and 23-1319 UNITED STATES OF AMERICA v. Anthony F. D’ambrosio

PRECEDENTIAL
UNITED STATES COURT OF APPEALS
FOR THE THIRD CIRCUIT
____________
Nos. 23-1310 and 23-1319
____________
UNITED STATES OF AMERICA
v.
ANTHONY F. D’AMBROSIO,
Appellant in 23-1310
UNITED STATES OF AMERICA
v.
ARMANDO ENRIQUE DELGADO,
Appellant in 23-1319
On Appeal from the United States District Court
for the Middle District of Pennsylvania
(District Court Nos. 1-15-cr-00003-002; 1-15-cr-00003-004)
District Judge: Honorable Christopher C. Conner
__________

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Argued on January 31, 2024
Before: CHAGARES, Chief Judge, RESTREPO and
FREEMAN, Circuit Judges
(Filed: June 26, 2024)
Patrick J. Bannon [Argued]
OFFICE OF THE U NITED STATES A TTORNEY
Middle District of Pennsylvania
235 North Washington Avenue
P.O. Box 309, Ste. 311
Scranton, PA 18503
Carlo D. Marchioli
OFFICE OF THE U NITED STATES A TTORNEY
1501 N ORTH 6TH STREET , 2ND FLOOR
P.O. BOX 202
H ARRISBURG , PA 17102
Counsel for Appellee
Edward J. Rymsza, III [Argued]
M IELE & RYMSZA
125 East Third Street
Williamsport, PA 17701
Counsel for Appellant D’Ambrosio

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Frederick W. Ulrich [Argued]
O FFICE OF THE FEDERAL PUBLIC D EFENDER
100 Chestnut Street, Ste. 306
Harrisburg, PA 17101
Counsel for Appellant Delgado
_________
OPINION OF THE COURT
_________
RESTREPO, Circuit Judge.
A sentencing judge bears the responsibility of depriving
or limiting a person’s liberty by ordering a period of
incarceration or probation. To assist with reintegration into
society after a custodial sentence, that judge can also impose
conditions of supervised release. Because a sentencing judge
imposes these conditions, a sentencing judge must also be
permitted to amend them. Accordingly, and for the following
reasons, we hold that a district court has the authority to modify
an arguably unlawful condition of supervised release raised in
a motion pursuant to 18 U.S.C. § 3583(e)(2) when properly
challenged below.
I.
From 2012 through 2015, a man named Albert Martinez

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operated a sex trafficking ring out of the Middle District of
Pennsylvania that spanned various states including Rhode
Island, New York, Pennsylvania, Maryland, Virginia, West
Virginia, Georgia, and Florida. Appellants Anthony
D’Ambrosio and Armando Delgado worked for Martinez in
various roles: transporting women and girls across state lines,
collecting money, providing security, and supplying drugs to
the victims.
In March 2015, a federal grand jury indicted Delgado
and D’Ambrosio, as well as others involved in the
organization, for their involvement in the sex trafficking
business.1 A jury convicted both Delgado and D’Ambrosio in
1 The seven-count Superseding Indictment charged Delgado
and D’Ambrosio with the following crimes:
(1) Sex Trafficking of Children [18 U.S.C. §
1591(a)];
(2) Transportation of an Individual to Engage in
Prostitution [18 U.S.C. § 2421(a)];
(3) Transportation of a Minor to Engage in
Prostitution [18 U.S.C. § 2423(a)];
(4) Conspiracy to Transport an Individual to
Engage in Prostitution [18 U.S.C. § 371];
(5) Conspiracy to Transport a Minor to Engage
in Prostitution [18 U.S.C. § 2423(a)];
(6) Conspiracy to Distribute and Possess with
Intent to Distribute Oxycodone, Cocaine,
Heroin, and Marijuana [21 U.S.C. § 846]; and
(7) Distribution and Possession with Intent to
Distribute Oxycodone [21 U.S.C. § 841(a)(1)].

