UNITED STATES COURT OF APPEALS 

FOR THE TENTH CIRCUIT 

_________________________________ 

UNITED STATES OF AMERICA, 

 Plaintiff - Appellee, 

v. 

BRIAN JOSEPH NIELSEN, 

 Defendant - Appellant. 

No. 21-8087 

(D.C. No. 1:10-CR-00193-SWS-1) 

(D. Wyo.) 

_________________________________ 

ORDER AND JUDGMENT*

_________________________________ 

Before HARTZ, BACHARACH, and EID, Circuit Judges. 

_________________________________ 

Defendant Brian Joseph Nielsen pleaded guilty in 2010 to one count of 

interstate shipment of child pornography. One of the conditions of his supervised 

release prohibited him from accessing “pornographic, sexually oriented, or sexually 

stimulating” materials. R., Vol. 1 at 20. After this court in United States v. Koch, 

978 F.3d 719, 722–23 n.1 (10th Cir. 2020), raised concerns about the potential 

overbreadth of this language, the district court issued a general order in November 

2020 stating that it amended the conditions of release of all defendants throughout 

the district who had the same supervised-release condition as Defendant. The only 

* This order and judgment is not binding precedent, except under the doctrines 

of law of the case, res judicata, and collateral estoppel. It may be cited, however, for 

its persuasive value consistent with Fed. R. App. P. 32.1 and 10th Cir. R. 32.1. 

FILED 

United States Court of Appeals 

Tenth Circuit 

August 10, 2022

Christopher M. Wolpert 

Clerk of Court

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 1
2 

change relevant to this case is that the new language narrowed the condition to 

encompass only depictions of sexually explicit material, as defined by 18 U.S.C. 

§ 2256(2)(A).1

 

Defendant’s supervised release was revoked in November 2021 after the 

district court found that he had committed four violations of the conditions of his 

supervised release. Two of his alleged violations were of the modified sexualmaterial condition. On appeal from the district court’s revocation order, he argues 

that those violations should have been dismissed because the court failed to make 

certain necessary findings before modifying his sexual-material condition in the 

general order, rendering the condition unlawful. Exercising jurisdiction under 

28 U.S.C. § 1291, we affirm. A defendant cannot challenge a revocation of 

supervised release on the ground that a condition of supervised release was not 

supported by adequate findings at the time it was imposed. 

I. BACKGROUND

In 2010 Defendant was indicted in the United States District Court for the 

District of Wyoming on three counts of interstate shipment of child pornography, in 

violation of 18 U.S.C. § 2252A(a)(1) and (b)(1), and one count of possession of child 

pornography, in violation of 18 U.S.C. § 2252A(a)(5)(B) and (b)(2). The alleged 

1 The revised condition also prohibited accessing child pornography, as 

defined in 18 U.S.C. § 2256(8), and material containing the obscene visual 

representation of the sexual abuse of children, as defined in 18 U.S.C. § 1466A. But 

these provisions are not at issue on appeal.

 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 2
3 

conduct was that on three separate occasions he sent images and videos of child 

pornography to an undercover police officer from New Hampshire (posing online as 

an 18-year-old male from Massachusetts) who was investigating child abuse and 

online exploitation of children. When the officer received the emails, he captured the 

sender’s IP address and was able to determine that it was assigned to Brian Nielsen 

of Mills, Wyoming. Law-enforcement officers in Wyoming obtained a warrant to 

search Defendant’s residence in Mills. They seized Defendant’s computer and three 

USB flash drives, which contained hundreds of videos and thousands of images, 

including photographs of an adolescent boy who appeared to be an inmate at the 

detention facility where Defendant had worked. During questioning at the police 

department, Defendant admitted to sending and possessing child pornography and 

said that he had been working as an activities director for the Boys and Girls Club of 

America for the past year. 

Defendant reached an agreement to plead guilty to one count of interstate 

shipment in exchange for dismissal of the other counts. The district court2

 sentenced 

Defendant to 135 months’ imprisonment and a life term of supervised release, noting 

the “chilling” nature of the crimes perpetrated on the victims depicted in the images. 

R., Vol. 3 at 63. One of the conditions of supervised release prohibited Defendant 

from possessing any “pornographic, sexually oriented, or sexually stimulating” 

2

 Then-Chief Judge William F. Downes was assigned to Defendant’s case at 

the time of sentencing. He retired from judicial service on July 24, 2011. On 

February 4, 2020, the case was reassigned to Chief Judge Scott W. Skavdahl. 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 3
4 

material. R., Vol. 1 at 20.3

 Defense counsel did not object to either the condition or 

the adequacy of the district court’s justification for it. Defendant did not appeal. 

In January 2020, one month after Defendant was released on supervision, a 

probation officer filed a Petition for Warrant or Summons for Offender Under 

Supervision alleging that Defendant committed four violations of his conditions of 

supervised release, including one violation of his sexual-material condition. At the 

hearing on the charges the government agreed to dismiss Defendant’s alleged 

violation of his sexual-material condition and he admitted the other violations. He 

was sentenced to six months’ imprisonment and 15 years of supervised release. The 

district court also ordered that Defendant “comply with all conditions of supervision 

previously imposed.” Id. at 31. 

