In the

United States Court of Appeals

For the Seventh Circuit ____________________

No. 14-1223

UNITED STATES OF AMERICA,

Plaintiff-Appellee,

v.

PARRISH KAPPES,

Defendant-Appellant.

____________________

Appeal from the United States District Court for the

Central District of Illinois.

No. 2:12-cr-20080-MPM-DGB-1 — Michael P. McCuskey, Judge.

____________________

No. 14-2135

UNITED STATES OF AMERICA,

Plaintiff-Appellee,

v.

DAVID L. CRISP, JR.,

Defendant-Appellant.

____________________

Appeal from the United States District Court for the

Central District of Illinois.

No. 2:13-cr-20050-MPM-DGB-1 — Michael P. McCuskey, Judge.
2 Nos. 14-1223, 14-2135 & 14-2482

____________________

No. 14-2482

UNITED STATES OF AMERICA,

Plaintiff-Appellee,

v.

JEFFREY J. JURGENS,

Defendant-Appellant.

____________________

Appeal from the United States District Court for the

Central District of Illinois.

No. 4:13-cr-40048-SLD-JEH-1 — Sara Darrow, Judge.

____________________

ARGUED NOVEMBER 14, 2014 — DECIDED APRIL 8, 2015

____________________

Before BAUER, FLAUM, and TINDER, Circuit Judges.

TINDER, Circuit Judge. We resolve three appeals in a single 

opinion because the appeals raise similar challenges to conditions of supervised release. Although supervised release 

has been a feature of the federal criminal justice system for 

nearly thirty years, with over a million federal defendants 

having been sentenced to supervised-release terms, during 

the past several years we have addressed certain aspects of 

supervised release for the first time.1 Some defendants, 

1 See, e.g., United States v. Sewell, --- F.3d ----, No. 14-1384, 2015 WL 

1087750 (7th Cir. Mar. 13, 2015); United States v. Thompson, 777 F.3d 368 

 
Nos. 14-1223, 14-2135 & 14-2482 3

judges, lawyers, and probation officers might characterize 

our recent focus on these issues as better late than never, 

while others might grumble that we are trying to fix an unbroken system. In any event, we hope our recent jurisprudence results in the imposition of supervised-release conditions that are properly-noticed, supported by adequate findings, and well-tailored to serve the purposes of deterrence, 

rehabilitation, and protection of the public.

The first section of this opinion provides an overview of 

the system of supervised release, including four general sentencing principles judges should consider. Next, we outline 

the history, crimes, and sentencings of the three defendants 

at issue. Then, we address the specific supervised-release 

challenges raised by each defendant, organized by the four 

general sentencing principles. Lastly, we consider Defendant 

Crisp’s contention that the sentencing judge failed to consider one of his principal mitigation arguments.

(7th Cir. 2015); United States v. Cary, 775 F.3d 919 (7th Cir. 2015); United 

States v. Hinds, 770 F.3d 658 (7th Cir. 2014); United States v. Johnson, 765 

F.3d 702 (7th Cir. 2014); United States v. Farmer, 755 F.3d 849 (7th Cir. 

2014); United States v. Baker, 755 F.3d 515 (7th Cir. 2014); United States v. 

Bryant, 754 F.3d 443 (7th Cir. 2014); United States v. Siegel, 753 F.3d 705 

(7th Cir. 2014); United States v. Poulin, 745 F.3d 796 (7th Cir. 2014); United 

States v. Shannon, 743 F.3d 496 (7th Cir. 2014); United States v. Adkins, 743 

F.3d 176 (7th Cir.), cert. denied, 134 S. Ct. 2864 (2014); United States v. Williams, 739 F.3d 1064 (7th Cir. 2014); United States v. Evans, 727 F.3d 730 

(7th Cir. 2013); United States v. Goodwin, 717 F.3d 511 (7th Cir.), cert. denied, 134 S. Ct. 334 (2013); United States v. Quinn, 698 F.3d 651 (7th Cir. 

2012).

 
4 Nos. 14-1223, 14-2135 & 14-2482

I. Supervised Release

In 1984, Congress passed the Sentencing Reform Act, 

which replaced the federal parole system with the system of 

supervised release. See 18 U.S.C. § 3583; see generally S. Rep. 

No. 98-225 (1983), reprinted in 1984 U.S.C.C.A.N. 3182. The 

parole system allowed a convicted defendant to be released 

prior to the expiration of his prison term on conditions designed to reduce the likelihood of his committing further 

crimes. Parole was criticized for creating uncertainty as to 

how long a particular defendant would actually spend in 

prison—i.e., the judicially-imposed sentence was not considered the “real sentence” because it was “subject to constant 

adjustment by the parole commission”—which was viewed 

as undermining public respect for the law and defendants’ 

morale. S. Rep. No. 98-225, at 56. 

Under the replacement system of supervised release, 

judges impose conditions at sentencing which take effect after the completion of the defendant’s prison term, and, in 

contrast to parole, do not reduce the length of the custodial 

portion of a defendant’s sentence.2 The purposes of supervised release have been variously described as rehabilitation, 

deterrence, training and treatment, protection of the public, 

2 However, as discussed below, it is probable (and proper) that sentencing judges impose both custody and supervised release for somewhat 

overlapping purposes, and if supervised release was not an option the 

same judge might impose a lengthier custodial sentence. In this way, the 

imposition of supervised release can be seen as potentially reducing the 

custodial sentence.

 
Nos. 14-1223, 14-2135 & 14-2482 5

and reduction of recidivism. See United States v. Johnson, 529 

U.S. 53, 59–60 (2000); United States v. Siegel, 753 F.3d 705, 708 

(7th Cir. 2014); United States v. Evans, 727 F.3d 730, 733 (7th 

Cir. 2013). Supervised release was not intended to be imposed for the purposes of punishment or incapacitation, 

“since those purposes will have been served to the extent 

necessary by the term of imprisonment.” S. Rep. No. 98-225, 

at 125; see also Johnson, 529 U.S. at 59 (“Supervised release 

fulfills rehabilitative ends, distinct from those served by incarceration.”); cf. 18 U.S.C. § 3583(c) (directing a court contemplating the imposition of supervised release to consider 

most sentencing factors set forth in 18 U.S.C. § 3553(a), except

the need for the sentence to provide just punishment for the 

offense). The Supreme Court has described supervised release as “the decompression stage” between prison and full 

release. Johnson v. United States, 529 U.S. 694, 709 (2000). 

“Prisoners may, of course, vary in the degree of help needed 

for successful reintegration. Supervised release departed 

from the parole system it replaced by giving district courts 

the freedom to provide postrelease supervision for those, 

and only those, who needed it. Congress aimed, then, to use 

the district courts’ discretionary judgment to allocate supervision to those releasees who needed it most.” Id. (citation 

omitted). 

In some felony cases, including certain cases involving 

drug-trafficking, sex offenses and domestic violence, supervised release is mandated by statute. See, e.g., 18 U.S.C. § 

3583(a), (k); 21 U.S.C. §§ 841(b), 960(b). Between 2005 and 

2009, approximately 41 percent of sentenced federal defendants were subject to statutes mandating supervised release. 

See U.S. Sentencing Comm’n, Federal Offenders Sentenced to 

Supervised Release at 69 n.275 (2010), available at
6 Nos. 14-1223, 14-2135 & 14-2482

http://www.ussc.gov/sites/default/files/pdf/research-andpublications/research-publications/2010/20100722_

Supervised_Release.pdf (last visited Mar. 26, 2015, as were all 

websites in this opinion). Although the sentencing guidelines 

call for supervised release in all remaining cases with a prison sentence of more than one year (with limited exceptions), 

see U.S.S.G. § 5D1.1(a)(2), the Supreme Court made the relevant provisions of the guidelines discretionary in 2005. See 

United States v. Booker, 543 U.S. 220, 245 (2005); United States 

v. Parker, 508 F.3d 434, 442 (7th Cir. 2007). The change from 

supervised release being mandatory to discretionary has 

made little practical difference: between 2005 and 2009, district courts imposed a term of supervised release in 99.1 percent of cases with a prison sentence in excess of one year but 

not subject to statutorily-mandated supervised release. U.S. 

Sentencing Comm’n, Federal Offenders Sentenced to Supervised Release at 7, 52 n.241. So while supervised release may 

have been intended “for those, and only those, who needed 

it,” Johnson, 529 U.S. at 709, the reality is that virtually all 

federal defendants who spend at least a year in custody are 

subject to supervised release.

The sentencing procedure generally is as follows. First 

the probation officer conducts a presentence investigation 

which culminates in the preparation of a presentence report. 

See 18 U.S.C. § 3552(a), (b); Fed. R. Crim. P. 32(c), (d). The 

presentence report identifies the kinds of sentences available, including the terms of supervised release which may be 

appropriate. See Fed. R. Crim. P. 32(d)(1)(C). The presentence report is disclosed to the parties at least 35 days before 

sentencing, and the parties state in writing any objections 14 

days later. See Fed. R. Crim. P. 32(e)(2), (f)(1). At least seven 

days before sentencing, the presentence report, including 
Nos. 14-1223, 14-2135 & 14-2482 7

any addenda addressing objections, is submitted to the court 

and the parties. See Fed. R. Crim. P. 32(g). 

At the sentencing hearing, the sentencing judge hears 

from the lawyers, the defendant and any victims who are 

present, and may receive evidence related to objections. See

Fed. R. Crim. P. 32(i). Ultimately, the judge engages in a twopart analysis. First, the judge determines the defendant’s 

sentencing range under the guidelines. United States v. Adkins, 743 F.3d 176, 189 (7th Cir.), cert. denied, 134 S. Ct. 2864 

(2014). Second, the judge makes “an individualized assessment of the appropriate sentence based on the § 3553(a) factors.” Id. (quotation omitted). Any term of supervised release 

is considered part of the overall sentence. Id. at 192. In determining whether to include a term of supervised release, 

and, if so, in determining the length of the term and the conditions of supervised release, the judge is required to consider the factors set out in 18 U.S.C. §§ 3553(a) and 3583(c)–

(d), which are discussed below.

The sentencing judge’s difficult task is not undertaken on 

a completely blank slate, but rather is structured by statutes 

and the guidelines, which recommend a range of terms of 

supervised release depending upon the category of offense, 

see 18 U.S.C. § 3583(b), and list certain mandatory and discretionary conditions, see id. §§ 3563(a)–(b), 3583(d); U.S.S.G.

§ 5D1.3. Some of the discretionary conditions are called 

“standard,” U.S.S.G. § 5D1.3(c), while others are called “special,” id. § 5D1.3(d)–(e), and are recommended for particular 

offenses. Sentencing judges also are empowered to “impose 

conditions of their own devising.” Siegel, 753 F.3d at 707.

After the sentencing judge exercises his or her “wide discretion in determining conditions of supervised release” at 
8 Nos. 14-1223, 14-2135 & 14-2482

sentencing, Adkins, 743 F.3d at 193 (quotation omitted), the

judge typically has no further occasion to consider the defendant’s supervised release until after the defendant has 

completed the custodial portion of his sentence, begun serving supervised release under supervision by a federal probation officer, and the district court is presented with a motion 

for modification, revocation, or termination of supervised 

release. See 18 U.S.C. § 3583(e). Although not currently mandated by statute or the guidelines, we have suggested that 

sentencing judges “[r]equire that on the eve of his release 

from prison, the defendant attend a brief hearing before the 

sentencing judge (or his successor) in order to be reminded 

of the conditions of supervised release.” Siegel, 753 F.3d at 

717. This “would also be a proper occasion for the judge to 

consider whether to modify one or more of the conditions in 

light of any changed circumstances brought about by the defendant’s experiences in prison.” Id. Adopting this suggestion would help mitigate the inherent difficulty in imposing 

conditions at sentencing which do not go into effect until the 

defendant is released from custody—often many years in the 

future. See id. at 708. A defendant may change substantially 

during a long prison sentence, and the world outside the 

prison walls may change even more. A judgeship does not 

come equipped with a crystal ball.

The sentencing judge may terminate supervised release 

at any time after one year of supervision, if the judge determines such action is warranted by the defendant’s conduct 

and serves the interests of justice. 18 U.S.C. § 3583(e)(1). For 

example, of the 42,984 active supervised release cases that

closed during the 12-month period ending September 30, 

2014, 13 percent were terminated early by the court. See

Admin. Office of the U.S. Courts, Post-Conviction Supervi-
Nos. 14-1223, 14-2135 & 14-2482 9

sion, Table E-7A, available at http://www.uscourts.gov/

uscourts/Statistics/JudicialBusiness/2014/appendices/E7ASep

14.pdf. Approximately 68 percent of supervised release cases 

closed during the same period were closed “successfully”, 

i.e., terminated (whether early or not) without revocation. Id. 

Approximately 61.3 percent of the supervised release violations during this period were for “technical violations” (such 

as failure of a drug test, failure to report to a supervising 

probation officer, or non-payment of financial conditions),

32.3 percent were for “major” violations (i.e., criminal offenses with a sentence of more than 90 days imprisonment), 

and 6.4 percent were for “minor” violations (i.e., criminal 

offenses with a sentence of 90 days or less of imprisonment). 

Id. 