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December 2017,2 and the two subsequently filed post-trial
motions.3 In May and July of 2019, respectively, United States
Probation prepared Presentence Investigation Reports for
D’Ambrosio and Delgado, which recommended both men
comply with the requirements of 34 U.S.C. § 20901, the Sex
Offender Registration and Notification Act (“SORNA”), as a
condition of supervised release. Sex offender registration is
triggered by an individual’s conviction for a sex offense.4 A
2 At the conclusion of the Government’s case, the Government
voluntarily dismissed Count 3, Transportation of a Minor to
Engage in Prostitution [18 U.S.C. § 2423(a)], for both
defendants.
3 Delgado and D’Ambrosio each filed a motion for judgment
of acquittal and a motion for a new trial. On the motions for
judgment of acquittal, the District Court vacated the
convictions on Count One, and entered judgment of acquittal
on Count Five. The District Court denied both motions for a
new trial. Thus, Delgado and D’Ambrosio stood convicted of
Count Two, Transportation of an Individual to Engage in
Prostitution [18 U.S.C. § 2421(a)], Count Four, Conspiracy to
Transport an Individual to Engage in Prostitution [18 U.S.C. §
371], and Counts Six and Seven, two controlled substances
violations.
4 A “sex offense” is defined as a criminal offense that (1) has
an element involving a sexual act or sexual contact with
another; (2) a criminal offense that is a specified offense
against a minor; (3) a federal offense under 18 U.S.C. § 1591,
or Chapters 109A, 110, or 117; (4) a military offense specified
by the Secretary of Defense; or (5) an attempt or conspiracy to
commit any of the aforementioned offenses. See 34 U.S.C. §
20911(5)(A).

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district court must decide, as a matter of law, if that person’s
conviction qualifies as a sex offense for purposes of imposing
SORNA. United States v. Icker, 13 F.4th 321, 330 (3d Cir.
2021) (holding that 18 U.S.C. § 3583(d) requires the court to
first determine whether the person has been convicted of a sex
offense as defined in 34 U.S.C. § 20911(5)(A)).
A.
At his sentencing in July 2019, Delgado objected to the
imposition of SORNA registration as a condition of his
supervised release. He argued that his offenses of conviction
did not require SORNA registration.5 The District Court
acknowledged that neither the court, counsel, nor Probation
knew whether the SORNA requirement applied to Delgado’s
offenses. As a result, the District Court delegated that
determination to Probation, noting that
we need to further investigate whether your
offenses of conviction are qualifying offenses,
and frankly at this juncture we simply don’t
know, but that is a matter for probation to
determine and you will obviously be apprised of
any registration requirements when you begin to
report to the probation office.
J.A. 81.
Delgado filed a direct appeal to this Court in August
2019, appealing his judgment of conviction and sentence. We
affirmed. United States v. Delgado, 827 F. App’x 180, 183 (3d
Cir. 2020). As to Delgado’s claim that the District Court
5 Delgado argued that his conviction fails to qualify due to an
exception for consensual sex under 34 U.S.C. § 20911(5)(C).

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erroneously required him to register under SORNA, we
concluded that the District Court did not impose any such
requirement. Id. at 184 (“The Judgement and Commitment
Order [did] not mandate that Delgado register as a sex offender
under SORNA.”).
Following his direct appeal, Probation required Delgado
to register under SORNA. In April 2021, Delgado challenged
that condition in a motion pursuant to § 3583(e)(2). The
District Court stayed the proceedings pending this Court’s
ruling in United States v. Icker, which held that 18 U.S.C. §
3583(d) requires the court to determine, as a matter of law,
whether a person has been convicted of a sex offense as defined
in 34 U.S.C. § 20911(5)(A). 13 F.4th at 330.
In February 2023, the District Court denied Delgado’s
§ 3583(e)(2) motion. Despite “acknowledging the facial
unconstitutionality of the challenged condition” in light of
Icker, J.A. 8, the District Court held it “lack[ed] jurisdiction to
consider [Delgado’s] legal challenge to his obligation to
comply with SORNA,” id. at 9. It reasoned that “challenges to
the legality of a condition of supervised release may not be
raised in a Section 3583(e)(2) motion.” Id.
Delgado timely appealed.
B.
Unlike Delgado, D’Ambrosio failed to object to the
SORNA registration requirement at his February 2020
sentencing. The only question that arose regarding SORNA
pertained to the length of D’Ambrosio’s registration. See J.A.
94 (“The only question that I have [ ] about [ ] SORNA . . . is
it a Tier 1? Is it a Tier 2? Or is it a Tier 3 requirement?”). His
counsel confirmed on the record that “as a result of that
conviction [ ] there would most likely be as part of [ ]
supervised release some SORNA requirements.”. J.A. 94.

