United States v. Holzer

(a)(2) and (d)(3), and one count of maliciously

 attempting to damage and destroy, by means of fire and explosives, a synagogue, in

 violation of

(i). The district court sentenced Holzer to a term of

 imprisonment of 235 months, to be followed by a fifteen-year term of supervised

 release. The district court also ordered Holzer to comply with eleven special

 conditions of supervised release, including Special Condition Nine, that prohibits him

 from acquiring, possessing, or using any material depicting support for or association

 with antisemitism or white supremacy.

       Holzer now appeals, arguing that the district court erred in imposing Special

 Condition Nine. Specifically, Holzer argues that Special Condition Nine infringes on

 his First Amendment rights, and that the district court failed to make any

 particularized findings to support the special condition. Exercising jurisdiction

 pursuant to

28 U.S.C. § 1291

, we conclude that Holzer’s challenge to Special

 Condition Nine is barred by the appellate waiver provision of his plea agreement.

 Consequently, we dismiss Holzer’s appeal.

                                            I

                                  Factual background

       Holzer, who was living in Pueblo, Colorado at the time of the offenses in this

 case, used multiple social media accounts to promote white supremacy ideology and

 acts of violence that were both racially and religiously motivated. In late September

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 2019, an Online Covert Employee (OCE) employed by the Federal Bureau of

 Investigation (FBI) contacted Holzer and told him that Facebook suggested that they

 should be friends. The OCE’s Facebook account portrayed the OCE as a white

 female who was supportive of white supremacy ideology. Holzer accepted the

 OCE’s friend request and soon thereafter began sending the OCE a variety of

 messages, photographs, and videos, all of which were focused on white supremacy

 and related acts of violence. For example, Holzer told the OCE that in October 2018,

 he had paid an individual to place arsenic in the pipes of a local synagogue.

       In early October 2019, Holzer told the OCE that he was preparing for a racial

 holy war and that he intended to poison the water supply at Temple Emanuel, a

 synagogue located in Pueblo, Colorado. Holzer invited the OCE to participate in

 those efforts, and proceeded to explain where he could obtain arsenic to carry out the

 poisoning. The OCE responded by telling Holzer that she had friends who would

 soon be in the area of Colorado Springs. Holzer replied that he was interested in

 meeting the OCE’s friends.

       On October 12, 2019, an FBI undercover agent (UC-1) contacted Holzer and

 presented himself as one of the OCE’s friends. UC-1 told Holzer that he and some

 friends planned to be in Colorado Springs the following week. Holzer sent UC-1

 several photos of himself with various images, paraphernalia, and clothing associated

 with white supremacy and Nazi ideology. Holzer also told UC-1 that he was

 planning to poison a synagogue in Pueblo. Over the next several days, Holzer



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 continued to send UC-1 images related to white supremacy and Nazi ideology.

 Holzer and UC-1 made plans to meet in person.

       On October 17, 2019, three undercover FBI agents (UCs) posing as the OCE’s

 friends met with Holzer in Colorado Springs. Holzer brought white supremacy

 paraphernalia as gifts for the UCs, including a flag, several patches, a metal Thor’s

 hammer, and a mask. Holzer told the UCs about his efforts in October 2018 to

 poison a synagogue’s water supply, and falsely claimed that he caused that

 synagogue to be shut down for months. Holzer then talked about poisoning the water

 supply at Temple Emanuel, with the goal of shutting the synagogue down and

 “mak[ing] them know they’re not wanted here.” ROA, Vol. I at 72. When one of the

 UCs asked Holzer an open-ended question about what other methods he was

 considering, Holzer mentioned welding the doors shut and suggested that he could

 put together Molotov cocktails to throw through the synagogue’s windows. Holzer

 also repeatedly expressed his hatred of Jewish people and discussed his efforts to

 drive them out of Pueblo.

       Following the meeting, Holzer and the UCs drove to Pueblo to visit Temple

 Emanuel and determine what type of attack would be most effective. While at

 Temple Emanuel, Holzer opined that Molotov cocktails would not be sufficient to

 destroy the entire building. Holzer and the UCs then discussed using pipe bombs.