In October 2020 this court decided Koch, 978 F.3d 719, in which we held that 

a district court plainly erred by imposing at sentencing a special condition of 

supervised release limiting access to “sexual materials that fall within the ambit of 

3

 The condition provided: 

The defendant shall not possess, send or receive any pornographic, 

sexually oriented, or sexually stimulating visual, auditory, telephonic or 

electronic signs, signals or sounds from any source, unless part of a 

treatment regimen. He shall not visit bulletin boards, chat rooms or other 

Internet sites where any pornographic, sexually oriented or sexually 

stimulating images or messages are discussed. He shall not send or receive 

e-mail or other documents discussing any pornographic, sexually oriented, 

or sexually stimulating images or messages. 

R., Vol. 1 at 20. 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 4
5 

the First Amendment” without first finding that the condition was supported by 

compelling and particularized justifications. Id. at 729; see id. at 724–28. The 

condition at issue in Koch (which also originated in the District of Wyoming) was 

virtually identical to Defendant’s sexual-material condition. Although the challenge 

in Koch was directed at the adequacy of the procedures employed by the district court 

in imposing the condition—and not at “any substantive aspects of the condition,” id. 

at 722 n.1—this court noted the “exceedingly broad nature” of the condition in 

rejecting the government’s implied request to view the condition as “a restriction on 

pornography alone,” id. at 722–23 n.1.

The United States District Court for the District of Wyoming responded 

promptly to our decision in Koch. On November 3, 2020, Chief Judge Scott W. 

Skavdahl sua sponte issued a “General Order Amending Sexual Material Prohibition 

Special Condition of Supervised Release,” which sought to address “concerns 

regarding the breadth of material potentially encompassed by the [Koch] special 

condition.” General Order 2020-13 at 1 (the General Order).4

 The order purported to 

“amend[] all Special Conditions of Supervised Release” that were identical to 

Defendant’s sexual-material condition to read as follows: 

The defendant shall not access, possess, send or receive any material 

that depicts sexually explicit conduct as defined in 18 U.S.C. § 2256(2)(A) 

in any format, including but not limited to images, books, writings, 

drawings, video games, or visual depiction of such conduct as defined in 

4

 General Order 2020-13 is publicly available on the district court’s website at 

https://www.wyd.uscourts.gov/sites/wyd/files/General%20Order%202020-13.pdf 

(last accessed July 11, 2022). 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 5
6 

18 U.S.C. § 2256(5); any material constituting or containing child 

pornography as defined in 18 U.S.C. § 2256(8), or any material constituting 

or containing the obscene visual representation of the sexual abuse of 

children as defined in 18 U.S.C. § 1466A. The defendant shall not visit 

bulletin boards, chat rooms, or other Internet sites where any material 

referenced above is discussed. 

Id. at 1–2. The General Order was not entered on Defendant’s docket, but it directed 

the probation office to “advise all Defendants to whom this amendment applies or 

will apply upon being place[d] on Supervised Release.” Id. at 2. Defendant does not 

contend that he lacked notice of the General Order.

In June 2021 a probation officer reported that Defendant “accessed 

pornography in March 2021” and then “accessed pornographic, sexually oriented and 

sexually stimulating material through a variety of applications between May 1, 2021, 

[and] May 31, 2021.” R., Vol. 1 at 33. Defendant consented to a modification of his 

supervised-release conditions that prohibited him from accessing the internet on any 

device for 90 days. He acknowledged in his consent form that he would be required 

to “abide by all the conditions previously imposed during the period of Supervised 

Release.” Id. at 34. The record does not reflect any mention of the General Order. 

In August 2021 the present proceedings to revoke Defendant’s term of 

supervised release were initiated. A probation officer reported that Defendant 

committed six violations of his supervised-release conditions, including several 

violations of the sexual-material condition as it appears modified in the General 

Order. As relevant here, Violation 1 charged that Defendant “view[ed] movies 

depicting sexual acts that showed full adult male nudity, masturbation, and sex.” Id.

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 6
7 

at 40. Violation 5 charged that Defendant was in possession of a diary containing a 

handwritten story that described a dream of a sexually explicit interaction between 

him and another adult man. And Violation 6 stemmed from Defendant’s admission 

that he viewed adult pornography on his cell phone. 

The initial revocation hearing was held on October 15, 2021. At the beginning 

of the hearing, defense counsel informed the court that the government had agreed to 

dismiss Defendant’s violations of his sexual-material condition in exchange for his 

admitting two other violations. As the district court questioned Defendant about the 

factual basis for one violation—contact with a minor outside the presence of an 

approved adult—Defendant denied the allegation that he was alone with the minor 

and would admit only that he made contact in the presence of an unapproved adult. 

The district court decided to continue the revocation hearing, stating, “[G]iven the 

nature of the allegations in this matter and given the circumstances and the history of 

this Defendant, I am not willing to accept a dismissal of the other charges and the 

violations[.]” R., Vol. 3 at 89. 

