In the

United States Court of Appeals

For the Seventh Circuit ____________________

No. 14-1316

UNITED STATES OF AMERICA,

Plaintiff-Appellee,

v.

DAVID M. THOMPSON,

Defendant-Appellant.

____________________

Appeal from the United States District Court for the

Southern District of Illinois.

No. 3:12-cr-30316-MJR-1 — Michael J. Reagan, Chief Judge.

____________________

No. 14-1521

UNITED STATES OF AMERICA,

Plaintiff-Appellee,

v.

DEREK ORTIZ,

Defendant-Appellant.

____________________

Appeal from the United States District Court for the

Northern District of Illinois, Eastern Division.

No. 10 CR 187-1 — Matthew F. Kennelly, Judge.

____________________
2 Nos. 14-1316, -1521, -1676, -1772

No. 14-1676

UNITED STATES OF AMERICA,

Plaintiff-Appellee,

v.

CHARLES BATES,

Defendant-Appellant.

____________________

Appeal from the United States District Court for the

Northern District of Illinois, Eastern Division.

No. 12 CR 700-1 — Charles R. Norgle, Sr., Judge.

____________________

No. 14-1772

UNITED STATES OF AMERICA,

Plaintiff-Appellee,

v.

DOMINGO BLOUNT,

Defendant-Appellant.

____________________

Appeal from the United States District Court for the

Northern District of Illinois, Eastern Division.

No. 11 CR 415-1 — Gary S. Feinerman, Judge.

____________________

ARGUED NOVEMBER 13, 2014 — DECIDED JANUARY 13, 2015

____________________
Nos. 14-1316, -1521, -1676, -1772 3

Before POSNER, KANNE, and ROVNER, Circuit Judges.

POSNER, Circuit Judge. We have consolidated for decision 

four appeals, heard on the same day, that present issues relating to supervised release. In a recent opinion, United States 

v. Siegel, 753 F.3d 705 (7th Cir. 2014), the court expressed 

concern with how the district courts of our circuit are administering supervised release. To recapitulate briefly the fuller 

discussion in the Siegel opinion, the Sentencing Reform Act 

of 1984 replaced parole for federal crimes with supervised 

release (to take effect in 1987). 18 U.S.C. § 3583. Parole of 

federal convicts is granted (though nowadays only in a very 

limited class of cases, see United States Parole Commission, 

Wikipedia, http://en.wikipedia.org/wiki/United_States_Parole

_Commission (visited Jan. 11, 2015, as was the other website

cited in this opinion)) by an administrative agency after a 

convicted defendant begins serving his sentence. An inmate 

granted parole is thus released from prison before the expiration of his term, but becomes subject to restrictions imposed by the agency on his conduct between his release and 

when, had he not been paroled, he would have been released upon the expiration of his prison sentence. The restrictions are intended to reduce the likelihood of his committing crimes in the future.

Supervised release, in contrast to parole, consists of restrictions, imposed by the judge at sentencing, called conditions or terms of supervised release, that are to take effect 

when the defendant is released from prison and continue for 

a specified term of years (which can be life). Parole shortens 

prison time, substituting restrictions on the freed prisoner. 

Supervised release does not shorten prison time; instead it 

imposes restrictions on the prisoner to take effect upon his 
4 Nos. 14-1316, -1521, -1676, -1772

release from prison. Parole mitigates punishment; supervised release augments it—most dramatically when the defendant, having been determined to have violated a condition or conditions of supervised release, is given, as punishment, a fresh term of imprisonment. 18 U.S.C. § 3583(e)(3). 

Supervised release is required by statute in fewer than half 

of cases subject to the sentencing guidelines. United States 

Sentencing Commission, Federal Offenders Sentenced to Supervised Release 3 (July 2010), www.ussc.gov/sites/default/files/

pdf/training/annual-national-training-seminar/2012/2_Feder

al_Offenders_Sentenced_to_Supervised_Release.pdf. In the 

other cases the sentencing judge has discretion to order or 

not order it, see 18 U.S.C. § 3583(a), but almost always the 

judge orders it in those cases too, United States Sentencing 

Commission, supra, at 69–70, often without explaining why.

Although the defendants in our four cases object to particular conditions of supervised release imposed on them, they 

do not challenge the propriety of the inclusion of some conditions of supervised release in their sentences.

Supervised release as it is designed and administered has

turned out to be problematic in a number of respects. See, 

e.g., Christine S. Scott-Hayward, “Shadow Sentencing: The 

Imposition of Federal Supervised Release,” 18 Berkeley J. 