The three cases here concern legal issues arising at the 

original sentencing hearing, when the sentencing judge imposed a term of supervised release and selected the conditions and length of the term. We organize our discussion of 

the defendants’ challenges around four general principles

sentencing judges should consider when imposing conditions of supervised release: (1) the importance of advance 

notice of conditions being considered; (2) the need to justify 

the conditions and the length of the term at sentencing by an 

adequate statement of reasons, reasonably related to the applicable § 3553(a) factors; (3) the goal of imposing only specific, appropriately-tailored conditions—which is to say, 

avoiding the imposition of vague or overbroad conditions; 

and (4) the requirement to orally pronounce all conditions, 

with the written judgment only clarifying the oral pronouncement in a manner that is not inconsistent with an unambiguous oral provision. Prior to turning to the defend-
10 Nos. 14-1223, 14-2135 & 14-2482

ants’ challenges, we outline the history and offenses of the 

three defendants at issue.

II. Defendants’ History and Offenses

A. Jeffrey Jurgens 

Defendant Jeffrey Jurgens is the product of a deplorable 

childhood. He grew up in a rural Illinois house that was 

strewn with garbage due to his mother’s hoarding; based 

upon the photos admitted at sentencing, his childhood home 

more closely resembled a landfill than a house. Jurgens’

mother was a neglectful alcoholic who “always had a beer in 

her hand,” and his father, also an alcoholic, abused her until 

they divorced when Jurgens was nine. No one taught 

Jurgens proper hygiene, and he was teased and bullied at 

school because he was dirty and smelled. Despite his upbringing, Jurgens graduated from high school in 2003 and 

from DeVry University in 2005 with an associate’s degree. 

He continued to live with his mother until she died in 2007. 

At the time of his mother’s death, Jurgens was 23. He 

moved into his own apartment and got a job with a tech 

company as a help-desk technician. He held that job for 

nearly six years until his arrest and detention in this case in

2013. During that time, he suffered severe social anxiety, left 

his apartment only for work and groceries, and allowed garbage to accumulate in his apartment because he feared encountering other people when he took out the trash. He had 

occasional social contact with co-workers, but he has never 

dated or had an intimate relationship.

Beginning in about 2007, Jurgens developed an interest in 

pre-pubescent and adolescent girls and in child pornography. For the next five years, he used file-sharing software to 
Nos. 14-1223, 14-2135 & 14-2482 11

find child pornography and downloaded files to his computer hard drives. On February 17, 2012, a Moline, Illinois, 

police detective executed a search warrant at Jurgens’ 

apartment and seized three computer hard drives containing 

69 videos of child pornography. After waiving his Miranda

rights, Jurgens told the detective that he had been watching 

child pornography for about five years and knew it was illegal. Jurgens said he did not pursue or have any contact with 

minors. He said, “I can’t do anything when they are not 

here.” 

On September 25, 2013, a grand jury charged Jurgens 

with one count of receipt and distribution of child pornography in violation of 18 U.S.C. § 2252A(a)(2)(A), and one 

count of possession of child pornography in violation of 18 

U.S.C. § 2252A(a)(5)(B). On October 24, 2013, Jurgens pleaded guilty to both counts without a written plea agreement.

On January 15, 2014, a probation officer filed an initial 

presentence report, which was later revised on March 13, 

2014, to reflect Jurgens’ objections. The report stated that the 

statute required a minimum sentence of five years’ imprisonment and a supervised-release term of five years to life on 

each count. The report indicated that the advisory guidelines 

range was 151 to 188 months of imprisonment and the 

guidelines recommended a life term of supervised release. 

The report stated, “[i]n addition to standard conditions of 

supervised release ... found at U.S.S.G. § 5D1.3, the Court 

may impose the following special conditions,” and listed 

seven “special conditions.” An addendum to the report indicated that Jurgens objected to five of the proposed special 

conditions.
12 Nos. 14-1223, 14-2135 & 14-2482

At a hearing originally scheduled for sentencing, the district court ordered Jurgens to undergo a psychosexual evaluation and reset the date for sentencing. A licensed counselor later diagnosed Jurgens with pedophilic disorder and social anxiety disorder. The counselor recommended the same 

conditions of “community supervision” that the presentence 

report listed and recommend that Jurgens receive counseling 

to address his social anxiety in addition to sex offender 

treatment. 

At the sentencing hearing on June 26, 2014, Jurgens’ attorney objected to the proposed conditions of supervised release which use “these very broad and vague terms about 

‘sexual arousal’ and ‘pornography’ and the like.” Jurgens’ 

attorney asked that the court fashion the conditions to “allow for Mr. Jurgens to have contact with minors who are relatives of his and allow him to have contact with minors that 

are incidental to employment.” Jurgens’ attorney then spoke 

of the “irrationality” of U.S.S.G. § 2G2.2,3 which produced a 

guidelines range of 151 to 188 months of imprisonment for 

Jurgens, and requested a sentence of 60 months of imprisonment and 10 years of supervised release. The government 

attorney requested a sentence of 108 months of imprisonment and 20 years of supervised release.

After hearing from Jurgens himself, the district judge addressed Jurgens’ offense in relation to other offenders, the 

harm to the victims, aggravating factors, and Jurgens’ personal history and characteristics. The district judge then im3 See generally United States v. Maulding, 627 F.3d 285, 287–88 (7th Cir. 

2010) (collecting cases addressing similar arguments).

 
Nos. 14-1223, 14-2135 & 14-2482 13

posed a sentence of 72 months of imprisonment and 20 years 

of supervised release. The judge imposed 13 standard conditions with no discussion, and six special conditions with discussion of each. The judge rewrote certain proposed special 

conditions to accommodate the objections raised by Jurgens’ 

counsel, and did not impose the special condition proposed 

by probation that Jurgens refrain from using the Internet for 

the purpose of sexual arousal.

Jurgens appeals, contending that the district judge procedurally erred when she imposed 20 years of supervised 

release without addressing his request for 10 years or making appropriate findings. On appeal, Jurgens also challenges 

each of the 19 standard and special conditions of supervised 

release on the basis that they were imposed without appropriate findings and are impermissibly vague and overbroad.

B. Parrish Kappes

The details of Defendant Parrish Kappes’ childhood are 

different from Jurgens’, but the themes are similar. Kappes’ 

parents separated when he was an infant, and his mother 

took him to live in Arizona. In 1972, when Kappes was six 

years old, he flew alone to Illinois, where his father and 

grandmother lived. He had been physically abused and neglected by his mother, and he “looked rough” when he arrived in Illinois. He was given the choice of living with his 

father or grandmother, and he chose the latter, feeling that 

his father had earlier abandoned him. He lived with his 

grandmother for most of the next 40 years until his arrest 

and detention in this case. Kappes had not seen his mother 

since he was a child, and he told the probation officer during 

a pre-sentence interview that he could not remember his 

mother’s name. Although Kappes graduated from high 
14 Nos. 14-1223, 14-2135 & 14-2482

school, he finished near the bottom of his class, and he told 

the probation officer he was illiterate. Although he maintained steady employment from 2006 to 2012, he grew “accustomed to being alone” and had difficulty socializing.

On October 15, 2012, law enforcement agents executed a 

search warrant at the Tuscola, Illinois, house that Kappes 

shared with his then-93-year-old grandmother. The agents 

found 2,319 images and 182 videos of child pornography on 

Kappes’ computer. Agents also found images taken by 

Kappes of a 17-year-old female in a bikini. After waiving his 

Miranda rights, Kappes admitted that he had been taking 

pictures of this female and others while they played in an 

outdoor pool adjacent to his home since the girl was approximately seven or eight years old. In a footlocker, the agents 

found over 30 pairs of children’s underwear which Kappes 

claimed to have stolen 20 years earlier when he worked as a 

furniture deliveryman. 

Kappes was charged with three counts of distributing 

child pornography and one count of possessing child pornography. After hearing two days of evidence, a jury found 

Kappes guilty on all counts. The presentence report stated 

that the guidelines range was 210 to 240 months of imprisonment and five years to life of supervised release. The report stated, “[i]n addition to standard conditions of supervised release ... found at U.S.S.G. § 5D1.3, the Court may 

impose the following special conditions,” and listed seven 

special conditions which largely mirrored those recommended in Jurgens’ presentence report. An addendum to the 

report stated that Kappes’ attorney had no objections to the 

report.
Nos. 14-1223, 14-2135 & 14-2482 15

At sentencing, Kappes’ attorney reiterated that Kappes 

had no objections to the presentence report. Counsel for the 

government requested a sentence of 240 months of imprisonment and 25 years of supervised release. Government 

counsel said she was requesting the statutory maximum because of, among other reasons, the graphic and violent images in Kappes’ child pornography collection. Kappes’ counsel commented upon Kappes’ positive employment record 

and record of caring for his grandmother. Kappes declined 

to speak. 

The district judge then discussed the “horrendous” nature and circumstances of the offense, and the “disturbing” 

character and history evidence of “taking pictures of neighbors’ children and saving panties for 20 years.” The district 

judge imposed a sentence of 240 months of imprisonment 

and 25 years of supervised release. The judge imposed 13 

standard conditions and the seven special conditions recommended in the presentence report.

Kappes appeals, contending that the district court erred 

by imposing (1) four special conditions which were not adequately supported by specific findings and are impermissibly vague or overbroad, (2) two special conditions which required Kappes to pay for court-ordered treatment and testing, and (3) three special conditions which appeared in the 

written judgment but were not orally pronounced at sentencing.

C. David Crisp, Jr.

Defendant David Crisp, Jr. (“Crisp”) followed in the 

footsteps of his father, David Crisp, Sr. At the time Crisp 

was charged in this case with possession with intent to dis-
16 Nos. 14-1223, 14-2135 & 14-2482

tribute crack cocaine, his father was serving a sentence in 

federal prison for similar crack cocaine trafficking offenses. 

Crisp later reported to probation that his father was involved in his life when he was not incarcerated; however, 

“he was incarcerated frequently.” Crisp likewise was involved in his children’s lives when not incarcerated; he 

claimed to have committed the instant offense because he 

wanted to raise his one-year-old daughter and five-year-old 

step-son in “relative comfort” and “the minimum wage job 

of $8.25 an hour was just not cutting it.” Like his father before him, Crisp—35 years old at the time of his last arrest—

had amassed a substantial criminal history consisting of 32 

arrests and 24 convictions (including four drug felonies) 

during the previous 18 years. 

Crisp pleaded guilty without a written plea agreement. 

The presentence report stated that the guidelines range was 

262 to 327 months of imprisonment and eight years of supervised release. The report stated, “[i]n addition to standard conditions of supervised release ... found at U.S.S.G. § 

5D1.3, the Court may impose the following special conditions,” and listed four special conditions. An addendum to 

the report stated that Crisp’s attorney had no objections to 

the report. 

On May 15, 2014, Crisp was sentenced in the same courtroom where his father was sentenced in 2011. At the outset 

of sentencing, defense counsel reiterated that she had no objections to the presentence report. Government counsel then 

recommended a sentence of 286 months of imprisonment 

and 10 years of supervised release. Defense counsel argued 

that, despite Crisp’s failure to enter into a plea agreement, 

“the Court can still consider the timeliness of [Crisp’s] coop-
Nos. 14-1223, 14-2135 & 14-2482 17

eration, the fact that he did render a proffer that was lengthy 

... and he did accept responsibility in a very, very quick 

manner.” Defense counsel asked the district judge “to depart 

from the bottom of the guideline range to the maximum 

amount that the Court feels is appropriate.”

After hearing from Crisp, the district judge discussed 

Crisp’s criminal history and said that his career offender status pursuant to the guidelines was appropriate. The judge 

said that Crisp had “rehabilitative potential” based upon 

Crisp’s allocution at sentencing and his “exceptional acceptance of responsibility.” The judge imposed a sentence of 

240 months of imprisonment and eight years of supervised 

release. The judge imposed 13 standard conditions and the 

four special conditions recommended in the presentence report.

Crisp appeals, contending that the district court erred by 

(1) imposing three conditions of supervised release which 

were not adequately supported by specific findings and are 

impermissibly vague or overbroad; and (2) failing to comment upon Crisp’s cooperation with law enforcement as a 

substantial mitigating factor.

III. Advance Notice of the Conditions

The first general principle sentencing judges should consider when imposing conditions of supervised release is that 

it is important to give advance notice of the conditions being 

considered. In most instances, this principle fits into the category of recommended “best practice” rather than mandatory requirement. Advance notice is only required of supervised release conditions that are not listed in a statute or the 

guidelines. United States v. Thompson, 777 F.3d 368, 377 (7th 
18 Nos. 14-1223, 14-2135 & 14-2482

Cir. 2015) (collecting cases). This is because “[d]efendant and 

lawyer are charged with knowledge of the sentencing guidelines, which list the standard conditions along with a number of special ones.” United States v. Bryant, 754 F.3d 443, 446 

(7th Cir. 2014).

Despite this charged knowledge, we have suggested that 

sentencing judges require the probation office to include any

recommended conditions of supervised release—and the 

reasons for the recommendations—in the presentence report 

that is disclosed to the parties prior to the sentencing hearing. See Thompson, 777 F.3d at 377; Siegel, 753 F.3d at 716–17. 

We also have suggested, as a matter of “best practices,” that 

sentencing judges: (a) send a list of the conditions that the 

judge is contemplating (including the reasons) to the parties 

prior to the sentencing hearing; and/or (b) explain at the sentencing hearing what conditions the judge is inclined to impose and why, then ask the parties whether they object to 

any of them or have a reasonable need for more time to decide whether to object, and adjourn the hearing if necessary. 

