### In the 

# United States Court of A p peals For the Seventh Circuit

____________________ No. 14

- 1316
U NITED S TATES OF A MERICA , Plaintiff

- Appell ee ,

v.

D AVID M. T HOMPSON , Defendant

- Appell ant

.

____________________ Appeal from t he United States District Court for th e Southern District of Illinois

. No. 3:12

- cr

- 30316

- MJR

- 1

— Michael J. Reagan , Chief Judge

.

____________________ No. 14

- 1521
U NITED S TATES OF A MERICA , Plaintiff

- Appell ee ,

v.

D EREK O RTIZ , Defendant

- Appell ant

.

____________________ Appeal from t he United State s District Court for the Northern District of Illinois , Eastern Division

. No. 10 CR 187

- 1

— Matthew F. Kennelly , Judge

.

____________________2 No s

. 14

- 1316,

- 1521,

- 1676,

- 1772

No

. 14

- 1676
U NITED S TATES OF A MERICA , Plaintiff

- Appell ee ,

v.

C HARLES B ATES , Defendant

- Appell ant

.

____________________ Appeal from t he 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
U NITED S TATES OF A MERICA , Plaintiff

- Appell ee ,

v.

D OMINGO B LOUNT , Def endant

- Appell ant

.

____________________ Appeal from t he United States District Court for the Northern District of Illinois , Eastern Division

. No. 11 CR 415

- 1

— Gary S. Feinerman , Judge

.

____________________ A R GUED N OVEMBER 13, 2014

— D ECIDED J AN U ARY 1 3 , 2 015

____________________No s

. 14

- 1316,

- 1521,

- 1676,

- 1772 3

Before P OSNER , K ANNE , and R OVNER , Circuit Judges

. P OSNER , Circuit Judge

. We have consolidated for d e cision four appeals, heard on the same day, that present issues r elating to supervised release. In a recent opinion, Uni t ed States v. Siegel , 753 F.3d 705 (7th Cir. 2014), the court expressed concern with how the district courts of our circuit are admi nistering supervised release. To recapitulate briefly the fuller discussion in the Siegel opinion, the Sentencing R e form Act of 1984 re placed parole for federal crimes with s u pervised 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, Wikip e dia , http://en.wikipedia.org/wiki/United_States_ Parole

_ Commission (visited Jan. 11 , 201 5 , as was the other website cited in this opinion )) by an administrative agency after a convicted defendan t begins serving his se n tence

. An inmate granted parole is thus released from prison before the exp iration of his term , but become s subject to restrictions i mposed by the agency on his conduct between his release and when, had he not been paroled, he would have been r eleased upon the expiration of his prison sentence. The r estrictions are intended to reduce the likelihood of his co mmitti ng crimes in the future

. Supervised release, in contrast to parole , consists of r estrictions , imposed by the judge at sent encing , called cond itions or terms of supe r vised re lease , that are to take effect when the defendant is released from prison and continue for a specified term of years (which can be life)

. P a role shortens prison time, substituting restrictions on the freed prisoner. Supervised release does not shorten prison time; instead it imposes restriction s on the prisoner to take effect upon his4 No s

. 14

- 1316,

- 1521,

- 1676,

- 1772

release from prison

. Parole mitigates punishment; supe rvised release augments it

— most dramatically when the d efendant, havin g been determined to have violated a cond ition or conditions of supervised release, is given, as punis hment, a fresh term of imprisonment. 18 U.S.C. § 3583(e)(3). Supervised release is required by sta t ute in fewer than half of cases subject to the sentenci ng guidelines . United States Sentencing Commission, Federal Offenders Sentenced to Supe rvised Release 3 (July 2010), www.ussc.gov/sites/ default/ files/ pdf/ training/ annu al

- nation al

- training

- seminar/2012/2_ Feder al_ Offenders_Sentenced _to

_ Sup er v is e d_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 alm ost always the judge orders it in those cases too, United States Sentencing Co m mission, supra , at 69

– 70 , often without explaining why. Although the defendants in our four cases object to partic ular conditions of supervised release imposed on them, they do not challenge the propriety of the inclusion of some co nditions of supe r vised release in their sentences.
S upervised release as it is designed and administered has turned out to be problematic in a number of respects

