned for a compliance review hearing because, it
asserted, Stuart violated two conditions of supervised release. It
represented that Stuart failed to make court-ordered restitution
payments and had moved to a new residence without notifying the
Probation Office or securing its approval.
Stuart was again arrested in January 2025. While working at
an organization providing services to people with disabilities, Stuart
had twice used a food stamp card taken from one of the residents to
run up more than $1,600 in charges. She had applied for this job by
using permutations of her name and misrepresenting her
employment history. Police initially interviewed Stuart about the
matter months before her eventual arrest, and she violated the
condition requiring her to report such a contact with police.
The government accordingly filed a petition alleging
violations of Stuart’s supervised release terms and moved to detain
her pending further proceedings. Stuart’s counsel instead raised the
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prospect of a new condition designed to address “further deception
with employment,” Gov’t App’x 152, under which employers would
be notified of Stuart’s criminal history. The court ordered Stuart
detained pending further proceedings.
The government later learned that Stuart had continued
collecting unemployment checks for weeks after securing
employment, and that she had previously secured a position (with
yet another employer) which she obtained by using a modification
of her legal name to bypass a background check.
Stuart was ultimately charged with three supervised release
violations, two for committing other crimes (food stamp and
unemployment frauds), and one for failing to notify the Probation
Office that she had been questioned by the police. Stuart admitted
to the third charge; Judge Nagala, to whom the case had by then
been assigned, found the first two by a preponderance of the
evidence.
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C. The Special Condition
The government sought a sentence of seven to ten months’
imprisonment, as well as the imposition of a new condition of
supervised release authorizing the Probation Office “to notify third
parties, including employers and potential employers, of [Stuart]’s
criminal history.” App’x 61. The probation officer proposed that
the condition require notification of Stuart’s personal history and
characteristics in addition to her criminal history. Stuart’s counsel
raised two objections.
[1] While conceding that a condition requiring Stuart to
“notify[] potential employers of her criminal history” would be
“incredibly . . . useful,” counsel objected that the expanded notice
about her characteristics and personal history would be overly
broad. App’x 105–06; see also App’x 108. The government agreed
that “the main thing is really her criminal history.” App’x 131–32.
[2] Stuart’s counsel also objected that the inclusion of “third
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parties” appeared “overly broad” since it was unclear “what a third
party would mean under that condition.” App’x 139. At the court’s
request, the probation officer explained that third parties included
only people in roles that would put them at risk of Stuart’s conduct:
A vulnerable person who hired Stuart or let her into their home
would be notified, while a friend of Stuart’s would not.
The court then proposed a revised condition authorizing the
Probation Office “to notify third parties . . . to whom Ms. Stuart may
present a risk, including employers and potential employers, of Ms.
Stuart’s criminal history and past criminal conduct.” App’x 142.
Stuart’s counsel asked that the condition be limited to people Stuart
lives with or to employers. The court ruled that doing so would
render the condition underinclusive; if for example Stuart started
her own business, the condition would not apply to “children or
other patients” to whom she provided services. App’x 143.
Acknowledging “some ambiguity” regarding “to whom Ms. Stuart
11
may present a risk,” the court “trust[ed] that the probation office
will use good judgment in determining who those people are.”
App’x 143.
Ultimately, the court imposed the following condition: “The
U.S. Probation Office is authorized to notify third parties, to whom
you may present a risk including employers and potential
employers, of your criminal history and past criminal conduct.”
App’x 164.
The court explained that this condition was “necessary in
order to ensure that anyone who hires Ms. Stuart is aware of her
criminal history and can make appropriate modifications to her job
responsibilities or otherwise just at least be on notice of them . . . .”
App’x 152. It reflected “the minimal condition necessary to ensure
that those with whom Ms. Stuart may come in contact and to whom
she poses a risk because of her criminal history can go in eyes wide
open as to her past criminal conduct.” App’x 154.
12
The court imposed this condition along with a sentence of ten
months’ incarceration and an additional two years’ supervised
release. Stuart was released from custody on September 19, 2025.
II
As a threshold matter, the government contends that Stuart’s
challenge to the condition is not fully ripe. Although it concedes
ripeness insofar as the condition authorizes notification to
employers, potential employers, people Stuart lives with, and
patients or customers she may serve if she becomes self-employed,
the government disputes ripeness as it applies to notification to any
other potential third party. But this approach recognizes as ripe
only delegation challenges that would be defeated.