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Although D’Ambrosio now asserts that “questions arose by the
parties and the [D]istrict [C]ourt regarding the applicability of
SORNA at all,” D’Ambrosio Br. at 5, the record reflects no
such questioning. Instead, his counsel affirmed its
applicability, noting that “[he] certainly recognize[d] that this
[was] a SORNA offense.” Id. As a result, the District Court
required D’Ambrosio to comply with SORNA as a condition
of supervised release.
D’Ambrosio did not file a direct appeal. He first
challenged the SORNA requirement in October 2021 via a pro
se motion, followed by a June 2022 counseled § 3583(e)(2)
motion to modify. In February 2023, the District Court denied
D’Ambrosio’s § 3583(e)(2) motion on the same grounds as
Delgado’s denial. D’Ambrosio timely appealed and we review
both cases together.
II.
As a threshold matter, we must address our jurisdiction
to review the District Court’s denial of a motion filed pursuant
to 18 U.S.C. § 3583(e)(2). The District Court had subject
matter jurisdiction of these underlying criminal cases under 18
U.S.C. § 3231. United States v. Styer, 573 F.3d 151, 153 n.2
(3d Cir. 2009). Section 1291 grants appellate jurisdiction
“from all final decisions of the district courts.” 28 U.S.C. §
1291. The District Court’s § 3583(e)(2) denials in these cases
constituted final decisions, closing the criminal cases below.
See, e.g., United States v. Rodriguez, 855 F.3d 526, 530–31 (3d
Cir. 2017) (determining appellate jurisdiction in the context of
Section 3582(c)(2) because “[f]inal judgment in a criminal
case means sentence” and “[l]ike sentencing judgments,
rulings on Section 3582(c)(2) motions are ‘unquestionably
final decisions of [a] district[] court because they close the

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criminal cases once again.’” (alterations in original) (internal
citations omitted)).
Nevertheless, our Court has yet to address whether we
possess jurisdiction over appeals concerning a district court’s
denial of an individual’s § 3583(e)(2) motion to modify
conditions of supervised release. We have, however, held that
we exercise jurisdiction over the imposition of additional
conditions of supervised release raised in a § 3583(e)(2)
motion. See United States v. Wilson, 707 F.3d 412, 414 (3d
Cir. 2013) (holding that appellate jurisdiction exists when
appealing an order modifying conditions of supervised release
under 18 U.S.C. § 3583(e)(2); United States v. Murray, 692
F.3d 273, 278 (3d Cir. 2012) (holding 28 U.S.C. § 1291 to grant
jurisdiction over appeals taken from a district court order
adding a condition of supervised release).
Given that we possess jurisdiction to review the
imposition of additional conditions of supervised release, it
would be prejudicial to defendants to decline jurisdiction when
reviewing the removal of such conditions. We thus exercise
appellate jurisdiction pursuant to § 1291 to review a district
court’s denial of a § 3583(e) motion.
III.
Before reaching the merits of the appeals—the District
Court’s finding that it lacked subject matter jurisdiction to
modify conditions of supervised release—we must review the
District Court’s delegation of the SORNA registration
condition to Probation. We review for abuse of discretion. See
Wilson, 707 F.3d at 414; see also United States v. Melvin, 978
F.3d 49, 52 (3d Cir. 2020) (internal citations omitted).
“A condition [of supervised release] is within the court’s
discretion if two criteria are met. First, the condition must be
reasonably related to the factors set forth in 18 U.S.C. §