. S ee, e.g., Christine S. Scott

- Hayward, “Shadow Sentencing: The Imposition of Federal Supervised Release,” 18 Berkeley J. Crim. L. 180 (2013) ; Fiona Doherty, “Indeterminate Senten cing Returns: The Invention of Supervised Release,” 88 N.Y.U. L. Rev. 958 (2013)

. One is that the list of cond i tions required or su g gested is very long. The supervised

- release statute, 18 U.S.C. § 3563(b), imposes 9 “mandatory” cond itions a nd 23 “discr e tionary conditions, ” for a total of 32. The sentencing guid e lines get into the act as well, see U.S.S.G. § 5B1.3, impos ing 10 “ mandatory ” cond i tions , 1 4 “standard” conditions , and 1 3 “special” or “additional cond i tions”

— aNo s

. 14

- 1316,

- 1521,

- 1676,

- 1772 5

to tal of 3 7

. The stat u tory and guideline conditions , where they overlap, are ge n erally the same substantively , but their wording often differs. Sentencin g judges usually use the guide line wording rather than the statutory wor d ing

. All but the mandatory conditions are optional

. And the judge is free to add or substitute (except with r e gard to the mandatory conditions) conditions of his own devising

. U n derst andably, 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 i mpos i tion

. Because conditions of supervised release do not take e ffe ct until the defendant completes his prison term and is r eleased , defendants given long prison se n tences

— and long prison sentences are common in federal senten c ing

— often have little interest in contesting conditions of supervised r elease at sentencing

. Cri minals who court long prison se ntences tend to have what economists call a high discount rate. That is, they give little weight to future costs and ben efits. Defendants or their lawyers may also worry that a su ccessful cha l lenge to a con dition or condition s of supervised release may induce the judge to impose a longer prison se ntence, thinking that resistance to supervised r e lease implies recidivist tendencies or intentions. And often a defendant is given no notice in a d vance of the sentencing hearing of th e conditions of supe r vised release that the judge is thinking of imposing, which can make it difficult for his lawyer to p r epare arg u ments in opposition. Many district judges appear to have overlooked the fact that because the imposition of conditions of s upervised r elease is part of the sentence, a sentencing judge is required6 No s

. 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 cond itions of supervised release that the judge is thinking of i mpos ing , by applying to the proposed conditions the senten cing considerations listed in 18 U.S.C. § 3553(a). The consi derations i n clude (in subsections (1), (2), and (3) respectively) “the n a ture and circumstances of the offense and the history and characteris tics of the defendant,” “the need for the se ntence imposed ,” and “the kinds of sentences available .” Any doubt that c onditions of supervised release are a part of the sentence and subject therefore to the requirement that the judge before imposing sentence apply the senten cing factors in section 3553(a) is dispelled by 18 U.S.C. § 3583(c) . It provides that “ t he court, in determining whether to include a term of supervised release, and, if a term of s upervised release is to be included, in determining the le ngth of the term and the conditions of supervised release, shall consider the factors set forth in [eight enumerated subse ctions of] section 3553 (a).” And being part of the sentence, the imposition of conditions of supervised release is subject to the further requirement s that “ t he court, at the time o f se ntencing, shall state in open court the reasons for its impos ition of the particular sentence , ” 18 U.S.C. § 3553(c) , and “ in determining the length of the term and the conditions of s upervised release, shall consider the factors set forth in ” eight

enu merated 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 th e 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), i n-No s

. 14

- 1316,

- 1521,

- 1676,

- 1772 7

ferred “that the primary purpose of supervised release is to facilitate the reentry of offenders into their communities, r ather than to inflict punishment. ” The omitted s ubsection (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 re c ommendations of the probation officer assigned to the case as to what conditions of supervised release to impose (if there are such reco mmendations