 The UCs offered to supply the pipe bombs, but cautioned that it would take some

 time because they would need to bring them in from out of state. Holzer stated in

 response, “Let’s get that place off the map.”

Id.


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       Following the meeting, Holzer continued to take steps in furtherance of

 bombing Temple Emanuel. On October 19, 2019, Holzer sent UC-1 a video showing

 him walking around the exterior of Temple Emanuel and commenting on various

 features of the building. Later that day, Holzer participated in a group chat with the

 UCs to discuss the bombing plot. During that chat, one of the UCs wrote, “Let me

 know what you want the end result to look like and I’ll get to work.”

Id. at 73

.

 Holzer responded the next day with a photo of a church, half of which had crumbled

 to the ground, and stated, “Let’s have it look something like that.”

Id.


       On October 31, 2019, Holzer met again with UC-1. The two discussed the

 plan to attack Temple Emanuel and agreed that Holzer would meet with the UCs at a

 motel around 9:00 p.m. on November 1 to examine the explosives before going to

 Temple Emanuel. At Holzer’s request, they went to a store to purchase gloves to use

 during the attack. Holzer repeatedly affirmed that he was prepared to go through

 with the attack the following night. When UC-1 raised the possibility of someone

 being inside Temple Emanuel when the explosives were detonated, Holzer stated that

 he did not think anyone would be there, but that he would not care if they were

 because they would be Jewish.

       On the evening of November 1, 2019, UC-1 picked up Holzer and drove him

 to a motel where two of the other UCs were waiting. One of the UCs showed Holzer

 two pipe bombs and two bundles each containing seven sticks of dynamite.1 Holzer


       1
         Although the UCs told Holzer that the pipe bombs and dynamite were
 functional, in fact they were all inert. Further, although the UCs told Holzer that two
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 examined the explosives and declared, “this is absolutely gorgeous.”

Id.

 at 74–75.

 Holzer then asserted that they should carry out the attack at 2:30 or 3:00 in the

 morning in order to avoid the police.

       Shortly thereafter, Holzer was arrested and transported to a police station

 where he waived his Miranda rights and agreed to speak with the FBI. Holzer

 admitted that he had been planning to blow up Temple Emanuel that night with the

 pipe bombs and dynamite in the motel room. He referred to the plan as “my

 mountain” and to Jews and Temple Emanuel as a “cancer” on the community.

Id. at 75

. Although Holzer stated that he had not planned on hurting anyone, when asked

 what he would have done if there had been someone inside Temple Emanuel when he

 arrived that night, he admitted that he would have gone through with the attack

 because anyone inside would have been Jewish.

                                 Procedural background

       On November 2, 2019, a criminal complaint was filed in the United States

 District Court for the District of Colorado charging Holzer with one count of

 attempting to obstruct religious exercise by force using explosives and fire, in

 violation of

(a)(2) and (d)(3).

       On November 21, 2019, a federal grand jury returned a three-count indictment

 against Holzer. Count 1 charged Holzer with intentionally attempting to obstruct


 of them brought the pipe bombs and dynamite to Colorado from out of state, in fact
 the dynamite and simulated black powder contained within the pipe bombs was
 shipped by the FBI from Quantico, Virginia, to Colorado to be used in the undercover
 operation.
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 persons in the enjoyment of their free exercise of religious beliefs through force and

 the attempted use of explosives and fire, in violation of

(a)(2) and

 (d)(3). Count 2 charged Holzer with maliciously attempting to damage and destroy

 Temple Emanuel by means of fire and explosives, in violation of

(i).

 Count 3 charged Holzer with using fire and an explosive to commit a federal felony,

 in violation of

(h)(1).

       On October 15, 2020, Holzer pleaded guilty, pursuant to a written plea

 agreement with the United States, to Counts 1 and 2 of the indictment. The plea

 agreement included a “Waiver of Appeal” section that stated as follows:

              The defendant is aware that

18 U.S.C. § 3742

 affords the right to
       appeal the sentence, including the manner in which that sentence is
       determined. Understanding this, and in exchange for the concessions
       made by the government in this agreement, the defendant knowingly
       and voluntarily waives the right to appeal any matter in connection with
       this prosecution, conviction, or sentence unless it meets one of the
       following criteria: (1) the sentence exceeds the maximum penalty
       provided in the statute of conviction; (2) the sentence exceeds 240
       months; or (3) the government appeals the sentence imposed. If any of
       these three criteria apply, the defendant may appeal on any ground that
       is properly available in an appeal that follows a guilty plea.