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3553(a)(1) & (2)(B)-(D). . . . Second, a condition must involve
no greater deprivation of liberty than is reasonably necessary
to achieve the deterrence, public protection and/or correctional
treatment for which it is imposed.” Loy, 237 F.3d at 256
(internal citations omitted). Thus, “[a]n abuse of discretion can
occur if a district court fails to apply the proper legal standard.”
Melvin, 978 F.3d at 52 (brackets, internal citations, and
quotations omitted).
When imposing SORNA as a condition of supervised
release for Delgado, the District Court acknowledged that it did
not know, as a matter of law, whether Delgado’s conviction
qualified as a sex offense triggering SORNA registration.
Instead of undertaking that legal determination, the District
Court improperly delegated that responsibility to Probation.
As it later admitted in its order denying the § 3583(e)(2)
motion, “it is beyond the power of Article III courts to delegate
the duty of determining who is a sex offender to the [P]robation
office, Bureau of Prisons or state agency.” J.A. 6 (quoting
Icker, 13 F.4th at 330)). The District Court failed to make the
same legal determination as to D’Ambrosio’s conviction and
likewise acknowledged that this error was facially
unconstitutional.
The District Court’s delegation of SORNA as a condition
of supervised release, for both Delgado and D’Ambrosio, is
therefore invalid. Without knowing if SORNA applies as a
matter of law, the requirement unfairly restricts both
Appellants’ fundamental rights. Because the District Court
abused its discretion, we remand for it (1) to reconsider if
Appellants’ offenses of conviction qualify as sex offenses
under 34 U.S.C. § 20911(5)(A) triggering SORNA registration
and (2) to engage in a § 3553(a) analysis to determine the
necessity of SORNA as a condition of supervised release.

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IV.
We now review de novo the District Court’s conclusion
that it lacked jurisdiction to consider a motion pursuant to 18
U.S.C. § 3583(e)(2) based on the legality of a supervised
release condition.6 See Ballentine v. United States, 486 F.3d
806, 808 (3d Cir. 2007).
A.
Supervised release is a form of post-imprisonment
supervision provided for by statute at 18 U.S.C. § 3583. The
purpose of supervised release is not to punish. Rather, it should
“fulfill[] rehabilitative ends” and is intended “to assist
6 The District Court’s decision to frame this issue as one of
“jurisdiction” misses the mark. “Jurisdictional requirements
mark the bounds of a ‘court’s adjudicatory authority.’” Culp
v. Comm’r of Internal Revenue, 75 F.4th 196, 200 (3d Cir.
2023) (quoting Boechler, P.C. v. Comm’r of Internal Revenue,
596 U.S. 199, 203 (2022)). Unmet jurisdictional requirements
“lock[] the courthouse doors.” Jaludi v. Citigroup & Co., 57
F.4th 148, 151 (3d Cir. 2023). For that reason, we “do not
apply the ‘jurisdictional’ label casually” and only treat a
provision as jurisdictional if Congress “clearly states” as
much. Culp, 75 F.4th at 200–01 (citations omitted). Here,
§ 3583(e)(2) appears to limit the court’s adjudicatory capacity
by restricting its decision-making to “any time prior to the
expiration or termination of the term of supervised
release.” But the provision does not contain any other express
jurisdictional language. The question then, is not whether the
District Court lacks power to adjudicate the defendants’
motions. Rather, it is simply whether the statute permits a
district court to consider the motion.