— often there are not ; there are not in any of the four cases before us ) and is doubtless a factor in judges’ fr equent omission to mention any of the sentencing factors in

sec tion 3553(a) or even any of the conditions re c ommended by the parties or the probation officer that the judge decides to i n clude in the sentence.
And b ecause conditions of supervised release, though imposed at sentencing, do not become oper a tional until th e defendant is released, the judge has to guess at the time of sentencing what cond i tions are likely to make sense in what may be the distant future . Conditions that may seem sens ible at sentencing may not be sensible many years later, when the defendant i s finally released from prison. Although nonmandatory conditions of supervised release can be mo dified at any time, 18 U.S.C. § 3583(e)(2), modification is a bother for a judge, e s pecially when, as is common in cases involving very long sentences, it becom es the responsibility of the sentencing judge’s su c cessor because in the meantime the sentencing judge has retired or died, resigned, or been promoted

. Fu r thermore, al though reducing recidivism is the purpose of supervised release, i t is difficult , often i mposs i-8 No s

. 14

- 1316,

- 1521,

- 1676,

- 1772

ble, to predict whether a defendant is likely upon r e lease to resume crim i nal activity

. Often rehabilitation is named as an additional purpose of supervised release, but being rehabil itated and going straight are as a practical matter synon ymous. Ano ther wrinkle is that beca use conditions of supervised release are imposed at sentencing, the conditions reco mmended to the judge at the sentencing hearing may be a product of negotiation between prosecution and defense. The defendant’s lawyer may o f fer the prosecution a trade

— more supervised release for a r e duced prison term

— and the prosecutor may agree . And when adversaries agree on the outcome of a legal proceeding the sentencing judge, habit uated as American judges are to a d versary procedure, may be relu ctant to subject the agreement to critical scrutiny, even though the law is clear that the fact that the pros e cution and defense agree on a sentence does not excuse the judge from having to determine the sentence’s conformity to the statut ory sentencing fa c tors. 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 co ncerning what conditions of supervised release to impose, spend disproportionate t ime on enforcement (that is, inve stigating violations of conditions of supervised release and recommending punishments for the vi o lator s ) and have little time left over for suggesting appropriate conditions and helping the probationer to comply with them

. This is a ser ious pro b lem 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 theNo s

. 14

- 1316,

- 1521,

- 1676,

- 1772 9

recommendations of the prob a tion officer assigned to the

ca se when the officer make s recommendations. A revocation of supervised release and recommital to prison relieves the probation se r vice of monitoring the person during his term of impriso n ment. According to Scott

- Hayward, supra , at 182 (footnotes omitted) , “ on average, one third of those indivi duals [on supervised release] will have their supervised r elease revoked, most as a result of technical violations, and receive, on average, a new pri s on se n tence of 11 months.”
And finally a number of the listed condit ions, along with a number of conditions that judges invent, are, as we’re about to explain , hopelessly vague. See also our Siegel opi nion, 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 conf usion that the applicable statutory and guidelines provisions have cr e ated

. We begin with United States v. Thompson . Thompson was 2 3 years old when he b e gan an online relationship with a girl of 14. They e x changed nude pictures of themselves. When she was 16 and he 2 5 she d e cided 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

. C onvicted in fe dera l district court of possession of child pornography , and of traveling in interstate co m merce for the purpose of engaging in sexual conduct , in violation of federal laws that fix the age10 No s

. 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 2 1 0 months in prison. He does not challenge the prison sentence, but o nly conditions of supervised r elease. Even with full credit for behaving himself in prison, Thompson will be just days short of 41 years old when r eleased, and it seems odd to be devising so far in advance r estrictions to impose on him then; but that is how supervised release operates. What is beyond odd

— what is unautho rized

— is that the judge imposed a lifetime of supervised r elease without any art iculated justification. The need for an express justification was acute because , as the judge r emarked, as a convicted sex offender Thompson will be su bject after he is released from prison to a lifetime of mandat ory state and local sex

- offender reporting quite apart from supervised release

. And sens i ble or not, the lifetime term is vitiated by the fact that in i m posing it the judge was laboring under the misapprehension that, in his words, “a term of supervised release can be r e duced but can’t be extended. ” That’s wrong; it can be e x tended. 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 b e ing release d from prison will be a menace to young girls u n til he dies perhaps as an octogenarian or even a non agenar i an

. It is rather, as the judge explained , that because the f u ture 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 e x tended , as the judge failed to understand . We are surprised that ne i-No s

