                               In the

    United States Court of Appeals
                 For the Seventh Circuit
                     ____________________
No. 19-1300
UNITED STATES OF AMERICA,
                                                   Plaintiff-Appellee,
                                 v.

SHAWN A. LEE,
                                               Defendant-Appellant.
                     ____________________

         Appeal from the United States District Court for the
                     Central District of Illinois.
          No. 3:18-cr-30011 — Sue E. Myerscough, Judge.
                     ____________________

ARGUED SEPTEMBER 26, 2019 — DECIDED FEBRUARY 18, 2020 —
                AMENDED JUNE 9, 2020
                ____________________

   Before BAUER, MANION, and ST. EVE, Circuit Judges.
   MANION, Circuit Judge. Shawn Lee sold a staggering
amount of ice methamphetamine in Central Illinois from early
2015 until his arrest in January 2018. He now appeals his sen-
tence after pleading guilty to one count of possessing 50
grams or more of methamphetamine with intent to distribute
and one count of possessing firearms in furtherance of a drug-
traﬃcking crime. Lee contends he should not have received
2                                                   No. 19-1300

two extra criminal history points under U.S.S.G. § 4A1.1(d)
for dealing methamphetamine while on supervision for a
drunk driving oﬀense. He also challenges the district judge’s
imposition of a fine and a term of supervised release that will
prohibit him from interacting with known felons unless he re-
ceives the probation oﬃcer’s permission. Because this super-
vision term commits an impermissible delegation of Article
III power relating to Lee’s liberty interest in familial associa-
tion, we vacate the condition and remand for reassessment.
We aﬃrm on all other grounds.
                        I. Background
    In late 2017 and early 2018, DEA agents and Illinois State
Police learned through multiple independent informants that
Shawn Lee had been distributing large quantities of ice meth-
amphetamine near Carlinville, Illinois. DEA agents confirmed
those reports by arranging a controlled buy between a confi-
dential source and Lee on January 16, 2018, during which the
source purchased over 83 grams of ice methamphetamine for
$1,500. On January 23, 2018, state troopers conducted a
planned traﬃc stop on a vehicle driven by Lee. Lee consented
to a K-9 walkaround of the vehicle and the dog alerted to the
presence of drugs. Troopers searched the car and found over
seven pounds of ice methamphetamine and $19,170 in cash,
including $900 of marked money used in the January 16 con-
trolled buy.
    Agents arrested and interviewed Lee. He told them he had
been dealing ice methamphetamine in the Carlinville area for
the last three years—since around January 2015—and admit-
ted he intended to ship the seized currency to his supplier in
partial satisfaction of a drug debt. Lee started out transacting
in eight-ounce quantities of methamphetamine but graduated
No. 19-1300                                                          3

to dealing pounds of drugs from about June 2017 until his ar-
rest. During that seven-month period alone, Lee distributed
approximately 100 pounds (45.36 kilograms) of methamphet-
amine. He purchased the drugs for $7,000 per pound (totaling
$700,000 worth of methamphetamine) and resold them at
$11,200 per pound ($1.12 million in sales). Investigators
lacked enough information to determine the amount of drugs
Lee dealt from the start of his illegal conduct until June 2017.
Lee informed agents he turned to selling methamphetamine
after losing his job because of his own drug use.
    Based on additional details gained during the
investigation, agents obtained and executed a search warrant
at Lee’s residence. Inside, agents discovered ice
methamphetamine and various other suspected narcotics
hidden throughout the house. Agents also discovered twelve
firearms1 in close proximity to the drugs, along with scales,
drug paraphernalia, and assorted ammunition and
magazines. The government charged Lee with one count of
distributing 50 grams or more of methamphetamine for the
January 16 controlled buy (Count 1), two counts of possessing
50 grams or more of methamphetamine with intent to
distribute (Counts 2 and 3), and one count of possessing
firearms in furtherance of a drug-traﬃcking crime (Count 4).
    Lee entered a blind guilty plea on Counts 2 and 4. As set
forth in the presentence report (“PSR”), the massive amount
of drugs prompted a base oﬀense level of 38 for Count 2. The
base level was then reduced for acceptance of responsibility,