On October 27, before the next hearing, the government and Defendant filed a 

joint motion to dismiss the three charges of violations of the sexual-material 

condition (Violations 1, 5, and 6). The basis for the motion was that “there [were] no 

particularized findings justifying the imposition of the underlying sexual materials 

special condition on [Defendant]”—referring to the condition as modified by the 

General Order. R., Vol. 1 at 43. The parties stated, “Based on Koch and the 

availability of an as-applied challenge to the sexual materials special condition, the 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 7
8 

parties believe that this court must make the findings required by Koch before it 

enforces the sexual materials special condition against [Defendant].” Id. at 46. 

A second revocation hearing was held on November 2. Defense counsel 

reiterated his Koch-based argument that it was unlawful to modify the sexualmaterial condition without individualized findings. He also argued that the General 

Order unlawfully modified the condition without a hearing. At issue was Federal 

Rule of Criminal Procedure 32.1(c), which provides that “the court must hold a 

hearing” before modifying conditions of supervised release, Fed. R. Crim. P. 

32.1(c)(1), unless, as relevant here, “(B) the relief sought is favorable to the person 

and does not extend the term of probation or of supervised release; and (C) an 

attorney for the government has received notice of the relief sought, has had a 

reasonable opportunity to object, and has not done so,” id. 32.1(c)(2). Defendant 

argued that this exception to the hearing requirement was inapplicable because 

(1) “no relief was sought” and (2) “this was not a modification that was favorable to 

[Defendant] as it continued to curtail constitutionally protected materials that he has 

a right to and not be limited by this Court without specific findings supporting such 

curtailing of his fundamental rights.” R., Vol. 3 at 105. Finally, defense counsel 

argued that the modified condition was unlawful as applied to the conduct underlying 

two of Defendant’s violations: 

[I]f that modified condition is applied [to Violation Number 1], it’s 

improper because the definition of “sexually explicit” would preclude 

[Defendant] from accessing movies that have artistic value that the 

average person, applying a contemporary community standard, would 

not find that it appeals to a prurient interest and that nothing in the 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 8
9 

movies that he was viewing that are the basis for Violation Number 1—

there’s nothing in them that is patently offensive. And in fact, when 

taken on the whole, they have serious artistic value. 

So as applied, . . . we’d ask the Court to dismiss Violation 1 on 

that basis . . . ; and we’d also ask the Court to dismiss Number 5 based 

on the fact that it is—keeping a diary is a protected First Amendment 

activity and that this—application of any modified condition like this 

would go well beyond the scope of what would be reasonable or 

necessary in regards to the sentencing factors. 

Id. at 106–07. 

The district court denied the motion to dismiss Violations 1 and 6. With 

respect to the Koch-based challenge, the court found that “additional information and 

findings were not required to preclude the scope of information and materials that 

were limited by the special condition.” Id. at 112. The court also rejected the notion 

that a hearing was required under Rule 32.1(c) before modifying the sexual-material 

condition through the General Order, ruling that Defendant received a favorable 

modification that “narrow[ed] the restriction.” Id. at 109. This ruling is not 

challenged on appeal.5

 With respect to the as-applied challenges, the district court 

dismissed Violation 5 concerning the diary entry as it presented a “colorable issue” 

but let the remaining violations go forward. Id. at 112. 

Two of Defendant’s probation officers testified at the November 2 hearing. 

Officer Aundrea Hines supervised Defendant from the beginning of his most recent 

5

 Nowhere in Defendant’s briefs does he argue that a hearing was required 

under Rule 32.1(c). He characterizes the original sexual-material condition as 

“stricter” than the modified condition. Aplt. Reply Br. at 6. 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 9
10 

term of supervised release until June 2021. According to Officer Hines, Defendant 

reported that “if he starts viewing pornography, it can oftentimes lead him down to 

viewing child pornography, specifically involving, usually, young boys.” Id. at 173. 

Officer Shelby Heatherly, who supervised Defendant from June until August 2021, 

similarly recalled that Defendant “talked about the consequences of continuing to 

look at porn or sexually oriented material, which included his stance that it was a 

progression, and it got worse the more he kind of fed into his addiction.” Id. at 133–

34.

At a final revocation hearing on November 19, the district court found that 

Defendant had committed Violations 1 and 6 of the modified sexual-material 

condition (in addition to the two other violations Defendant admitted). The court 

prefaced its findings with a discussion of Defendant’s history and characteristics, 

including (i) the conduct underlying his 2011 sentence; (ii) a clinical interview from 

June 2012 in which “Defendant described . . . that, quote, I got on my computer, 

looked at legal porn and then child porn. I sought it out, and it was not accidental,” 

id. at 221; and (iii) the testimony of the probation officers from the November 2 

hearing. The court reiterated its rejection of Defendant’s Koch argument, adding that 

“at least since revocation in February of 2020,” the record in this case “supported 

imposing the [sexual-material] Special Condition.” Id. at 227. Also, the district court 

rejected Defendant’s as-applied challenge to Violation 1, noting the graphic nature of 

the material accessed by Defendant. 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 10
11 

The district court imposed a 14-month sentence, followed by 15 years of 

supervised release. It commented that a sentence of 12 months and one day would be 

appropriate if it erred with respect to the two violations of the sexual-material 

condition. Defendant filed a notice of appeal of the revocation order that same day. 