Crim. L. 180 (2013); Fiona Doherty, “Indeterminate Sentencing Returns: The Invention of Supervised Release,” 88 

N.Y.U. L. Rev. 958 (2013). One is that the list of conditions

required or suggested is very long. The supervised-release

statute, 18 U.S.C. § 3563(b), imposes 9 “mandatory” conditions and 23 “discretionary conditions,” for a total of 32. The 

sentencing guidelines get into the act as well, see U.S.S.G. 

§ 5B1.3, imposing 10 “mandatory” conditions, 14 “standard” 

conditions, and 13 “special” or “additional conditions”—a 
Nos. 14-1316, -1521, -1676, -1772 5

total of 37. The statutory and guideline conditions, where 

they overlap, are generally the same substantively, but their 

wording often differs. Sentencing judges usually use the 

guideline wording rather than the statutory wording. All but 

the mandatory conditions are optional. And the judge is free 

to add or substitute (except with regard to the mandatory 

conditions) conditions of his own devising. Understandably, 

given the number of conditions, many district judges simply 

list the conditions that they impose, devoting little or no

time at sentencing to explaining them or justifying their imposition.

Because conditions of supervised release do not take effect until the defendant completes his prison term and is released, defendants given long prison sentences—and long 

prison sentences are common in federal sentencing—often 

have little interest in contesting conditions of supervised release at sentencing. Criminals who court long prison sentences tend to have what economists call a high discount 

rate. That is, they give little weight to future costs and benefits. Defendants or their lawyers may also worry that a successful challenge to a condition or conditions of supervised 

release may induce the judge to impose a longer prison sentence, thinking that resistance to supervised release implies 

recidivist tendencies or intentions. And often a defendant is 

given no notice in advance of the sentencing hearing of the 

conditions of supervised release that the judge is thinking of 

imposing, which can make it difficult for his lawyer to prepare arguments in opposition.

Many district judges appear to have overlooked the fact

that because the imposition of conditions of supervised release is part of the sentence, a sentencing judge is required 
6 Nos. 14-1316, -1521, -1676, -1772

by the Supreme Court’s decision in United States v. Booker, 

543 U.S. 220 (2005), to evaluate the propriety of any conditions of supervised release that the judge is thinking of imposing, by applying to the proposed conditions the sentencing considerations listed in 18 U.S.C. § 3553(a). The considerations include (in subsections (1), (2), and (3) respectively) 

“the nature and circumstances of the offense and the history 

and characteristics of the defendant,” “the need for the sentence imposed,” and “the kinds of sentences available.”

Any doubt that conditions of supervised release are a 

part of the sentence and subject therefore to the requirement 

that the judge before imposing sentence apply the sentencing factors in section 3553(a) is dispelled by 18 U.S.C. 

§ 3583(c). It provides that “the court, in determining whether 

to include a term of supervised release, and, if a term of supervised release is to be included, in determining the length 

of the term and the conditions of supervised release, shall 

consider the factors set forth in [eight enumerated subsections of] section 3553(a).” And being part of the sentence, the 

imposition of conditions of supervised release is subject to 

the further requirements that “the court, at the time of sentencing, shall state in open court the reasons for its imposition of the particular sentence,” 18 U.S.C. § 3553(c), and “in 

determining the length of the term and the conditions of supervised release, shall consider the factors set forth in” eight 

enumerated subsections of section 3553(a). 18 U.S.C. 

§ 3583(c).

Subsection (a) of section 3553 lists the sentencing factors 

that the judges are to consider in determining the sentence. 

From the omission of subsection 3553(a)(2)(A), the court in 

United States v. Murray, 692 F.3d 273, 280 (3d Cir. 2012), in-
Nos. 14-1316, -1521, -1676, -1772 7

ferred “that the primary purpose of supervised release is to 

facilitate the reentry of offenders into their communities, rather than to inflict punishment.” The omitted subsection 

(a)(2)(A) is “the need for the sentence imposed ... to reflect 

the seriousness of the offense, to promote respect for the law, 

and to provide just punishment for the offense.”

The sheer number of conditions may induce haste in a 

sentencing judge’s evaluation of the recommendations of the 

probation officer assigned to the case as to what conditions 

of supervised release to impose (if there are such recommendations—often there are not; there are not in any of the 

four cases before us) and is doubtless a factor in judges’ frequent omission to mention any of the sentencing factors in 

section 3553(a) or even any of the conditions recommended 

by the parties or the probation officer that the judge decides 

to include in the sentence.