   1  Agents discovered a thirteenth gun—an antique that did not meet
the technical “firearm” definition. The government did not charge Lee’s
possession of that gun.
4                                                           No. 19-1300

resulting in a total oﬀense level of 35. Lee’s record earned him
three criminal history points: one point for a 2015 drunk driv-
ing conviction and two points for committing the instant
crimes while on supervision for the drunk driving oﬀense.
The three total points placed Lee in criminal history category
II, which, combined with the total oﬀense level of 35, resulted
in a sentencing range of 188 to 235 months’ imprisonment on
Count 2. The Guidelines range for Count 4 equaled the statu-
tory minimum: 60 months’ imprisonment.
    The PSR also included information about Lee’s finances,
including a list of assets (totaling nearly $190,000) and a net
worth greater than $102,000.2 Despite this information, the
probation oﬃcer opined, “it appears [Lee] does not have the
ability to pay a fine or community restitution.” (PSR ¶ 96.) The
Guidelines called for a fine range of $40,000 to $10,000,000.
    At sentencing, the district judge adopted the PSR’s factual
findings as her own. She calculated the same Guidelines
ranges as set forth in the PSR: 188 to 235 months’ imprison-
ment on Count 2 and 60 months’ imprisonment on Count 4.
Neither party objected.
    The district judge sentenced Lee to 210 months’
imprisonment, consisting of 150 months on Count 2—a
below-Guidelines sentence—and 60 months on Count 4, to be
served consecutively. The judge further imposed a $20,000
fine—a below-Guidelines amount—after weighing the huge
amount of ice methamphetamine Lee sold, the dangerousness
of that drug, and the need to deprive oﬀenders of ill-gotten

    2 We note Lee’s primary asset, his home, is in foreclosure, meaning his

total assets and net worth will be substantially less upon his release from
prison.
No. 19-1300                                                      5

gains against Lee’s available assets. Upon release, the judge
ordered Lee to a term of five years’ supervision. Among the
several terms Lee must comply with during that period is
Condition No. 7, which limits his ability to interact with
known felons unless granted permission by the probation
oﬃcer. Two of Lee’s sons are convicted felons.
                         II. Discussion
    Lee challenges his criminal history score, the $20,000 fine,
and supervisory Condition No. 7. We aﬃrm his sentence with
one narrow exception. First, the district judge calculated Lee’s
criminal history score correctly when she assessed two extra
points under U.S.S.G. § 4A1.1(d). Second, the judge provided
adequate consideration of the necessary factors to support the
fine. And finally, Condition No. 7 implicates Lee’s familial as-
sociation interests on a prospective level only, so, at this point,
we need not wade into his constitutional argument’s merits.
The same term of supervision, however, improperly delegates
Article III power to the probation oﬃcer, requiring reassess-
ment.
   A. Lee’s Criminal History
    Lee maintains his criminal history score should not have
been enhanced by U.S.S.G. § 4A1.1(d), which adds two points
“if the defendant committed the instant oﬀense while under
any criminal justice sentence, including probation, parole, su-
pervised release, imprisonment, work release, or escape sta-
tus.” This challenge lacks merit because Lee engaged in
6                                                         No. 19-1300

conduct related to his oﬀense while on supervision for his
state drunk driving conviction.3
   The commentary to § 4A1.1(d) instructs courts to add two
points if the defendant committed the instant oﬀense, includ-
ing any relevant conduct, while on supervision. U.S.S.G.
§ 4A1.1(d), Application Note 4. When investigators inter-
viewed Lee in January 2018, he admitted to dealing metham-
phetamine in the region for the previous three years. This
course of dealing constitutes relevant conduct. See, e.g., United
States v. Stephenson, 557 F.3d 449, 456–57 (7th Cir. 2009) (hold-
ing defendant’s continuous dealing of the same drug in the
same locale using the same few distributors during the com-
mon eight-year time frame qualified as conduct related to the
charged transaction). His July 2015 drunk driving conviction
and resulting year of supervision fall squarely within this
time period. The district judge therefore awarded two extra
criminal history points correctly under § 4A1.1(d).
    Lee’s only response to the relevant conduct hurdle is that
his statements to investigators cannot be used to enhance his
sentence (by way of his criminal history calculation). This ar-
gument misses the mark. Lee invokes language extracted
from the safety-valve provision at 18 U.S.C. § 3553(f): “Infor-
mation disclosed by a defendant under this subsection may
not be used to enhance the sentence of the defendant unless
the information relates to a violent oﬀense.” That provision
does not apply here. The district court made no finding re-
garding the safety valve (the record does not indicate the
safety valve ever came up at all), and in any event, Lee would


