In the 

United States Court of Appeals 

For the Seventh Circuit ____________________

No. 15‐3090

UNITED STATES OF AMERICA,

Plaintiff‐Appellee,

v.

ADAM BRENT HILL,

Defendant‐Appellant.

____________________

Appeal from the United States District Court for the

Southern District of Illinois.

No. 3:14‐cr‐30207‐NJR‐1 — Nancy J. Rosenstengel, Judge.

____________________

SUBMITTED MARCH 10, 2016 — DECIDED APRIL 7, 2016

____________________

Before WOOD, Chief Judge, and POSNER and ROVNER, Cir‐

cuit Judges.

POSNER, Circuit Judge. The defendant pleaded guilty to

receiving child pornography and was sentenced to 10 years

in prison plus a fine and restitution and 5 years of super‐

vised release. He filed a notice of appeal, but his lawyer, a

federal public defender, asserting that the appeal is frivo‐

lous—in which event it should be dismissed without ado—

has filed an Anders brief asking us for leave to withdraw as
2 No. 15‐3090   

the defendant’s lawyer and also advising us that the defend‐

ant does not wish to challenge his guilty plea. See Anders v.

California, 386 U.S. 738 (1967).

We are troubled by only one thing, but an important

thing, in the handling of the case so far—how defense coun‐

sel and the district judge dealt with conditions of supervised

release. At the sentencing hearing defense counsel advised

the judge that the defendant did not wish to challenge his

guilty plea or any of the proposed conditions of supervised

release. All those conditions had been proposed by the pro‐

bation service in its presentence report, but are nowhere

mentioned in the Anders brief. The judge did not recite the

conditions at the sentencing hearing; and although the de‐

fendant said that he had read the proposed conditions and

discussed them with his lawyer before the sentencing hear‐

ing, the judge didn’t ask him whether he was waiving any or

all (or none) of the possible objections to them. Before the

sentencing hearing the defendant’s lawyer had objected to a

single condition, the condition forbidding the defendant to

use or possess electronic devices able to take photographs or

record videos; the probation service had responded to the

objection by deleting the condition from the report.

At the sentencing hearing the judge asked the defendant

whether he’d “had enough time to review [the presentence

report] and discuss it with counsel,” and the defendant said

he had. Telling the defendant “you have the right for me to

read each one of [the conditions of supervised release sug‐

gested in the presentence report] and go over them with

you,” the judge asked him whether he was willing to waive

the reading. The lawyer chimed in that he hadn’t had an op‐

portunity to discuss waiver with his client, and he asked the
No. 15‐3090 3

judge to give them “just ... a moment” to confer about the

matter. The judge obliged, and after what must have been

only a brief conference in the courtroom (remember that the

judge had given them “just ... a moment” to confer) the de‐

fendant signed the waiver, which stated that he had no ob‐

jection to the conditions of supervised release and waived

the judge’s reading of them.

We cannot be confident that without additional guidance

from either his lawyer or the district judge the defendant

was capable of knowingly waiving a challenge to any, let

alone all, of the conditions of supervised release. A recurrent

problem regarding waivers of objections to conditions of su‐

pervised release is that because the conditions don’t take ef‐

fect until the defendant is released from prison and criminals

often have a high discount rate (meaning they give little

weight to events in the future other than the immediate fu‐

ture), a defendant sentenced to a long term of prison (10

years in Hill’s case) is quite likely to register no interest in

the conditions without prompting by his lawyer; this under‐

scores the importance of guidance from the lawyer and care‐

ful inquiry by the judge.

That importance was magnified in this case by the prob‐

lematic nature of several of the 20 conditions (apart from the

5 mandatory conditions, for which the judge of course was

not responsible, see 18 U.S.C. § 3583(d)). One of the prob‐

lematic conditions is that “the defendant shall not knowing‐

ly possess a firearm, ammunition, or destructive device. The

defendant shall not knowingly possess a dangerous weapon

unless approved by the Court.” Does this mean that with the

approval of the court the defendant can be permitted to pos‐

sess a “destructive device,” such as live ammunition, which
4 No. 15‐3090   

is not a weapon, just as water is not a cup? Could the judge

allow the defendant to own a gun, which of course is “a

dangerous weapon”?