And because conditions of supervised release, though 

imposed at sentencing, do not become operational until the 

defendant is released, the judge has to guess at the time of 

sentencing what conditions are likely to make sense in what 

may be the distant future. Conditions that may seem sensible at sentencing may not be sensible many years later, when 

the defendant is finally released from prison. Although 

nonmandatory conditions of supervised release can be modified at any time, 18 U.S.C. § 3583(e)(2), modification is a 

bother for a judge, especially when, as is common in cases 

involving very long sentences, it becomes the responsibility 

of the sentencing judge’s successor because in the meantime

the sentencing judge has retired or died, resigned, or been 

promoted. Furthermore, although reducing recidivism is the 

purpose of supervised release, it is difficult, often impossi-
8 Nos. 14-1316, -1521, -1676, -1772

ble, to predict whether a defendant is likely upon release to 

resume criminal activity. Often rehabilitation is named as an 

additional purpose of supervised release, but being rehabilitated and going straight are as a practical matter synonymous.

Another wrinkle is that because conditions of supervised 

release are imposed at sentencing, the conditions recommended to the judge at the sentencing hearing may be a 

product of negotiation between prosecution and defense. 

The defendant’s lawyer may offer the prosecution a trade—

more supervised release for a reduced prison term—and the 

prosecutor may agree. And when adversaries agree on the 

outcome of a legal proceeding the sentencing judge, habituated as American judges are to adversary procedure, may be 

reluctant to subject the agreement to critical scrutiny, even 

though the law is clear that the fact that the prosecution and 

defense agree on a sentence does not excuse the judge from 

having to determine the sentence’s conformity to the statutory sentencing factors. Freeman v. United States, 131 S. Ct. 

2685, 2692 (2011).

Still another problem is that probation officers, upon 

whom district judges rely heavily for recommendations concerning what conditions of supervised release to impose,

spend disproportionate time on enforcement (that is, investigating violations of conditions of supervised release and 

recommending punishments for the violators) and have little 

time left over for suggesting appropriate conditions and 

helping the probationer to comply with them. This is a serious problem given the severe understaffing of the probation 

service that we discussed in the Siegel opinion, 753 F.3d at 

710, and the reliance that most district judges repose in the 
Nos. 14-1316, -1521, -1676, -1772 9

recommendations of the probation officer assigned to the 

case when the officer makes recommendations. A revocation 

of supervised release and recommital to prison relieves the 

probation service of monitoring the person during his term 

of imprisonment. According to Scott-Hayward, supra, at 182

(footnotes omitted), “on average, one third of those individuals [on supervised release] will have their supervised release revoked, most as a result of technical violations, and 

receive, on average, a new prison sentence of 11 months.”

And finally a number of the listed conditions, along with 

a number of conditions that judges invent, are, as we’re 

about to explain, hopelessly vague. See also our Siegel opinion, 753 F.3d at 712–16, for a fuller discussion of vagueness 

and ambiguity in conditions of supervised release.

Given the problems we’ve enumerated, it is no surprise 

that the administration of supervised release by the district 

courts has not run smoothly. The types of oversights that 

we’ll be discussing—well illustrated by our four cases—are 

understandable, perhaps indeed inevitable, given the confusion that the applicable statutory and guidelines provisions

have created.

We begin with United States v. Thompson. Thompson was 

23 years old when he began an online relationship with a girl 

of 14. They exchanged nude pictures of themselves. When 

she was 16 and he 25 she decided to run away from home.

Thompson picked her up and drove her across state lines, 

and they had sex in a state in which the age of consent was 

16 and their sexual activity therefore legal. Convicted in federal district court of possession of child pornography, and of 

traveling in interstate commerce for the purpose of engaging 

in sexual conduct, in violation of federal laws that fix the age 
10 Nos. 14-1316, -1521, -1676, -1772

of consent as 18 rather than, as in many states, 16, see, e.g., 

18 U.S.C. § 2423(a), Thompson was sentenced to 210 months 

in prison. He does not challenge the prison sentence, but only conditions of supervised release.