Thompson, 777 F.3d at 377. An exception to these “best practice” suggestions would be conditions of supervised release 

which are “administrative requirements applicable whenever a term of supervised release is imposed,” such as “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.” Thompson, 777 F.3d 

at 378. “Once the judge has explained why supervised release is necessary, he should be permitted to impose the necessary incidents of supervision without explanation.” Id.

The goal of providing the parties with advance notice of 

the conditions at issue is to allow the parties to present an 
Nos. 14-1223, 14-2135 & 14-2482 19

informed response. Cf. Irizarry v. United States, 553 U.S. 708, 

715 (2008) (“Sound practice dictates that judges in all cases 

should make sure that the information provided to the parties in advance of the [sentencing] hearing, and in the hearing itself, has given them an adequate opportunity to confront and debate the relevant issues.”); United States v. Scott, 

316 F.3d 733, 735 (7th Cir. 2003) (“Knowledge that a condition of this kind was in prospect would have enabled the 

parties to discuss such options intelligently.”). To the extent 

not required by rule or the sentencing judge, we recommend

that defense counsel and government counsel make recommendations and/or objections regarding the proposed conditions of supervised release in advance of the sentencing 

hearing. Cf. Fed. R. Crim. P. 32(f)(1) (requiring parties to 

state in writing any objections to the presentence report 

within 14 days of receipt). 

Jurgens’ sentencing offers an example of the utility of advance notice by probation and timely objections by the defendant. Jurgens objected to four of the special conditions 

proposed in the presentence report, and the sentencing

judge responded by changing the language in three of the 

objected-to conditions and declining to impose the fourth 

one entirely. It is our hope that the combination of advance 

notice, timely objections, and appropriate judicial response 

to the objections will result in conditions better tailored to 

fulfill the purposes of supervised release, less confusion and 

uncertainty, and perhaps—Jurgens’ case notwithstanding—

fewer appeals.

The issue of advance notice of the proposed conditions is 

potentially relevant to our standard of review. See United 

States v. Farmer, 755 F.3d 849, 853 (7th Cir. 2014) (“[I]t seems 
20 Nos. 14-1223, 14-2135 & 14-2482

problematic to conclude that the defendant waives objections to special conditions if he does not properly confront 

conditions presented for the first time at the sentencing hearing.”). “We recently recognized some tension in our cases as 

to the proper standard of review” when a defendant fails to 

“object” (or, more accurately, take “exception”) after the sentencing judge imposes a condition to which the defendant 

had no notice, because, for example, the probation officer 

did not recommend it. United States v. Shannon, 743 F.3d 496, 

499 (7th Cir. 2014) (collecting cases). In general, our rule has 

been that the imposition of contested conditions are reviewed for an abuse of discretion, while uncontested conditions are reviewed for plain error. United States v. Ross, 475 

F.3d 871, 873 (7th Cir. 2007); cf. United States v. Baker, 755 

F.3d 515, 522 (7th Cir. 2014) (allegations of procedural error, 

such as whether a judge adequately explained his chosen

sentence, are reviewed de novo). Under either standard of review, we must be mindful of the fact that “[t]he sentencing 

judge is in a superior position to find facts and judge their 

import under § 3553(a) in the individual case,” and “district 

courts have an institutional advantage over appellate courts 

in making these sorts of determinations, especially as they 

see so many more Guidelines cases than appellate courts 

do.” Gall v. United States, 552 U.S. 38, 51–52 (2007) (quotations and alterations omitted).

The government contends that Jurgens, Kappes and 

Crisp received notice of the conditions they now challenge 

because all challenged conditions were recommended in the 

respective presentence reports. Accordingly, the government 

contends that plain error review is appropriate in each case 

because Kappes and Crisp did not object to the presentence 

report and each of Jurgens’ objections were accommodated 
Nos. 14-1223, 14-2135 & 14-2482 21

by the conditions ultimately imposed by the sentencing 

judge. Kappes concedes that plain error review applies to his 

vagueness and overbreadth challenges. Jurgens argues that 

abuse of discretion review is appropriate to his challenges of 

the standard conditions because the presentence report 

merely incorporated the standard conditions by reference, 

rather than listing each standard condition in the report itself. Crisp offers no opinion on the standard of review, arguing that the errors are reversible regardless of the standard 

of review. 

We find that, with respect to the challenges we consider 

here, the outcome is the same regardless of the standard of 

review. See United States v. Hinds, 770 F.3d 658, 665 (7th Cir. 

2014) (same); Farmer, 755 F.3d at 854 (same); Shannon, 743 

F.3d at 500 (same). Despite this finding, we caution future 

defendants against withholding objections under the belief 

that we will continue to treat the abuse-of-discretion and 

plain-error standards of review as functionally interchangeable in this context. Under plain-error review, unlike abuseof-discretion review, we are permitted but not required to 

order correction of an error.4 United States v. Olano, 507 U.S. 

725, 735 (1993) (“[Federal Rule of Criminal Procedure] 52(b) 

[governing plain error] is permissive, not mandatory. If the 

forfeited error is plain and affects substantial rights, the 

court of appeals has authority to order correction, but is not 

4 An argument could be made that a sentencing judge may adopt any 

unobjected-to conditions in the presentence report without the need to 

make findings. Cf. Fed. R. Crim. P. 32(i)(3)(A) (a sentencing judge may 

accept any undisputed portion of the presentence report). Because the 

issue has not been raised by the parties, we do not consider it here.

 
22 Nos. 14-1223, 14-2135 & 14-2482

required to do so.” (quotation omitted)). A sentencing hearing is not meant to be a dress rehearsal.

IV. Statement of Reasons and Appropriate Tailoring

The second principle—justifying the conditions by an adequate statement of reasons—and the third—imposing appropriately-tailored conditions—are interrelated. Accordingly, after outlining the parameters of each principle, we discuss the defendants’ challenges to specific conditions in connection with both rules.

A. Statement of Reasons

The second general principle regarding the imposition of 

conditions of supervised release that we address is that a 

sentencing court must justify the conditions and the length 

of the term at sentencing by an adequate statement of reasons, reasonably related to the applicable § 3553(a) factors. 

See Bryant, 754 F.3d at 445. This “allow[s] for meaningful appellate review”; it “promote[s] the perception of fair sentencing”; and it is a vital element in maintaining the “uniform 

and constant” principle in the federal judicial tradition that 

“the sentencing judge ... consider[s] every convicted person 

as an individual and every case as a unique study in the 

human failings that sometimes mitigate, sometimes magnify, 

the crime and the punishment to ensue.” Gall, 552 U.S. at 50, 

52 (quotation omitted).

The applicable factors are set out in 18 U.S.C. §§ 3553(a)

and 3583(c)–(d). Section 3583(d) places the factors into three 

groups. First, the conditions of supervised release “must be 

reasonably related to (1) the defendant’s offense, history and 

characteristics; (2) the need for adequate deterrence; (3) the 

need to protect the public from further crimes of the defend-
Nos. 14-1223, 14-2135 & 14-2482 23

ant; and (4) the need to provide the defendant with treatment.” United States v. Angle, 598 F.3d 352, 360–61 (7th Cir. 

2010); see 18 U.S.C. § 3583(d)(1). Next, the conditions “cannot 

involve a greater deprivation of liberty than is reasonably 

necessary to achieve the goal of deterrence, incapacitation, 

and rehabilitation.” United States v. Goodwin, 717 F.3d 511, 

522 (7th Cir.), cert. denied, 134 S. Ct. 334 (2013); see 18 U.S.C. 

§ 3583(d)(2). Finally, the conditions must be consistent with 

any pertinent statement that the United States Sentencing 

Commission issues.5 18 U.S.C. § 3583(d)(3); cf. Siegel, 753 

F.3d at 708 (noting that, logically, this factor is not applicable 

to conditions already listed in the guidelines). Unfortunately, applying this “vague and general” list of unweighted factors to a specific case is unwieldy in practice, “and cannot 

yield an objective result.” Siegel, 753 F.3d at 707.

The judge need not address every factor “in checklist 

fashion, explicitly articulating its conclusions regarding each 

one.” Shannon, 518 F.3d at 496; see United States v. Starko, 735 

F.3d 989, 992 (7th Cir. 2013) (“Courts do not have to engage 

in a discourse of every single § 3553(a) factor; however, it is 

also the case that a rote statement that the judge considered 

all relevant factors will not always suffice.” (quotation omitted)). “[T]he court may simply give an adequate statement of 

5 The statute requires that each discretionary condition be “consistent 

with any pertinent policy statements” by the Sentencing Commission. 18 

U.S.C. § 3583(d)(3). The defendants in these cases appear to argue that a 

sentencing judge is required to identify a particular policy statement issued by the Sentencing Commission prior to imposing any discretionary 

condition of supervised release. We do not agree. However, if a challenged condition is inconsistent with a pertinent policy statement, then 

the condition would violate § 3583(d)(3).

 
24 Nos. 14-1223, 14-2135 & 14-2482

reasons, consistent with § 3553(a), for thinking the sentence 

it selects is appropriate.” Shannon, 518 F.3d at 496. “[T]he 

more onerous the term [of supervised release], the greater 

the justification required—and ... a term can become onerous because of its duration as well as its content.” United 

States v. Quinn, 698 F.3d 651, 652 (7th Cir. 2012); cf. Gall, 552

U.S. at 50 (“We find it uncontroversial that a major departure [from the guidelines range] should be supported by a 

more significant justification than a minor one.”). “Special” 

conditions often require more justification than “standard” 

conditions—but not always—and a condition’s label in the 

guidelines is ultimately irrelevant. All discretionary conditions, whether standard, special or of the judge’s own invention, require findings. See Bryant, 754 F.3d at 445. We emphasize that the judge need not give a speech about each condition, but conversely, we believe sentencing judges rarely, if 

ever, should list a multitude of conditions without discussion. This rule, however, is subject to a harmless error analysis. See Siegel, 753 F.3d at 713.

The fact that a sentencing judge may reduce or modify 

terms of supervised release at any time, see 18 U.S.C. 

§ 3583(e)(2), may lead the judge to resolve uncertainties at 

the time of sentencing in favor of a long but reducible period. “[S]till this is a subject that requires an explicit decision 

by the judge after considering the defendant’s arguments.” 

Quinn, 698 F.3d at 652. We also have advised sentencing 

judges to “consider the possibility of setting sunset dates for 

some of the more onerous terms, so that [the defendant] can 

regain more control of his own activities without needing a 

public official’s advance approval, while enough supervision 

remains to allow intervention should [the defendant] relapse.” Id. at 652–53. In Quinn, we vacated a term of super-
Nos. 14-1223, 14-2135 & 14-2482 25

vised release and remanded for resentencing when the judge 

rejected the defendant’s request for a 10-year term of supervised release and instead imposed a lifetime term without 

discussion of the length of defendant’s supervision, the 

terms that he would be required to follow, or much of the 

defendant’s evidence that he presented a lower-than-normal 

risk of recidivism. See id. at 652. 

Jurgens contends that the sentencing judge erred in imposing a 20-year term of supervised release without discussion of his request for a 10-year term. Jurgens points to the 

statement in Quinn that it is not sufficient to simply choose a 

supervised release term within the guidelines range; “a 

judge still must consider a defendant’s serious arguments 

for a sentence below the Sentencing Commission’s recommendations.” Id. Jurgens contends that we should vacate the 

20-year term and “remand with instructions that the district 

court consider the § 3583(c) factors when addressing Mr. 

Jurgens’s requested 10 year term of supervised release.” 

The Sentencing Commission recommends the statutory 

maximum term of supervised release for every sex offense, 

see U.S.S.G. § 5D1.2(b)(2), and any sentence within the guidelines range is “entitled to a presumption of substantive reasonableness.” Quinn, 698 F.3d at 652 (citing, inter alia, Rita v. 

United States, 551 U.S. 338 (2007)). The 20-year supervisedrelease term Jurgens received is below the statutory maximum of life and thus below the term recommended by the 

Sentencing Commission. However, even in this situation, 

while the sentencing judge “need not discuss each section 

3553(a) factor at sentencing and need not respond to every 

pithy argument that a defendant raises,” a defendant is enti-
26 Nos. 14-1223, 14-2135 & 14-2482

tled to a discussion of his “principal” arguments. United 

States v. Villegas-Miranda, 579 F.3d 798, 801 (7th Cir. 2009).

Prior to sentencing, Jurgens submitted a 21-page “commentary on sentencing factors.” This document contains extensive discussion of factors favoring leniency in the term of 

imprisonment, culminating with a request for a custodial 

sentence of 60 months. The document contains a brief discussion of supervised release, focused exclusively on his objections to four terms of supervised release recommended in 

the presentence report. The document contains no recommendation as to—or even mention of—the length of the term 

of Jurgens’ supervised release. Jurgens’ objections in the addendum to the presentence report likewise contain nary a 

mention of the length of supervised release. In his remarks at 

the sentencing hearing, Jurgens’ counsel spoke expansively 

on Jurgens’ history and need for sex-offender treatment, the 

irrationality of the guidelines imprisonment-range, and the 

lack of evidence of “hands-on sex offenses.” At the conclusion of his remarks, after asking for 60 months in custody, 

Jurgens’ counsel devoted a single sentence to the length of 

the term of supervised release: “We ask for a ten-year period 

of supervised release with appropriate conditions therein.”