. 14

- 1316,

- 1521,

- 1676,

- 1772 11

ther the government nor the defense poin t ed out the judge’s

error at the senten c ing hearing

. The judge committed other errors. One was his failure to include in the oral sentence a condition of supervised r e lease requiring that the defendant receive treatment for drug a ddiction. 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 a p pears 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, 7 10

– 11 (7th Cir. 2014); United States v. A l buray , 415 F.3d 782, 788 (7th Cir. 2005).
A more serious error was a condition of supervised r elease that Thompson not have “any contact with persons under the age of 18 unless in the presence of a responsib l e adu lt who is aware of the nature of the defendant’s bac kground and instant offense and who had been approved by the pr o bation officer.” This can’t have been meant literally , since understood literally it would include male s un der 18 as well as females, though there is no suggestion that Thom pson 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 wai t ress, paying a cashier, sitting next to a girl (a stranger) a t a baseball game, replying to a girl asking directions, or b e ing shown a friend’s baby girl

— or his own baby, for that matter. We have warned against imposing a restrictive cond i tion that is not reasonably related to the defendant’s “offense, history and c haracteristics. ... Moreover, given the potentia lly severe r e strictions on [the defendant’s] day

- to

- day life that this condition imposes, the district court’s lack of explan a-12 No s

. 14

- 1316,

- 1521,

- 1676,

- 1772

tion of why it thinks this condition involves no greater de privation of liberty than nece s sary to achieve the penological goals stated in 18 U.S.C. § 3553(a) is troubling. ... Because the district court has not provided any explan a tion of how this condition is reasonably related to [the defendant’s] o ffense and background or to the goals of punishment, invol ving no greater deprivation of liberty than is reasonably ne cessary to achieve these goals, we vacate the condition.” Uni ted States v. Goodwin , 717 F.3d 511, 523

– 24 (7th Cir. 2013). The judge in Thompson’s case imposed a total of 2 4 non

mandatory conditions of supervised release. Because all those conditions were part of the se n tence, 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 t he 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 ina ppropriate or vague. Among the ina p propriate ones is that the “d efendant shall support his or her depen d ents and meet other family r e sponsibilities.” Of course “or her” should not be in there; its inclusion suggests the rote nature of the judge’s impos i tion of conditions of supervised release. More i mportant, the condition assumes arbitrarily and maybe i naccurately that should Thompson ever acquire dependents he will have, d e spite being an ex

- con subject to conditions of supervised release and state and local sex

- offender r estrictions and reporting re quirements , the resources nece ssary to support his depen d ents

. Among the vague conditions is that “d efendant shall r efrain from excessive use of alcohol,” where “excessive use”No s

. 14

- 1316,

- 1521,

- 1676,

- 1772 13

is not defined , tho ugh it could readily be defined, as we e xplained in United S tates v. Siegel , supra , 753 F.3d at 715

– 16

. Fatally vague is a condition forbidding the defendant to “a ssociate with any person convicted of a felony, unless granted permission to do so by the prob a tion officer.” How would the defendant know whether someon e he was assoc i ating with had ever been convicted of a felony? There is no stated requirement that he know; the condition appears to i m pose strict liability. If so, to protect himself he would have to submit the name of any person he met to his probation o fficer to determine whether the name appeared in any dat abase of felons

. Maybe liability for violating the condition isn’t strict; so might it be enough that a reasonable pe r son would know that a person whom the defendant was assoc iating 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, a cquaintanceship, or frequent meetings? What if a dependent whom Thompson will be required to support when he is r eleased from prison is convicted of a felony? Must he stop a ssociating 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 ot h erwise interact with a person whom he knows to be engaged, or planning to be

e n gaged, in criminal activity ” ? The government offers the blanket defense that Thom pson waived any objection to the conditions of supervised r elease that the judge imposed

. The judge had sent a list of the conditi ons, with checkmarks next to the ones he was consi dering imposing, to the parti es in advance of the se n tencing hearing and the government argues that this was the d efendant’s (more realistically, his lawyer’s) last chance to o p-14 No s

. 14

- 1316,

- 1521,

- 1676,

- 1772

pose them. But the judge didn ’t indicate why he was thin king 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 consider ation of these factors he decides that he’s leaning toward i mposing pa r ticular conditions, he should inform the parties of the conditions and the possible reasons for impo s ing them , so that they can develop arguments pro or con to present at the sentencing hearing. ( It would likewise be a better pra ctice f or the presentence report to give reasons for any cond itions of supervised release that it suggests, b ut as we said the pr e sentence reports in these four cases did not suggest any conditions of supe r vised release