II. ANALYSIS 

Defendant’s sole argument on appeal is that the two remaining violations of 

his sexual-material condition—Violations 1 and 6—“should have been dismissed 

because the district court failed to make particularized findings, at the time it 

imposed the applicable special condition, as to whether the intrusion on [his] 

fundamental First Amendment right was justified by compelling circumstances.” 

Aplt. Br. at 1–2. As we understand his point, he is complaining that the district court 

purported to modify his sexual-material condition by the General Order, and that the 

modification was procedurally inadequate. 

Defendant’s argument relies primarily on our recent decisions in Koch and 

United States v. Englehart, 22 F.4th 1197 (10th Cir. 2022). But there is a dispositive 

difference between those cases and the case at hand. In Koch the defendant directly 

appealed from the district court’s imposition at sentencing of a sexual-material 

condition. See 978 F.3d at 722–23. In Englehart the government petitioned to modify 

the conditions of a defendant who was already on supervised release and had 

committed several violations; the defendant directly appealed from the district court’s 

order modifying his sexual-material condition and imposing new burdensome 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 11
12 

conditions. See 22 F.4th at 1201–02. In this case, by contrast, Defendant appeals 

from an order revoking his supervised release. 

This distinction controls the outcome. As we declared in United States v. 

LeCompte, 800 F.3d 1209, 1214 n.6 (10th Cir. 2015), “Courts have consistently said 

that a defendant cannot challenge the condition [of supervised release] on its face at a 

revocation hearing.” Accord United States v. Helton, 612 F. App’x 906, 909 

(10th Cir. 2015) (“We are in alignment with other circuits in holding that a 

supervisee cannot challenge a condition itself when responding to a petition to revoke 

supervised release.”). The typical way to challenge an improper condition of 

supervised release is by an appeal. See United States v. Wayne, 591 F.3d 1326, 1334 

(10th Cir. 2010) (The supervisee “should have challenged the legal and factual basis 

of the initial supervised release condition on direct appeal from the sentencing 

court’s judgment.”); United States v. Preacely, 702 F.3d 373, 376 (7th Cir. 2012) 

(“The primary problem with [the defendant’s] argument is that he raises it too late. 

The time for [him] to challenge the condition was at sentencing or on direct appeal, 

not at his revocation hearing.”).6

 

6

 We do not foreclose the possibility of seeking relief through a collateral 

attack under 28 U.S.C. § 2255, or by a motion to modify conditions under 18 U.S.C. 

§ 3583(e)(2), cf. United States v. Begay, 631 F.3d 1168, 1169–71 (10th Cir. 2011). 

We note that this court has yet to squarely rule on the proper scope of a § 3583(e)(2) 

motion in a precedential opinion. But cf. United States v. Grigsby, 737 F. App’x 375, 

378 & n.5 (10th Cir. 2018) (citing United States v. Lussier, 104 F.3d 32, 35 (2d Cir. 

1997), for the proposition that the “legality of condition[s] of supervised release may 

only be challenged on direct appeal or as collateral attack under § 2255”). 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 12
13 

The rule barring a challenge to a condition of release at the revocation hearing 

is a specific application of a more general proposition that court orders are to be 

obeyed. “The orderly and expeditious administration of justice by the courts requires 

that an order issued by a court with jurisdiction over the subject matter and person 

must be obeyed by the parties until it is reversed by orderly and proper proceedings.”

Maness v. Meyers, 419 U.S. 449, 459 (1975) (internal quotation marks omitted). It 

follows from this rule that even if a condition of supervised release is appealed, it 

must be obeyed while appeal is pending unless a stay is granted. See id. at 458 (“If a 

person to whom a court directs an order believes that order is incorrect the remedy is 

to appeal, but, absent a stay, he must comply promptly with the order pending 

appeal.”). It is important to note, however, that the supervisee may, of course, still 

dispute the factual basis for an asserted violation of his condition. And the supervisee 

may raise at the revocation hearing an as-applied claim that the condition cannot 

properly be applied to the particular circumstances of the alleged violation. See 

LeCompte, 800 F.3d at 1213–14. 

The problem for Defendant is that he is not making an as-applied challenge to 

his condition of supervised release and the condition of supervised release 

purportedly imposed by the General Order had not been set aside or stayed at the 

time he violated it. He claims that he has timely appealed from the General Order 

because it was never entered on the docket in his case. See United States v. Mendoza, 

698 F.3d 1303, 1308–09 (10th Cir. 2012) (“[W]e conclude that a judgment is not 

‘entered on the criminal docket’ for purposes of Fed. R. App. P. 4(b)(6) unless 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 13
14 

judgment is noted on the docket in a publicly accessible manner. . . . Because the 

criminal docket in [the defendant’s] case does not reflect the entry of final judgment, 

we deny the government’s motion to dismiss [the appeal as untimely].”). But even if 

the appeal from that order is timely, he did not obtain, or even seek, a stay of the 

order before violating the challenged condition of supervised release. And he has 

never argued that he lacked notice of the condition. 

The dissent suggests that this did not matter because Defendant was unable to 

appeal the General Order before it was entered in the docket of his case. But this 

suggestion is misconceived in several respects. 

