Estrada v. Smart

Appellate Case: 23-1189    Document: 010111079946   Date Filed: 07/16/2024   Page: 1
                                                                            FILED
                                                                United States Court of Appeals
                                                                        Tenth Circuit
                                     PUBLISH
                                                                        July 16, 2024
                   UNITED STATES COURT OF APPEALS
                                                                    Christopher M. Wolpert
                            FOR THE TENTH CIRCUIT                       Clerk of Court
                          _________________________________

  BRIAN ESTRADA,

        Plaintiff - Appellant,

  v.                                                    No. 23-1189

  JACOB SMART,

        Defendant - Appellee.
                     _________________________________

               Appeal from the United States District Court
                        for the District of Colorado
                   (D.C. No. 1:20-CV-00549-WJM-STV)
                    _________________________________

 Nicole L. Masiello (Robert Reeves Anderson, Arnold & Porter Kaye Scholer
 LLP, Denver, Colorado, and Andrew T. Tutt, Arnold & Porter Kaye Scholer
 LLP, Washington, DC, with her on the briefs), Arnold & Porter Kaye Scholer
 LLP, New York, New York, for Appellant.

 Abigail L. Smith, Senior Assistant Attorney General (Philip J. Weiser,
 Colorado Attorney General, with her on the brief), Colorado Department of
 Law, Denver, Colorado, for Appellee.
                      _________________________________

 Before McHUGH, MURPHY, and FEDERICO, Circuit Judges.
                 _________________________________

 FEDERICO, Circuit Judge.

       When Congress enacted the Prison Litigation Reform Act (“PLRA”) in

 1996, it declared that “[w]hat this country needs . . . is fewer and better
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 prisoner suits.” Jones v. Bock, 

 (2007). The PLRA elevated

 mandatory administrative exhaustion to its current height in 42 U.S.C.

 § 1997e(a). Section 1997e(a) states: “No action shall be brought with

 respect to prison conditions under . . . Federal law, by a prisoner

 confined in any jail, prison, or other correctional facility until such

 administrative remedies as are available are exhausted.” 42 U.S.C.

 § 1997e(a) (emphasis added).

       Section 1997e(a) requires a prisoner to exhaust all available

 administrative remedies “prior to filing a lawsuit regarding prison

 conditions in federal court.” Little v. Jones, 

 (10th Cir.

 2010) (citing § 1997e(a)). Exhaustion under the PLRA is “mandatory” and

 “unexhausted claims cannot be brought in court.” Jones, 

 (citing Porter v. Nussle, 

 (2002)).

       In May 2018, Plaintiff Brian Estrada was a prisoner confined in the

 custody of the Colorado Department of Corrections (“CDOC”). While

 attempting to escape a Colorado county courthouse, he was shot three times

 by Defendant Jacob Smart, a CDOC officer. Estrada later sued Smart under

 

 and alleged excessive force, but the district court granted

 Smart’s summary judgment motion. It concluded that Estrada had failed to

 exhaust all available CDOC administrative remedies by not following

 CDOC’s three-step grievance process.

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       Final judgment was entered, and Estrada timely appealed, so we have

 jurisdiction under 

. Estrada now argues that a county

 courthouse is not a CDOC prison, so his lawsuit is not “with respect to

 prison conditions” under the PLRA. He also claims the CDOC grievance

 procedures apply only to CDOC prisons, so his claim is outside the scope of

 when and where they apply.

       Having considered the record, briefing, and oral argument in full, we

 affirm the entry of summary judgment. In this PLRA case, geography is not

 the controlling factor. Instead, as the district court correctly determined,

 the PLRA and CDOC’s grievance procedures both applied to the shooting of

 a CDOC inmate by a CDOC officer.

                                        I

       In May 2018, Estrada was an inmate of CDOC. That month, CDOC

 transported him to the Logan County Courthouse in northeastern Colorado

 for a hearing in a pending criminal case. While in the jury box of a

 courtroom on the second floor, Estrada attempted to escape. His hands and

 ankles were shackled to his waist, so he could only shuffle across the floor.

 During Estrada’s shuffle across the courtroom, he was shot three times by

 Smart, a CDOC officer, who was posted in the courtroom and in charge of

 guarding Estrada. No other officer in the courtroom had reached for their

 gun. Estrada was unarmed.

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       Estrada survived being shot and returned to custody as a CDOC

 inmate. In 2020, while in CDOC custody, he sued Smart, in his personal

 capacity, in federal district court in Colorado. His complaint alleged a single

 claim for excessive force in violation of the Eighth Amendment under

 § 1983.

       After Estrada filed his First Amended Complaint, Smart moved to

 dismiss under Federal Rule of Civil Procedure (“Rule”) 12(b)(6) based on

 qualified immunity. The district court denied that motion, ruling that

 Smart “should have been on notice that use of deadly force on an unarmed

 prisoner restrained in the manner as was Plaintiff would violate Plaintiff’s

 Eighth Amendment right to be free of the use of excessive force[.]” Aplt.

 App’x at 79–80.

       The case then entered the discovery phase. Beyond Estrada’s

 deposition, it is unclear whether any other depositions occurred. The parties

 cite to no depositions in the record, nor do they mention written discovery.

       After discovery concluded, Smart filed a motion for summary

 judgment under Rule 56 based on his affirmative defense of failure to

 exhaust administrative remedies. Estrada was a CDOC inmate at the time

 of the shooting and when he filed suit, yet he did not pursue CDOC’s three-

 step grievance process regarding the courthouse shooting.



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       In support of the summary judgment motion, Smart introduced the

 following evidence: (1) a declaration from Anthony DeCesaro (the “DeCesaro

 Declaration”), a CDOC Step 3 Grievance Officer with personal knowledge

 about Estrada’s grievance filings and the scope of the CDOC’s grievance

 procedures; (2) CDOC Administrative Regulation (“AR”) 850-04; and (3)

 portions of Estrada’s deposition testimony.