    3 The parties debate whether Lee waived this challenge, but we do not

address waiver here.
No. 19-1300                                                    7

not be eligible to receive its benefits because he fails the fol-
lowing criteria: the defendant must not have “possess[ed] a
firearm or other dangerous weapon … in connection with the
oﬀense.” § 3553(f)(2); United States v. Collins, 924 F.3d 436,
440–41 (7th Cir. 2019). He possessed twelve firearms too many
in connection with his drug business.
   B. Lee’s $20,000 Fine
    Lee claims the district judge failed to justify his below-
Guidelines fine, which the judge imposed over the probation
oﬃcer’s recommendation that Lee did not appear able to pay
one. “When a district court determines that a fine is in order,
we will only reverse its factual finding if it is clearly errone-
ous.” United States v. Artley, 489 F.3d 813, 826 (7th Cir. 2007).
In other words, the record must clearly indicate whether the
district judge “properly has considered the relevant factors”
set forth below. United States v. Bauer, 129 F.3d 962, 968 (7th
Cir. 1997).
    Section 5E1.2 of the Guidelines mandates the imposition
of a fine unless “the defendant establishes that he is unable to
pay and is not likely to become able to pay any fine.” U.S.S.G.
§ 5E1.2(a). “This language is to be taken seriously: the judge
must impose a fine, unless the defendant demonstrates that he
cannot pay anything, either at sentencing or in the foreseeable
future.” United States v. Gomez, 24 F.3d 924, 926–27 (7th Cir.
1994). The defendant’s burden here is a heavy one “because
almost everyone has or will acquire some assets.” Id. at 927.
The Guidelines state the district judge “shall consider” eight
factors before imposing a fine:
       (1) the need for the combined sentence to reflect
       the seriousness of the oﬀense (including the
8                                                         No. 19-1300

        harm or loss to the victim and the gain to the
        defendant), to promote respect for the law, to
        provide just punishment and to aﬀord adequate
        deterrence;
        (2) any evidence presented as to the defendant’s
        ability to pay the fine (including the ability to
        pay over a period of time) in light of his earning
        capacity and financial resources;
        (3) the burden that the fine places on the defend-
        ant and his dependents relative to alternative
        punishments;
        (4) any restitution or reparation that the defend-
        ant has made or is obligated to make;
        (5) any collateral consequences of conviction, in-
        cluding civil obligations arising from the de-
        fendant’s conduct;
        (6) whether the defendant previously has been
        fined for a similar oﬀense;
        (7) the expected costs to the government of any
        term of probation, or term of imprisonment and
        term of supervised release imposed; and
        (8) any other pertinent equitable considerations.
U.S.S.G. § 5E1.2(d). Similar “factors to be considered” can be
found at 18 U.S.C. § 3572(a).4
   When imposing a fine, a district judge need not make ex-
press or specific findings regarding each of the relevant