              The defendant also knowingly and voluntarily waives the right to
       challenge this prosecution, conviction, or sentence in any collateral
       attack (including, but not limited to, a motion brought under

28 U.S.C. § 2255

). This waiver provision does not prevent the defendant from
       seeking relief otherwise available in a collateral attack on any of the
       following grounds: (1) the defendant should receive the benefit of an
       explicitly retroactive change in the sentencing guidelines or sentencing
       statute; (2) the defendant was deprived of the effective assistance of
       counsel; or (3) the defendant was prejudiced by prosecutorial
       misconduct. Should the plea of guilty be vacated on the motion of the
       defendant, the government may, in its sole discretion, move to reinstate
       any or all of the counts dismissed pursuant to this agreement.


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Id. at 63

.

        A presentence investigation report (PSR) was prepared and submitted to the

 district court and the parties in December 2020. Attached to the PSR was an exhibit

 titled “SENTENCING RECOMMENDATION.” ROA, Vol. 2 at 34. That exhibit,

 consistent with the calculations in the PSR, recommended that the district court

 impose sentences of 204 months’ custody on each of Counts 1 and 2, with the

 sentences to run concurrently. The exhibit also recommended a three-year term of

 supervised release as to Count 1 and a fifteen-year term of supervised release as to

 Count 2, with the two terms to run concurrently. The exhibit listed mandatory,

 standard, and special conditions of supervised release that it recommended the

 district court adopt. Among the proposed special conditions of supervised release

 was the following: “You shall not possess, view, access, or otherwise use material

 that is primarily associated with extremist views or organizations (including but not

 limited to anti-Semitic material).”

Id. at 35

.

        Holzer filed a written objection to the above-quoted special condition of

 supervised release recommended in the exhibit to the PSR. Holzer argued that the

 proposed special condition was “impermissibly vague” because it would “allow[] the

 U.S. Probation Office to determine, within its own discretion and without definition,

 what is ‘extremist’ and what material is ‘primarily associated with’ extremism.”

Id. at 61

. Further, Holzer argued that the proposed special condition would infringe on

 his First Amendment rights because it would “amount[] to a severe restriction on

 [his] freedoms of religion, thought, and expression.”

Id. at 64

.

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          On January 25, 2021, the district court provided the probation officer and the

 parties with its own proposed special conditions of supervised release. Included

 among those proposed special conditions was Proposed Special Condition Nine,

 which stated:

          You shall not knowingly acquire, possess or otherwise use any
          photograph, flag, clothing, patch, imagery, jewelry, literature, or other
          material depicting support for or association with anti-Semitism or
          white supremacy. Specifically included in this prohibition, without
          limitation, are Mein Kampf, swastikas, iron crosses, other Nazi
          memorabilia or logos; Thor’s hammer; KKK symbolism; numeric
          symbols: 12, 14, 18, 88, 311, or 1488; the Aryan Fist; 14 words; the
          Celtic cross; the Sonnenrad; the Valknut; and the Blood Drop Cross.

Id.,

Vol. 2 at 841. Holzer objected to proposed Special Condition Nine, arguing that

it was impermissibly vague, impermissibly delegated the court’s authority to Holzer’s

probation officer, and infringed on his First Amendment rights.

The district court held a sentencing hearing on February 26, 2021. Holzer’s

counsel repeated the objection to proposed Special Condition Nine. The district

court overruled defense counsel’s objection. The district court imposed a term of

imprisonment of 235 months, to be followed by a fifteen-year term of supervised

release. The district court ordered that, during the period of supervised release,

Holzer would be required to comply with standard conditions of supervision and

eleven special conditions of supervised release, including Special Condition Nine

(which was worded identically to the district court’s proposed Special Condition

Nine).

