FILED
                                                                      United States Court of Appeals
                                       PUBLISH                                Tenth Circuit

                      UNITED STATES COURT OF APPEALS                         June 10, 2019

                                                                          Elisabeth A. Shumaker
                            FOR THE TENTH CIRCUIT                             Clerk of Court
                        _________________________________

 UNITED STATES OF AMERICA,

       Plaintiff - Appellee,
                                                              No. 18-1263
 v.

 JON JULIAN CABRAL,

       Defendant - Appellant.
                      _________________________________

                     Appeal from the United States District Court
                             for the District of Colorado
                          (D.C. No. 1:18-CR-00024-RM-1)
                       _________________________________

Kathleen Shen, Assistant Federal Public Defender (Virginia L. Grady, Federal Public
Defender, and Veronica S. Rossman, Assistant Public Defender, with her on the briefs),
Denver, Colorado, for Defendant - Appellant.

Karl L. Schock (Jason R. Dunn, United States Attorney, and Paul Farley, Assistant
United States Attorney, on the brief), Denver, Colorado, for Plaintiff - Appellee.
                        _________________________________

Before LUCERO, BACHARACH, and McHUGH, Circuit Judges.
                  _________________________________

McHUGH, Circuit Judge.
                    _________________________________


      Jon Julian Cabral pleaded guilty to being a felon in possession of a firearm and

ammunition in violation of 18 U.S.C. § 922(g)(1). The district court sentenced him to

forty-six months’ imprisonment followed by three years’ supervised release. Among
other supervised-release conditions, the court imposed Standard Condition Twelve,

which allows a probation officer to require Mr. Cabral to notify third parties if the

probation officer determines Mr. Cabral poses a risk to them. Apart from a reference

to “making sure the public is protected,” the district court gave little guidance on how

the probation officer should determine whether Mr. Cabral poses a risk to another

person. Indeed, the court admitted that it “can’t say what the risk is now” and that

unforeseen risks, unrelated to Mr. Cabral’s crime of conviction, might arise in the

future and trigger the condition.

      Mr. Cabral challenges Standard Condition Twelve, arguing it is

unconstitutionally vague and impermissibly delegates judicial power to a probation

officer. Our prudential ripeness doctrine prevents us from reaching his vagueness

challenge. However, his improper-delegation challenge is ripe for review, and we

hold the risk-notification condition, as imposed by the district court, improperly

delegates judicial power to a probation officer.

                                I.     BACKGROUND

      Early in the morning on December 30, 2017, Denver police officers responded

to the report of a fight at a nightclub. Based on live security footage, a dispatcher told

the responding officers that a male had just arrived in a white Chevy sedan and

pulled a handgun out of his pocket. Upon arrival, the officers quickly identified

Mr. Cabral as the man the dispatcher had described. But when they tried to detain

him, Mr. Cabral walked toward the Chevy and tossed the handgun into the car



                                            2
through an open door. The officers then arrested Mr. Cabral and retrieved the

handgun, which was loaded with three rounds of ammunition.

      Mr. Cabral has an extensive criminal history: along with several misdemeanor

convictions (some, but not all, juvenile offenses), he had previously been convicted

of felony menacing with a weapon, possession of a controlled substance, and felony

robbery. After the incident at the nightclub, the Government charged Mr. Cabral with

a single count of being a felon in possession of a firearm and ammunition in violation

of 18 U.S.C. § 922(g)(1). Mr. Cabral pleaded guilty on March 28, 2018.

      The Presentence Investigation Report recommended a within-Guidelines

sentence of 42 months’ imprisonment and three years’ supervised release. The report

also recommended that the district court order the standard conditions of supervised

release, including Standard Condition Twelve (“the risk-notification condition”).

This condition provides:

      If the probation officer determines that you pose a risk to another person
      (including an organization), the probation officer may require you to
      notify that person about the risk and you must comply with that
      instruction. The probation officer may contact the person and confirm
      that you have notified the person about the risk.