    4 In addition to its own factors, § 3572(a) requires consideration of
those listed under 18 U.S.C. § 3553(a).
No. 19-1300                                                     9

factors, Bauer, 129 F.3d at 966, although an express finding
may nonetheless be made by adopting the PSR’s facts, id. (cit-
ing United States v. Monem, 104 F.3d 905, 912 (7th Cir. 1997)).
This approach keeps the focus on the need for the judge to
weigh the necessary factors without requiring her to give an
“often unnecessary” articulation of her findings. Id. at 967–68;
see also United States v. Petty, 132 F.3d 373, 382 (7th Cir. 1997)
(reciting Bauer’s standard and explaining, “We desired to re-
lieve the district courts, when possible, from the substantial
burden of making express findings when simply adopting the
PSR will do as well.”).
    The record reveals the district judge considered the rele-
vant factors suﬃciently. Before imposing Lee’s fine, the judge
emphasized the seriousness of Lee’s oﬀense, which created “a
significant danger to the community”: Lee distributed a “mas-
sive amount” of ice methamphetamine—a “very dangerous”
drug—and possessed a dozen firearms in connection with
that oﬀense. (Lee’s Br. App. at 66.) See U.S.S.G. § 5E1.2(d)(1),
and 18 U.S.C. § 3553(a)(1–2) (the sentencing court shall con-
sider the nature, circumstances, and seriousness of the of-
fense). She also underscored the need to deprive Lee of his ill-
gotten gains and to deter others from attempting to profit
through similar illicit enterprises, see 18 U.S.C. §§ 3572(a)(5),
3553(a)(2)(B), by rejecting his sentencing argument that he
used drug proceeds to help others. As the district judge
stated, “So did El Chapo. He helped out his community as
well with the ill-gotten gains that he received from illegal
drugs.” (Lee’s Br. App. at 67.) Put diﬀerently, good deeds do
not excuse the illegal acts that make them possible, nor do
they outweigh the danger and harm Lee’s drug trade posed
to the public.
10                                                           No. 19-1300

    The PSR also contained information about other relevant
factors, such as Lee’s financial resources and the lack of de-
pendents, pecuniary loss, and restitution. See U.S.S.G.
§ 5E1.2(d)(2–4); 18 U.S.C. § 3572(a)(1–3); see also United States
v. Patterson, 698 F. App’x 840, 841 (7th Cir. 2017) (aﬃrming the
district judge’s justification for the imposed fine where he
adopted the PSR’s factual findings regarding these same
items). Notably, the PSR detailed several assets with a com-
bined value exceeding the ultimate fine amount, including
Lee’s two automobiles and two all-terrain vehicles ($7,300 to-
tal), his work tools ($15,000), and $14,2005 in savings bonds.
(PSR ¶ 94.) By adopting the PSR’s contents, the district judge
made express findings for each of these factors, further sup-
porting the imposed fine. Bauer, 129 F.3d at 966 (citing Monem,
104 F.3d at 912).
    Because the district judge accepted the PSR’s factual find-
ings yet departed from the probation oﬃcer’s estimate re-
garding Lee’s ability to pay a fine, Lee insists the fine be va-
cated under Bauer. In that case, we held the underpinnings of
a fine may be lacking when, for example, “the district court
adopts the factual findings contained in the presentence re-
port but deviates from the fine recommendation, if any, made

     5The PSR listed the savings bonds’ value erroneously as $20,000. Lee
filed a post-sentencing motion under Fed. R. Crim. P. 35(a) seeking a re-
duced fine equal to the bonds’ actual worth ($14,200). The district judge
denied Lee’s request and reiterated the bases for the fine in a written or-
der. (Doc. 39.) Both the Rule 35(a) motion and the resulting order were
entered after Lee filed his notice of appeal, however, so the parties debate
whether we have jurisdiction to consider the order’s contents when ad-
dressing Lee’s fine challenge. We need not consider the order; it cites only
Lee’s assets and the nature, circumstances, and severity of his crimes. The
record already reflects a consideration of these factors.
No. 19-1300                                                    11