“Ripeness is a constitutional prerequisite to the exercise of
jurisdiction by federal courts.” United States v. Traficante, 966 F.3d
99, 106 (2d Cir. 2020) (alteration adopted and citation omitted). “The
ripeness doctrine springs from both Article III limitations on judicial
13
power and prudential concerns about avoiding premature judicial
interference in an evolving situation.” United States v. VillafaneLozada, 973 F.3d 147, 150 (2d Cir. 2020). Thus, federal courts avoid
entanglement in abstract disputes over matters “that are premature
for review because the injury is merely speculative and may never
occur.” United States v. Fell, 360 F.3d 135, 139 (2d Cir. 2004) (citation
omitted).
“In addressing any and all ripeness challenges, courts are
required to make a fact-specific determination as to whether a
particular challenge is ripe by deciding whether (1) the issues are fit
for judicial consideration, and (2) withholding of consideration will
cause substantial hardship to the parties.” United States v. Balon, 384
F.3d 38, 46 (2d Cir. 2004) (alteration adopted) (quoting United States
v. Quinones, 313 F.3d 49, 58 (2d Cir. 2002)).
“[W]hen a challenge to a condition of supervised release
involves a pure question of law, we regularly allow that challenge to
14
proceed years or even decades before the defendant begins his term
of supervision,” United States v. Salvador, 180 F.4th 470, 476 (2d Cir.
2026) (internal quotation marks and citation omitted), so long as “the
delegation is not conditioned on future events.” Villafane-Lozada, 973
F.3d at 152. That is because the court has already delegated the
challenged authority to the probation officer, and future events
would not change our analysis. See id. at 151–52. Accordingly,
arguments that conditions vest impermissible discretion in a
probation officer are generally ripe. Id. “We do not need to know
anything about how the condition will actually be operationalized”
to resolve such challenges; “[w]e just need the words on the page.”
Salvador, 180 F.4th at 477.
We have occasionally dismissed challenges to special
conditions as unripe when those challenges depend on the future
state of a rapidly evolving technology that will be used to effectuate
the condition. Id. at 476. But Stuart is “challenging the already
15
realized delegation of judicial power to a probation officer, not some
hypothetical decision that this delegation might allow in the future.”
Villafane-Lozada, 973 F.3d at 151.
The government relies on United States v. Traficante, in which
we ruled unripe a challenge to a standing order that replaced in all
judgments a prior standard risk condition with a new one. 966 F.3d
at 104, 106–07. The new condition authorized risk notification only
if the district court determined in consultation with the probation
officer that the defendant posed a risk of further offenses, which
might never happen. Id. at 104, 107. And even if it made that
determination, the district court could itself require the defendant to
notify the at-risk individual or order the probation officer to require
the defendant to do so. Id. at 107. “In either scenario, the probation
officer would lack discretion over whether to impose a notification
obligation.” Id. Because “the ostensibly improper delegation may
never actually occur,” we concluded that the defendant’s challenge
16
was unripe. Id. at 106–07.
We have distinguished Traficante when, as here, the delegation
“has already occurred and is not contingent on future judicial
action.” Villafane-Lozada, 973 F.3d at 151. Stuart’s challenge
implicates the probation officer’s “already-granted authority” to
notify certain categories of people to whom she presents a risk,
rather than any choice to notify a particular person at a particular
time. Id. “That delegation was either proper or not — and its
propriety does not depend on how (or even whether) the probation
officer might later choose to wield the delegated power.” Id.
(quoting United States v. Cabral, 926 F.3d 687, 696 (10th Cir. 2019)); see
also United States v. Jimenez, 175 F.4th 341, 354 (2d Cir. 2026)
(“Villafane-Lozada directs our attention to whether a challenge hinges
on a ‘hypothetical’ situation that may or may not occur, or on the
plain terms of the condition itself.”). Addressing the propriety of
this already-realized delegation now rather than later avoids
17
hardship for Stuart and the government alike. Stuart’s delegation
challenge is therefore ripe.
III
Operating in the field, a probation officer can take account of
risks that a judge is in no position to monitor; and the scope of
delegation may properly be expanded when, as here, the
defendant’s risk-creating conduct is especially opportunistic and
creative.