U.S.S.G. § 5D1.3(c)(12). Mr. Cabral filed an objection to the PSR’s recommendation

that the risk-notification condition be imposed, arguing the condition is vague,

constitutes an unlawful occupational restriction,1 and improperly delegates authority


      1
        Mr. Cabral abandoned the occupational restriction argument on appeal,
asserting only that Condition Twelve is unconstitutionally vague and is an improper
delegation.

                                           3
to a probation officer. At Mr. Cabral’s sentencing hearing, the district court

expressed its concern about Mr. Cabral’s history of violent crime and imposed the

risk-notification condition over Mr. Cabral’s renewed objection. But rather than

providing guidance for narrow application of the condition, the sentencing court

justified the need for broad discretion in the probation officer when making the risk

assessment:2

         I don’t care if I can’t say what the risk is now. That’s the whole
      point. I can’t say what the risk is now. Any number of things can
      happen. There are some things that have happened now. There are
      things that could happen after he is convicted and sentenced by me. For
      example, and I am—to be clear I’m just making stuff up here. It could
      be that two years after he is sentenced by me, some DNA evidence
      shows that he involved [sic] in the perpetrator [sic] of a rape involving
      some victim, somewhere and he gets convicted for that. I can’t sit here
      now, and predict or project that risk. It could be that he has a mental-
      health issue or a drug issue, that happens afterwards, while he is on
      supervised release, that creates a risk.
         The way this is being defined to me is that I, the all-powerful Judge,
      should be able to say exactly what risk is or is not worthy of requiring
      him to notify those affected by the risk, and it’s absurd, because I can’t
      anticipate every risk, and I am not going to sit here and pretend that I
      can.
         This is not a condition which is imposed and says based on—what
      has transpired, from today backwards, and only based on those things
      that are temporally current as of today, as defined and understood by me
      in matter X, Y, and Z without the prospect for further evidence coming
      along down the road, but based on that cabin, in the manner I just
      described, here are the people he presents them to, and here is—here are


      2
         Mr. Cabral challenges the text of U.S.S.G. § 5D1.3(c)(12), as interpreted by
the district court orally at sentencing. United States v. Barwig, 

, 855
(10th Cir. 2009) (“an oral pronouncement of sentence from the bench controls over
written language” (quotation marks and alteration omitted)); see also United States v.
Villano, 

, 1451 (10th Cir. 1987) (“The sentence orally pronounced
from the bench is the sentence.”). Therefore, we quote at length the district court’s
description of the condition.
                                           4
       the things that you may, probation, tell him to notify people of. It’s just
       nonsense.

ROA, vol. III at 60–61. The court rejected Mr. Cabral’s vagueness challenge,

reasoning that “there’s nothing vague about [the condition]. Again, he is told to

advise someone about the risk. He either does it or he doesn’t.” 

And the

sentencing court decided the term “risk” was not vague because it should be given its

“ordinary meaning.” 

to the improper-delegation argument, the court

reasoned that “[t]his is a matter of supervision, and . . . supervision decisions are

appropriate for the probation department. There is nothing here that even rationally

says that I now could say what the risk is that presents . . . itself . . . in the future, and

that I am in a better position to assess that risk today, not even knowing what it is,

than the probation officer may be, once it presents itself.” 

Although the

court tied the condition’s enforcement to public safety, see 

(“Part of [the

responsibility of the parole officer] is making sure that the public is protected, that’s

all that this is.”), the court also acknowledged that the risk-notification provision

“[c]ould affect girlfriends, family, living. It could, in theory, impact an occupation.”

       The district court sentenced Mr. Cabral to 46 months’ imprisonment, followed

by three years’ supervised release subject to all the standard supervised-release

conditions, including Standard Condition Twelve—the risk-notification condition.

Mr. Cabral timely appealed his sentence.




                                              5
                                 II.    DISCUSSION

      Mr. Cabral argues on appeal that the risk-notification condition is

unconstitutionally vague.3 He also argues the condition improperly delegates judicial

power to a probation officer by allowing the probation officer to decide the scope of

the “risk” that should trigger the notification requirement, thereby delegating the

power to “decide the nature or extent of [Mr. Cabral’s] punishment.” Appellant’s Op.

Br. at 15 (quoting United States v. White, 

, 1141 (10th Cir. 2015)).