by the United States Probation Oﬃce, or alternatively, if the
district court declines to adopt the findings in the presentence
report and makes no findings of its own.” 129 F.3d at 968.
    But Bauer’s language describes situations in which the dis-
trict court either imposes a fine inconsistent with its stated in-
tentions or fails to make any findings of fact at all. Id. at 967.
We pointed to Monem as illustrative of the former, where the
probation oﬃcer recommended a below-Guidelines fine be-
cause of the defendant’s financial status. Bauer, 129 F.3d at 967
(discussing Monem, 104 F.3d at 911–12). But at Monem’s sen-
tencing, the judge stated: “The Court will accept the recom-
mendation of the presentence report and impose a fine of
$15,000, which is the minimum fine.” Monem, 104 F.3d at 912
(emphasis added). So, the judge imposed a fine higher than
the PSR’s recommendation while purporting to accept it. We
therefore could not “accept the district court’s blanket state-
ment that it accepted the recommendation of the PSR when
an unexplained contradiction [was] evident from the record.”
Id.
   The same ambiguity does not exist here. True, the district
judge adopted the factual findings of the PSR as her own near
the start of Lee’s sentencing. But the record does not end on
that rote announcement. Rather, the judge entertained argu-
ment from the parties regarding Lee’s financial status, rejected
the probation oﬃcer’s recommendation of no fine, and in do-
ing so reached her own conclusion that Lee could pay a
$20,000 fine. And by adopting the PSR’s findings regarding
Lee’s total assets worth well in excess of that amount, the
judge supported this conclusion suﬃciently. Lee’s fine did
not result from any error, clear or otherwise.
12                                                  No. 19-1300

     C. Supervised Release Condition No. 7
   The district judge also sentenced Lee to five years’ super-
vised release on each count of conviction, to be served con-
currently. Among the various terms of supervision, the judge
ordered Lee not to:
        knowingly meet, communicate, or otherwise in-
        teract with any person whom he knows to be a
        convicted felon or to be engaged in, or planning
        to engage in, criminal activity, unless granted
        permission to do so by the probation oﬃcer.
(Lee’s Br. App. at 78.) Lee’s challenge to this condition is two-
fold, and both prongs stem from the fact that two of his sons—
Ethan and Charles—are felons themselves. First, Lee argues
the condition commits an improper delegation of Article III
power because it allows the probation oﬃcer—instead of the
district judge—to determine whether Lee can enjoy the com-
pany of his own children. Second, Lee contends the condition
will unjustifiably deprive him of the constitutional right of fa-
milial association.
        1. Article III Delegation
    “Article III judges lack constitutional authority to delegate
the duty of imposing a defendant’s punishment to a non-
Article III judge, such as a probation oﬃcer or treatment
provider.” United States v. Wagner, 872 F.3d 535, 543 (7th Cir.
2017). At the outset, the government claims Lee did not
preserve his delegation argument for appeal. We disagree. In
his sentencing memorandum, Lee requested Condition No. 7
not be imposed, or, in the alternative, “that he be allowed to
visit with his family without prior approval from the probation
oﬃce.” (Doc. 30 at 8, emphasis added.) He reiterated this
No. 19-1300                                                     13

objection at sentencing. By contesting the need to receive prior
approval from the probation oﬃcer, Lee’s objection went to
the heart of the non-delegation rule, even if not so articulated.
See United States v. Billups, 536 F.3d 574, 578 (7th Cir. 2008) (An
objection may be suﬃcient to preserve an appellate argument
even if the objector “oﬀers a new twist on that argument
based upon additional authority on appeal.”). We therefore
review Lee’s delegation claim de novo. United States v. Schrode,
839 F.3d 545, 554 (7th Cir. 2016).
    To determine whether a condition of supervised release
violates the non-delegation rule, “we distinguish between
permissible conditions that merely task the probation oﬃcer
with performing ministerial acts or support services related
to the punishment imposed and impermissible delegations
that allow the oﬃcer to decide the nature or extent of the de-
fendant’s punishment.” Wagner, 872 F.3d at 543 (internal quo-
tation marks and citations omitted). An example of a permis-
sible, ministerial delegation would be “a condition requiring
a defendant to attend treatment as approved by the probation
oﬃcer” because “the court itself ordered participation in the
program and only provides the probation oﬃcer authority to
manage the details and supervision of the program.” Id.
    Here, the district court delegated the decision of whether
Lee can associate with his two sons to the probation oﬃcer.
The probation oﬃcer’s future task, then, is not merely to man-
age or supervise, but to determine whether, when, and how
Lee can exercise his constitutional liberty interest in familial
association. We think that is much more than a “ministerial
act.” In this context, the clause “unless granted permission to
do so by the probation oﬃcer” is overbroad and violates the
non-delegation principle. Thus, it must be stricken from
14                                                   No. 19-1300