Another condition states that “the defendant shall report

to the probation officer in a manner and frequency directed

by the Court or [the] probation officer.” Requiring the de‐

fendant to report to his probation officer is unexceptionable,

United States v. Thompson, 777 F.3d 368, 378 (7th Cir. 2015),

but shouldn’t “manner” and “frequency” be defined, or at

least be qualified by “reasonable”? And while in United

States v. Poulin, 809 F.3d 924, 932 (7th Cir. 2016), we called

this condition “a classic administrative requirement that can

be imposed without explanation after the judge has ex‐

plained why supervised release is necessary,” the judge in

the present case did not explain the why or what of the sub‐

stantive need for supervised release as distinct from the ad‐

ministrative conditions that she was imposing, saying only

that “a five‐year term will allow probation to get the defend‐

ant with any mental health, sex offender treatment, any

treatment that he needs at all to assist him with his employ‐

ment needs and reintegration back into society, to reduce

recidivism, and to protect the public from crimes, and afford

specific deterrence. Certainly, we will know within five

years if Mr. Hill is true to his word that he is going to turn

his life around and become a productive member of society.”

Thus in effect she left everything to the probation service.

As for the condition that requires the defendant to “fol‐

low the instructions of the probation officer,” shouldn’t there

be a hint at least at what those instructions might be? Can a

probation officer instruct the defendant to do yoga, attend

church, or shave off his beard? It’s true that a defendant can
No. 15‐3090 5

always ask the judge to modify or eliminate a condition of

supervised release, but how likely is he to do so, at the risk

of irritating the judge? Shouldn’t “instructions” be qualified

by “reasonable”?

Another condition of supervised release requires the de‐

fendant to “notify the probation officer at least ten days pri‐

or to, or within seventy‐two hours after, any change in resi‐

dence or employment.” But would the defendant know

when he must notify the probation officer at least ten days

prior to a change and when he may wait until after the

change? Maybe the idea is that if fired from a job without

notice he has 3 days in which to notify his probation officer;

but if the employer notifies him that he’s being fired at least

10 days in advance of his termination date the defendant

must notify his probation officer immediately. Who knows

what is meant.

A further problem with this condition is the absence of

any indication of what types of change in employment must

be reported. We answered that question in United States v.

Armour, 804 F.3d 859, 869 (7th Cir. 2015), noting approvingly

that “the district court [had] required [the defendant] to ‘no‐

tify Probation ... any time you leave a job or accept a job.’”

In contrast, in United States v. Kappes, 782 F.3d 828, 849 (7th

Cir. 2015), we said, quoting United States v. Thompson, supra,

777 F.3d at 379, that a condition requiring the defendant to

notify his probation officer of any “change in ... employ‐

ment” is too vague, because it fails to indicate “whether

change in employment just means changing employers or

also includes changing from one position to another for the

same employer at the same workplace.” The same vagueness

attends the change‐in‐employment condition in the present
6 No. 15‐3090   

case. The failure of Hill’s lawyer to note this defect seems

inexcusable, as it would be unrealistic to suppose that Hill

himself would have noticed it.

Another condition imposed in this case, criticized for

vagueness in our recent decision in United States v. Henry,

813 F.3d 681, 683 (7th Cir. 2016), requires the defendant to

“permit a probation officer to visit the defendant ... at home

or elsewhere and shall permit confiscation of any contraband

observed in plain view of the probation officer” (emphasis

added). We are troubled by the vagueness of “or elsewhere.”

Again this is a problem neither remarked by the defendant’s

lawyer nor likely to be identified as problematic by the de‐

fendant himself.

Another questionable condition requires the defendant,

“while any financial penalties are outstanding, ... [to] apply

all monies received from income tax refunds, lottery win‐

nings, judgments, and/or any other anticipated or unex‐

pected financial gains to the outstanding court‐ordered fi‐

nancial obligation.” What if the defendant is unemployable,

and one or more of these financial gains is his only source of

income? Shouldn’t his elementary needs be balanced against

the government’s revenue needs and (less certainly) against

claims for restitution by victims of the defendant’s crimes?