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Final judgment in the case was entered on March 2, 2021. Holzer filed a notice of

appeal on March 5, 2021.

Holzer argues in his appeal that Special Condition Nine of his supervised

release infringes on his First Amendment rights and was not supported by any

particularized findings made by the district court. The government argues in

response that Holzer’s challenge to Special Condition Nine is barred by the appellate

waiver provision of his written plea agreement. For the reasons outlined below, we

agree with the government and therefore dismiss Holzer’s appeal.

In United States v. Hahn,

359 F.3d 1315

 (10th Cir. 2004) (en banc), we

  considered “how we should resolve appeals brought by defendants who have waived

  their appellate rights in a plea agreement.”

Id. at 1324

. “In fashioning our analysis,”

  we identified four guiding principles.

 “First, every circuit that has considered

  enforcement of appellate waivers enforces at least some forms of appellate waivers.”

 “Second, contract principles govern plea agreements.”

 at 1324–25. “Third, a

  defendant who waives his right to appeal does not subject himself to being sentenced

  entirely at the whim of the district court.”

Id. at 1325

 (quotation marks omitted).

  And “[f]ourth, appellate waivers benefit the government by saving the costs of

  prosecuting appeals; and only through the efficient dismissal of an appeal will the

  government receive the benefit of its bargain.”

 (quotation marks and brackets

  omitted).



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         We in turn adopted a “three-prong analysis” for deciding whether a criminal

  defendant has waived his appellate rights in an enforceable plea agreement.


  “This analysis” requires us to determine: “(1) whether the disputed appeal falls

  within the scope of the waiver of appellate rights; (2) whether the defendant

  knowingly and voluntarily waived his appellate rights; and (3) whether enforcing the

  waiver would result in a miscarriage of justice.”


         Applying this three-prong enforcement analysis to the case at hand, we

  conclude that all three prongs weigh against Holzer and require us to enforce the

  appellate waiver provision of his plea agreement.

         a) Scope of the waiver

         As previously noted, Holzer’s written plea agreement included a section entitled

  “Waiver of Appeal” that stated, in pertinent part:

                The defendant is aware that

18 U.S.C. § 3742

 affords the right to
         appeal the sentence, including the manner in which that sentence is
         determined. Understanding this, and in exchange for the concessions
         made by the government in this agreement, the defendant knowingly
         and voluntarily waives the right to appeal any matter in connection with
         this prosecution, conviction, or sentence unless it meets one of the
         following criteria: (1) the sentence exceeds the maximum penalty
         provided in the statute of conviction; (2) the sentence exceeds 240
         months; or (3) the government appeals the sentence imposed. If any of
         these three criteria apply, the defendant may appeal on any ground that
         is properly available in an appeal that follows a guilty plea.

  ROA, Vol. 1 at 63.

         The government argues that Holzer’s appeal falls within the scope of the

  above-quoted waiver language because Holzer seeks in his appeal to challenge one of the

  terms of supervised release imposed by the district court. Aple. Br. at 17 (citing United

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  States v. Sandoval,

477 F.3d 1204, 1207

 (10th Cir. 2007)). Holzer effectively concedes

  that point, but argues in response that the issue he seeks to assert in his appeal falls within

  the first listed exception in the above-quoted language because the challenged condition

  “exceeds the maximum penalty provided in the statute of conviction.” Aplt. Reply Br. at

  1–2. More specifically, Holzer argues that “special supervised release condition number

  nine exceeds the statutory limits of § 3583(d) and is unconstitutional.” Id. at 2. In other

  words, Holzer argues, condition number nine is “illegal” and “[a]n illegal sentence

  exceeds the maximum penalty permitted by law.” Id.

         To resolve this question, we must first determine what the parties intended when

  they employed in the appellate waiver provision of the plea agreement the phrase “the

  maximum penalty provided in the statute of conviction.” In doing so, “[w]e interpret a

  plea agreement as we would any contract and in light of what the defendant reasonably

  understood when she entered her plea.” United States v. Porter,

905 F.3d 1175, 1178


  (10th Cir. 2018) (quotation marks and brackets omitted). “[B]ecause the government

  drafted the Plea Agreement, we construe all ambiguities against the government.” United

  States v. Rubbo,

948 F.3d 1266, 1268

 (10th Cir. 2020).