Even with full credit for behaving himself in prison, 

Thompson will be just days short of 41 years old when released, and it seems odd to be devising so far in advance restrictions to impose on him then; but that is how supervised 

release operates. What is beyond odd—what is unauthorized—is that the judge imposed a lifetime of supervised release without any articulated justification. The need for an 

express justification was acute because, as the judge remarked, as a convicted sex offender Thompson will be subject after he is released from prison to a lifetime of mandatory state and local sex-offender reporting quite apart from 

supervised release. And sensible or not, the lifetime term is 

vitiated by the fact that in imposing it the judge was laboring 

under the misapprehension that, in his words, “a term of 

supervised release can be reduced but can’t be extended.” 

That’s wrong; it can be extended. 18 U.S.C. §§ 3583(e)(1)-(2); 

Fed. R. Crim. P. 32.1(c).

It’s not that the judge thought that Thompson after being

released from prison will be a menace to young girls until he 

dies perhaps as an octogenarian or even a nonagenarian. It is 

rather, as the judge explained, that because the future cannot 

be predicted, any term of supervised release shorter than life 

would create a risk that Thompson would commit further 

crimes at an advanced age. But should that risk seem acute

many years from now when Thompson completes his prison 

term, a finite term of supervised release could be extended, 

as the judge failed to understand. We are surprised that nei-
Nos. 14-1316, -1521, -1676, -1772 11

ther the government nor the defense pointed out the judge’s 

error at the sentencing hearing.

The judge committed other errors. One was his failure to 

include in the oral sentence a condition of supervised release 

requiring that the defendant receive treatment for drug addiction. Not because it’s a mandatory condition or one that 

the judge would have been remiss in failing to impose, but 

because, though he intended to impose it, it appears only in 

the written judgment, and the oral sentencing, which omits 

it, takes precedence over the written. United States v. Johnson, 

765 F.3d 702, 710–11 (7th Cir. 2014); United States v. Alburay, 

415 F.3d 782, 788 (7th Cir. 2005).

A more serious error was a condition of supervised release that Thompson not have “any contact with persons 

under the age of 18 unless in the presence of a responsible 

adult who is aware of the nature of the defendant’s background and instant offense and who had been approved by 

the probation officer.” This can’t have been meant literally, 

since understood literally it would include males under 18 as 

well as females, though there is no suggestion that Thompson is bisexual. Furthermore, even if males are excluded 

from the no-contact rule, “contact,” being undefined, could 

be understood to mean being served by a waitress, paying a 

cashier, sitting next to a girl (a stranger) at a baseball game, 

replying to a girl asking directions, or being shown a friend’s 

baby girl—or his own baby, for that matter.

We have warned against imposing a restrictive condition 

that is not reasonably related to the defendant’s “offense, 

history and characteristics. ... Moreover, given the potentially severe restrictions on [the defendant’s] day-to-day life that 

this condition imposes, the district court’s lack of explana-
12 Nos. 14-1316, -1521, -1676, -1772

tion of why it thinks this condition involves no greater deprivation of liberty than necessary to achieve the penological 

goals stated in 18 U.S.C. § 3553(a) is troubling. ... Because 

the district court has not provided any explanation of how 

this condition is reasonably related to [the defendant’s] offense and background or to the goals of punishment, involving no greater deprivation of liberty than is reasonably necessary to achieve these goals, we vacate the condition.” United States v. Goodwin, 717 F.3d 511, 523–24 (7th Cir. 2013).

The judge in Thompson’s case imposed a total of 24 nonmandatory conditions of supervised release. Because all 

those conditions were part of the sentence, the judge was, as 

we noted earlier in this opinion (as well as in Goodwin and 

Siegel) not permitted to impose them without determining 

their conformity to the sentencing factors in 18 U.S.C. 

§ 3553(a). There is no indication that he did so. He just 

checked boxes in a list of conditions. Some of the conditions

seem appropriate or innocuous, but others are either inappropriate or vague. Among the inappropriate ones is that the 

“defendant shall support his or her dependents and meet 

other family responsibilities.” Of course “or her” should not 

be in there; its inclusion suggests the rote nature of the 

judge’s imposition of conditions of supervised release. More 

important, the condition assumes arbitrarily and maybe inaccurately that should Thompson ever acquire dependents 

he will have, despite being an ex-con subject to conditions of 

supervised release and state and local sex-offender restrictions and reporting requirements, the resources necessary to support his dependents.

Among the vague conditions is that “defendant shall refrain from excessive use of alcohol,” where “excessive use” 
Nos. 14-1316, -1521, -1676, -1772 13

is not defined, though it could readily be defined, as we explained in United States v. Siegel, supra, 753 F.3d at 715–16. 