Condition No. 7—only the district judge can permit or deny
Lee’s association with his sons. See Wagner, 872 F.3d at 543
(holding supervised release term improperly delegated dis-
trict court’s Article III authority to determine the nature of de-
fendant’s punishment where language left imposition of sex
oﬀender treatment up to probation oﬃcer); see also United
States v. Voelker, 489 F.3d 139, 153–54 (3d Cir. 2007) (vacating
condition that prohibited defendant from associating with
minors absent the probation oﬃcer’s prior approval because
it delegated “the sole authority for deciding if Voelker will
ever have unsupervised contact with any minor, including his
own children, for the rest of his life.”).
    We recognize that the probation oﬃcer is an authority on
a supervisee’s record of compliance. With that knowledge
comes the ability to identify associations and settings that
jeopardize a supervisee’s progress. But the same expertise
does not supply unlimited Article III power to bar Lee from
interacting with his children. Still, our decision today does not
remove the probation oﬃcer’s insight from the equation. If
Lee requests to communicate with Ethan and Charles follow-
ing his release, the district judge may (and should) invite the
probation oﬃcer to present the necessary evidence and make
a recommendation. With the oﬃcer’s input in hand, the judge
“can properly exercise [her] authority to determine whether
such punishment is necessary to serve the principles and
goals of supervised release.” Wagner, 872 F.3d at 543.
    For these reasons, we vacate Condition No. 7 and remand
for the district court to revise its language in a way that keeps
the authority to permit familial association with the judge. We
emphasize that our holding is limited to the extent Lee’s del-
egation challenge relates to this fundamental liberty interest.
No. 19-1300                                                              15

Indeed, his argument on appeal rests on this narrow ground
only. But more to the point, the magnified nature of Lee’s fa-
milial interest, as we highlight below, sets this case apart from
those that require no more than routine review by the proba-
tion oﬃcer. See United States v. Armour, 804 F.3d 859, 870 n.3
(7th Cir. 2015) (Letting the probation oﬃcer decide whether
an oﬀender may associate with his children while on super-
vised release is more serious than delegating authority to per-
mit a defendant’s interaction with any ordinary felon.). Our
holding does not reach run-of-the-mill probationer requests
to attend barbecues, church services, or other benign commu-
nity gatherings where known felons might be encountered.
Those determinations remain appropriately with the proba-
tion oﬃcer. This is an exceptional case.
        2. Constitutional Challenge
    We are sympathetic to Lee’s second concern, and it is a se-
rious one. The liberty interest he raises—a parent’s right to
enjoy the companionship of his children—“is perhaps the old-
est of the fundamental liberty interests recognized by [the Su-
preme Court].” Troxel v. Granville, 530 U.S. 57, 65 (2000).6 And
in no way do we diminish Lee’s liberty interest by

    6  Ethan and Charles, however, are not minors—they were both 23
years old as of November 2018. (PSR ¶ 65.) Query whether their age de-
tracts from Lee’s claimed liberty interest. See Russ v. Watts, 414 F.3d 783,
788 (7th Cir. 2005) (Observing several circuits have been “reluctant to ex-
tend the constitutional protections afforded the parent-child relationship
to cases involving adult children.”). While we declined in Russ to “impose
an absolute rule that parents of adult children lack any liberty interest in
their relationship with their children,” we nonetheless stated, “minor chil-
dren’s need for the guidance and support of their parents warrants
sharply different constitutional treatment.” Id. at 790 (internal quotation
marks and citations omitted).
16                                                  No. 19-1300