To begin with, it is worth noting that even if Defendant had filed an appeal, 

that would not in itself excuse his violation of the condition of supervised release. He 

would be required to comply with the condition while the appeal was pending unless 

it was stayed during appeal. 

Moreover, Defendant had avenues to seek relief from the condition of 

supervised release before he violated it. He has not disputed that he had notice of the 

General Order. If he thought that the General Order was valid, he could have filed a 

notice of appeal even before entry in his docket. Federal Rule of Appellate Procedure 

4(b)(2) states: “A notice of appeal filed after the court announces a decision, 

sentence, or order—but before the entry of the judgment or order—is treated as filed 

on the date of and after the entry.” Even if additional steps would need to be taken 

before we would consider the merits, but see Mendoza, 698 F.3d at 1309 n.3 

(“Although final judgment was never properly entered, we nevertheless have 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 14
15 

jurisdiction over this appeal. As long as no question exists as to the finality of the 

district court’s decision, defects in the proper entry of judgment do not affect our 

appellate jurisdiction.” (internal quotation marks omitted)), Defendant could have 

acted to be sure those steps would be taken so that his appeal could be promptly 

addressed by this court. For example, he could have filed with us a petition for writ 

of mandamus to require the district court to enter the General Order on his docket; if 

the petition noted that Defendant wished to challenge the condition of supervised 

release and could not appeal until entry on the docket, there is little doubt that this 

court would have taken prompt action. 

As an alternative, Defendant could have pursued relief in district court. He 

could have filed a motion challenging the General Order and seeking a stay pending 

further proceedings in district court or on appeal. And he could, of course, have 

requested the district court to enter the General Order on his docket so that he could 

appeal. 

The one thing that Defendant could not do is take the law into his own hands 

and decide to disobey an undisturbed order of a court with jurisdiction. 

In the above discussion, we have assumed that the General Order was a valid 

order of the district court. We think, however, that Defendant would have a strong 

argument that the district court acted beyond its authority in modifying a special 

condition of his supervised release by means of a general order.7

 But Defendant has 

7

 The term general order (or standing order) refers to “orders . . . adopted by 

district courts . . . as district-wide or division-wide orders, without an opportunity for 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 15
16 

not pursued this argument and we dispose of his appeal on other grounds. We note, 

however, that even if the General Order was a nullity and could supply him with an 

excuse for not complying with the sexual-material condition as modified, then his 

original sexual-material condition would still have been in effect. Because the 

notice or public comment.” Committee on Rules of Practice and Procedure of the 

Judicial Conference of the United States, Report and Recommended Guidelines on 

Standing Orders in District and Bankruptcy Courts at 1 (2009). But the power to 

issue such orders is limited. To be sure, a court has “inherent authority to regulate the 

practice of litigants before it.” United States v. Ray, 375 F.3d 980, 992 (9th Cir. 

2004). This authority is recognized in Federal Rule of Criminal Procedure 57(b), 

which states that a “[a] judge may regulate practice in any manner consistent with 

federal law, [the Federal Rules of Criminal Procedure], and the local rules of the 

district.” General Order 2020-13, however, does not regulate practice or procedure—

it purports to substantively modify existing special conditions of supervised release 

for a class of defendants. We are not aware of any law authorizing such a 

modification by general order rather than by proceeding in each applicable case. One 

could therefore assume that the General Order was a nullity. Perhaps a viable 

alternative would have been a general order instructing probation officers on the 

enforcement of a supervised-release condition. See 18 U.S.C. § 3602(a) (Probation 

officers serve “under the direction of the court making the appointment.”). This 

approach has been used to restrict the application of already-imposed conditions in 

response to changes in the law governing supervised-release conditions. See, e.g., In 

the Matter of: Enforcement and Imposition of Standard Conditions of Supervised 

Release and Probation No. Twelve, No. 19-MC-00004-27 (D.N.M. July 10, 2019) 

(“In accordance with [United States v. Cabral, 926 F.3d 687, 691 (10th Cir. 2019)], 

the United States Probation Office . . . shall cease enforcing the risk-notification 

condition for those Defendants already under supervision, unless Court approval is 

first obtained.”); Standing Order Pursuant to 18 U.S.C. § 3583(e)(2) Ordering the 

Probation Office to Construe the Thirteen Standard Conditions of Supervised Release

(N.D. Ill. May 24, 2015) (Reinhard, J.) (“Based on recent caselaw authority from the 

Seventh Circuit regarding the impermissible vagueness of certain conditions of 

supervised release, the court hereby orders the probation office to construe and apply 

the above thirteen conditions as hereinafter modified to defendants currently on 

supervised release or sentenced but not yet on supervised release in the following 

manner . . . .” (citations omitted)). 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 16
17 

conduct underlying his revocation would have violated both conditions—he has not 

argued otherwise—the outcome here would remain the same. 

III. CONCLUSION 

We AFFIRM the sentence imposed by the district court upon revocation of 

Defendant’s term of supervised release. 

Entered for the Court 

Harris L Hartz 

Circuit Judge 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 17
United States v. Brian Joseph Nielsen, No. 21-8087 

BACHARACH, J., dissenting 

I respectfully dissent. The district court broadly prohibited Mr. 