Fatally vague is a condition forbidding the defendant to “associate with any person convicted of a felony, unless granted 

permission to do so by the probation officer.” How would 

the defendant know whether someone he was associating 

with had ever been convicted of a felony? There is no stated

requirement that he know; the condition appears to impose 

strict liability. If so, to protect himself he would have to

submit the name of any person he met to his probation officer to determine whether the name appeared in any database of felons. Maybe liability for violating the condition 

isn’t strict; so might it be enough that a reasonable person 

would know that a person whom the defendant was associating with was a felon, even if the defendant didn’t know? 

And what exactly is “association”? Is a single meeting 

enough, or is the word intended to denote friendship, acquaintanceship, or frequent meetings? What if a dependent 

whom Thompson will be required to support when he is released from prison is convicted of a felony? Must he stop associating with that person as well? Would it not be more 

sensible to scrap the quoted condition and instead forbid the 

defendant “to meet, communicate, or otherwise interact with 

a person whom he knows to be engaged, or planning to be 

engaged, in criminal activity”?

The government offers the blanket defense that Thompson waived any objection to the conditions of supervised release that the judge imposed. The judge had sent a list of the 

conditions, with checkmarks next to the ones he was considering imposing, to the parties in advance of the sentencing 

hearing and the government argues that this was the defendant’s (more realistically, his lawyer’s) last chance to op-
14 Nos. 14-1316, -1521, -1676, -1772

pose them. But the judge didn’t indicate why he was thinking of imposing these conditions. A judge cannot properly 

decide what sentence to impose without consideration of the 

sentencing factors in 18 U.S.C. § 3553(a). If upon consideration of these factors he decides that he’s leaning toward imposing particular conditions, he should inform the parties of 

the conditions and the possible reasons for imposing them, 

so that they can develop arguments pro or con to present at 

the sentencing hearing. (It would likewise be a better practice for the presentence report to give reasons for any conditions of supervised release that it suggests, but as we said 

the presentence reports in these four cases did not suggest 

any conditions of supervised release.) An alternative would 

be for the judge to explain at the sentencing hearing what 

conditions he was inclined to impose and why, and ask the 

defendant’s lawyer whether he objects to any of them; if the 

lawyer had a reasonable need for more time to decide

whether he has grounds for objection, the judge could adjourn the hearing.

Either of our suggested approaches would be a “best 

practice,” which is different from a required practice; for except with regard to conditions of supervised release not 

listed in the statute or the guidelines, United States v. Bryant, 

754 F.3d 443, 446 (7th Cir. 2014), no advance notice is required. Id. at 446–47; United States v. McKissic, 428 F.3d 719, 

725–26 (7th Cir. 2005); United States v. Lopez, 258 F.3d 1053, 

1055–56 (9th Cir. 2001); United States v. Barajas, 331 F.3d 1141, 

1143–45 (10th Cir. 2003). This conclusion follows from the 

Supreme Court’s decision in Irizarry v. United States, 553 U.S. 

708 (2008). The district judge in that case had imposed a sentence in excess of the sentence recommended in the presentence report without prior notification to the parties. The 
Nos. 14-1316, -1521, -1676, -1772 15

Supreme Court held that this lack of notice didn’t require 

reversal.

But that holding is consistent with Barajas, where we read

that “there may be occasions when a defendant has a good 

reason for not being prepared to address at sentencing the 

imposition of a condition of supervised release listed in the 

Sentencing Guidelines. In such a circumstance the district 

court can exercise its sound discretion to grant a continuance,” id. at 1145—though we would be inclined to substitute “should” for “can” in the last clause of the quoted passage. For in Irizarry itself we read that

Rule 32(i)(1)(C) [of the Federal Rules of Criminal Procedure] requires the district court to allow the parties 

to comment on “matters relating to an appropriate sentence,” and given the scope of the issues that may be 

considered at a sentencing hearing, a judge will normally be well advised to withhold her final judgment 

until after the parties have had a full opportunity to 

present their evidence and their arguments. Sentencing 

is “a fluid and dynamic process and the court itself 

may not know until the end whether a variance will be 

adopted, let alone on what grounds.” ... Sound practice dictates that judges in all cases should make sure 

that the information provided to the parties in advance 

of the hearing, and in the hearing itself, has given them 

an adequate opportunity to confront and debate the 

relevant issues. We recognize that there will be some 

cases in which the factual basis for a particular sentence will come as a surprise to a defendant or the 

Government. The more appropriate response to such a 

problem is not to extend the reach of Rule 32(h)’s notice requirement categorically, but rather for a district 

judge to consider granting a continuance when a party 
16 Nos. 14-1316, -1521, -1676, -1772

has a legitimate basis for claiming that the surprise was 

prejudicial.”