commenting that his situation is both rare and unfortunate
when it comes to family relationships. According to the PSR,
Ethan is serving three concurrent sentences in Illinois for pos-
session of methamphetamine. His expected release date is
November 2021. Charles is serving an eighteen-year sentence
in Illinois for aggravated delivery of methamphetamine. His
projected release date is March 2026. (PSR ¶ 65.) Fortunately
for Lee, he enjoys a good relationship with his youngest son,
Zander, who has maintained regular contact with and visited
Lee in prison. We hope Ethan and Charles will do the same
once their prison terms end, although that could depend in
part on their own conditions of supervision.
    Still, whereas the improper delegation has already been
committed by the district court’s final judgment, Lee’s con-
cern about a constitutional infringement is too prospective for
us to address at this juncture. Lee received a sentence of 210
months’ imprisonment (seventeen and a half years) and his
terms of supervision will not take eﬀect until his release. See
United States v. Kappes, 782 F.3d 828, 859 (7th Cir. 2015) (hold-
ing claimed violation of right to familial association imposed
by supervision terms not yet ripe in light of twenty-year sen-
tence). A lot can happen during that time. See id. at 838 (rec-
ommending district judges reassess defendants’ conditions of
supervision on the eve of release from prison; “A defendant
may change substantially during a long prison sentence, and
the world outside the prison walls may change even more.”);
United States v. Siegel, 753 F.3d 705, 708 (7th Cir. 2014) (“Con-
ditions that may seem sensible at sentencing may not be sen-
sible many years later, when the defendant is finally released
from prison.”). For example, Lee might rehabilitate his seri-
ous drug addiction (detailed at length in the PSR) through the
Bureau of Prison’s substance abuse programs such that
No. 19-1300                                                   17

associating with felons—especially those who are involved in
drugs, like Lee’s sons—no longer presents a risk of recidivism
or relapse. As the PSR explains, Lee interacted with criminals
as part of his oﬀense conduct, but he only turned to dealing
methamphetamine in the first place after losing his job be-
cause of his own drug use. (PSR ¶¶ 23, 118.)
    Moreover, the condition Lee challenges might never
threaten his liberty interest at all if the district judge grants
Lee permission to interact with Ethan and Charles. By its own
language, Condition No. 7 does not completely bar Lee from
associating with his sons; the judge “may allow contact … if
[she] deems it appropriate; the condition is not a blanket ban.”
See United States v. Llantada, 815 F.3d 679, 685 (10th Cir. 2016)
(rejecting defendant’s associational rights challenge to nearly
identical supervised release condition). Lee has provided no
reason to believe that, with the probation oﬃcer’s recommen-
dation in hand, the judge will refuse permission to communi-
cate or associate with Ethan and Charles. And we assume the
probation oﬃcer will address requests to associate and make
recommendations in a reasonable manner. Kappes, 782 F.3d at
857–58. At sentencing, the probation oﬃcer explained his de-
partment reviews requests to associate simply for whether the
desired interaction will “generate any additional risk for non-
compliance” with the conditions of supervised release. (Lee’s
Br. App. at 9.) Speaking hypothetically, the probation oﬃcer
noted his oﬃce would grant (now, recommend granting) per-
mission for Lee to contact Ethan and Charles if the two sons
abide by their own terms of probation and supervision.
   The record reflects a preference for allowing contact be-
tween Lee and his sons provided all parties are progressing
in their respective rehabilitative sentences. Receiving
18                                                  No. 19-1300

permission to associate, therefore, is largely up to all three
men. See United States v. Edwards, 944 F.3d 631, 637 (7th Cir.
2019) (rejecting defendant’s vagueness challenge to a condi-
tion that prohibited unauthorized contact with minors be-
cause defendant gave “no reason to believe that the probation
oﬃcer would refuse” permission to spend time with his mi-
nor nephew).
    By declining to review Lee’s constitutional challenge at
this time, we do not mean a defendant can never immediately
appeal a condition of supervised release following entry of
judgment. We have reviewed many such challenges, includ-
ing where the terms of supervision required the defendant to
submit to drug testing or to participate in sex oﬀender treat-
ment, or prohibited the defendant from associating with
white supremacy groups or from using the internet entirely.
See United States v. Rhodes, 552 F.3d 624, 629 (7th Cir. 2009)
(collecting cases). But the conditions in those cases were defi-
nite, unlike here. The district judge must first deny a request
to contact Lee’s sons for any liberty interest to be implicated,
and such a denial would likely flow only from Lee’s or his
sons’ hypothetical noncompliance with their respective terms
of supervision. If the judge prohibits contact between Lee and
his sons down the line, Lee may bring a challenge then to as-
sert his constitutional rights, Llantada, 815 F.3d at 685, and he
can seek to modify his supervised release terms at any time
before his supervision ends. See 18 U.S.C. § 3583(e)(2); United
States v. St. Clair, 926 F.3d 386, 389 (7th Cir. 2019). Our ap-
proach here promotes eﬃciency over “perpetuating expen-
sive and time-consuming appeals and resentencings … .”
United States v. Silvious, 512 F.3d 364, 371 (7th Cir. 2008).
No. 19-1300                                           19