         The plea agreement in this case does not expressly define the phrase “the

  maximum penalty provided in the statute of conviction,” and the parties now offer

  differing interpretations of that phrase. To begin with, the parties disagree as to whether

  the “statute[s] of conviction” in this case are confined solely to the statutes that Holzer

  pleaded guilty to violating, i.e.,

(a)(2), (d)(3) and 844(i), or whether they

  also include the penalty provisions contained in

18 U.S.C. § 3583

. Holzer, for his part,

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  concedes that the specific statutes that he pleaded guilty to violating do not expressly

  mention supervised release. But, Holzer argues, these statutes of conviction effectively

  “incorporat[e] all of the penalty provisions contained in § 3583,” which itself authorizes

  the imposition of supervised release on all criminal defendants convicted of violating

  federal law. Aplt. Reply Br. at 3. In support, Holzer argues that “[b]y enactment of the

  umbrella statute § 3583, Congress ensured that the penalty of supervised release, and the

  accompanying conditions of supervised release, would be incorporated into every federal

  criminal statute unless a specific statute provides otherwise.” Id. Thus, he argues,

  “[s]ection 3583 is provided for in every federal criminal statute unless the statute says

  otherwise.” Id. at 4.

         The government, on the other hand, argues that Holzer’s “‘statutes of conviction’

  are

(a)(2), (d)(3) and . . . 844(i), and not § 3583(d).” Aple. Br. at 12

  (emphasis in original). The government in turn asserts that because the statutes of

  conviction refer only to terms of imprisonment and fines and do not expressly refer to

  supervised release, exception (1) in the appellate waiver provision was therefore intended

  to focus solely on the maximum term of imprisonment (or fine) that could be imposed

  under each statute of conviction. And in turn, the government argues, because Special

  Condition Nine does not involve either a term of imprisonment or a fine, it necessarily

  does not “exceed the maximum penalty provided in the statute[s] of conviction” and thus

  the exception does not apply.

         We conclude that the specific language in the parties’ plea agreement provides an

  answer to this question. As Holzer correctly notes, the parties’ plea agreement includes a

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  section entitled “STATUTORY PENALTIES.” That section, which was presumably

  intended, at least in part, to help provide context to exception (1) set forth in the appellate

  waiver provision, specifically mentions supervised release:

         Based on the defendant’s criminal history known at this time, the applicable
         maximum statutory penalty for a violation of

18 U.S.C. § 247

(a)(2) and
         (d)(3) is not more than 20 years of imprisonment, not more than a $250,000
         fine, or both, not more than three years of supervised release. The
         applicable maximum statutory penalty for a violation of

(i)
         is not more than 20 years of imprisonment, not more than a $250,000 fine,
         or both, not more than lifetime supervised release.

  ROA, Vol. 1 at 67 (emphasis added). Further, as Holzer notes in his reply brief, the

  district court mentioned these statutory maximum terms of supervised release at the

  change-of-plea hearing when it was explaining to Holzer “the maximum penalties” he

  was facing.

Id.,

Vol. 3 at 23–24.

In light of this language in the plea agreement, the district court’s reference to the

maximum terms of supervised release at the change-of-plea hearing, and the fact that any

ambiguities in the plea agreement are construed against the government, we conclude that

the phrase “maximum penalty provided in the statute of conviction” set forth in this plea

agreement should be construed to include both the statutory terms of imprisonment that

are set forth in the criminal statutes that Holzer pleaded guilty to violating and the terms

of supervised release that are authorized in § 3583 for Holzer’s crimes of conviction.

That is not the end of the matter, however, because the government makes one

additional, and indeed critical, argument. According to the government, the term

“‘maximum’ generally refers to something that can be quantified,” and thus the phrase

“‘maximum penalty’ denotes a specific quantity of time or restitution.” Aple. Br. at 12.