553 U.S. at 715–16. Because we’re remanding in Thompson’s 

case, the defendant’s lawyer should be permitted to wait until the sentencing hearing to present his objections to whatever conditions of supervised release the judge is minded to 

impose.

We need to note an exception to our “best practice” suggestion, however. Some conditions of supervised release are 

administrative requirements applicable whenever a term of 

supervised release is imposed, regardless of the substantive 

conditions that are also imposed. Examples are requiring the 

defendant to report to his probation officer, answer the officer’s questions, follow his instructions, and not leave the 

judicial district without permission. Once the judge has explained why supervised release is necessary, he should be 

permitted to impose the necessary incidents of supervision 

without explanation. It is not correct, however, as has been 

suggested, that all the standard conditions are “‘basic administrative requirement[s] essential to the functioning of 

the supervised release system.’” United States v. Truscello, 168 

F.3d 61, 63–64 (2d Cir. 1999). To similar effect see United 

States v. Tulloch, 380 F.3d 8, 13–14 (1st Cir. 2004). Most of 

them are substantive rather than administrative.

So much for Thompson’s sentence; on to United States v. 

Ortiz. This defendant pleaded guilty to three bank robberies 

and was sentenced to prison for 135 months. Twenty-one

conditions of supervised release were imposed, all but one 

to remain in force for three years after his release from prison. As in Thompson’s case, the appeal does not challenge the 

prison sentence but only conditions of supervised release.
Nos. 14-1316, -1521, -1676, -1772 17

The presentence report, prepared (as is normal) by the 

probation officer assigned to the case, contained no suggested conditions of supervised release at all. Nor had the prosecution suggested any. They were sprung on the defendant at 

the sentencing hearing, and with such brevity that we don’t

think his lawyer can be faulted for having failed to object.

The judge’s entire discussion of supervised release consisted 

of the following sentence: “The conditions of supervised release will include the normal conditions, plus drug testing 

up to the maximum that’s permitted, drug counseling and 

treatment at the direction of the probation office, and mental 

health counseling and treatment at the direction of the probation office, which may include taking necessary prescription medications.” It’s not clear what the judge meant by 

“normal conditions,” but the written judgment lists 3 mandatory conditions (DNA collection, drug testing, and a prohibition against committing further crimes), 13 standard 

conditions (judges usually exclude from the guidelines list of 

14 standard conditions the last one, which relates to the 

payment of the financial obligations imposed by the sentence; for some reason not known to us this requirement is 

incorporated into another part of the standard form that is 

issued to defendants when they receive their sentences), and 

5 additional conditions (a firearm prohibition, a drug treatment program, mental health counseling, a requirement that 

the defendant report to the probation office within 72 hours 

of his release from prison, and that he pay restitution). Far 

from applying the sentencing factors in 18 U.S.C. § 3553(a) to 

the conditions of supervised release that he was imposing, 

the judge gave no reasons at all for any of the conditions.

The conditions imposed are riddled with ambiguities. 

Example: “as directed by the probation officer, the defendant 
18 Nos. 14-1316, -1521, -1676, -1772

shall notify third parties of risks that may be occasioned by 

the defendant’s criminal record or personal history or characteristics.” There is no indication of what is meant by “personal history” and “characteristics” or what “risks” must be 

disclosed to which “third parties.” The defendant is to notify 

his probation officer of any “change in ... employment,” but

there is no indication 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 defendant is forbidden to “frequent places 

where controlled substances are illegally sold, used, distributed, or administered,” but there is no requirement that he 

know or have reason to know or even just suspect that such 

activities are taking place. Nor is there any indication of how 

many trips constitute “frequent[ing]” such places. Instead of 

being forbidden to use a controlled substance he “shall have 

no use of controlled substance,” a puzzling expression. And 

he is required to pay substantial restitution (more than 

$13,000) “at a rate of at least 10% of new monthly income,” 

but there is no explanation of what “new” is meant to signify. Nor did the district court specify a penalty should the defendant fail to pay the restitution ordered.