In this context, we do not consider Jurgens’ request for a 

10-year term to be one of his “principal” arguments, requiring discussion by the sentencing judge. Villegas-Miranda, 579 

F.3d at 801. We find that the judge did not err in focusing her 

discussion on the topics focused upon by Jurgens’ counsel. 

Of course, a sentencing judge must always adequately explain his or her choice as to the length of custody and supervised release, consistent with the relevant § 3553(a) factors. 

See Farmer, 755 F.3d at 852. In this case, we find that was 
Nos. 14-1223, 14-2135 & 14-2482 27

done, particularly given that the length of custody and supervised release were both significantly below the guidelines range. Cf. Quinn, 698 F.3d at 652 (more onerous terms 

require greater justification, and “a term can become onerous because of its duration as well as its content”). The judge 

chose to discuss her reasons for imposing the sentence as a 

whole, and we find this to be a reasonable choice in this case. 

The judge discussed Jurgens’ troubled personal history and 

characteristics and also discussed her “concern” that, after 

he was caught but prior to incarceration, he continued to 

watch “simulated depictions” of child pornography. Moreover, even if the judge erred by not adequately explaining her 

decision to follow the six-year custodial sentence (near the 

low end of the statutory range) with 20 years of supervised 

release (meaning Jurgens will complete his supervised release when he is approximately 54 years old), we find this 

error to be harmless in this case. “[A] district court may find 

it proper to impose a longer term of supervised release to 

follow a relatively shorter term of imprisonment,” United 

States v. Albertson, 645 F.3d 191, 198 (3d Cir. 2011), and that is

what the sentencing judge did in this case.

Jurgens also argues that the sentencing judge erred by 

failing to provide an adequate statement of reasons for each 

of the 19 standard and special conditions of supervised release the judge imposed. We address those arguments below

in conjunction with our discussion of the individual conditions.

B. Specific, Appropriately Tailored Conditions

The third sentencing principle we address is that sentencing judges should impose conditions of supervised release 

which are (a) appropriately tailored to the defendant’s of-
28 Nos. 14-1223, 14-2135 & 14-2482

fense, personal history and characteristics; (b) involve no 

greater deprivation of liberty than is reasonably necessary to 

achieve the goals of deterrence, protection of the public, and 

rehabilitation; and (c) sufficiently specific to place the defendant on notice of what is expected. See Adkins, 743 F.3d at 

196 (discussing “the importance of notice and reasonably 

narrow tailoring,” in crafting conditions of supervised release); Goodwin, 717 F.3d at 525 (“[E]ach special condition 

imposed must be tailored to Goodwin and his needs and involve no greater deprivation of liberty than is reasonably 

necessary to achieve the goals of deterrence, protection of 

the public, and rehabilitation.” (citation omitted)); United 

States v. Schave, 186 F.3d 839, 843 (7th Cir. 1999) (“A condition of supervised release is unconstitutionally vague if it 

would not afford a person of reasonable intelligence with 

sufficient notice as to the conduct prohibited.”). This rule 

functions as a limit to a sentencing judge’s “wide discretion 

in determining conditions of supervised release.” Adkins, 743 

F.3d at 193 (quotation omitted). 

We have recognized “the difficulty of drafting special 

conditions.” Id. at 196. We have suggested that sentencing 

judges define the crucial terms in a condition in a way that 

“provides clear notice to [the defendant] (preferably through 

objective rather than subjective terms),” and/or “includes a 

mens rea requirement (such as intentional conduct).” Id. We 

have further suggested that the judge “[m]ake sure that each 

condition imposed is simply worded, bearing in mind that, 

with rare exceptions, neither the defendant nor the probation officer is a lawyer and that when released from prison 

the defendant will not have a lawyer to consult.” Siegel, 753 

F.3d at 717.
Nos. 14-1223, 14-2135 & 14-2482 29

1. Standard Conditions

As we have said, the fact that certain non-administrative 

conditions are labeled “standard” does not render them immune from the requirements that they be adequately supported and not vague or overbroad. See Thompson, 777 F.3d 

at 376–78.

In Jurgens’ case, the sentencing judge imposed 13 standard conditions without giving reasons. Jurgens challenges 

each standard condition as having been improperly imposed 

without notice and without findings, and further challenges 

most of them as being vague, overbroad, and/or an excessive 

deprivation of his liberties. Jurgens first contends that the 

standard conditions were omitted from the presentence report, which deprived him of notice and an opportunity to 

object. Jurgens’ presentence report referred to the “standard 

conditions of supervised release ... found at U.S.S.G. § 

5D1.3.” While it would be better practice for probation officers to detail each condition being proposed, along with reasons why they would be applicable in a particular defendant’s case, we cannot say that Jurgens was deprived of notice 

that each of the standard conditions listed in U.S.S.G. § 

5D1.3 would be considered by the sentencing judge. 

Jurgens finds more solid ground for his contention that 

the judge imposed 13 standard conditions without making

findings consistent with the § 3553(a) factors. With respect to 

the substantive standard conditions, Jurgens is correct that 

the sentencing judge imposed them without explanation as 

to why they were appropriate in Jurgens’ case and involved 

no greater deprivation of liberty than is reasonably necessary to achieve the permissible goals of supervised release. 

See Goodwin, 717 F.3d at 523–24. However, we nonetheless 
30 Nos. 14-1223, 14-2135 & 14-2482

must look at the conditions to determine whether the failure 

to give reasons was harmless. See Siegel, 753 F.3d at 713. As 

we did in Thompson and Siegel, we highlight the ambiguities

and/or overbreadth in many of the standard conditions, and 

suggest modifications for improving them.

The condition forbidding the defendant from “associat[ing] with any persons engaged in criminal activity” and 

“associat[ing] with any person convicted of a felony, unless 

granted permission to do so by the probation officer,” is “fatally vague” because it appears to impose strict liability and 

does not define “associate.” Thompson, 777 F.3d at 376–77. A 

suggested modification would be to 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.” Id. at 377.

The condition that the defendant “refrain from excessive 

use of alcohol,” is vague because “excessive use” is not defined. Id. at 376. A suggested definition for “excessive” alcohol use for men is “binge drinking or heavy drinking,” with 

“heavy drinking” being defined as “consuming 15 drinks or 

more per week.” Siegel, 753 F.3d at 715 (quotation omitted). 

While the government points to no evidence contradicting 

Jurgens’ claim he was a teetotaler, the government nonetheless contends the condition banning excessive alcohol use is 

appropriate because Jurgens is the child of alcoholics. The 

sentencing judge did not say this, and given the lack of any 

apparent connection between alcohol use and Jurgens’ offense, we think the imposition of this condition without findings was not harmless.

The condition that “the defendant shall support his or 

her dependents and meet other family responsibilities” is 
Nos. 14-1223, 14-2135 & 14-2482 31

inappropriate in Jurgens’ case because he has no dependents, see Thompson, 777 F.3d at 376, and it is not apparent 

what “other family responsibilities” means, given that it appears to mean something different than “support[ing]” 

Jurgens’ as-yet nonexistent dependents. To the extent the 

condition requires only financial support, as argued by the 

government, the condition should make that explicit and 

should include a limitation which takes into account the defendant’s ability to pay. Cf. Siegel, 753 F.3d at 714 (“Revoking 

a defendant’s supervised release and recommitting him to 

prison for mere inability to pay would constitute imprisonment for debt.”). 

The condition that “the defendant shall notify third parties of risks that may be occasioned by the defendant’s criminal record or personal history or characteristics” contains 

numerous ambiguities. “There is no indication of what is 

meant by ‘personal history’ and ‘characteristics’ or what 

‘risks’ must be disclosed to which ‘third parties.’” Thompson, 

777 F.3d at 379. Presumably, the meaning of these terms 

would change from defendant to defendant, which makes 

definitions particularly important with this condition.

The condition that the defendant is to notify his probation officer of any “change in ... employment” 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.” Id. 

Likewise, the condition requiring the defendant to work 

“regularly at a lawful occupation” fails to define “regularly.” 

The condition prohibiting the defendant from “frequent[ing] places where controlled substances are illegally 

sold, used, distributed, or administered,” contains no “indi-
32 Nos. 14-1223, 14-2135 & 14-2482

cation of how many trips constitute ‘frequent[ing]’ such 

places.” Id. More importantly, the condition, read literally, 

improperly imposes strict liability because “there is no requirement that [the defendant] know or have reason to 

know or even just suspect that such activities are taking 

place.” Id. Likewise, the condition that “the defendant shall 

not leave the judicial district without ... permission” would 

be improved by explicitly adding a scienter requirement, 

particularly in a case where it is foreseeable that a defendant 

will reside near the boundary of two judicial districts within 

the same state. 

The condition that “the defendant shall answer truthfully 

all inquiries by the probation officer” “essentially asks for a 

waiver of the right not to be forced to incriminate oneself, 

because the condition would require the defendant to answer ‘yes’ if he were asked whether he had committed another crime and he had.” Id. at 379–80. In the context of probation, the Supreme Court has held that a state probation 

requirement that the probationer “be truthful with the probation officer ‘in all matters,’” was insufficient to require Miranda warnings because such a condition does not penalize 

the right to remain silent. Minnesota v. Murphy, 465 U.S. 420, 

422, 434 (1984). The Court said that the “the State could not 

constitutionally carry out a threat to revoke probation for the 

legitimate exercise of the Fifth Amendment privilege,” but 

the “probation condition [at issue] proscribed only false 

statements; it said nothing about [the defendant’s] freedom 

to decline to answer particular questions and certainly contained no suggestion that his probation was conditional on 

his waiving his Fifth Amendment privilege with respect to 

further criminal prosecution.” Id. at 437, 438. We have interpreted Murphy as drawing a line between “a merely plausi-
Nos. 14-1223, 14-2135 & 14-2482 33

ble fear that invoking one’s Fifth Amendment privilege will 

get one into trouble with the probation authorities,” and 

“the police tell[ing] the probationer that unless he talks his 

probation will be revoked.” United States v. Cranley, 350 F.3d 

617, 622 (7th Cir. 2003). The former does not require Miranda

warnings, while the latter does. Id. Because we are remanding for resentencing for other reasons, we decline to decide 

on which side of the Murphy line this condition falls. On remand, Jurgens may request that the standard condition that 

“the defendant shall answer truthfully all inquiries by the 

probation officer” should include language indicating that 

the condition does not prevent the defendant from invoking 

his Fifth Amendment privilege against self-incrimination.

We do not, however, hold here that such language is required. 

Jurgens contends that his Fifth Amendment rights also 

are implicated by the separate standard condition requiring 

him to “notify the probation officer within seventy-two 

hours of being arrested or questioned by a law enforcement 

officer.” We do not see how the mere fact of an arrest or law 

enforcement contact is itself incriminating, and Jurgens 

points us to no authority so holding. And unlike the previous condition, which required “all inquiries” to be answered, 

there is nothing in this condition which requires the defendant to answer any follow-up questions by the probation officer which may tend to elicit incriminating answers. With 

respect to the lack of findings to support this condition, we 

think it is harmless in this instance. Clearly, this condition 

assists the probation officer in monitoring the defendant’s 

conduct and compliance with the other conditions of release, 

most notably, the mandatory condition that the defendant 

commit no other criminal offenses.
34 Nos. 14-1223, 14-2135 & 14-2482

Jurgens challenges the standard condition that “the defendant shall permit a probation officer to visit him or her at 

any time at home or elsewhere and shall permit confiscation 

of any contraband observed in plain view of the probation 

officer” as infringing on his Fourth Amendment right to be 

free from warrantless nighttime searches. This condition is 

not as broad as the conditions we vacated in Farmer, 755 F.3d 

at 854–55, and Goodwin, 717 F.3d at 523,6 and thus does not 

implicate the defendant’s Fourth Amendment rights to the 

same extent. However, the visitation standard condition is 

nonetheless broadly worded, and “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.” 

Thompson, 777 F.3d at 380. The sentencing judge made no effort to explain why this condition—especially in its current, 

broadly worded form—is connected to Jurgen’s offense, history, and personal characteristics, or how it is reasonably 

necessary to furthering the deterrence, public protection, 

and rehabilitation goals referred to in 18 U.S.C. § 3583(d)(2). 

Given that Jurgens’ offense exclusively involved images on a 

computer—which presumably would not be left in plain 

view when Jurgens heard a knock on the door—and there is 

no indication Jurgens has ever possessed any other form of 

“contraband,” there is no readily apparent justification for 

this condition to be imposed upon Jurgens. Accordingly, we 

cannot find that the lack of explanation was harmless. See

Thompson, 777 F.3d at 380 (“Regardless of any possible con6 A modified version of that broader search condition was imposed upon 

Jurgens as a “special condition,” and is discussed infra.

 
Nos. 14-1223, 14-2135 & 14-2482 35

stitutional concern, [this condition is] too broad in the absence of any effort by the district court to explain why [it is] 

needed.”); cf. Goodwin, 717 F.3d at 523 (“Although we stop 

short of stating that such [search] restrictions could never be 

appropriate in these circumstances, our skepticism leads us 

to conclude that the district court must provide some justification for these particular conditions.”).