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The government in turn argues that “[a] condition of release—as opposed to a term of

release—even if it is an unreasonable one, does not exceed a ‘statutory maximum.’” Id.

(emphasis in original).

We agree with the government’s argument for three reasons. First, we note that

the term “maximum” is commonly defined to mean “[t]he highest value or extreme

limit,” “[t]he highest possible magnitude or quantity of something which is attained,

attainable, or customary; an upper limit of magnitude or quantity,” and “[a]n upper limit

imposed by authority.” Oxford English Dictionary (3d ed. 2001). And the term

“magnitude,” which is employed in these dictionary definitions, means “[s]ize,”

“absolute value,” and “[a] quantity, an amount.”2 Id.

Second, we note that the statutes of conviction that are expressly referenced in the

exception to the appellate waiver provision in the parties’ plea agreement themselves

refer to numerical quantities. As noted, Holzer admitted to violating

18 U.S.C. § 247

(a)(2), which makes it illegal to “intentionally obstruct[], by force or threat of force,

  including by threat of force against religious real property, any person in the enjoyment

  of that person’s free exercise of religious beliefs, or attempts to do so.” The parties

  agreed in the plea agreement that the statutory “punishment for” violating § 247(a)(2)

  was “a fine in accordance with [Title 18] and imprisonment for not more than 20 years,


         2
           Notably, the district court at the change-of-plea hearing couched exception
  (1) to the appellate waiver in terms of quantity or length of the sentence imposed.
  ROA, Vol. 1 at 18 (“The three things that would permit you to appeal are these; one,
  if I were to give you a sentence that was greater than the maximum penalty provided
  for in the statutes of conviction. In other words, greater than the statutory
  maximum.”).
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  or both.”

18 U.S.C. § 247

(d)(3). Holzer also admitted to violating

(i),

  which makes it illegal to “maliciously damage[] or destroy[], or attempt[] to damage or

  destroy, by means of fire or an explosive, any building . . . or other real . . . property used

  in interstate or foreign commerce or in any activity affecting interstate or foreign

  commerce.” Anyone convicted of violating the statute “shall be imprisoned for not less

  than 7 years and not more than 40 years, fined under this title, or both.”

(i). And § 3583, which we have concluded, given the unique wording of the plea

  agreement in this case, is encompassed by the plea agreement’s phrase “maximum

  penalty provided in the statute of conviction,” provides for maximum terms of supervised

  release in terms of years. Notably, the district court expressly referred to those maximum

  terms at the change-of-plea hearing. See

18 U.S.C. § 3583

(b) (authorizing terms of

  supervised release ranging from one year to five years, depending upon the nature of the

  felony);

id.

 § 3583(j) (authorizing supervised release for “any term of years or life” for

  certain terror offenses).

         Third, our own case law supports the conclusion that the phrase “maximum

  penalty” denotes a specific quantity of time or restitution. In United States v. Green,

405 F.3d 1180

 (10th Cir. 2005), we held, in the context of interpreting the meaning of Hahn’s

  miscarriage of justice exception, that “[o]rdinarily and naturally, the phrase ‘statutory

  maximum’ refers to the longest sentence that the statute punishing a crime permits a court

  to impose.”

 at 1191–92 (emphasis added).

         Holzer’s only response to the government’s argument is that it is foreclosed by our

  decision in United States v. Williams,

10 F.4th 965

 (10th Cir. 2021). We disagree. The

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  defendant in Williams, who pleaded guilty to bank fraud, sought on appeal to challenge

  the amount of restitution that the district court ordered him to pay to his bank victims.

  The government argued in response that the defendants’ arguments were precluded by an

  appellate waiver provision in the parties’ written plea agreement. That appellate waiver

  provision, like the one at issue here, stated that the defendant waived the right to appeal

  any matter in connection with his sentence unless “the sentence exceed[ed] the maximum

  penalty provided in the statutes of conviction.”