Before we can reach the merits of Mr. Cabral’s appeal, we first consider the

government’s contention that the challenge is not ripe for judicial review.4




      3
         Citing our dicta in United States v. Hull, 

(10th Cir. 2018), the
Government contends that Mr. “Cabral’s vagueness challenge is foreclosed by the
Supreme Court’s decision in Beckles v. United States,” 

(2017). See
Response Br. at 4. This is incorrect. In Hull, we mentioned the Beckles Court’s
conclusion that “the advisory Sentencing ‘Guidelines are not subject to a vagueness
challenge under the Due Process Clause’ because . . . they only ‘guide the exercise of
a court’s discretion in choosing an appropriate sentence within the statutory range.’”

, 1224 n.1 (10th Cir. 2018) (quoting 

). But
Beckles simply held that a residual clause in the Guidelines identical to that struck
down in Johnson v. United States, 

(2015), could not similarly be void
for vagueness because the Guidelines, which “merely guide the district courts’
discretion, . . . are not amenable to a vagueness challenge.” 

. The Court never suggested that a defendant cannot challenge a supervised-
release condition for vagueness where it is merely derived from the Guidelines.
      4
        In Hull, we heard a challenge to Standard Condition Twelve on similar
grounds to those Mr. Cabral raises, and we resolved that challenge on the merits
without considering ripeness. 

, 1224–27 (10th Cir. 2018). However,
neither party raised the issue of prudential ripeness in that case, see 

is
generally not our practice to raise the issue sua sponte, see Fourth Corner Credit
Union v. Fed. Reserve Bank of Kan. City, 

, 1076 (10th Cir. 2017)
(Bacharach, J., concurring).
                                            6
                                      A. Ripeness

       “We review the issue of ripeness de novo.” Roe No. 2 v. Ogden, 

, 1231 (10th Cir. 2001). The ripeness doctrine involves both constitutional

requirements and prudential concerns. See Tex. Brine Co. v. Occidental Chem. Corp.,

, 1229 (10th Cir. 2018). “The purpose of the ripeness doctrine is to

prevent the premature adjudication of abstract claims.” 

is

based on Article III’s requirement that federal courts hear only “[c]ases” and

“[c]ontroversies.” See U.S. Const. art. III, § 2; see also Fourth Corner Credit Union

v. Fed. Reserve Bank of Kan. City, 

, 1059 (10th Cir. 2017). Because

federal courts cannot give advisory opinions, the matter must come to the court in

“clean-cut concrete form.” New Mexicans for Bill Richardson v. Gonzales, 

, 1499 (10th Cir. 1995); see also Preiser v. Newkirk, 

, 401 (1975)

(“[A] federal court has neither the power to render advisory opinions nor ‘to decide

questions that cannot affect the rights of litigants in the case before them.’” (quoting

North Carolina v. Rice, 

, 246 (1971) (per curiam))).

       Even when an appeal satisfies Article III’s “case or controversy” requirement,

we may still decline to review it under the prudential ripeness doctrine. Application

of this doctrine turns on two factors: (1) “the fitness of the issue for judicial review,”

and (2) “the hardship to the parties from withholding review.” United States v.

Bennett, 

, 1326 (10th Cir. 2016); see also Abbott Laboratories v.

Gardner, 

, 148–49 (1967). “As for whether the issue is fit for judicial

review, we focus on whether the determination of the merits turns upon strictly legal

                                            7
issues or requires facts that may not yet be sufficiently developed.” United States v.

Ford, 

, 1283 (10th Cir. 2018) (internal quotation marks omitted). Thus,

“[a] claim is not ripe for adjudication if it rests upon ‘contingent future events that

may not occur as anticipated, or indeed may not occur at all.’” Texas v. United States,

, 300 (1998) (quoting Thomas v. Union Carbide Agric. Prod. Co., 

, 580–81 (1985)). As for the hardship to the parties from withholding

review, we consider whether Mr. Cabral “face[s] a direct and immediate dilemma”

arising from the supervised-release condition he is challenging. Bennett, 823 F.3d at

at 1328 (internal quotation marks omitted).