Nielsen’s viewing of adult pornography. After entering this broad 

prohibition, the court issued a general order, modifying the conditions for 

many defendants (including Mr. Nielsen) subject to supervised release. Mr. 

Nielsen argues that the district court erred by imposing the modified 

conditions without making particularized findings. The government 

conceded error. 

Faced with this concession, the district court tried to cure its error by 

conducting a hearing and making new findings. The resulting question is 

whether the new findings cured the error. 

The majority declines to answer this question, reasoning that we 

don’t consider facial challenges initiated in revocation proceedings. But 

we decline to consider those challenges only when the defendant could 

have appealed the conditions earlier. 

That’s not the case here. Mr. Nielsen couldn’t appeal the conditions 

any earlier than he did because the district court hadn’t entered the 

disputed conditions in his docket. So I would consider the merits of Mr. 

Nielsen’s challenge to the conditions. 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 18
2 

In considering this challenge, I would reverse because the district 

court didn’t cure its failure to make particularized findings when entering 

the general order. 

1. Mr. Nielsen appealed the disputed conditions at his first 

opportunity. 

Defendants can challenge supervised release conditions in two ways: 

facially and as applied. The parties agree that Mr. Nielsen could raise an 

as-applied challenge now even though he didn’t appeal when the district 

court modified the conditions. But at oral argument, Mr. Nielsen 

disavowed an as-applied challenge. The only challenge left would be a 

facial challenge. 

The majority points out that ordinarily, a defendant can’t wait until a 

revocation proceeding to make a facial challenge to the conditions. We and 

other circuits have generally held that waiting until the revocation 

proceeding is too late because the defendant could have appealed the 

supervised release conditions when they were imposed. See, e.g., United 

States v. Helton, 612 F. App’x 906, 909 (10th Cir. 2015) (unpublished) 

(attributing the bar on facial challenges in revocation proceedings to the 

presumed ability of the supervisee to “timely challenge a condition ‘on 

direct appeal from the sentencing court’s judgment’” (quoting United 

States v. Wayne, 591 F.3d 1326, 1334 (10th Cir. 2010))); see also Wayne, 

591 F.3d at 1334 (concluding that the defendant was time-barred from 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 19
3 

making a facial challenge to a supervised release condition at a compliance 

hearing because she had failed to appeal from the judgment imposing the 

sentence); accord United States v. Johnson, 138 F.3d 115, 117–18 (4th Cir. 

1998) (declining to review the defendant’s facial challenges to his 

conditions of supervised release after revocation of his supervised release 

because he should have appealed the sentence); United States v. Preacely, 

702 F.3d 373, 376 (7th Cir. 2012) (concluding that a supervisee couldn’t 

wait until the revocation hearing to challenge a condition of supervised 

release because the time “to challenge the condition [had been] at the 

sentencing or on direct appeal”); United States v. Key, 832 F.3d 837, 840 

(8th Cir. 2016) (“We are skeptical that a defendant who failed to appeal 

the imposition of a condition of release can bring a facial challenge to the 

condition following revocation.”). But what if the defendant couldn’t have 

appealed the supervised release conditions when they were imposed? 

That’s the situation here. 

In every criminal case, the district court must enter orders in the 

defendant’s criminal docket. Fed. R. Crim. P. 55. Entry in the docket is 

essential to “start[] the appeal deadline.” United States v. Mendoza, 

698 F.3d 1303, 1307 (10th Cir. 2012) (citing Advisory Committee Note to 

1966 Amendments, reprinted in 39 F.R.D. 69, 200 (1966)); see also 

Bankers Trust Co. v. Mallis, 435 U.S. 381, 384 (1978) (per curiam) 

(explaining that the Federal Rules of Civil Procedure governing entry of 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 20
4 

orders in the docket serve “to clarify when the time for appeal . . . begins 

to run”). Given this purpose, the time to appeal begins with entry of an 

appealable order in the docket of the criminal case. Fed. R. App. 

P. 4(b)(1); see Fed. R. App. P. 4(b)(6) (“A judgment or order is entered for 

purposes of this Rule 4(b) when it is entered in the criminal docket.”). 

Until the order is entered in the criminal case, an appeal is premature. See 

United States v. West, 240 F.3d 456, 458–59 (5th Cir. 2001) (concluding 

that the defendant’s appeal of her criminal judgment was premature 

because the district court had not yet entered the judgment (under review) 

in the docket). So a defendant can’t appeal until the district court has 

entered an appealable order in the docket. See Constien v. United States, 

628 F.3d 1207, 1210 (10th Cir. 2010) (“When prematurity of a notice of 

appeal cannot be ‘cured’ by [Federal Rule of Appellate Procedure 4(a)(2)], 

the aggrieved party must await a final judgment before filing a notice of 

appeal to challenge the allegedly erroneous ruling.”).1

 

1

 The Federal Rules of Appellate Procedure provide an exception when 

 the district court announces an otherwise appealable ruling and 

 a party files a notice of appeal before the district court enters 

the order in the docket. 