Ortiz’s counsel takes particular issue with two standard 

conditions of supervised release that might be thought to 

impinge on constitutional rights: that “the defendant shall 

answer truthfully all inquiries by the probation officer” and 

that he “shall permit a probation officer to visit him or her 

[there is of course no “her” in the case] at any time at home 

or elsewhere and shall permit confiscation of any contraband observed in plain view of the probation officer.” The 

first of these conditions essentially asks for a waiver of the 

right not to be forced to incriminate oneself, because the 
Nos. 14-1316, -1521, -1676, -1772 19

condition would require the defendant to answer “yes” if he 

were asked whether he had committed another crime and he 

had. The second condition would allow the probation officer 

to “visit” the defendant at 3:00 a.m. every morning and look 

around for contraband, and also allow him to follow the defendant everywhere, looking for contraband. Regardless of 

any possible constitutional concern, both conditions are too 

broad in the absence of any effort by the district court to explain why they are needed.

A number of decisions in other circuits brush aside objections to the breadth and ambiguity of the many conditions 

of supervised release imposed by district judges. See, e.g., 

United States v. Phillips, 704 F.3d 754, 767–68 (9th Cir. 2012); 

United States v. Zobel, 696 F.3d 558, 574–75 (6th Cir. 2012); 

United States v. Albertson, 645 F.3d 191, 200–01 (3d Cir. 2011); 

United States v. Mike, 632 F.3d 686, 696–97 (10th Cir. 2011). 

However, in all those cases, and others that we might cite as 

well, the court interpreted an overbroad or ambiguous condition narrowly. For example, in Phillips after noting that the 

district court had imposed “a condition prohibiting Phillips 

from ‘frequent[ing] places where controlled substances are 

illegally sold, used, distributed, or administered,’” a condition that Phillips contended on appeal was “’vague and 

overbroad,’” the Ninth Circuit held that the condition “prohibits Phillips from knowingly going to a specific place where 

drugs are illegally used or sold, but ... does not prohibit him 

from ... going to a given neighborhood simply because a 

person is selling drugs somewhere within that neighborhood.” 704 F.3d at 767–68 (emphasis in original). It is preferable for the district court to specify limitations in a condition 

of supervised release in the condition itself, rather than leaving it to the appellate court to interpolate the limitations; 
20 Nos. 14-1316, -1521, -1676, -1772

otherwise the defendant may think himself bound by the 

broader interpretation. If you’re 90 percent certain that purchasing girl-scout cookies from someone who rings your

doorbell wouldn’t violate a condition of supervised release, 

do you want to risk going back to prison because you may 

have guessed wrong? If out of caution therefore you decline 

to purchase the cookies, the sentencing guideline will deter 

lawful conduct, and thus be overbroad. Like any other part 

of a criminal sentence, the conditions of supervised release 

that are imposed should be clear.

That is one teaching of our Siegel decision and in addition 

we believe and endeavored to make clear in that decision

that conditions of supervised release imposed in a sentence 

require careful appellate consideration when the sentencing 

judge fails to explain or justify or narrow ambiguous or inappropriate-seeming conditions and fails to apply the statutory sentencing factors.

Our third case is United States v. Bates. The defendant 

was sentenced to 188 months in prison for dealing in crack 

cocaine. With regard to supervised release, the case is essentially identical to Ortiz. No conditions of supervised release 

were mentioned in the presentence report. The judge sprang 

them on the parties in the sentencing hearing, imposing the 

usual 13 standard conditions and five others (though for 

eight years, rather than the three years in Ortiz’s case). He 

gave no reasons for any of them. All he said was: “The 

standard conditions are adopted by the Court” (actually, as 

we just noted, not all of them). Our criticisms of the handling 

of supervised release by the judge in Ortiz’s case are equally 

applicable to Bates’s case.
Nos. 14-1316, -1521, -1676, -1772 21

In our final case, United States v. Blount, the defendant

challenges not only the conditions of supervised release but 

also the prison sentence (300 months, for running an extensive organization engaged in the sale of heroin), specifically 

the four-level enhancement in the defendant’s base offense 

level by reason of his being “an organizer or leader of a 

criminal activity that involved five or more participants or 

was otherwise extensive.” U.S.S.G. § 3B1.1(a). For the persuasive reasons given by the district judge and unnecessary 

for us to repeat or amplify, the enhancement, and so the 300-

month sentence, were proper. As in our other three cases, 

however, the district judge’s handling of supervised release 

was seriously flawed.

There was again no discussion of any section 3553(a) factors that the judge may have thought justified the length and 

conditions of supervised release. His discussion of the conditions of supervised release that he was imposing on the defendant is difficult even to understand. He listed only 8 conditions, but said that the defendant “shall comply with the 

standard conditions that have been adopted by this court,” 

and the written judgment lists the 13 usual standard conditions—with all their ambiguities uncorrected. The 8 conditions he discussed are a mixture of mandatory and “additional” conditions.