      Here, only prudential ripeness is at issue. Analyzing each of the prudential

ripeness factors, we conclude Mr. Cabral’s vagueness challenge is unripe but his

improper-delegation challenge is ripe for review.

1. Ripeness of Mr. Cabral’s Vagueness Challenge

      Mr. Cabral alleges the risk-notification condition is unconstitutionally vague.

Prudential ripeness prevents us from reaching this challenge both because it is

presently unfit for judicial review and because Mr. Cabral will face little hardship if

we decline to review it now.

      First, it would be virtually impossible to resolve Mr. Cabral’s vagueness

challenge without factual development. The vagueness doctrine requires supervised

release conditions to “be written so that ordinary people can understand what conduct

is prohibited and in a manner that does not encourage arbitrary and discriminatory

enforcement.” United States v. Llantada, 

, 683 (10th Cir. 2016)

                                            8
(quotation marks omitted); cf. City of Chicago v. Morales, 

, 56 (1999)

(articulating standards for vagueness challenges). Applying these standards generally

requires some factual context: in particular, information on what sort of conduct the

provision was intended to regulate and how an officer might reasonably enforce the

challenged provision. See City of 

–64 (considering purpose of

anti-loitering provision and discussing its “perverse consequence of excluding from

its coverage much of the [gang-related] conduct that motivated its enactment”). Here,

we do not know how (or even whether) the probation officer would choose to enforce

the risk-notification condition. Absent such factual development, it is impossible for

us to assess how the condition would be applied—or, indeed, even whether it would

be applied—with sufficient particularity to determine whether it fails on either of

these vagueness grounds.

      Even if we could resolve this pre-enforcement challenge as a pure question of

law, our precedent strongly disfavors deciding challenges to supervised-release

conditions that might never be applied. The doctrine of prudential ripeness

“prevent[s] courts from entangling themselves in [such] abstract disagreements”

without concrete application to guide their analysis. Utah Republican Party v. Cox,

, 1092 (10th Cir. 2018) (quotation marks omitted). Even assuming a

condition is facially problematic, “the mere existence” of a provision such as the

risk-notification condition “is ordinarily not enough to sustain a judicial challenge,

even by one who reasonably believes that the law applies to him and will be enforced

against him.” New Mexicans for Bill 

(quoting Nat’l

                                           9
Student Ass’n v. Hershey, 

, 1110 (D.C. Cir. 1969)). Because the

scenarios Mr. Cabral alludes to “may not occur as anticipated, or indeed may not

occur at all,” depending on the probation officer’s future decisions, this challenge is

not yet fit for judicial review. 

(quoting 

–81)); cf. Nat’l Park Hospitality Ass’n v. Dep’t of Interior, 

, 808

(2003) (“[A] regulation is not ordinarily considered . . . ‘ripe’ for judicial review . . .

until the scope of the controversy has been reduced to more manageable proportions,

and its factual components fleshed out, by some concrete action applying the

regulation to the claimant’s situation in a fashion that harms or threatens to harm

him.” (quoting Lujan v. Nat’l Wildlife Fed’n, 

, 891 (1990))).

       United States v. Ford demonstrates this rule’s application in the supervised-

release context. 

. The defendant in that case challenged, in

relevant part, a “condition requiring him to submit to a polygraph examination if

directed to do so by his probation officer or treatment provider.” 

the

challenge was unripe, reasoning: “When a condition of supervised release is, by its

own terms, contingent on the decision of a different actor, that condition is not ripe

for immediate review.” 

We explained that “the condition that [the

defendant] submit to polygraph testing is only required if (1) treatment is

recommended in the sex-offense-specific assessment [the defendant would be

required to take] and (2) polygraph testing in particular is directed by the probation

officer and/or treatment provider.” 

marks omitted). Likewise,

in United States v. Bennett, we held a challenge to a plethysmograph testing

                                            10
condition unripe where a “treatment provider must evaluate [the defendant] and find

that testing is appropriate” before testing could be 

.5 In

sum, the first prudential-ripeness factor weighs against review because the risk-

notification condition, contingent as it is upon a third party’s decision, implicates

myriad circumstances that may never occur or, if they occur, could trigger different

legal concerns.