. ) An alternative would be for the judge to explain at the sentencing hearing what cond i tions he was inclined to impose and why , and ask the defe n dant’s lawyer whether he objects to any of them; if the law yer had a reasonable need for more time to decide whether he has grounds for objection , the jud ge could a djourn the hea r ing. Either of our suggested approaches would be a “best practice,” which is different from a required practice ; for e xcept with regard to conditions of supervised release not listed in the statute or the guid e lines , United States v. Bryant , 754 F.3d 443, 446 (7th Cir. 2014) , n o advance notice is r equired

. 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 d e cision in Irizarry v. United States , 553 U.S. 708 (2008). The district judge in that case had imposed a se ntence in excess of the sentence recommended in the prese ntence rep ort without prior notification to the parties. TheNo s

. 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 d e fendant has a good reason for not being prepared to address at senten c ing the imposition of a condition of supervised r e lease listed in the Sentencing Guidelines . In such a circumstance the di s trict court can exercise its sound discretion to grant a contin uance , ” id . at 1145

— though we would be inclined to subst itute “should” for “can” in the last clause of the quoted pa ssage. For in Irizarry itself we read that

Rule 32(i)(1)(C) [of the Federal Rules of Criminal Pr ocedure] requires the district court to allow the parties to comment on “matters re lating to an appropriate se ntence,” and given the scope of the issues that may be considered at a sentencing hearing, a judge will no rmally be well advised to withhold her final judgment until after the parties have had a full opportunity to present their ev i dence 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 pra ctice dictates that judges in all cases should make sure tha t 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 p articular se ntence 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 n otice requirement categorically, but rather for a district judge to consider granting a contin u ance when a party16 No s

. 14

- 1316,

- 1521,

- 1676,

- 1772

has a legitimate basis for claiming that the su r prise was prejudicial .”

553 U.S. at 715

– 16

. B ecause we’re remanding in Thompson’s

case , the defendant’s lawyer should be permitted to wait u ntil the sentencing hearing to present his objections to wha tever conditions of supervised release the judge is minded to i m pose.
We need to note an exception to our “best practice” su ggestion , however . Some conditions of supervised release are administrative requirements applicable whenever a ter m of supe r vised release is imposed, regardless of the substantive cond i tions that are also imposed. Examples are requiring the defendant to report to his probation officer, an swer the o fficer’s questions, follow his instructions, and not leave the judicial district without permission. Once the judge has e xplained why supervised release is ne c essary, 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 sta ndard conditions are “ ‘ basic a dministrative 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 (1s t Cir. 2004). Most of them are su b stantive 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. Twe n ty

- one conditions of supervised release were imposed, all but one
to remain in force for three years after his release from pri son. As in Thompson’s case, the appeal does not cha l lenge the prison sentence but only conditions of supe r vised release.No s

. 14

- 1316,

- 1521,

- 1676,

- 1772 17

The presentence report , pr epared (as is normal) by the probation officer assigned to the case, contain ed no sugges ted conditions of supervised release at all . Nor had the pros ecution suggested any. They w ere sprung on the defe n dant at the se n tencing hearing , and with such brevity t hat we don’t think his lawyer can be faulted for having failed to object

. The judge’s entire discussion of s u pervised release consisted of the following sentence: “The conditions of supervised r elease will include the normal cond i tions, plus drug testing

u p to the maximum that’s permitted, drug counsel ing and treatment at the direction of the pr o bation office, and mental health counseling and treatment at the direction of the pr obation office, which may include taking necessary prescri ption medications.” It ’s not clear what the judge meant by “normal conditions,” but the written judgment lists 3 ma ndatory conditions ( DNA collection, drug testing, and a pr ohibition against committing further crimes) , 13 standard conditions (judges usually exclude from the gui d e lines list of 1 4 standard conditions the last one , which relate s to the payment of the financial obligations imposed by the se ntence ; for some reason not known to us this requirement is incorporated into an other part of the sta n dard form that is issued t o defendants when they receive their sentences ) , and 5 additional conditions ( a firearm prohibition, a drug trea tment program, mental health counse l ing, a requirement that the defendant report to the prob a tion office within 72 hours of his release from pri son, and that he pay restitution) . Far from a p plying the sentencing factors in 18 U.S.C. § 3553(a) to the conditions of supe r vised release that he was imposing, the judge gave no re a sons at all for any of the conditions.
The conditions imposed are riddled with ambigui ties. Example: “as directed by the probation offi c er, the defe n dant18 No s