Since financial gain could refer to any income, this condition

potentially conflicts with the payment schedule set by the

court, which requires Hill to pay either $50 per month or 10

percent of his net monthly income, whichever is greater.

Still another questionable condition, this one also criti‐

cized in United States v. Kappes, supra, 782 F.3d at 849, re‐

quires the defendant to “work regularly at a lawful occupa‐

tion unless excused by the probation officer for schooling,
No. 15‐3090 7

training, or other acceptable reasons.” The assumption must

be that the defendant can find regular work. But what if he’s

unemployable? Is that an “acceptable reason” for not work‐

ing?

Hopelessly vague is the further condition, again also crit‐

icized in Kappes, id. at 849, that the defendant “shall notify

third parties of risks that may be occasioned by the defend‐

ant’s criminal record or personal history or characteristics.”

Does this mean that if he happens to be standing next to a

six‐year‐old girl at a soda fountain he has to warn her that he

has been convicted of receipt of child pornography? Does he

have to explain to her what child pornography is?

The vagueness of so many of the conditions of super‐

vised release imposed in this case is important because the

more vague a condition is, the harder it is for the defendant

to determine what restrictions it actually imposes and

whether any of them are so onerous that he should object.

There is more to criticize but we have said enough to in‐

dicate that the conditions of supervised release imposed in

this case should have received more careful scrutiny by de‐

fense counsel and the district judge—unless there was in‐

deed a knowing waiver by the defendant. We cannot tell,

because the judge did not confirm with the defendant that

he had knowingly waived objections to the conditions, and

because the record does not reveal how long the defendant

and his lawyer huddled in the courtroom before the defend‐

ant agreed to sign the waiver. Probably the huddle was brief,

since as we noted earlier the judge said that she was giving

them “just ... a moment” to decide whether there would be a

waiver.  
8 No. 15‐3090   

But out of an abundance of caution we have decided to

remand the case for a determination of the length of the

huddle and, relatedly, whether the defendant knowingly

waived all objections to the conditions of supervised release.

It might seem that we should go further, and remand the

case for revision of the conditions of supervised release and

for a full resentencing. There is potential substitutability be‐

tween prison and the conditions. Both types of punishment

restrict the defendant’s freedom. And therefore other things

being equal (which often they are not, however), the more

restrictive the conditions the less the need for a very long

prison sentence, while the longer the prison sentence the less

the need for very strict conditions. E.g., United States v.

Downs, 784 F.3d 1180, 1182 (7th Cir. 2015). But a remand of

such scope would be premature, given the possibility just

discussed that the defendant made a knowing waiver of ob‐

jections to the conditions of supervised release. Should the

limited remand we are ordering reveal that the defendant

did not make a knowing waiver of all challenges to the con‐

ditions of supervised release recommended in the presen‐

tence report and imposed by the judge, the defendant, with

advice of counsel, will still need to decide whether correct‐

ing the unsound or questionable conditions that we’ve iden‐

tified would carry too great a risk that the corrections would

lead the district judge to increase the length of the defend‐

ant’s prison sentence. Of course the judge might decide in‐

stead to reduce it, but this just means that there is both up‐

side and downside risk, and a defendant is entitled to an

opportunity to decide whether to take a chance that the up‐

side risk will not materialize. United States v. Bryant, 754 F.3d

443, 447 (7th Cir. 2014).
No. 15‐3090 9

So, to conclude, if the limited remand that we’re ordering

results in a determination that the defendant knowingly

waived all challenges to the conditions of supervised release,

we will grant the Anders motion and that will be the end of

the case. If instead the determination is that he did not

knowingly waive all challenges to the conditions, the case

will again come before us and he will need to decide (and

through his counsel advise us of the decision) whether or not

to challenge the conditions, since a successful challenge, fol‐

lowed by a remand for resentencing, will leave the judge

free to impose a longer, as well as in the alternative a short‐

er, prison sentence. For now, however, we need only remand

the case for a determination of whether the defendant know‐

ingly waived all objections to the conditions of supervised

release imposed by the district court. The defendant’s lawyer

shall continue to represent the defendant on remand, and is

ordered to file a status report with this court within 14 days

of the district court’s ruling on remand.

CASE REMANDED WITH DIRECTIONS