       The second prudential ripeness factor, hardship to the parties, also weighs

against review of the vagueness challenge. Mr. Cabral’s risk-notification

obligation—and thus, the “dilemma” whether to comply or challenge that obligation

in court—arises only if his probation officer directs him to notify someone. Thus,



       5
         Several of our sister circuits have adopted similar rules. See, e.g., United
States v. Magana, 

, 459 (5th Cir. 2016) (“An appeal . . . is not ripe if it is ‘a
matter of conjecture’ whether the requirements of the condition will take effect.” (quoting
United States v. Carmichael, 

, 761–62 (5th Cir. 2003))); United States v.
Rhodes, 

, 629 (7th Cir. 2009) (collecting cases) (describing ripeness inquiry
in challenges to supervised-release conditions as turning on whether a condition is
“determinate” or depends on “a string of contingencies”); United States v. Lee, 

, 448, 450 (6th Cir. 2007) (condition requiring participation “in a specialized sex
offender treatment program that may include the use of plethysmograph or polygraph” is
unripe because “we have no idea whether the Probation Office will determine that such
treatment will be necessary”); but see United States v. Rock, 

, 833 n.1 (D.C.
Cir. 2017) (rejecting government's ripeness argument in plethysmograph challenge,
reasoning “supervisory conditions are ordinarily ripe for challenge upon imposition” and
“this court's ruling will provide [defendant] with ‘an immediate, concrete, and valuable
benefit: certainty’ regarding whether he will have to face such testing” (quoting
VanderKam v. VanderKam, 

, 889 (D.C. Cir. 2015))); United States v.
Weber, 

, 556–57 (9th Cir. 2006) (entertaining challenge to plethysmograph
condition even though “it is not certain that [defendant] will ever be ordered to” undergo
such testing because “[a] term of supervised release, even if contingent, is part and parcel
of the defendant's sentence and can be challenged on direct appeal”).

                                             11
Mr. Cabral does not currently face the sort of “direct and immediate dilemma” that

would support judicial review. To be sure, the risk-notification condition as imposed

by the district court vests Mr. Cabral’s probation officer with exceptionally broad

power, and Mr. Cabral convincingly articulates hypothetical scenarios in which his

probation officer could use that broad power to infringe on Mr. Cabral’s rights. But,

as the Government observes, these scenarios “ha[ve] not yet occurred (and may never

occur).” Response Br. at 8 (quoting United States v. Davis, 

, 52 (1st Cir.

2001)). If Mr. Cabral’s probation officer never invokes the risk-notification

condition, then Mr. Cabral will never experience any hardship from the condition,

whether or not we reach the merits of his challenge. “When a condition of supervised

release is, by its own terms, contingent on the decision of a different actor,” Ford’s

holding is unequivocal: “that condition is not ripe for immediate 

. This holds true even if the potential hardship is significant, and even if the

challenge could theoretically be analyzed without waiting for its application. See 

      Mr. Cabral observes that if we decline to review his challenge now and the

probation officer does invoke the condition, he would have only two ways to

challenge it. First, he could move for modification of the condition under 18 U.S.C.

§ 3583(e), but he would be left to do so without the benefit of appointed counsel.

Second, he could simply violate the condition and “risk re-incarceration.”

Appellant’s Reply Br. at 9 (quoting 

). It is true that, assuming

the probation officer invokes the risk-notification condition, Mr. Cabral would suffer

                                           12
a burden from the lack of appointed counsel to challenge the condition. But we

identified a similar burden in Ford, and we still withheld review under the prudential

ripeness doctrine as to the polygraph condition that would be imposed only upon the

future decision of a medical provider. 

(“But to challenge the

condition by violating it would risk re-incarceration. And a request to modify the

condition—unlike this direct appeal—will require he proceed pro se or retain an

attorney near the end of his incarceration . . . .”). Because neither prudential ripeness

factor supports immediate review, we decline to consider Mr. Cabral’s vagueness

challenge on the merits.

2. Ripeness of Mr. Cabral’s Improper-Delegation Challenge

       Unlike his vagueness challenge, Mr. Cabral’s improper-delegation challenge is

presently ripe for review. First, the challenge is fit for judicial resolution because it

presents “a legal [question] that can be easily resolved” without additional factual

development. 