Fed. R. App. P. 4(a)(2) (civil cases), 4(b)(2) (criminal cases). Under this 

exception, we treat the appeal as filed when the district court enters the 

order in the docket. Fed. R. App. P. 4(a)(2), 4(b)(2). Even when the district 

court doesn’t ever enter the order in the docket, we obtain jurisdiction 

when there’s “no question as to the finality of the district court’s 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 21
5 

The district court never entered the general order in Mr. Nielsen’s 

docket. As a result, he couldn’t appeal the modification of his conditions 

through the general order. If he had appealed any earlier than he did, we’d 

have lacked jurisdiction. See note 1, above (citing Warren v. Am. Bankers 

Ins. of Fla., 507 F.3d 1239, 1245 (10th Cir. 2007)). 

The only reason that we have jurisdiction now is that when the 

district court revoked supervised release, the court reinstituted the 

modified conditions and entered the order in Mr. Nielsen’s docket. He filed 

a notice of appeal the same day. But he couldn’t have appealed the 

conditions until entry of the order in Mr. Nielsen’s docket. 

decision.” United States v. Mendoza, 698 F.3d 1303, 1309 n.3 (10th Cir. 

2012) (quoting Burlington N. R.R. Co. v. Huddleston, 94 F.3d 1413, 1416 

n.3 (10th Cir. 1996)). 

This exception doesn’t apply here. The district court didn’t announce 

the modification of Mr. Nielsen’s conditions, and a substantial question 

exists regarding the finality of the general order in Mr. Nielsen’s case. No 

one suggests that his deadline to appeal would have started once he learned 

of the modification. 

He did eventually learn of the general order and its application to 

him. But we don’t know when that was. Because the court didn’t announce 

its modification of Mr. Nielsen’s conditions and the court’s failure to enter 

the general order in the docket affects timeliness of the appeal, the 

exception doesn’t apply and jurisdiction never passed to us. See Warren v. 

Am. Bankers Ins. of Fla., 507 F.3d 1239, 1245 (10th Cir. 2007) (concluding 

that jurisdiction didn’t pass to us when the notice of appeal remained in 

suspension prior to entry of an order of dismissal). 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 22
6 

In these limited circumstances, we can’t fault Mr. Nielsen for waiting 

until the revocation proceeding to challenge the disputed conditions. He 

needed to wait because any prior appeal would have been premature. I 

would thus address the merits of Mr. Nielsen’s challenge. 

The majority doesn’t question prematurity had Mr. Nielsen filed a 

notice of appeal to the general order, but speculates on a series of possible 

events that might have led to an appealable order: 

1. Under the federal rules, an “announcement” of the decision (the 

general order) meant that the appeal would have been treated as 

filed upon entry of the general order in Mr. Nielsen’s criminal 

case. Fed. R. App. P. 4(b)(2); see note 1, above. 

2. Because of this federal rule, we could not have considered Mr. 

Nielsen’s appeal until the district court entered the general 

order in Mr. Nielsen’s criminal case. 

3. Mr. Nielsen could have requested a mandamus petition to 

require entry of the general order in his docket. 

The majority’s speculation overlooks the reason for prohibiting facial 

challenges initiated in revocation proceedings and stems from a 

misinterpretation of the federal rule. 

The majority relies on the general prohibition of facial challenges to 

a supervised release condition made in revocation proceedings. That 

prohibition stems from the assumption that the defendant could have 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 23
7 

appealed the condition when it was imposed. See pp. 2–3, above.2

 And Mr. 

Nielsen couldn’t appeal before entry of the revocation order. 

Despite his inability to appeal, the majority speculates about other 

actions that Mr. Nielsen could have taken. The majority rests that 

speculation on Federal Rule of Appellate Procedure 4(b)(2), which 

provides that when a party files a notice of appeal “after the court 

announces a decision, sentence, or order—but before the entry of the 

judgment or order—[the notice of appeal] is treated as filed on the date of 

and after the entry.” Fed. R. App. P. 4(b)(2) (emphasis added); see note 1, 

above. The majority says that given this rule, Mr. Nielsen could have taken 

“additional steps” to obtain entry of the general order in his docket. Maj. 

Order & Judgment at 14. 

But this rule wouldn’t apply if Mr. Nielsen had prematurely appealed 

the general order. The rule applies only when a district court “announces” 

its order, decision, or sentence; and neither party has suggested that the 

court announced its general order, much less announced it as a decision or 

2

 The majority attributes this restriction to the need for compliance 

with a condition while it’s in place. Maj. Order & Judgment at 13. For this 

proposition, the majority relies on Maness v. Meyers, 419 U.S. 449 (1975). 

There the Court discussed only the availability of contempt when an 

attorney advises a client to disobey a subpoena. Id. at 459. In that 

discussion, the Court observed that people must comply with orders absent 

a stay, pointing out that “the remedy is to appeal” the order. Id. The Court 

said nothing about supervised release or the ability to challenge orders that 

can’t be appealed. 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 24
8 

order in Mr. Nielsen’s case. Because the rule doesn’t apply, we would have 

had to dismiss the premature appeal for lack of jurisdiction. See pp. 3–5, 

above. 

But let’s suppose that we would have applied the rule anyway and 

waited for “additional steps . . . to be taken.” Maj. Order & Judgment 

at 14. And let’s suppose further that Mr. Nielsen would have requested 

mandamus to require entry of the general order in his docket. And we can 

even suppose further that we’d have granted mandamus. Why would this 

theoretical set of possibilities bear on Mr. Nielsen’s right to challenge his 

conditions? Regardless of what might have happened, he appealed the 

conditions at his first actual opportunity. So there’s no reason to prohibit 

consideration of his facial challenge. 