Jurgens contends that the condition prohibiting him from 

entering “into any agreement to act as an informer or a special agent of a law enforcement agency without the permission of the court” prevents him “from pursuing a key avenue for reducing his criminal exposure in the event he commits a new crime.” But this argument presumes the court 

unreasonably denies him permission, which seems to be an 

unlikely enough event that the imposition of this condition 

does not constitute an abuse of discretion, much less plain 

error. Moreover, the lack of findings to support this condition is harmless because, although there are occasions “when 

the law enforcement benefits to the community justify permitting the offender to engage in this high-risk activity,” 

“[a]cting as a confidential informant is generally inconsistent 

with the rehabilitative and re-integrative goals of supervision.” Admin. Office of the U.S. Courts, Guide to Judiciary 

Policy, Vol. 8, pt. E, § 460.60.20 (2011), available at

https://wvn.fd.org//pdf/Part_E%20109.pdf.

We have focused upon Jurgens’ challenges to the standard conditions imposed upon him because Jurgens challenges each of the standard conditions on appeal. The same 13 

standard conditions imposed upon Jurgens were imposed 

upon Kappes and Crisp, with the exception that Crisp was 

prohibited from “any” use of alcohol instead of “excessive” 
36 Nos. 14-1223, 14-2135 & 14-2482

use. The ban on “excessive” use of alcohol is the only standard condition challenged on appeal by Kappes, and it must 

be vacated for the same reasons this condition was vacated 

as to Jurgens. Because we are ordering a resentencing for 

Kappes, our comments above regarding the other 12 standard conditions should be considered by Kappes’ sentencing 

judge as well. 

On appeal, Crisp challenges the standard conditions 

banning “any” use of alcohol and requiring him to “support” his dependents and “meet other family responsibilities.” Unlike Jurgens and Kappes, there is evidence that 

Crisp consumed alcohol: he reported to the probation officer 

that he drank alcohol three to four times a week, but not to 

intoxication. The sentencing judge imposed the alcohol ban 

with no explanation for how it connected to Crisp’s offense 

or history. Perhaps a rationale could be offered adequate to 

support a total or—more likely—an “excessive” alcohol ban, 

but that rationale is not sufficiently apparent that we may 

declare harmless the failure to make any findings in support 

of the condition as written. See Baker, 755 F.3d at 524 (vacating a complete ban on alcohol despite defendant’s statement 

that he consumed a six-pack of beer or more twice per week, 

because “there is no evidence that Baker’s alcohol use has 

contributed to his repeated criminal conduct or that Baker is 

dependent on alcohol”).

The failure to give reasons for imposing the condition requiring Crisp to “support” his dependents and “meet other 

family responsibilities” was harmless given the central role 

Crisp’s family played in the presentence report and the 

comments made by the defense and the judge at sentencing. 

However, our other comments made above regarding this 
Nos. 14-1223, 14-2135 & 14-2482 37

condition apply with equal force to Crisp. The meaning of 

the phrase, “other family responsibilities,” is not apparent, 

given that it appears to mean something different than 

“support[ing]” Crisp’s dependents. To the extent the condition requires only financial support, the condition should 

make that explicit and should include a limitation which 

takes into account the defendant’s ability to pay. As with 

Kappes, because we are ordering a resentencing for Crisp, 

our comments above regarding the other 11 standard conditions which were not challenged by Crisp should be considered by Crisp’s sentencing judge.

We are not the first court to be presented with at least 

some of these objections to the standard conditions. “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.” Thompson, 777 

F.3d at 380 (collecting cases). Other courts have interpreted 

an overbroad or ambiguous condition narrowly, for example, by reading a scienter requirement into a condition that is 

silent on the issue. See United States v. Phillips, 704 F.3d 754, 

767–68 (9th Cir. 2012) (construing the standard condition 

prohibiting the defendant from “frequent[ing] places where 

controlled substances are illegally sold” as “prohibit[ing] 

Phillips from knowingly going to a specific place where drugs 

are illegally used or sold, but ... not prohibit[ing] him from ... 

going to a given neighborhood simply because a person is 

selling drugs somewhere within that neighborhood”); United 

States v. Green, 618 F.3d 120, 123 (2d Cir. 2010) (same, regarding a condition prohibiting association with street gangs). 

Likewise, we have imposed “an appropriate limiting construction” to a condition of supervised release prohibiting a 

defendant from “associat[ing] ... with any member or organ-
38 Nos. 14-1223, 14-2135 & 14-2482

ization which espouses violence or the supremacy of the 

white race,” despite “the absence of an explicit scienter requirement in the restriction.” Schave, 186 F.3d at 843. Similarly, we have previously decided that the erroneous imposition of two overbroad conditions does not amount to plain 

error requiring our intervention because “conditions of supervised release are readily modifiable at the defendant’s 

request.” United States v. Silvious, 512 F.3d 364, 371 (7th Cir. 

2008); accord United States v. McKissic, 428 F.3d 719, 726 (7th 

Cir. 2005) (same, regarding the imposition of a condition 

without notice to the defendant). 

However, as in Adkins, “this is not a case where we can 

tweak the relevant condition[s] easily.” 743 F.3d at 195 (quotation omitted).We have identified numerous conditions 

with troublesome provisions, and “we would need to define 

multiple key terms or provide multiple limiting constructions.” Id. at 196. “[B]ecause the district court will retain jurisdiction over this case for many years, including the power 

to amend the conditions of supervised release at any time, it 

is in a superior position to write a new condition, if it so 

chooses.” Id. (citing 18 U.S.C. § 3583(e)(2)). As for declining 

to remand in favor of requiring the defendant to request 

modification at a later time, once a defendant is serving supervised release, he typically finds himself without the right 

to counsel and may lack the legal sophistication to recognize 

the potential infirmities in the conditions he has been ordered to obey. Also, in an effort to avoid the ire of the probation officer and judge who hold his liberty in their hands, the 

unrepresented defendant on supervised release may opt to 

forgo his right to request modification, and either attempt to 

abide by an overbroad condition or ignore the condition and 

hope it is not discovered. Accordingly, in this instance, we 
Nos. 14-1223, 14-2135 & 14-2482 39

find “[i]t is preferable for the district court to specify limitations in a condition of supervised release in the condition 

itself” at the time of sentencing, rather than leaving it to either the appellate court to introduce limitations or the defendant on supervised release to make a motion for modification. Thompson, 777 F.3d at 380.

2. Special Conditions

a. Bans on Mood-Altering Substances, 

Pornography, and Internet

Both Kappes and Crisp are subject to special conditions 

banning the purchase, possession or use of any “mood altering substance.” This phrase is not defined nor is its meaning 

self-evident. Siegel, 753 F.3d at 713 (“It could include coffee, 

cigarettes, sugar, and chocolate, among many others; yet 

these substances are not causal factors of recidivist behavior.”). A better definition for “mood altering substances,” 

although not the only one, would be “psychoactive substances that impair physical or mental functioning, including 

street, synthetic, or designer drugs.” Id. (quotation marks 

omitted). We also have suggested simply prohibiting “illegal

mood-altering substances.” United States v. Cary, 775 F.3d 

919, 924 (7th Cir. 2015). In Kappes’ case, the sentencing judge 

offered no reasons for imposing the condition, and the record offers no indication Kappes has ever used psychoactive 

substances, so we cannot say that the lack of findings as to 

this condition was harmless. Therefore, Kappes’ special condition number one is vacated. The same condition also contains limitations on the use of alcohol (a total ban for Crisp 

and a ban on “excessive” use for Kappes), and our comments made above related to the standard condition limiting 

the use of alcohol apply with equal force to this duplicative 
40 Nos. 14-1223, 14-2135 & 14-2482

special condition. The special condition also permits testing 

for use of alcohol, but to the extent the defendant is allowed

to consume non-excessive amounts of alcohol, the sentencing judge should indicate the purpose of this testing if this 

condition is reimposed in some form. See Baker, 755 F.3d at 

525; Siegel, 753 F.3d at 716.

Kappes is subject to special condition numbers four and 

seven, banning him from receiving or viewing “any material, legal or illegal, that contains pornography,” and forbidding him from “us[ing] the Internet ... for the purpose of 

sexual arousal.” “Adult pornography, unlike child pornography, enjoys First Amendment protection, and so we must 

be especially cautious when considering a ban on possessing 

adult pornography.” Shannon, 743 F.3d at 500. We have

found that special conditions such as Kappes’ special condition numbers four and seven do not survive a vagueness or 

overbreadth challenge, irrespective of whether plain-error 

review or abuse-of-discretion review applied. See id.; Adkins, 

743 F.3d at 194; Goodwin, 717 F.3d at 525. We again so find 

here. 

In Jurgens’ case, the presentence report recommended 

the identical pornography and Internet-usage conditions 

imposed upon Kappes, but the sentencing judge declined to 

impose the Internet-usage condition and modified the pornography condition to prohibit Jurgens from receiving or 

viewing “any material, legal or illegal, that contains illegal 

pornography as that is defined in the U.S. Code.” Despite 

the sentencing judge’s modifications, Jurgens complains that 

the reference to “legal” material is “plainly a scrivener’s error,” and the condition is “redundant given that the mandatory condition banning the commission of federal or state 
Nos. 14-1223, 14-2135 & 14-2482 41

offenses prohibits the [same] conduct.” Jurgens is correct, 

but any error is harmless. Moreover, given Jurgens’ offense, 

the sentencing judge may have wished to emphasize that 

Jurgens is prohibited from possessing illegal pornography. If 

so, the sentencing judge may make that clear on remand.

b. Treatment Programs and Computer 

Monitoring

Jurgens is required by special condition numbers one, 

two, and five to participate in “psychiatric services and/or a 

program of mental health counseling and treatment,” “sex 

offender treatment,” and probation’s “Computer and Internet Monitoring Program.” Jurgens contends on appeal that 

these special conditions are greater than necessary deprivations of his liberty and were not supported by adequate findings.

With respect to the conditions requiring mental-health 

counseling and treatment and sex-offender treatment, 

Jurgens did not object to these special conditions despite 

their appearance in the presentence report. Jurgens himself 

told the sentencing judge: “I want to use this as an opportunity to turn my life around by making use of any and all 

education, counseling and guidance that is made available to 

me.”7 Prior to sentencing, the judge ordered a psychosexual 

evaluation of Jurgens. Jurgens was diagnosed with an anxiety disorder and a pedophilic disorder. Jurgens’ attorney emphasized Jurgens’ “abusive childhood situation,” requested 

7 Jurgens came close to waiving this challenge. See Cary, 775 F.3d at 927 

(“We will not second-guess conditions of supervised release imposed 

consistent with an offender’s request in the district court.”).

 
42 Nos. 14-1223, 14-2135 & 14-2482

a “ten-year period of supervised release with appropriate 

conditions,” and asked for Jurgens to be housed in a prison 

where “he gets the benefit of sex offender ... treatment.” The 

sentencing judge then commented upon Jurgens’ wretched 

childhood wherein Jurgens “never learned to value 

[him]self” and attributed Jurgens’ anxiety disorder to his 

childhood. The judge commented on her concern that, after 

being caught with child pornography but prior to his arrest 

and incarceration, Jurgens collected anime, which is “just 

animated, simulated depictions of the same kinds of things 

that ... you understood you could no longer look at.” The 

judge found that the length of time Jurgens viewed the videos depicting child pornography and the nature of the images 

were aggravating factors. The judge ordered the mentalhealth treatment and sex-offender treatment conditions “because of the information contained about your mental health 

in the [presentence report] and also in the psychosexual 

evaluation regarding concerns about pedophilia, [and] also

concerns about your high level of social anxiety and avoidance issues.” We find that these findings are sufficient pursuant to § 3583(d) to survive plain-error or abuse-ofdiscretion review of both conditions.8 See Evans, 727 F.3d at 

733–35; Ross, 475 F.3d at 875. 

8 We have encouraged judges to “consider the possibility of setting sunset dates for some of the more onerous terms.” Quinn, 698 F.3d at 652. 

Although we find no plain error in the imposition of the treatment conditions for the full term of Jurgens’ supervised release, on remand the 

sentencing judge may consider imposing sunset dates on the treatment

conditions. If treatment continues to be warranted beyond the sunset 

dates, the term may be extended. See Thompson, 777 F.3d at 375.

 
Nos. 14-1223, 14-2135 & 14-2482 43

On appeal, Jurgens takes particular exception to the condition that he “will submit to physiological testing, including polygraph testing, which may be part of a sex offender 

treatment program as directed by the U.S. Probation Office.”9 Jurgens contends that physiological testing includes 

plethysmograph testing,10 which he contends is a greater 

than necessary deprivation of his liberty interests. Plethysmograph testing is physically intrusive and controversial, 

but it “has been recognized by some psychologists and researchers as a useful technique in the treatment of sexual offenders,” United States v. Weber, 451 F.3d 552, 565 (9th Cir. 

2006), and “courts have upheld conditions requiring offenders to undergo [plethysmograph] testing under various legal 

challenges.” United States v. Rhodes, 552 F.3d 624, 626 (7th 

Cir. 2009). To the extent this condition might require Jurgens 

to submit to plethysmograph testing—which is not mentioned in the condition—it involves too many contingencies 

to make the issue ripe for review at this time. See id. at 628–

29 (holding that the defendant’s challenge to a similar condition was not ripe for review because it is “based on a number of contingencies,” including that the treatment program 

9 The condition as a whole reads: “You shall participate in a sex offender 

treatment program as deemed necessary by the U.S. Probation Office. 