10 F.4th at 971

. In addressing the

  government’s argument, we noted that the parties’ plea agreement also included “a

  section entitled ‘STATUTORY PENALTIES’” that outlined the maximum term of

  imprisonment, the maximum fine, the maximum term of supervised release, and also

  stated “plus restitution.”

at 971–72. In light of the plea agreement’s express reference

to “plus restitution,” we concluded as follows:

We recognize that restitution presents a less-obvious sort of “maximum”
than do the other categories of penalties. For instance, the statutory
maximum prison time of 30 years is self-evident. Determining the
maximum restitution requires more work. In identifying the MVRA’s
limits in a particular case, a district court must find facts and then apply
them through a multi-layered legal framework. For instance, the amount of
restitution a court may order to most victims is limited to the losses directly
and proximately caused by the defendant’s conduct underlying the offense
of conviction, though the amount of restitution a court may order to some
victims is limited to the losses directly caused by a defendant’s conduct in a
scheme. See 18 U.S.C. § 3663A(a)(2).

But the government drafted the Plea Agreement, including the appeal
waiver and associated provisions. And we read any ambiguities in appeal
waivers against the government and in favor of a defendant’s appellate
rights. Lonjose, 663 F.3d at 1297 (citations omitted). On appeal, Williams
has made a sufficient threshold argument that the total restitution exceeds
the MVRA’s limit (i.e., what the district court had authority to order paid to
WebBank) that he may proceed to the merits. See Gordon, 480 F.3d at

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1208–10 (reading the plea agreement as a whole in determining that the
terms of the appeal waiver didn't waive the defendant's ability to challenge
the restitution order as illegal under the MVRA); cf. United States v.
Cooper,

498 F.3d 1156

, 1158–60 (10th Cir. 2007) (enforcing an appeal
waiver of the “sentence as imposed by the Court and the manner in which
the sentence is determined” against a challenge to restitution). If the
government expects us to enforce an appeal waiver in circumstances like
these, it needs to write a better appeal waiver. We conclude that Williams’s
appeal waiver doesn’t bar his appeal of the restitution order.

Id. at 972.

Williams is not controlling here. To begin with, Williams involved an award of

restitution under the MVRA, and not a special condition of supervised release imposed

under § 3583. An award of restitution always involves a quantifiable amount of money,

whereas a special condition of supervised release, such as Special Condition Nine in this

case, is typically not quantifiable in nature. Indeed, Special Condition Nine is not

quantifiable at all, and instead prohibits Holzer from possessing items of a certain

character. Although Holzer argues that there is no real “distinction between a sentence

that exceeds the limits of the law and a sentence that exceeds the statutory maximum,”

we reject his position and conclude that there is in fact a material distinction between

those two things. Aplt. Reply Br. at 9.

Ultimately, we conclude that the phrase “maximum penalty provided in the statute

of conviction,” which is employed in the appellate waiver provision of the parties’ plea

agreement, cannot, as Holzer suggests, reasonably be construed to refer to both quantities

of time (i.e., months, years) and to limitations on the type of actions a defendant can take

while on supervised release. Those limitations, while subject to statutory constraints, are

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not quantifiable in the same manner as quantities of time or, for that matter, quantities of

money.

We therefore conclude, in sum, that the issues that Holzer seeks to raise on appeal

fall within the scope of the appellate waiver provision of his plea agreement, but do not

fall within the scope of exception (1) to the appellate waiver provision.3

b) Knowing and voluntary

“The second prong of the [Hahn] analysis requires [us] to ascertain whether

[Holzer] knowingly and voluntarily waived his appellate rights.”

359 F.3d at 1325

.

  Notably, Holzer does not dispute that he knowingly and voluntarily waived his appellate

  rights. And, in any event, the record on appeal firmly indicates that he did. More

  specifically, the language of the parties’ plea agreement expressly states that Holzer

  “knowingly and voluntarily waive[d] the right to appeal any matter in connection with

  th[e] prosecution, conviction, or sentence” unless it met one of the specified exceptions.