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individuals in their transition to community life.” United
States v. Johnson, 529 U.S. 53, 59 (2000); see also United
States v. Sheppard, 17 F.4th 449, 454 (3d Cir. 2021) (“The
primary purpose of supervised release is to facilitate the
integration of offenders back into the community rather than to
punish them.” (brackets, internal citations, and quotations
omitted)); S. Rep. No. 98–225, at 124 (1983) (indicating that
the “primary goal” of supervised release is to rehabilitate)).
Individuals returning to their communities following a period
of incarceration face countless barriers: housing insecurity;
access to health care; difficulty finding lawful employment;
and emotional obstacles with family reunification. The
sentencing judge bears the burden of crafting a sentence as well
as a period of supervised release that not only deters future
recidivism, but also facilitates successful reentry into society.
When initially imposing conditions of supervised
release, § 3583(c) instructs the district court to consider certain
factors set forth in § 3553. These factors include: (1) the nature
and circumstances of the offense and the individual’s history
and characteristics; (2) the need for the sentence to afford
adequate deterrence, protect the public, and provide the
individual with educational training, medical care, or other
correctional treatment; (3) the Guidelines range; (4) the
pertinent policy statements of the Sentencing Commission; (5)
the need to avoid unwarranted sentencing disparities; and (6)
the need to provide restitution. 18 U.S.C. § § 3583(c);
3553(a)(1)–(2), (a)(4)–(7). Although the statute does not
explicitly direct a sentencing judge to consider the
rehabilitative needs of a person, the nature and circumstances
of the offense, as well as a that person’s personal history, often
inform these needs.
Following sentencing, the opportunities to challenge a
sentence or conditions of a sentence are limited. For example,

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a defendant may file: (1) a direct appeal; (2) a timely motion
pursuant to Federal Rules of Criminal Procedure 35(a) –(c); or
(3) a petition to vacate an illegal sentence under 28 U.S.C. §
2255. Each of these avenues includes temporal and procedural
restrictions. In addition, § 3583(e)(2) grants a District Court
broad discretion to “modify, reduce, or enlarge the conditions
of supervised release, at any time prior to the expiration or
termination of the term of supervised release.” 18 U.S.C. §
3583(e)(2) (emphasis added). But a District Court must first
“consider the factors set forth in section 3553(a)(1), (a)(2)(B),
(a)(2)(C), (a)(2)(D), (a)(4), (a)(5), (a)(6), and (a)(7).” Id.
Although § 3583(e)(2) provides an additional pathway
to challenge conditions of supervised release, “[a]n individual
may not use § 3583(e)(2) as a substitute for an appeal, belatedly
raising challenges to the original conditions of supervised
release that were available at the time of his initial sentencing.”
United States v. McLeod, 972 F.3d 637, 643–44 (4th Cir.
2020); see also United States v. Nestor, 461 F. App’x 177, 179
(3d Cir. 2012) (“[A defendant] may not [] use section
3583(e)(2) to gain review over issues which should have been
raised in earlier proceedings.”). We refuse to read
§ 3583(e)(2)’s “at any time” language as a detour from other
procedural avenues. Requiring individuals to exhaust all
timely challenges provides a necessary procedural check to the
potentially endless challenges that might otherwise be
available pursuant to § 3583(e)(2).
B.
Assuming a person properly exhausts all challenges to
the legality of a condition of supervised release, we hold that a
district court may consider legality as grounds for modification
in a § 3583(e)(2) motion.

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Courts take different positions with respect to the scope
of § 3583(e)(2). For example, some Courts of Appeal have
found that illegality does not provide a proper ground for a §
3583(e)(2) motion,7 while others have held that § 3583(e)(2)
permits challenges based on legality in some circumstances.8
Decisions denying challenges to legality are primarily based
on two reasons: (1) § 3583(e)(2)’s enumerated factors that a
district court must consider constitute an exclusive list of
factors, of which legality is not included;9 and (2) permitting a
challenge based on legality would undermine the overall
“scheme of appellate and collateral review” established by
7 See, e.g., United States v. Faber, 950 F.3d 356, 358–59 (6th
Cir. 2020); United States v. Gross, 307 F.3d 1043, 1044 (9th
Cir. 2002); United States v. Hatten, 167 F.3d 884, 885 (5th Cir.
1999); United States v. Lussier, 104 F.3d 32, 35 (2d Cir. 1997).
8 See, e.g., McLeod, 972 F.3d at 644 (permitting § 3583(e)(2)
challenges based on legality on “the basis of new or unforeseen
developments” and not “as a substitute for a [belated] appeal”);
United States v. Neal, 810 F.3d 512, 518 (7th Cir. 2016)
(holding that § 3583(e)(2) may be used to challenge legality,
even after the time for appellate review has ended).
9 See, e.g., Gross, 307 F.3d at 1044 (“Conspicuously absent
from this list of relevant factors is illegality.”); Hatten, 167
F.3d at 886 (“The enumerated factors that the court must
consider in making a modification determination . . . do not
include a consideration of the legality of the supervised release
itself.”); Lussier, 104 F.3d at 34 (“The plain language of
subsection 3583(e)(2) indicates that illegality of a condition of
supervised release is not a proper ground for modification
under this provision.”).