. 14

- 1316,

- 1521,

- 1676,

- 1772

shall notify third parties of risks that may be occ a sioned by the defendant’s criminal record or personal history or cha racteris tics.” There is no indication of what is meant b y “pe rsonal history” and “characteristi c s” or what “risks” must be disclosed to which “third parties

. ” The defendant is to n o tify his prob a tion officer of any “change in ... employment,” but there is no indication whether change in employment just means chan ging employers or also includes changing from one p o sition to another for the same employer at the same workplace. The defendant is forbidden to “frequent places where controlled substances are illegally sold, used, distri buted, or admini s tered,” but there is no requirement that he know or have reason to know or even just suspect that such
act i vities are taking place. Nor is there any indication of how many trips const i tute “frequent[ing]” such places. Instead of being forbidden to use a controlled substanc e he “shall have

n o 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 sign ify

. Nor did the district court specify a penalty should the d efendant fail to pay the restit u tion ordered.
Ortiz’s counsel takes particular issue with two standard conditions of supervised release that might be thought to impinge on constitutional rights: th at “the defendant shall

a n swer 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 contr aband observed in plain view of the probation off i cer.” The first of these conditions essentially asks for a waiver of the right not to be forced to incriminate oneself, because theNo s

. 14

- 1316,

- 1521,

- 1676,

- 1772 19

condition would require the defendant to a n swer “yes” if he

were asked whether he had committed another crime and he had. The second condition would allow the probation o f ficer to “visit” the defendant at 3:00 a.m. every morning and look around for contraband, and also allow him to follow the d efendant everywhere, looki ng for contr a band. Regardless of any possible constitutional concern, both conditions are too broad in the absence of any effort by the district court to e xplain why they are needed

. A number of decisions in other circuits brush aside o bjections to the br eadth and ambiguity of the many conditions of supervised release imposed by di s trict 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. Albertso n , 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 co ndition narrowly. For example, in Ph illips 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 cond ition that Phillips contended on appeal was “’v ague and overbroad,’” the Ninth Cir cuit held that the condition “ pr ohibits Phillips from knowingly going to a sp e cific place where drugs are illegally used or sold, but ... does not prohibit him from ... going to a given neighborhood simply because a person i s selling drugs somewhere within that neighbo rhood

. ” 704 F.3d at 767

– 68 (emphasis in original). It is prefe rable for the district court to specify limitations in a cond i tion of supervised release in the condition itself, rather than lea ving it to the appel late court to interpolate the limitations ;20 No s

. 14

- 1316,

- 1521,

- 1676,

- 1772

otherwise the defendant may think himself bound by the broader interpretation . If you’re 90 percent certain that pu rchasing girl

- scout cookies from someone who rings your doorbell wouldn’t violate a condition of s upervised r e lease, do you want to risk going back to prison because you may have guessed wrong? If out of caution ther e fore you decline to purchase the cookies, the sentencing guideline will deter lawful co n duct, and thus be overbroa d. Like any other part of a criminal sentence, the conditions of supe r vised release that are i m posed should be clear. That is one teaching of our Siegel decision and in add i tion we believe and endeavored to make clear in that dec i sion that conditions of supervised release impose d in a se n tence require careful appellate consideration when the se n tencing judge fail s to explain or justify or narrow ambiguous or i nappropriate

- seeming conditions and fail s to apply the stat utory 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 esse ntially identical to Ortiz . No conditions of supervised r e lease were mentioned in the presentence report. The judge sprang them on the parties in the sentencing hearing, impo s ing 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 co n d it ions 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

a p plicable to Bates’s case.No s

. 14

- 1316,

- 1521,

- 1676,

- 1772 21

In our final case, United States v. Blount , the defenda nt challenge s not only the conditions of supervised release but also the prison sentence (300 months, for running an exte nsive organization engaged in the sale of heroin), specif i cally the four