(quotation marks omitted). In Ford, the

challenged condition would be triggered, and therefore would implicate the

defendant’s constitutional rights, only in the event a medical provider recommended

polygraph testing. 

Here, by contrast, Mr. Cabral is challenging the

already-realized delegation of judicial power to a probation officer, not merely some

hypothetical future violation that delegation might allow. Contrary to the

Government’s assertion, we need not “adjudicate hypothetical scenarios” to resolve

this challenge.” Response Br. at 8. The district court’s delegation to the probation

officer occurred at the moment the district court tasked the probation officer with

                                            13
assessing Mr. Cabral’s risk and did so without any meaningful direction. 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.

Thus, the question whether the risk notification condition improperly delegated

judicial power is presently fit for judicial review.

      The burden Mr. Cabral would face if we do not consider his challenge now

weighs at least slightly in favor of review. As explained above, the probation officer

might never invoke the risk-notification condition, and so Mr. Cabral might never

experience any hardship stemming from the alleged improper delegation. But, as with

Mr. Cabral’s vagueness challenge, if we do not decide his improper-delegation

challenge now and the probation officer later invokes the risk-notification condition,

Mr. Cabral could challenge it only without the benefit of appointed counsel or “risk

re-incarceration” by violating the condition. 

. This dilemma,

although still only potential, would certainly place a heavier burden on Mr. Cabral

than if we entertained his challenge on direct appeal, while he is represented by

appointed counsel. To be sure, this potential hardship alone would not justify review

where contingency on a third party’s decision hampers meaningful judicial resolution

of the issue in a factual vacuum, as with Mr. Cabral’s vagueness challenge. See 

But given that Ford is distinguishable in the case of a pure improper-delegation

challenge, the prospect that Mr. Cabral would otherwise have to retain private

counsel or proceed pro se to challenge the condition further supports our immediate

review of his challenge, with the benefit (to him and to us) of counsel’s briefing. See

                                            14
United States v. White, 

, 1204 (10th Cir. 2001) (court’s “interest in

judicial efficiency” impacts prudential ripeness analysis). Because Mr. Cabral’s

improper delegation challenge is ripe for review, we now proceed to consider that

challenge on the merits.

                                B. Improper Delegation

      “We review constitutional non-delegation challenges to conditions of

supervised release de novo.” United States v. Ullmann, 

, 1264 (10th

Cir. 2015). “Article III of the United States Constitution confers the authority to

impose punishment on the judiciary, and the judiciary may not delegate that authority

to a nonjudicial officer.” United States v. Bear, 

, 1230 (10th Cir.

2014). Mr. Cabral argues the risk-notification condition improperly delegates the

power to define the term “risk”—and thus “to determine what conduct the condition

proscribes, and when it will be enforced”—without meaningful guidance from the

district court. Appellant’s Op. Br. at 14–15.

      In an improper-delegation challenge to a supervised-release condition, “we

distinguish between permissible delegations that merely task the probation officer

with performing ministerial or support services related to the punishment imposed

and impermissible delegations that allow the officer to decide the nature or extent of

the defendant’s punishment.” 

(quotation marks omitted). This

inquiry turns “on the liberty interest affected by the probation officer’s discretion.”

a probation officer to make the decision to restrict a defendant’s

significant liberty interest constitutes an improper delegation of the judicial authority

                                           15
to determine the nature and extent of a defendant’s punishment.” 

Mr. Cabral’s probation officer with determining whether Mr. Cabral poses a “risk” to

others in any facet of his life and requiring Mr. Cabral to comply with any order to

notify someone of any such risk, the district court delegated broad decision-making

authority to the probation officer that could implicate a variety of liberty interests.

      To be sure, we try to interpret “open-ended” supervised release conditions

such that they comply with the law. United States v. Mike, 

, 696 (10th

Cir. 2011). Thus, “where a broad condition of supervised release is ambiguous and

could be read as restricting a significant liberty interest, we construe the condition

narrowly so as to avoid affecting that significant liberty interest.” 