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Congress. United States v. Lussier, 104 F.3d 32, 36 (2d Cir.
1997).
First, although § 3583(e)(2) does not explicitly list
legality as a factor which must be considered, it also does not
prohibit legality as a consideration. Legality is at the heart of
every decision made by a judge. To forbid a judge from
considering legality would render the position, and every
judicial determination, virtually meaningless. The legality of
sentences and conditions of supervised release is a necessary
and obvious consideration; nothing in the text of § 3583(e)(2)
explicitly prevents its consideration.
Looking at a separate subsection of § 3583 supports this
conclusion. Subsection § 3583(c) lists the factors that a court
must consider when initially imposing a condition of
supervised release. Like § 3583(e)(2), § 3583(c) also omits
any mention of the condition’s legality. But it would make no
sense to say that a court, in imposing a supervised release
condition, is prohibited from considering whether that
condition is lawful.
Second, we acknowledge the concern shared among our
sister Circuits regarding the use of § 3583(e)(2) as a “backdoor
[] challenge”, Gross, 307 F.3d at 1044 (internal citations
omitted), which “would evade the detailed statutory scheme for
orderly and timely appellate review,” Neal, 810 F.3d at 517.
Nevertheless, we agree with the Fourth Circuit’s decision in
United States v. McLeod, which highlighted the balance
between finality and flexibility. 972 F.3d at 642–43.
Individuals must first exhaust all timely challenges and cannot
“raise forfeited procedural arguments” via a § 3583(e)(2)
motion years later. Id. at 643. But Congress also implicitly
recognized the need for flexibility when including the “at any
time” language in § 3583(e)(2). The need for flexibility is
particularly important when evaluating conditions of

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supervised release, which may change over time as a person’s
rehabilitative needs evolve. See Murray, 692 F.3d at 278
(“[P]robation conditions should be subject to modification, for
the sentencing court must be able to respond to changes in the
probationer’s circumstances as well as new ideas and methods
of rehabilitation.”) (alteration in original) (quoting Fed. R.
Crim. P. 32.1(b) advisory committee’s note)).
C.
Applying the principles and restrictions discussed
above, we remand for the District Court to reconsider
Appellants’ § 3583(e)(2) motions, with the understanding that
Delgado and D’Ambrosio present different procedural
histories. Delgado and D’Ambrosio’s § 3583(e)(2) motions
challenged the applicability of the imposed SORNA condition
on the basis that their underlying convictions qualify for an
exception to SORNA’s registration requirements. These
challenges raise not only legal questions, but factual ones.
Because factfinding falls squarely within the purview of the
district court, we defer the review of the underlying argument
to the District Court on remand. See Pullman-Standard v.
Swint, 456 U.S. 273, 291–92 (1982).
V.
The District Court erred as a matter of law in two ways:
(1) improperly delegating its Article III powers to Probation to
determine if SORNA applied to Appellants’ convictions and
(2) concluding that it lacked jurisdiction pursuant to §
3583(e)(2) in denying Appellants’ motions to modify
conditions of their supervised release. We will therefore
reverse the District Court’s orders and remand for further
proceedings consistent with this opinion.

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