We review the imposition of a condition of supervised release
for abuse of discretion. United States v. MacMillen, 544 F.3d 71, 74
(2d Cir. 2008). When such a challenge raises an issue of law, “we
review the imposition of that condition de novo, bearing in mind that
any error of law necessarily constitutes an abuse of discretion.” Id.
at 74–75. We may construe the condition’s terms “in a manner that
avoids the problematic implications that might be suggested by an
18
aggressively literal reading of their text.” United States v. Kunz, 68
F.4th 748, 761 (2d Cir. 2023); see also id. at 764–65.
Stuart’s challenge concerns one issue: the district court’s
delegation of third-party risk notification authority to the Probation
Office. 2 “[T]here are limits on a [d]istrict [c]ourt’s ability to delegate
judicial authority to a probation officer.” United States v. Young, 910
F.3d 665, 669 (2d Cir. 2018). They are rooted in the principle that
“[t]he power to impose special conditions of supervised release . . . is
vested exclusively in the district court.” United States v. Matta, 777
2 Stuart does not challenge the condition insofar as it authorizes the
Probation Office to notify employers of criminal history and criminal conduct other than her offense of conviction. We accordingly do not reach the question whether such a condition is an “occupational restriction” that must be specifically “based on the offense of conviction.” United States v. Peterson, 248 F.3d 79, 85 (2d Cir. 2001) (per curiam). Compare id. at 85–86 (vacating condition insofar as it required notification of offenses other than the instant offense of conviction, citing 18 U.S.C. § 3563(b)(5) and U.S.S.G. § 5F1.5(a)(1), which require occupational restrictions to be “based on the offense of conviction”) with United States v. Brown, 173 F.4th 45, 51 (2d Cir. 2026) (“[S]ince Peterson, we have upheld employer-notification requirements without subjecting them to the special requirements for occupational restrictions.”).
19
F.3d 116, 122 (2d Cir. 2015). Consequently, “the extensive
supervision mission of federal probation officers includes executing
the sentence but not imposing it.” Kunz, 68 F.4th at 765 (citation
omitted); see also United States v. Franklin, 838 F.3d 564, 568 (5th Cir.
2016) (“The imposition of a sentence, including the terms and
conditions of supervised release, is a core judicial function that
cannot be delegated.” (internal quotation marks and citation
omitted)).
The question becomes whether a district court has crossed the
line of permissible delegation by giving a probation officer the
power to impose a condition, rather than merely execute one. A
court crosses this line when it delegates “authority which would
make a defendant’s liberty itself contingent on a probation officer’s
exercise of discretion,” Matta, 777 F.3d at 122, since doing so is
“tantamount to allowing the probation officer to decide the extent of
the defendant’s punishment — authority reserved exclusively for
20
the district court.” United States v. Carlineo, 998 F.3d 533, 537–38 (2d
Cir. 2021); see Matta, 777 F.3d at 122–23.
The government, in passing, expresses doubt that this
condition implicates a protected liberty interest. But we need not
resolve the question. Stuart contends that the district court gave
Probation powers that we have prohibited district courts from
delegating. See MacMillen, 544 F.3d at 76–78; United States v.
Peterson, 248 F.3d 79, 85–86 (2d Cir. 2001) (per curiam); United States
v. Boles, 914 F.3d 95, 110–12 (2d Cir. 2019). Regardless of whether
these cases [1] establish that third-party risk-notification conditions
like this one implicate a liberty interest or [2] impose limits on
delegation in this context for another reason, we remain bound by
them. The government does not argue otherwise, opting instead to
“assum[e] arguendo that notification implicates a protected liberty
interest.” Appellee’s Br. 43.
To determine whether a district court impermissibly
21
delegated judicial power, we ask whether the court left a condition’s
implementation to the officer’s “unfettered discretion.” See Peterson,
248 F.3d at 86; MacMillen, 544 F.3d at 77; Boles, 914 F.3d at 112.
In United States v. Peterson, we remanded for clarification of
two conditions of supervised release that concerned third-party risk
notification. 248 F.3d at 85–86. A challenged standard condition
provided for notice, “as directed by the probation officer,” to “third
parties of risks that may be occasioned by the defendant's criminal
record or personal history or characteristics.” Id. at 85 (second
emphasis added). A related special condition granted the probation
officer discretion to determine, “due to the defendant’s criminal
history and/or offense conduct,” whether “a third-party risk
notification may be required. If required, the defendant must notify his
employer of his conviction and/or criminal history.” Id. (emphasis
added).