–31 (interpreting a condition not to delegate authority to impose invasive

medical and psychiatric treatments because such a condition would implicate liberty

interests). But here, we cannot help construing the risk-notification condition as

granting the probation officer broad discretion to make decisions implicating Mr.

Cabral’s liberty interests. First, it would be impossible for us to cabin the condition

without contradicting the express language of the district court refusing to limit its

scope. See ROA, vol. III at 60 (“I don’t care if I can’t say what the risk is now.

That’s the whole point.”); see also 

(repudiating notion that risk assessment

depends only on “what has transpired, from today backwards, and only based on

those things that are temporally current as of today, as defined and understood by me

in matter X, Y, and Z”). Second, given the district court’s wide-ranging speculation

about how the risk-notification condition might apply to “any number of things,”

                                            16
from a future “mental-health issue” or “drug issue” to a hypothetical future rape

investigation, it would be impossible for us to delineate all the ways in which the

condition may or may not be permissibly enforced. See 

. Unlike Bear, where

it was clear how the challenged condition might infringe on a liberty interest, 

–31, the district court here emphatically opened the door to boundless

scenarios implicating various liberty interests.

       As the district court observed, the condition could implicate a multitude of

liberty interests, depending on how it is enforced: it “[c]ould affect girlfriends,

family, living. It could, in theory, impact an occupation.” ROA, vol. III at 65. In the

interest of providing some guidance on remand, we will elaborate on some (though

certainly not all) of the ways in which the risk-notification condition implicates

Mr. Cabral’s liberty interests and therefore improperly delegates judicial power to the

probation officer.

       If Mr. Cabral’s probation officer orders him to notify family members that he

poses a risk to them, the condition may infringe on his “fundamental right of familial

association.” United States v. Lonjose, 

, 1303 (10th Cir. 2011). “Where

a condition of supervised release interferes with that right, compelling circumstances

must be present to justify the condition.” Id.; see also 

(“Given

the importance of this liberty interest, . . . conditions that interfere with the right of

familial association can do so only in compelling circumstances, and it is imperative

that any such restriction be especially fine-tuned to achieve the statutory purposes of

sentencing.” (quotation marks and citations omitted)).

                                             17
      Similarly, Mr. Cabral’s probation officer might order him to warn an employer

or prospective employer about a perceived risk unrelated to the offense of

conviction—relying, as the probation officer reasonably might, on the district court’s

emphatic refusal to “cabin” the condition to “things that are temporally current as of”

Mr. Cabral’s conviction. ROA, vol. III at 61. This could be an impermissible

occupational restriction, depending upon the circumstances. See 

(striking down third-party notification condition to the extent it “requires

[defendant] to notify potential employers . . . about his criminal convictions” because

“such notification constitutes an occupational restriction and the court did not make

the findings required by law”); see also U.S.S.G. § 5F1.5(a)(1)–(2) (allowing

occupational restrictions only where district court makes specific findings linking

defendant’s occupation to “the conduct relevant to the offense of conviction” and

establishing that such a restriction is “reasonably necessary to protect the public”).6

And we have repeatedly held that occupational restrictions implicate liberty interests.

See, e.g., Stidham v. Peace Officer Standards And Training, 

, 1153

(10th Cir. 2001).

      Because the risk-notification condition, as imposed by the district court, grants

Mr. Cabral’s probation officer decision-making authority that could infringe on a



      6
        Although Mr. Cabral claimed in the district court that Standard Condition
Twelve was an improper occupational restriction, he has not made that argument on
appeal, or even referred to U.S.S.G. § 5F1.5(a) (requiring special findings of fact to
support occupational restrictions). Nonetheless, a probation officer’s future
interpretation of the risk-notification condition may raise such concerns.
                                           18
wide variety of liberty interests, it is an improper delegation of judicial power.

Therefore, we vacate Mr. Cabral’s sentence and remand to the district court for

resentencing.

                                III.   CONCLUSION

      For the foregoing reasons, we DISMISS Mr. Cabral’s vagueness challenge as

prudentially unripe, but we reach the merits of his improper delegation claim, and we

VACATE Mr. Cabral’s sentence and remand to the district court for resentencing

consistent with our decision.




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