You shall pay for such services, if financially able, as directed by the U.S. 

Probation Office. You will submit to physiological testing, including polygraph testing, which may be part of a sex offender treatment program 

as directed by the U.S. Probation Office. You shall pay for such services, 

if financially able, as directed by the U.S. Probation Office.”

10 Plethysmograph testing involves placing a device on a man’s penis in 

order to measure his sexual response to various visual and auditory 

stimuli. See United States v. Weber, 451 F.3d 552, 561–62 (9th Cir. 2006).

 
44 Nos. 14-1223, 14-2135 & 14-2482

may only require “polygragh testing alone, which is not unusual,” and/or “the development of science or the law may 

render the [plethysmograph] testing irrelevant or even illegal, or maybe the movement will be in a different direction 

altogether”). If Jurgens ultimately is ordered to undergo plethysmograph testing as part of a sex offender treatment program on supervised release, he may petition the district 

court to modify the condition if he then objects to it. See id. at 

629.

As for polygraph testing, which is mentioned in the condition (although as a contingency), Jurgens contends this 

possibility infringes on his Fifth Amendment right to be free 

from self-incrimination. Our earlier discussion related to 

Jurgens’ prior Fifth Amendment challenge applies with 

equal force here. A defendant on supervised release retains 

the privilege to invoke his Fifth Amendment rights. On remand, Jurgens may request that the sentencing judge include language indicating that this condition does not prevent him from invoking the privilege against selfincrimination, although we do not hold that such language 

is required. Jurgens also contends that the condition gives 

“the probation office 20 years of unlimited ability to test” 

Jurgens with a polygraph. However, we read this condition 

as delegating to probation the selection of the treatment provider; only the treatment provider is authorized to select the 

type(s) and amount of testing. We encourage the sentencing 

judge on remand to consider rewording the condition to 

make this point clear. Cf. Siegel, 753 F.3d at 713 (addressing 

issues with, and ambiguities in, a similarly worded condition).
Nos. 14-1223, 14-2135 & 14-2482 45

Jurgens also challenges the condition requiring him to 

participate in probation’s “Computer and Internet Monitoring Program.” A similar condition was proposed in the 

presentence report. See U.S.S.G. § 5D1.3(d)(7). The proposed 

condition required Jurgens to install, “on any computer” he 

used, filtering software that would “monitor/block access to 

sexually oriented websites.” Jurgens objected because he 

planned to use computers on his job and the term “sexually 

oriented” was vague and overbroad. The sentencing judge 

accommodated Jurgens’ objections by replacing the term 

“sexually oriented websites” with “websites that contain illegal child, or illegal pornography,” and adding a clarification that the condition applies only to “personal computers” 

and not to any computer Jurgens needs to access through his 

employment.11 The judge explained at sentencing that the 

11 The condition reads in full:

You shall participate with the U.S. Probation Office’s 

Computer and Internet Monitoring Program during 

your term of supervision. This shall apply to any personal computers that you have, not to any computers 

that you need to access through your employment. The 

monitoring program will start as soon as possible after 

your supervision term begins. You shall sign the rules of 

the Computer and Internet Monitoring Program and 

comply with the conditions of this program. During this 

time, you shall install filtering software on any computer 

you possess or use which will monitor and block access 

to any websites that contain illegal child, or illegal pornography. You shall allow the U.S. Probation Officer 

and Office unannounced access to any computer you 

possess or use, other than that you use through your 

employment, to verify that the filtering software is func-

 
46 Nos. 14-1223, 14-2135 & 14-2482

condition was necessary to help ensure compliance with the 

other conditions of supervised release. 

Jurgens contends that the judge’s findings were inadequate to support this condition. We disagree. Jurgens’ use of 

a computer facilitated his offense, and the sentencing judge 

reasonably found that the monitoring program will “ensure 

compliance” with the other conditions, most notably the 

condition prohibiting Jurgens from receiving, transmitting,

or viewing illegal pornography. The deterrent effect of filtering software—and unannounced checks to determine the 

software remains functional—is apparent. “[W]e try to take 

careful note of context and the practical realities of a sentencing hearing. District judges need not belabor the obvious. 

The judge need not be explicit where ‘anyone acquainted 

with the facts would have known without being told why 

the judge had not accepted the argument’ ....” United States 

v. Gary, 613 F.3d 706, 709 (7th Cir. 2010) (quoting United 

States v. Cunningham, 429 F.3d 673, 679 (7th Cir. 2005)). 

Moreover, we endorse the sentencing judge’s efforts to respond to the objections Jurgens made at sentencing. We find 

that the modified condition was adequately supported by 

the sentencing judge.

Jurgens also argues that this condition violates his Fourth 

Amendment rights because it permits the probation officer 

unlimited, unannounced access to Jurgens’ personal computer(s) “to verify that the [child pornography] filtering 

software is functional.” Jurgens characterizes this condition 

tional. You shall pay of [sic] the cost of this software, if 

financially able.

 
Nos. 14-1223, 14-2135 & 14-2482 47

as allowing “warrantless, suspicionless, nighttime searches 

of Mr. Jurgens’ home to occur for the next 20 years.” While 

the possibility that a probation officer may knock on 

Jurgens’ door at 3:00 a.m. seeking to verify that the filtering 

software is functional is troubling, cf. Thompson, 777 F.3d at 

380, this condition is narrower than the home-visit condition 

discussed earlier.12 Indeed, if Jurgens’ personal computer is 

a laptop computer, presumably he may comply with this 

condition by bringing the computer to the probation officer 

at Jurgens’ door or elsewhere, and the officer would not 

need to enter Jurgens’ residence. We find that this condition 

does not violate Jurgens’ Fourth Amendment rights.

This issue highlights the dissonance between defense 

counsel’s and government counsel’s respective views of 

probation officers. Defense counsel appears to view the typical probation officer as Inspector Javert,13 obsessively en12 Likewise, this condition is significantly narrower than the condition at 

issue in the primary case relied upon by Jurgens in his reply, United 

States v. Malenya, 736 F.3d 554 (D.C. Cir. 2013). In Malenya, the court vacated a condition which provided that the defendant “shall not possess 

or use a computer or have access to any on-line service without the prior 

approval of the United States Probation Office ... and [shall] allow installation of a computer and Internet-monitoring program.” Id. at 560. The 

court vacated this condition because “the record contains no evidence ... 

that Malenya indulged in adult or child pornography” and “[a] ban on 

computer and internet usage, qualified only by the possibility of probation office approval, is obviously a significant deprivation of liberty.” Id. 

at 560–61. Not only is the computer monitoring condition in this case 

significantly less restrictive than the condition at issue in Malenya, but 

the monitoring condition in this case is closely tailored to Jurgens’ offense, unlike in Malenya.

13 See Victor Hugo, Les Misérables (1862).

 
48 Nos. 14-1223, 14-2135 & 14-2482

gaged in a misguided and destructive pursuit of defendants. 

Government counsel appears to view the typical probation 

officer as Mr. Chips,14 a kindly educator (or rehabilitator) 

who disciplines only when absolutely necessary. This dissonance finds its root in a probation officer’s dual function: “to 

guide the [defendant] into constructive development” and to 

prevent “behavior that is deemed dangerous to the restoration of the individual into normal society.” Morrissey v. 

Brewer, 408 U.S. 471, 478 (1972). While the balance a particular probation officer strikes between supervision and enforcement may vary, we think it remains true that the ongoing supervisory relationship of a probation officer to a defendant “is not, or at least not entirely, adversarial.” Griffin v. 

Wisconsin, 483 U.S. 868, 879 (1987). It is inherent in this system that conditions allow probation officers a degree of discretion in performing their difficult job. Of course, we cannot 

allow conditions to be worded in such a way as to endow 

probation officers with “essentially unlimited discretion.” 

Thompson, 777 F.3d at 382. But at some point, we must “fairly 

presume [the defendant]’s probation officer will apply the 

conditions in a reasonable manner.” United States v. Smith, 

606 F.3d 1270, 1283 (10th Cir. 2010). And if a particular probation officer exercises his or her discretion in an unreasonable manner, this exercise will be subject to review by the 

district court. 

Finally, Jurgens argues that the provision in each treatment/monitoring condition requiring him to pay “if financially able” should “have stated that Mr. Jurgens’ inability to 

14 See James Hilton, Goodbye Mr. Chips (1934).

 
Nos. 14-1223, 14-2135 & 14-2482 49

pay could not be a basis for revocation.” We think it is apparent from each condition that Jurgens’ supervised release 

may not be revoked for not paying the costs of treatment or 

monitoring if he is not financially able to pay. Cf. Baker, 755 

F.3d at 529 (“A defendant may not be recommitted to prison 

‘for mere inability to pay’....” (quoting Siegel, 753 F.3d at 

714)). Indeed, we recently referred to the use of the phrase, 

“if financially able,” as a “best practice for district courts to 

follow” in crafting conditions of supervised release. Cary, 

775 F.3d at 928–29.

At Kappes’ sentencing, the judge imposed special conditions requiring Kappes to participate in sex-offender treatment and probation’s Computer and Internet Monitoring 

Program, and requiring him to pay for the treatment and filtering software “if financially able.” Kappes challenges the 

pay-if-able language in the treatment condition, contending

that there is no statutory authority for a court to require a 

defendant to pay for treatment programs.15 Kappes overlooks 18 U.S.C. § 3672, which authorizes a court to order repayment by the recipient of treatment “services, training, or 

guidance,” and 18 U.S.C. § 3583(d), which authorizes a court 

to impose “any other condition it considers appropriate.” See 

Cary, 775 F.3d at 928 (holding that a district court is empowered to impose payment conditions pursuant to § 3672 and § 

3585(d)). To the extent the sentencing judge failed to make 

adequate findings to support the payment portion of the 

15 Kappes also challenges the pay-if-able language in special condition 

one, which prohibits him from excessive use of alcohol and use of moodaltering substances and requires him to undergo substance-abuse treatment. We have already vacated this condition.

 
50 Nos. 14-1223, 14-2135 & 14-2482

challenged condition, we find this error to be harmless. It is 

self-evident that the pay-if-able language will incentivize defendants to succeed with their rehabilitative efforts, see United States v. Williams, 739 F.3d 1064, 1066–67 (7th Cir. 2014), 

and “reimburse [the Administrative Office of the U.S. Courts 

for] the appropriations obligated and disbursed in payment 

for such services, training, or guidance.” 18 U.S.C. § 3672. 

Finally, although not challenged by Kappes, we encourage 

Kappes’ sentencing judge on remand to consider modifying 

the language of the computer-monitoring condition in the 

same manner as was done by the sentencing judge in 

Jurgens’ case—i.e., in the absence of additional findings on 

remand, the filtering software should only block websites 

containing illegal pornography (e.g., child pornography), 

rather than all “sexually oriented websites.” Cf. Cary, 775 

F.3d at 926–27 (indicating that any internet ban “must be defined to some degree of precision”). 

c. No-Contact Condition

Both Kappes and Jurgens challenge a special condition 

prohibiting contact with minors. In Quinn, we singled out a 

term of supervised release prohibiting unapproved contact 

with minors—including the defendant’s minor child, whom 

defendant had never been accused of abusing—and stated 

that “[p]utting the parent-child relationship under governmental supervision for long periods ... requires strong justification.” 698 F.3d at 652. After Quinn, we have vacated similar no-contact conditions due to a lack of adequate findings. 

See Baker, 755 F.3d at 526–27; United States v. Poulin, 745 F.3d 

796, 802 (7th Cir. 2014); Goodwin, 717 F.3d at 524. 

In Kappes’ case, the judge adopted in toto the condition 

recommended in the presentence report banning Kappes 
Nos. 14-1223, 14-2135 & 14-2482 51

from contact with all minors except in the presence of an 

adult approved by probation, in the course of normal commercial business, or other cases of unintentional and incidental contact. During the sentencing hearing, the judge recited this condition without discussion. Were we to view this 

portion of the transcript in isolation, the judge’s findings 

would be inadequate to sustain such a condition, despite the 

fact that—unlike the defendant in Quinn—Kappes has no 

children and has not identified any extended family member 

with minor children. However, we review the judge’s comments at the entire sentencing hearing. Prior to listing the 

conditions, the judge discussed the “much more disturbing 

information here than just a desire to see young children 

have sex with adults.” The judge said that “a lengthy period 

of supervised release” is necessary because Kappes, while 

working as a furniture deliveryman, stole “over 30 female 

panties, many of which apparently belonged to children,” 

and kept the collection for 20 years. The judge told Kappes 

that the length of time he kept the collection was “concerning,” and “[m]ore disturbing” was Kappes’ surreptitious 

photographing of children playing in a neighboring outdoor 

pool for approximately ten years. The judge concluded that 

the conditions of supervised release were necessary because 

of “worry about any future crimes or possible acting out, 

stealing panties, pictures of young girls next door.” We think 

the sentencing judge’s explanation is sufficient to justify imposing upon Kappes an appropriately tailored no-contact condition. 

However, the no-contact condition actually imposed upon Kappes is somewhat overbroad. The condition prohibits 

non-incidental “contact” with males as well as females under 18, despite the fact that we are not aware of any evidence 
52 Nos. 14-1223, 14-2135 & 14-2482

that Kappes is bisexual. See Thompson, 777 F.3d at 376 (“A[n] 

... error was a condition of supervised release that Thompson not have ‘any contact with persons under the age of 

18....’ 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.”). 