                     III. Conclusion
    For all these reasons, Condition No. 7 is VACATED and
REMANDED to the district court for reconsideration con-
sistent with this opinion. Lee’s sentence is otherwise
AFFIRMED.
20                                                    No. 19-1300

    ST. EVE, Circuit Judge, concurring in part. I agree with my
colleagues that the district court correctly calculated Shawn
Lee’s criminal history score and that Lee’s fine did not result
from any error. I further agree that Supervised Release Con-
dition No. 7 raises an issue of improper delegation of Article
III power to a probation oﬃcer because of Lee’s underlying
constitutionally protected liberty interest in associating with
his children. I disagree, however, that Lee’s challenge to Con-
dition No. 7 is prospective such that it precludes our review
of Lee’s constitutional argument.
    A condition of supervised release is unripe for purposes
of our review only if it is “subject to a string of contingencies.”
United States v. Wagner, 872 F.3d 535, 542 n.2 (7th Cir. 2017)
(rejecting an argument that a condition of supervised release
is not ripe for review). The condition that Lee challenges to-
day does not rely on any contingencies: it sets as a default rule
that Lee cannot speak with his two sons over his term of su-
pervised release. See United States v. Johnson, 756 F.3d 532,
539–40 (7th Cir. 2014) (concluding that a challenge to a condi-
tion of supervised release is ripe because “if we do nothing
the default will be that the special condition is in place.”). The
majority suggests that for this condition to impinge on Lee’s
constitutionally protected liberty interest, Lee would have to
request to communicate with his children, and the district
court would have to deny that request. I respectfully disagree
that a challenge to a properly preserved condition of super-
vised release is premature because the court or a probation
oﬃcer would first need to deny a request for an exception to
the rule.
  Indeed, we have already resolved Lee’s constitutional ar-
gument: we determined that the delegation to probation of
No. 19-1300                                                    21

the administration of Condition No. 7 was impermissible be-
cause of Lee’s underlying constitutionally protected liberty in-
terest in associating with his children. Slip Op. 13–15. We
have said before that a condition of supervised release may
infringe on a constitutionally protected right or interest, but
the condition must be “reasonably related to the ends of reha-
bilitation and protection of the public from recidivism.”
United States v. Armour, 804 F.3d 859, 870 (7th Cir. 2015) (quot-
ing United States v. Sines, 303 F.3d 793, 801 (7th Cir. 2002)). A
district court must “provide some rationale for why it believed
[a challenged condition of supervised release] would be help-
ful” to these ends, rather than merely state that it is so. United
States v. Canfield, 893 F.3d 491, 496 (7th Cir. 2018). We further
have explained that courts must consider the infringement
“more scrupulously” when it impacts deep, personal relation-
ships. Sines, 303 F.3d at 801–02.
    Here, the district court did not discuss why a bar on com-
municating with his children would aid in Lee’s rehabilitation
or prevent his recidivism, and instead dismissed Lee’s objec-
tion on the ground that probation would address it upon his
release from custody. Given the fundamental importance of
the constitutionally protected liberty interest at stake—that
Lee will risk returning to prison if he communicates with his
own children while on supervised release—this explanation
is woefully insufficient. Accordingly, I would vacate the con-
dition and remand to the district court not only to remedy the
impermissible delegation, but also to carve out a limited ex-
ception to Condition No. 7 for Lee’s children, or to otherwise
provide a sufficient rationale for their inclusion in the terms
of the condition.