- level enhancement in the defendant’s base o f fense level by rea son of his being “an organizer or leader of a cri m inal activity that involved five or more participants or was otherwise extensive.” U.S.S.G. § 3B1.1(a). For the pe rsuasive reasons given by the district judge and unnecessary for us to repeat or amplify, th e enhancement, and so the 300

- month sentence, were proper. As in our other three cases, however, the district judge’s handling of supervis ed release

was seriously flawed.
There was again no discussion of any section 3553(a) fa ctors that the judge may have thought justified the length and conditions of supervised release. His discussion of the cond itions of supervised release that he was imposing on the d efendant is difficult even to understand. He listed only 8 co nditions, but said that the defendant “shal l comply with the standard conditions that have been adopted by this court,” and the written judgment lists the 13 usual standard cond itions

— with all their ambiguities uncorrected . The 8 cond itions he discussed are a mix ture of mandatory and “add itional” c on ditions.
Two of them are seriously questionable. One is that “if [the defendant is] unemployed after the first 60 days of s upervision or if unemployed for 60 days after ter min a tion or layoff from employment, he shall perform at least 20 hours of comm u nit y service work per week at the direction of and in the discretion of the Probation Office until gainfully e mployed.” Taken literally, this means that if at, say, age 68 he22 No s

. 14

- 1316,

- 1521,

- 1676,

- 1772

is unemployed, he will have to perform 20 hours of comm unity se r vice per week

— indefi nitely (till he dies?). No doubt the judge, if he thought about this cond i tion, would not have wanted it interpreted literally, esp e cially since an application note to U.S.S.G. § 5F1.3 states that “community service ge nerally should n ot be imposed in e x ces s of 400 hours.” The judge did not mention that application note, and the go vernment is incorrect when it says in its brief that the judge’s community

- service condition “did not amount to the imp osition of more than 400 hours of service.” The judge placed no limit on the amount of community service that the d efendant could be ordered to do

. Another unsound condition was that the defendant “o btain his GED within the first year of supervision.” (The go vernment ’s brief mistakenly states that the judge merely o rdered the defendant to “seek” his GED.) The GED is a ba ttery of five tests; if you pass, you get a certificate roughly equivalent to a high

- school diploma (though try co n vincing a prospective employer of the equivalence) . There is no a ssurance 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 i mproper condition of supervised release that could be fixed by chan g ing a single word, and would have been years ago if the Se n tencing Commission, the probation services, and the judiciary paid closer attention to the precise scope and wor ding of conditions of supervised r e lease . We are mindful that both the emplo y ment 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 e xpressed.No s

. 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 r e duce the sentence
to just under 22 years ; h e will therefore be b e tween 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, a lthough this would have consequen ces 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 defe ndant to reenter the her oin trade , or engage in other criminal activity, at that age? He has a long criminal record but all related it seems to dea l ing in heroin

. He may be burned out by the time he’s r e leased from prison. To impose a 10

- year term of super vised release to take effect in 2 2 to 25 years requires ju s tification; and while the term can be modified at any time , a superior alte rnative might well be to impose at the outset a nominal term, with the understanding (contrary to the e r ror by the distric t 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 supe rvised release i m posed in these four cases relies not on case law but rather on the proposition that the defendant can ask the probation o f ficer 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 li ke telling a defendant he’ll be on supervised release until the probation o f ficer decides he’s24 No s

. 14

- 1316,

- 1521,

- 1676,

- 1772

been on it long enough, or that if he isn’t sure what is “e xcessive use of a l cohol” he should ask the probation officer. As a practical matter the terms of super vised r e lease would be determined not by a judge but by a probation officer e xercising 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 (7t h Cir. 2007). It’s true that probation off i cers are employees of the federal judiciary, but so are law clerks and judges’ secreta ries, yet they are not allowed to decide the sentences of co nvicted d e fendants. 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 isol ation from the conditions of supervised release, we vacate the entire se n tences because reconsideration of thos e conditions may co n ceivably induce one or more of the judges to alter the prison sentence that he imposed.

R EVERSED AND R EMANDED

.