Kappes contends that, “[a]lthough he has no children, if he 

did (or if an extended family member does), his fundamental 

right to familial association would be violated by a limitation 

on contact with minors.” Given that Kappes was sentenced 

to a 20-year term of imprisonment at the age of 47, we think 

that any violation of his rights by this condition is too contingent to be ripe for review at this time. See Rhodes, 552 F.3d 

at 628–29. After Kappes is released from custody, if he or a 

family member has minor children, he may petition the district court to modify this condition. See id. at 629; see also 18 

U.S.C. § 3583(e)(2).

In Jurgens’ case, the presentence report recommended a 

special condition identical to the one imposed in Kappes’ 

case. Prior to sentencing, the judge ordered a psychosexual 

evaluation, and the evaluator diagnosed Jurgens with pedophilia and recommended imposition of the same no-contact 

provision. Jurgens objected that this proposed condition infringed on his constitutional right to familial association because Jurgens has a nephew who is a minor. At sentencing, 

the judge accommodated this objection by revising the recommended condition to prohibit contact with “non-related” 

minors except in the presence of an adult approved by probation, in the course of normal commercial business, or other 

cases of unintentional and incidental contact. The judge said 

that the no-contact condition was “especially necessary in 

[Jurgens’] case because the target age of most of your child 
Nos. 14-1223, 14-2135 & 14-2482 53

pornography was ... seven- to eight-year-olds and, further 

... [Jurgens] made a statement that he ‘can’t do anything [to 

minors] when they are not here.’” The judge said that 

Jurgens’ statement was “troublesome enough, given the nature of this offense, that I think it’s an appropriate condition 

to impose in this case.” Although this is perhaps the minimum of what might be sufficient to justify a no-contact provision in a possession-only child-pornography case, we 

think the judge’s explanation is sufficient. 

Despite the judge’s modification of the condition in response to Jurgens’ objection, the no-contact provision actually imposed in Jurgens’ case is overbroad. The condition prohibits non-incidental “contact” with males as well as females 

under 18, despite the lack of evidence that Jurgens is bisexual. See Thompson, 777 F.3d at 376. Likewise, the judge’s 

statements at sentencing suggest that Jurgens is attracted to 

seven- and eight-year-olds, making a restriction on contact 

with 17-year-olds seem unsupported by the judge’s findings. 

Because this case must be remanded for other reasons, the 

sentencing judge should address the overbreadth of this 

condition on remand.

d. Search Condition

The final special condition imposed upon Jurgens requires him to “submit to the search of [his] person, automobile, and property under [his] control” when “there is reasonable suspicion to believe that [he is] in violation of a condition of supervised release,” subjects his computers and related devices to “periodic unannounced examinations,” and 

allows “retrieval and copying of all data ... to ensure compliance with this condition, and/or removal of such equipment 

for the purpose of conducting a more thorough examina-
54 Nos. 14-1223, 14-2135 & 14-2482

tion.”16 Jurgens concedes that because he failed to object to 

this condition—which was proposed in the presentence report—it now is subject to plain error review. Jurgens nonetheless contends that the condition must be vacated because 

the sentencing judge failed to support it with adequate findings, the condition infringes on his Fourth Amendment right 

to keep his property free from unreasonable searches and

seizures, and the condition is an excessive deprivation of his 

Fifth Amendment right to property.

The sentencing judge stated that this condition was being 

imposed “to ensure compliance with these conditions.” 

Combined with the judge’s other comments at sentencing 

which we have summarized above, we think this is sufficient 

to support this condition. And even if the judge did not say 

enough, this would not be the type of error which affects 

Jurgens’ substantial rights, see Olano, 507 U.S. at 735, because 

the consistency of this condition with the sentencing factors 

and the other conditions “is plain, given the nature of [the 

16 The condition states in full:

If there is reasonable suspicion to believe that you are in 

violation of a condition of supervised release, you shall 

submit to the search of your person, automobile, and 

property under your control by the U.S. Probation Office. You shall also allow the U.S. Probation Office to 

conduct periodic unannounced examinations of your 

computer equipment, Internet capable devices, similar 

electronic devices, related computer peripherals, which 

may include retrieval and copying of all data from your 

device to ensure compliance with this condition, and/or 

removal of such equipment for the purpose of conducting a more thorough inspection.

 
Nos. 14-1223, 14-2135 & 14-2482 55

defendant’s] crime,” see Siegel, 753 F.3d at 713. This condition 

clearly relates to the goals of rehabilitation, deterrence and 

protection of the public, and is reasonably related to the nature and circumstances of Jurgens’ computer-facilitated offense. Compare Goodwin, 717 F.3d at 523 (vacating a similar 

condition because there was no “indication in the record that 

Goodwin has ever used a computer to commit any crime”). 

We next turn to Jurgens’ challenge to the merits of the 

condition, which authorizes searches when “there is reasonable suspicion to believe that [Jurgens is] in violation of a 

condition of supervised release.” Jurgens highlights the 

standard condition requiring him to follow his probation officer’s instructions, and says when that standard condition is 

combined with the search condition, “the mind runneth over 

when imagining how many ways an unheeded instruction 

provides a springboard for searching Mr. Jurgens’s person, 

automobile and property.” Jurgens posits that, “[i]f he commits a traffic infraction,” a Javert-like probation officer may 

use the infraction to confiscate Jurgens’ computer pursuant 

to this condition, and “[m]aybe the deprivation is just for a 

day, but maybe that was the day that Mr. Jurgens was supposed to make a presentation for work and cannot do so because materials for the presentation are on the computer the 

government took.” Jurgens points to no case in which anything remotely similar has happened to a defendant on supervised release, despite the fact that this search condition is 

common. We do not find that Jurgens’ hypothetical conjecture is sufficient to establish plain error. Cf. United States v. 

Westerfield, 714 F.3d 480, 489 (7th Cir. 2013) (“This hypothetical conjecture is baseless, and certainly does not establish 

plain error.”). 
56 Nos. 14-1223, 14-2135 & 14-2482

In the context of probation, the Supreme Court has held 

that the Fourth Amendment balance of “the degree to which 

[a search of a probationer’s residence] intrudes upon an individual’s privacy and, ... the degree to which it is needed 

for the promotion of legitimate governmental interests,” requires “no more than reasonable suspicion to conduct a 

search of th[e] probationer’s house.” United States v. Knights, 

534 U.S. 112, 119, 121 (2001) (quotation omitted); cf. United 

States v. Montiero, 270 F.3d 465, 469, 473 (7th Cir. 2001) (upholding, pre-Knights, a suspicionless-search supervisedrelease condition because the condition was necessary to 

“curb the sort of criminal activity in which a defendant had a 

history of engaging,” but vacating the condition’s suspicionless seizure authorization as vague and overbroad, and remanding to the district court “to craft more precisely the seizure authority of the special condition”). Post-Knights, the 

First Circuit has upheld a supervised-release condition materially the same as the computer-search-and-removal condition challenged by Jurgens. See United States v. Stergios, 659 

F.3d 127, 131 n.6, 134 (1st Cir. 2011). The court noted that, “if 

the district court could not mandate compliance with the 

rules of the treatment program, the required participation 

would be ineffectual.” Id. at 134 (quotation and alteration

omitted); but see United States v. Lifshitz, 369 F.3d 173, 193 (2d 

Cir. 2004) (vacating, under de novo review, a similar condition on the basis that “[t]he scope of the computer monitoring condition as it stands may ... be overbroad,” and ordering “the district court to evaluate the privacy implications of 

the proposed computer monitoring techniques as well as 

their efficacy as compared with computer filtering”). 

Given the legal authority cited above, we cannot find that 

the district court plainly erred in imposing the search condi-
Nos. 14-1223, 14-2135 & 14-2482 57

tion upon Jurgens. See Olano, 507 U.S. at 734 (“At a minimum, court of appeals cannot correct [a plain] error ... unless the error is clear under current law.”). We do note that 

both the defense and the government assume that, as stated 

in the government’s brief, “[t]he removal provision requires 

Mr. Jurgens to release his computer for more thorough inspection by his probation officer only if there is reasonable 

suspicion that Mr. Jurgens has violated the terms of his release.” However, the language of the condition is not as clear 

as it could be on this point. On remand, the sentencing judge 

should consider rewording the condition to clarify that the 

“periodic unannounced examinations of [Jurgens’] computer 

equipment ... which may include ... removal of such 

equipment for the purpose of conducting a more thorough 

inspection” may only be done if the probation officer has 

reasonable suspicion to believe that Jurgens is in violation of 

a condition of supervised release. See 18 U.S.C. § 3583(d) (authorizing a supervised-release condition requiring a sex offender to submit to search “by any law enforcement or probation officer with reasonable suspicion concerning a violation 

of a condition of supervised release or unlawful conduct by

the person” (emphasis added)); U.S.S.G. § 5D1.3(d)(7)(C) 

(recommending the same special condition for sex offenders); cf. Farmer, 755 F.3d at 854 (vacating a search condition 

that required “no suspicion, reasonable or otherwise, to trigger a search”). The identical condition was imposed upon 

Kappes, and we similarly encourage Kappes’ sentencing 

judge to consider rewording the condition.

V. Pronounce All Conditions

The fourth sentencing principle that we address in the 

context of imposing conditions of supervised release is the 
58 Nos. 14-1223, 14-2135 & 14-2482

need to orally pronounce all conditions from the bench. 

“[W]hen there is a conflict between an oral and later written 

sentence, the oral judgment pronounced from the bench controls.” United States v. Johnson, 765 F.3d 702, 710–11 (7th Cir. 

2014). However, if “[t]he specifications in the written judgment clarify the oral pronouncement” and the written provisions “are not inconsistent with an unambiguous [oral] provision,” then the differing written provisions will not be vacated. Baker, 755 F.3d at 529 n.2. The parameters of this rule 

can be seen by comparing examples of how we have applied 

it. Compare Johnson, 765 F.3d at 711 (“[T]he district court unambiguously announced several specific conditions of supervised release at Johnson’s sentencing hearing and did not 

include any statement as to whether other standard conditions would apply.... [A]ny new conditions imposed in the 

later written judgment are inconsistent with the court’s oral 

order and must be vacated.”), and United States v. Alburay, 

415 F.3d 782, 788 (7th Cir. 2005) (“The written version contradicts the oral version in that the oral version does not order ‘immediate deportation’ in any shape or form.”), with 

Baker, 755 F.3d at 529 n.2 (“Any argument that the payment 

conditions should be vacated because the written judgment, 

explicitly stating the entity or official who can direct Baker to 

pay, is inconsistent with the oral pronouncement, which only says ‘as directed’ without specifying by whom, is unavailing.”), and United States v. Bonanno, 146 F.3d 502, 511–12 (7th 

Cir. 1998) (holding that when the district court orally imposed “all the standard conditions of supervised release 

adopted by this Court” but did not enumerate those conditions until the written order, the written order was merely a 

clarification of the vague oral pronouncement and the enumerated standard conditions would not be vacated). “We 
Nos. 14-1223, 14-2135 & 14-2482 59

review a claim of an inconsistency between the oral and 

written judgments de novo, comparing the sentencing transcript with the written judgment to determine whether an 

error occurred as a matter of law.” Johnson, 765 F.3d at 710. 

Kappes contends that the sentencing judge violated this 

rule three times, and requests that the allegedly inconsistent 

provisions in the written judgment be vacated. First, during 

the sentencing hearing, the judge orally stated that Kappes 

will have to submit to “psychological testing, including polygraph testing, which may be part of a sex offender treatment

program.” The written judgment states that Kappes will 

have to submit to “physiological testing, including polygraph 

testing, which may be part of a sex offender treatment program.” Given that, strictly speaking, polygraph testing is a 

physiological, rather than psychological, test, there was an 

ambiguity in the judge’s oral sentence. Accordingly, we may 

look to the written judgment to help determine the intended 

sentence. See Bonanno, 146 F.3d at 511. After looking to the 

written judgment, it is clear that the sentencing judge simply 

misspoke when he said “psychological testing,” and intended the condition to impose “physiological testing,” as stated 

in the judgment (as well as in the unobjected-to presentence 

report). Accordingly, this provision is not vacated for violating the rule that conditions must be orally pronounced.

Next, the sentencing judge orally required Kappes to “allow Probation to conduct periodic, unannounced examination of your computer, Internet capable devices, electronic 

devices, or related computer peripherals; and they may retrieve or copy all data from your devices to ensure compliance.” The written judgment adds the requirement that 

Kappes allow the “removal of such equipment for the pur-
60 Nos. 14-1223, 14-2135 & 14-2482

pose of conducting a more thorough inspection.” Here, the 

oral pronouncement was unambiguous. If “the oral version 

is unambiguous, there is no need to look beyond the oral 

version for any clarification from the written version. The 

written version is thus a nullity, not requiring further discussion.” Alburay, 415 F.3d at 788 (citation omitted). Therefore, the inconsistent provision in the written judgment, allowing the removal of Kappes’ computer equipment, is vacated. However, this may be a hollow victory for Kappes 

since we are remanding for resentencing on other grounds. 

If, after hearing from the parties and otherwise complying 

with the appropriate sentencing procedures, the judge wishes to include the computer-removal provision in special 

condition number six, he may do so during resentencing.