Because “the court must determine, rather than leaving to the
22
discretion of the probation officer, whether such notification is
required,” we remanded for the district court to clarify whether
notification was mandatory. Id. at 86. And if the court on remand
believed notification should only be mandatory “for certain types of
employment but not others,” it could “specify guidelines to direct
the probation officer,” but could not “simply leave the issues of
employer notification to the probation officer’s unfettered
discretion.” Id.
Similarly, in United States v. Boles, we vacated a condition
requiring the defendant to give notice “[i]f the probation officer
determines that [he] pose[s] a risk to another person . . . .” 914 F.3d
at 110–11. Because the condition gave the probation officer
“unfettered discretion with respect to the [employer] notification
requirement,” it was “largely indistinguishable” from the condition
we vacated in Peterson. Id. at 112.
But we upheld a similar condition in United States v.
23
MacMillen. 544 F.3d at 76–78. The defendant was convicted of
possessing computerized images of child pornography accessed via
the internet; a special condition “authorize[d] the probation office to
address third-party risk issues [with] the Defendant’s employers.”
Id. at 73–74 (alterations in original). The district court at sentencing
explained that since employers often provide access to computers, it
was important to ensure that the defendant’s employers
“underst[oo]d the potential risks.” Id. at 74.
MacMillen distinguished Peterson because the condition was
limited to specific types of employment, and the nature of the
offense provided the probation officer with sufficient guidance to
identify risk. Id. at 77–78. While the district court in Peterson
“provided no guidance to Probation as to what types of employment
might require risk notification,” the district court in MacMillen tied
the defendant’s “risk issues” to jobs where the defendant could
access computers. Id. at 77. And the child pornography offense
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“adequately inform[ed] Probation” of the relevant risk; notification
was required when the defendant could access child pornography
on a work computer. Id. So when considering “whether and in
what situations an employer should be informed” of the conviction,
the probation officer would not “be operating in a vacuum.” Id.
In essence, we ask whether the probation officer “is equipped
with a standard of decision that constrains its discretion and avoids
arbitrary use of its delegated authority.” Kunz, 68 F.4th at 766.
Here, the district court sufficiently cabined the probation
officer’s discretion. It adequately defined the risks Stuart poses and
therefore gave the probation officer sufficient guidance to identify
the people subject to them. In context, the “risk” is that Stuart will
engage in opportunistic fraud and larceny that fits no pattern, at the
expense of anyone in her orbit to whose property she enjoys access.
The district court explained as much when it articulated the need for
those “to whom she poses a risk because of her criminal history” to “go
25
in eyes wide open as to her past criminal conduct.” App’x 154
(emphasis added).
Stuart acted by impersonation, false credentials,
misrepresentations of her history and name, doctored instruments,
food stamp fraud and unemployment fraud, stealing a bank card,
pilfering from hosts, and purloining a purse. She stole from a
landlord, her roommates, her roommates’ families, the government,
large institutions, and vulnerable individuals alike, in amounts large
and small.
That criminal history and conduct also make clear enough the
wide categories of people endangered and the risks they face. They
include, as the district court explained, employers and potential
employers, people Stuart lives with, and people to whom Stuart may
provide services if self-employed. Given Stuart’s range and pattern
of similar criminal conduct, the district court gave the probation
officer as much guidance as the defendant’s protean offenses
26
allowed, without imposing parameters that create means of evasion.
The probation officer is free in these circumstances to identify new
areas in which this judicially defined risk may materialize, even
though the district court could not enumerate every opportunity for
fraud and larceny that may present itself; a judge, who is not in the
field, cannot be expected to do so.
The district court sufficiently defined the risks posed by Stuart
and found it necessary to notify third parties of them. It determined
that third-party notification was warranted and identified the class
of vulnerable people requiring such notice. The Probation Office’s
remaining task is to identify instances where that risk materializes
on the ground. That function is more akin to “executing” the
condition than “imposing it.” Kunz, 68 F.4th at 765 (citation
omitted).
For the foregoing reasons, we AFFIRM the judgment of the
district court.
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