2. Mr. Nielsen’s other alleged options shouldn’t affect our 

disposition. 

The majority relies not only on speculation about what might have 

happened if Mr. Nielsen had prematurely appealed, but also on the 

availability of three other options: 

1. comply with the allegedly unconstitutional conditions and 

forgo an appeal, 

2. challenge the conditions in district court and move for a stay of 

the conditions while those proceedings remained pending, or 

3. ask the district court to enter the general order in his docket so 

that he could appeal.

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 25
9 

Mr. Nielsen presumably did have other options. But those options 

didn’t include the ability to appeal the conditions. And we’ve disallowed 

facial challenges to supervised release conditions through revocation 

proceedings only because we’ve assumed that the defendant could have 

appealed the conditions when they had been imposed. See pp. 2–3, above 

(citing cases). And we would have lacked jurisdiction if Mr. Nielsen had 

appealed from the order imposing the supervised release conditions. So 

regardless of other options for Mr. Nielsen, we’d have no reason to 

disallow his challenge to the conditions. 

The majority suggests that the district court might have revoked the 

supervised release even if the conditions had been unconstitutional. 

Perhaps the majority is right. That seems unlikely because the district 

court said that if the disputed conditions were deemed invalid, the sentence 

would have been shorter by roughly two months (twelve months and a day 

rather than fourteen months). See p. 11, below. 

Regardless of what the district court would have done, though, we 

shouldn’t decline to consider Mr. Nielsen’s challenge to the conditions 

themselves. No one suggests that Mr. Nielsen could have appealed the 

conditions any earlier than he did. And the only reason that we’ve ever 

given for disallowing facial challenges to conditions in revocation 

proceedings is that the defendant could have appealed those conditions 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 26
10 

when they were imposed. That’s not the case here, so we have no reason to 

disallow Mr. Nielsen’s facial challenge to the conditions. 

3. The district court erred by failing to make particularized findings 

when modifying Mr. Nielsen’s conditions. 

On the merits, I would credit that challenge. 

Everyone appears to agree that 

 the district court conducted the revocation proceedings based 

on alleged violations of the condition stated in the general 

order, 

 the district court applied the general order to Mr. Nielsen 

without particularized findings, and 

 the lack of particularized findings constituted an error. 

Despite agreeing that the district court erred, the government argues 

that the district court cured that error by later making particularized 

findings that would have validated the general order. I disagree. 

The district court did make particularized findings when revoking 

supervised release. In making those findings, however, the district court 

relied in part on events taking place in 2021—after the court had imposed 

the condition from the general order on Mr. Nielsen. R. vol. III, at 222, 

226. A court cannot support a decision based on evidence that hadn’t 

existed at the time of the decision. So the district court’s new findings, 

even if particularized, wouldn’t have cured the lack of particularized 

findings when the court imposed the condition from the general order. 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 27
11 

4. The district court’s error wasn’t harmless. 

The government argues that even if the court had erred in modifying 

the conditions, any error would have been harmless. 

Nonconstitutional errors are harmless unless they “had a ‘substantial 

influence’ on the outcome or leave[] one in ‘grave doubt’ as to whether 

[they] had such effect.” United States v. Griffin, 389 F.3d 1100, 1104 

(10th Cir. 2004) (quoting United States v. Mejia-Alarcon, 995 F.2d 982, 

990 (10th Cir. 1993)). For constitutional errors, the government must prove 

harmlessness beyond a reasonable doubt. See Chapman v. Cal., 386 U.S. 

18, 24 (1967); Malone v. Carpenter, 911 F.3d 1022, 1029 (10th Cir. 2018). 

Regardless of which standard applies, the error wasn’t harmless. The 

district court said that Mr. Nielsen’s sentence would have been shorter by 

about two months without reliance on the disputed conditions. R. vol. III, 

at 242 (“[J]ust so it’s clear, to the extent a court would somehow 

unreasonably conclude that the Special Condition was not enforceable at 

the time the violations occurred in this matter as noted in 1 and 6, then the 

sentence would be 12 months and a day. . . [rather than] 14 months.”). The 

district court’s statement shows that the error was not harmless. See United 

States v. Serrano-Dominguez, 406 F.3d 1221, 1224 (10th Cir. 2005) 

(finding that the district court’s announcement of an alternative sentence 

under the methodology proposed by the defendant “eliminates any need to 

speculate about what it would do on remand”); see also United States v. 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 28
12 

Gieswein, 887 F.3d 1054, 1061 (10th Cir. 2018) (stating that a procedural 

error is harmless only if “the district court would have imposed the same 

sentence” without the error (quoting United States v. Kieffer, 681 F.3d 

1143, 1165 (10th Cir. 2012))). So I would reverse and remand with 

instructions to vacate the disputed conditions and resentence Mr. Nielsen 

for the revocation of supervised release. 

Appellate Case: 21-8087 Document: 010110722909 Date Filed: 08/10/2022 Page: 29