Kappes’ third challenge involves the oral omission of the 

written judgment’s ban on “paraphernalia related to any 

controlled substance or mood altering substance,” which 

appears in special condition number one. As we have already vacated this special condition for other reasons (due to 

its ban on “excessive” use of alcohol and possession and use 

of any “mood altering substance”), we decline to consider 

this additional challenge to the condition. 

VI. Mitigation Argument

Apart from his challenges to the conditions of supervised 

release, Crisp contends that the sentencing judge erred by 

failing to consider or comment upon one of his principal arguments in mitigation, namely, that he cooperated with law 

enforcement despite the lack of a government motion for a 

reduced sentence. See United States v. Leiskunas, 656 F.3d 732, 

737 (7th Cir. 2011) (“A district court may consider a defendant’s cooperation with the government as a basis for a re-
Nos. 14-1223, 14-2135 & 14-2482 61

duced sentence, even if the government has not made a

[U.S.S.G.] § 5K1.1 or [Federal] Rule [of Criminal Procedure]

35 motion.”).

We review de novo whether a judge followed proper procedures in sentencing, including whether the judge adequately explained his or her chosen sentence. United States v. 

Davis, 764 F.3d 690, 694 (7th Cir. 2014). “A sentencing judge 

must address a defendant’s principal arguments in mitigation when those arguments have recognized legal merit.” Id.; 

see Cunningham, 429 F.3d at 679.17 The judge, however, “need 

17 “[S]ince 2005 we have decided nearly 200 cases presenting questions 

under the Cunningham duty to explain the reasons for rejecting principal 

arguments in mitigation.” United States v. Donelli, 747 F.3d 936, 941 (7th 

Cir. 2014). In an effort to address this recurring issue, we offered a suggestion to sentencing judges in United States v. Garcia-Segura, 717 F.3d 566 

(7th Cir.), cert. denied, 134 S. Ct. 667 (2013), which we repeat here:

In order to ensure that defendants feel that they have 

had such arguments in mitigation addressed by the 

court and to aid appellate review, after imposing sentence but before advising the defendant of his right to 

appeal, we encourage sentencing courts to inquire of defense counsel whether they are satisfied that the court 

has addressed their main arguments in mitigation. If the 

response is in the affirmative, a later challenge for failure 

to address a principal mitigation argument under the 

reasoning of Cunningham would be considered waived. 

If not, the trial court would have the opportunity to clarify whether it determined that the argument was so 

weak as not to merit discussion, lacked a factual basis, or 

has rejected the argument and provide a reason why. An 

affirmative answer, however, would not waive an argument as to the merits or reasonableness of the court’s 

treatment of the issue.

 
62 Nos. 14-1223, 14-2135 & 14-2482

not address arguments that have no apparent merit, and 

need not spend time addressing an argument if ‘anyone acquainted with the facts would have known without being 

told why the judge had not accepted the argument.’” United 

States v. Castaldi, 743 F.3d 589, 595 (7th Cir. 2014) (quoting 

Cunningham, 429 F.3d at 679). “The explanation need not be 

exhaustive, but it must be sufficient to satisfy this court that 

the sentencing judge has given meaningful consideration to 

the section 3553(a) factors and the parties’ arguments in determining how long the defendant’s sentence should be. This 

will entail some discussion of any significant argument the 

defendant has made with respect to his characteristics that 

might bear on the length of the sentence.” United States v. 

Schmitz, 717 F.3d 536, 541 (7th Cir. 2013) (citations omitted). 

“The amount of explanation needed in any particular case 

depends on the circumstances, and less explanation is typically needed when a district court sentences within an advisory guidelines range.” United States v. Curby, 595 F.3d 794, 

797 (7th Cir. 2010) (quotation and citations omitted).

At sentencing, defense counsel said there was no motion 

to deviate from career offender status because “there was a 

cooperation agreement that was signed,” and “a proffer was 

conducted,” and “there may have been a 5K1.1 motion if Mr. 

Crisp had entered into a cooperation plea agreement, which 

he elected not to do, to preserve his rights to appeal and the 

other things that would have been waived under the cooperation plea agreement.” The judge responded: “So what 

you’re saying to me is: There may have been an attempt at 

Id. at 569 (quotation and citation omitted).

 
Nos. 14-1223, 14-2135 & 14-2482 63

cooperation, or he may actually have taken the first step towards it. But, in the end, no cooperation agreement was 

signed and incorporated into a plea agreement [and] we 

ended up with an open plea?” Defense counsel said the 

judge was “correct” and explained, “I would say that we 

went all the way through the entire procedure up to the 

point where he would have entered into a cooperation plea 

agreement, a written agreement, which was not actually performed.” The judge then outlined the facts of the case and 

commented: “So while there isn’t a cooperation agreement 

here, there certainly is an exceptional early acceptance of responsibility by his being Mirandized, waiving his constitutional rights, telling [agents], ‘Yes, you got me, and this is 

what I’ve been doing.’ So no obstruction of justice, resisting 

arrest, a cooperation in the execution of the search warrant,

and admissions took place immediately.”

Later in the hearing, defense counsel made several mitigating arguments, including Crisp’s family history, his drug 

addiction, his status as a “a neighborhood level dealer” rather than a “drug kingpin,” the lack of weapons in his criminal history, his effort to support his daughter, his conduct 

compared to that of most career offenders, and his sentencing range had he not been a career offender. Defense counsel 

then argued: “[H]e cooperated right away. The second he 

was arrested he said, ‘You got me. I admit it. I waive my Miranda. I confess.’ He was pled out within three months after 

the indictment came down. And ... between the indictment 

and the actual change of plea, he did cooperate. I sat in the 

Ford County Jail basement for three and a half hours with 

agents while he regaled them with all the information he 

could possibly give them.” Defense counsel said that, although the Government did not make a substantial assistance 
64 Nos. 14-1223, 14-2135 & 14-2482

motion pursuant to U.S.S.G. § 5K1.1, “the Court can still 

consider the timeliness of the cooperation, the fact that he 

did render a proffer that was lengthy, that even though the 

government doesn’t have to mention it because he didn’t 

comply with the rest of that cooperation agreement by entering into that binding plea, he still tried his best; and he did 

accept responsibility in a very, very quick manner.”

The judge then discussed Crisp’s lengthy criminal history 

(35 arrests and 23 convictions, including four drug felonies), 

and said that a sentence of the mandatory minimum of 10

years (as suggested by defense counsel) “would depreciate 

the seriousness of his history of crime.” The judge said that 

he would sentence Crisp below the guidelines imprisonment 

range (262 to 327 months), because the judge would “take 

into consideration the fact that maybe he has rehabilitative 

potential by his allocution today; and by the time he was arrested, he gave it up quickly. He admitted it. So I think the 

exceptional acceptance of responsibility here immediately 

shows that there is an opportunity of hope for rehabilitation.... So how far do I depart from the career offender 

guidelines? I will depart 22 months to 240 months.”

Given the judge’s below-guidelines sentence, and 

“[p]aying close attention to the context and practical realities,” Castaldi, 743 F.3d at 595–96, we find that the judge did 

not err by failing to mention Crisp’s proffer to law enforcement agents when the judge was discussing the § 3553(a)

factors. During sentencing, each time defense counsel raised 

the subject of cooperation, counsel mentioned it in conjunction with Crisp’s quick acceptance of responsibility. The district court explicitly considered and credited Crisp’s “exceptional acceptance of responsibility.” Although the judge did 
Nos. 14-1223, 14-2135 & 14-2482 65

not go on to discuss Crisp’s proffer specifically, the judge 

considered the mitigation argument in the same context as it 

was argued by counsel—acceptance of responsibility. And 

the judge’s earlier discussion with counsel shows that the 

judge recognized the proffer and understood it to be “the 

first step” toward a cooperation plea agreement. In this circumstance, we are satisfied that the judge, “even if implicitly 

and imprecisely,” considered Crisp’s principal arguments in 

mitigation. United States v. Spiller, 732 F.3d 767, 769 (7th Cir. 

2013) (“[A]s long as the sentencing court considers the arguments made in mitigation, even if implicitly and imprecisely, the sentence imposed will be found reasonable.” 

(quotation omitted)); see also United States v. Poetz, 582 F.3d 

835, 839 (7th Cir. 2009) (“[I]t is apparent from this record that 

the judge fully understood [the defendant’s] argument on 

this point and implicitly considered ... it in imposing a lenient, below-guidelines term of imprisonment.”).

Moreover, defense counsel did not give the judge any 

meaningful specifics about Crisp’s proffer—such as whether 

Crisp identified suppliers, customers, the location of contraband, or any other specifics about his drug deals. Even defense counsel refrained from describing the single session 

with law enforcement agents as “substantial assistance,” and 

she never indicated that Crisp’s “regaling” the agents with 

information prompted, advanced, or assisted any investigation or prosecution. Given our conclusion that the judge adequately considered Crisp’s arguments, we need not determine whether this argument was “so weak as not to merit 

discussion.” Cunningham, 429 F.3d at 679. It is enough to say 

that a weaker argument, lacking specific factual support, 

does not merit as much discussion as a stronger one. See Davis, 764 F.3d at 694 (“[T]he amount of explanation required 
66 Nos. 14-1223, 14-2135 & 14-2482

from the district court varies with the circumstances. A brief 

explanation can certainly suffice.” (quotation and citation 

omitted)). 

VII. Relief

Our final order of business is deciding upon the relief to 

issue in each case. In prior cases in which we found error in 

the supervised release portion of the sentence, but no error 

in the custodial portion, we have sometimes remanded for 

resentencing of the supervised release issue only, and sometimes simply remanded “for resentencing consistent with 

this opinion.”18 Recently, we remanded for an entire resen18 Compare Siegel, 753 F.3d at 717 (“So the prison sentences in both our 

cases stand, but the cases must be remanded for reconsideration of the 

conditions of supervised release that we have determined to be inappropriate, inadequately defined, or imposed without the sentencing judge’s 

having justified them by reference to the sentencing factors in 18 U.S.C. 

§ 3553(a).”), and Goodwin, 717 F.3d at 526 (“[W]e affirm Goodwin’s conviction, vacate the supervised release portion of his sentence, and remand to the district court for resentencing consistent with this opinion. 

The resentencing shall be limited to a reassessment of the length of 

Goodwin’s supervised release and any special conditions imposed during this period.”), and Quinn, 698 F.3d at 653 (“The term of supervised 

release is vacated, and the case is remanded for resentencing on that issue only.”), with United States v. Sewell, --- F.3d ----, No. 14-1384, 2015 WL 

1087750, at *12 (7th Cir. Mar. 13, 2015) (“We vacate ... each of Sewell’s 

conditions of supervised release. We vacate each condition because reconsideration of some conditions may impact the imposition of others. 

The sentence is affirmed in every other respect. The case is remanded to 

the district court for proceedings consistent with this opinion.”), and 

Baker, 755 F.3d at 529 (“We vacate Baker’s supervised release term, special conditions 1 and 4, and the payment provision in conditions 1, 3, and 

8; and remand for resentencing consistent with this opinion. We affirm 

Baker’s prison term and all of the other terms in the special conditions 

 
Nos. 14-1223, 14-2135 & 14-2482 67

tencing “because reconsideration of those [vacated] conditions may conceivably induce one or more of the judges to 

alter the prison sentence that he imposed.” Thompson, 777 

F.3d at 382. 

We hesitate to require a complete resentencing in the cases before us, especially in Crisp’s case, as only a small number of his conditions have been affected by this opinion. But 

because the custodial and supervised release portions of a 

sentence serve somewhat, though not entirely, overlapping 

purposes, there might properly be an interplay between 

prison time and the term and conditions of supervised release.19 See Albertson, 645 F.3d at 198. If certain supervised 

release conditions are vacated, the balance struck by the sentencing judge might be disrupted to a degree where the 

judge would wish to alter the prison term and/or other conditions to ensure that the purposes of deterrence, rehabilitation, and protecting the public are appropriately furthered

by the overall sentence. Accordingly, as we did in Thompson, 

we vacate the entire sentences and remand for a complete 

resentencing.

After this long march through these defendants’ challenges and our recent supervised-release jurisprudence, a 

sentencing judge might be frustrated with the task of naviimposed.”), and Shannon, 743 F.3d at 503 (“We vacate Special Condition 

No. 10 of Shannon’s supervised release and remand for further proceedings consistent with this opinion.”).

19 While an interplay may be proper, the prison term and supervised 

release term should not be treated as interchangeable. See Johnson, 529 

U.S. at 60.

 
68 Nos. 14-1223, 14-2135 & 14-2482

gating the maze of rules and principles that we—

interpreting the strictures of Congress—have outlined. A 

sentencing judge might be tempted to conclude that the imposition of discretionary conditions of supervised release is

more trouble than it is worth. And perhaps in certain cases,

only a small number of well-tailored discretionary conditions may be all that is necessary to accomplish the purposes 

of supervised release. A comparatively small number of 

conditions might also make compliance easier on defendants 

and supervision easier on understaffed probation departments. But no matter the number of conditions, so long as 

they are appropriately tailored, adequately justified, and 

orally pronounced after proper notice, they will be upheld. 

Whether the system of supervised release is worth its human 

and financial costs is a matter beyond our mandate and 

competence. We trust that the supervised-release system 

represents a worthwhile method of rehabilitating defendants, deterring future crimes and protecting the public.

In all three cases, the judgments are REVERSED, and the 

cases are REMANDED for resentencing.