  ROA, Vol. 1 at 63; see Hahn,

359 F.3d at 1325

 (directing courts to “examine whether the

  language of the plea agreement states that the defendant entered the agreement knowingly

  and voluntarily”). Further, the transcript of the change-of-plea hearing indicates that the

  district court thoroughly questioned Holzer regarding his understanding of the terms of

  the plea agreement, including the appellate waiver provision, and the district court

  “f[ou]nd, explicitly, the waiver of appellate rights . . . [wa]s one which [wa]s knowingly


         3
          Contrary to our ruling in Hahn, the Ninth Circuit would exclude from a
  general appellate waiver a constitutional challenge to a condition of supervised
  release unless specifically waived in the plea agreement. United States v. Wells,

29 F.4th 580, 587

 (9th Cir. 2022).
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  and voluntarily made.” ROA, Vol. 3 at 20; see Hahn,

359 F.3d at 1325

 (directing courts

  to “look for an adequate Federal Rule of Criminal Procedure 11 colloquy”).

        c) Miscarriage of justice

        “The third prong of [Hahn’s] enforcement analysis requires [us] to determine

  whether enforcing the waiver will result in a miscarriage of justice.” Hahn,

359 F.3d at 1327

. A miscarriage of justice will occur only “in one of . . . four situations”:

  (1) “where the district court relied on an impermissible factor such as race” in

  crafting its sentence; (2) “where ineffective assistance of counsel in connection with

  the negotiation of the waiver renders the waiver invalid”; (3) “where the sentence

  exceeds the statutory maximum”; or (4) “where the waiver is otherwise unlawful,”

  meaning that “the error must seriously affect the fairness, integrity or public

  reputation of judicial proceedings, as that test was employed in United States v.

  Olano,

507 U.S. 725, 732

 (1993).” Hahn,

359 F.3d at 1327

 (internal quotation marks

  and brackets omitted).

        Holzer argues that enforcing the appellate waiver provision would result in a

  miscarriage of justice in this case. Aplt. Reply Br. at 10. In support, Holzer again

  asserts that the district court lacked authority under § 3583 to impose Special

  Condition Nine, and he asserts that, in any event, Special Condition Nine infringes on

  his First Amendment rights, specifically his right to freely practice his religion and

  his right to receive information.

        It is not entirely clear which of the four situations outlined in Hahn Holzer is

  relying on in asserting his miscarriage of justice argument. Clearly, neither the first

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  nor second apply here because the district court did not rely on an impermissible

  factor in crafting its sentence and there is no allegation that defense counsel was

  ineffective in connection with the negotiation of the appellate waiver. That leaves

  the last two situations.

         We have held, in interpreting the third situation identified in Hahn, i.e.,

  “where the sentence exceeds the statutory maximum,” that the phrase “‘statutory

  maximum’ . . . refers to the upper limit of punishment that Congress has legislatively

  specified for the violation of a given statute.” Green,

405 F.3d at 1194

. For the

  reasons previously discussed, we conclude that this includes only the quantifiable

  aspects of punishment, such as the length of supervised release, and not any special

  conditions of supervised release that impose limits on a defendant’s conduct.

         That leaves only the final situation listed in Hahn, i.e., where the waiver is

  otherwise unlawful.4 We have held that “[t]his [fourth Hahn] exception looks to

  whether ‘the waiver is otherwise unlawful,’ not to whether another aspect of the

  [sentencing] proceeding may have involved legal error.” United States v. Smith,

500 F.3d 1206, 1213

 (10th Cir. 2007) (emphasis in original) (internal quotation marks and

  citation omitted). In other words, our “inquiry is not whether the sentence is

  unlawful, but whether the waiver itself is unlawful because of some procedural error


         4
           The lead opinion in Hahn stated that this fourth situation will arise only when
  “the alleged error . . . satisf[ies] the fourth prong of the . . . plain error test” outlined
  in United States v. Olano,

507 U.S. 725

 (1993).

359 F.3d at 1329

. Importantly,
  however, this portion of the Hahn opinion did not garner a sufficient number of votes
  to constitute a majority of the en banc court and therefore is not considered part of
  the holding in the case.
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  or because no waiver is possible.” United States v. Sandoval,

477 F.3d 1204, 1208


  (10th Cir. 2007). “An appeal waiver is not ‘unlawful’ merely because the claimed

  error would, in the absence of waiver, be appealable.”

 And “[t]he defendant

  bears the burden of persuasion” in establishing the unlawfulness of the waiver itself.