Two of them are seriously questionable. One is that “if 

[the defendant is] unemployed after the first 60 days of supervision or if unemployed for 60 days after termination or 

layoff from employment, he shall perform at least 20 hours 

of community service work per week at the direction of and 

in the discretion of the Probation Office until gainfully employed.” Taken literally, this means that if at, say, age 68 he 
22 Nos. 14-1316, -1521, -1676, -1772

is unemployed, he will have to perform 20 hours of community service per week—indefinitely (till he dies?). No doubt 

the judge, if he thought about this condition, would not have 

wanted it interpreted literally, especially since an application 

note to U.S.S.G. § 5F1.3 states that “community service generally should not be imposed in excess of 400 hours.” The 

judge did not mention that application note, and the government is incorrect when it says in its brief that the judge’s 

community-service condition “did not amount to the imposition of more than 400 hours of service.” The judge placed

no limit on the amount of community service that the defendant could be ordered to do.

Another unsound condition was that the defendant “obtain his GED within the first year of supervision.” (The government’s brief mistakenly states that the judge merely ordered the defendant to “seek” his GED.) The GED is a battery of five tests; if you pass, you get a certificate roughly 

equivalent to a high-school diploma (though try convincing 

a prospective employer of the equivalence). There is no assurance of passing the tests, let alone within a year. There is 

no means of “requiring” that a person pass the GED tests, 

unless cheating is permitted. This is an example of an improper condition of supervised release that could be fixed by 

changing a single word, and would have been years ago if 

the Sentencing Commission, the probation services, and the 

judiciary paid closer attention to the precise scope and wording of conditions of supervised release. We are mindful that 

both the employment and GED conditions were upheld in 

United States v. McKissic, supra, 428 F.3d at 724–25, but 

against objections different from those that we have just expressed.
Nos. 14-1316, -1521, -1676, -1772 23

An added wrinkle is that the defendant was 39 years old 

when sentenced; his prison sentence is (300 months ÷ 12 =) 

25 years, though good-time credit could reduce the sentence 

to just under 22 years; he will therefore be between 61 and 64 

when he is released. The judge imposed a 10-year term of 

supervised release for some though not all of the counts. For

others it was 3 years, although this would have consequences only if the 10-year counts were vacated, which we are not 

doing.

The judge should have explained the need for a 10-year

term of supervised release to take effect when this defendant 

is in his 60s. How likely is the defendant to reenter the heroin trade, or engage in other criminal activity, at that age? He 

has a long criminal record but all related it seems to dealing 

in heroin. He may be burned out by the time he’s released 

from prison. To impose a 10-year term of supervised release 

to take effect in 22 to 25 years requires justification; and

while the term can be modified at any time, a superior alternative might well be to impose at the outset a nominal term, 

with the understanding (contrary to the error by the district 

judge in Thompson’s case) that it can be extended, if that 

seems needful, on the eve of the defendant’s completion of 

his prison sentence.

The government in defending the conditions of supervised release imposed in these four cases relies not on case 

law but rather on the proposition that the defendant can ask 

the probation officer what a condition means, and the officer 

will give him a sensible answer. This is some protection 

against unreasonable or ambiguous conditions, but not 

enough. It is too much like telling a defendant he’ll be on 

supervised release until the probation officer decides he’s 
24 Nos. 14-1316, -1521, -1676, -1772

been on it long enough, or that if he isn’t sure what is “excessive use of alcohol” he should ask the probation officer. 

As a practical matter the terms of supervised release would 

be determined not by a judge but by a probation officer exercising an essentially unlimited discretion (for example to 

define “excessive use of alcohol”). The law doesn’t authorize 

that. United States v. Tejeda, 476 F.3d 471, 473–74 (7th Cir. 

2007). It’s true that probation officers are employees of the 

federal judiciary, but so are law clerks and judges’ secretaries, yet they are not allowed to decide the sentences of convicted defendants.

To conclude, in all four cases the judgments are reversed 

and the cases remanded for resentencing. Although we find 

no reversible error in the prison sentences treated in isolation from the conditions of supervised release, we vacate the 

entire sentences because reconsideration of those conditions 

may conceivably induce one or more of the judges to alter 

the prison sentence that he imposed.

REVERSED AND REMANDED.