       As described by Estrada in his Opening Brief, the DeCesaro

 Declaration “appended a complete copy of the operative administrative

 regulation governing grievances, and the regulation in effect at the time

 this suit was filed.” Aplt. Br. at 15 (citations omitted). The DeCesaro

 Declaration detailed CDOC’s “formalized three-step grievance process for

 inmates set forth in Administrative Regulation (‘AR’) 850-04.” Aplt. App’x

 at 116.

       At summary judgment, Estrada disputed only the scope of AR 850-04.

 He argued it did not apply to the courthouse shooting, as he pointed out

 that the Logan County Courthouse is not a CDOC facility.

       As to the scope of the administrative regulation, both sides focused on

 AR 850-04(IV)(D)(1), which states that the CDOC grievance procedures

 cover “a broad range of complaints including, but not limited to: policies,

 conditions, and incidents within the facility that affect the offender



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 personally; actions by employees and offenders and for resolving offender

 issues relating to health care concerns.” Id. at 123.

       Smart also showed that other language in AR 850-04 supported his

 interpretation. He pointed to AR 850-04(IV)(D)(2), which lists several

 exclusions for which CDOC’s grievance procedures do not apply; it states

 that “[t]his grievance procedure may not be used to seek review” of the

 excluded topics listed. Id. Yet incidents external to a CDOC facility,

 including a courthouse, are not part of this exclusions list. Id.

       DeCesaro next declared: “Inmates may also file grievances regarding

 incidents that occur outside of the facility while they are in the custody of

 the CDOC, such as during transport to court appearances or medical visits.”

 Aplt. App’x at 117 (citing AR 850-04(IV)(D)(1)-(2)). AR 850-04 supports this

 statement because it says the CDOC grievance procedures are available “to

 offenders sentenced to the [C]DOC. This includes [C]DOC offenders housed

 in private facilities and offenders who have been released to parole,

 community, or ISP supervision.” Aplt. App’x at 121 (AR 850-04(IV)(A)(2));

 see also Aplt. App’x at 117 (DeCesaro Declaration, at ¶ 10) (citing AR 850-

 04(IV)(A)(2)).

        DeCesaro further established that Estrada had filed three grievances

 on unrelated topics in the year following the shooting, which ranged from

 May 1, 2018, to May 30, 2019. Thus, the CDOC grievance system was

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 “available” to Estrada, and he utilized it three times in the year following

 the courthouse shooting. But, as DeCesaro established, Estrada did not file

 a grievance for the courthouse shooting.

       By introducing the DeCesaro Declaration and attachments, Smart

 met his burden of proof on his affirmative defense. He established that

 Estrada failed to exhaust the available CDOC administrative remedies,

 while simultaneously filing three grievances on unrelated topics.

       At this point, the summary judgment burden shifted to Estrada, the

 nonmovant, to show that the CDOC regulations did not apply or were not

 available. To survive summary judgment, Estrada needed to offer evidence.

 But he provided only bare allegations and legal arguments made by his

 counsel about the scope of AR 850-04. And he did not make the definitional

 challenges to the PLRA that he now raises on appeal. Estrada failed to

 attach or cite any evidence or deposition testimony (for example, deposition

 testimony from DeCesaro or a Federal Rule 30(b)(6) deposition of CDOC);

 his response included as exhibits only an inmate orientation video and

 handbook from a CDOC facility. He failed to establish the factual or legal

 significance of either exhibit. Nor did he offer his own declaration or

 deposition testimony to describe what he received from CDOC regarding the

 grievance procedures, when he received it, where he received it, from whom

 he received it, or anything else. Indeed, in support of his argument before

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 the district court, Estrada effectively provided no summary judgment

 evidence.

       The district court granted the motion for summary judgment without

 holding an evidentiary hearing. It ruled that both the PLRA and CDOC’s

 three-step grievance procedures applied to the May 2018 courthouse

 shooting,   and    that    Estrada   failed   to   exhaust   CDOC’s     available

 administrative remedies.

       On appeal, Estrada argues the May 2018 courthouse shooting is

 beyond the scope of both the PLRA, generally, and the CDOC’s specific

 three-step grievance process. According to Estrada, a courthouse is not a

 prison, so his claim about the courthouse shooting is not “with respect to

 prison conditions,” as the scope of § 1997e(a) requires.

                                        II

       “We review de novo the district court’s finding of failure to exhaust

 administrative remedies.” Little, 

 (quoting Jernigan v.

 Stuchell, 

 (10th Cir. 2002)).

       “Failure to exhaust under the PLRA is an affirmative defense.” Tuckel

 v. Grover, 

 (10th Cir. 2011). When a defendant moves

 for summary judgment based on an affirmative defense, Rule 56 puts the

 burden on the defendant to “demonstrate that no disputed material fact

 exists regarding the affirmative defense asserted.” Hutchinson v. Pfeil, 105

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, 564 (10th Cir. 1997). “If the defendant meets this initial burden,

 the plaintiff must then demonstrate with specificity the existence of a

 disputed material fact.” 

 “If the plaintiff fails to make such a showing,

 the affirmative defense bars his claim, and the defendant is then entitled to

 summary judgment as a matter of law.” 

 Applied to this case, “[o]nce”

 Smart “prove[d] that [Estrada] failed to exhaust,” then “the onus f[ell] on

 [Estrada] to show that remedies were unavailable to him[.]” Tuckel, 

.

                                       III

       First, we must decide whether the district court correctly decided the

 exhaustion question, without a hearing, and instead of sending that

 question to a jury. Estrada argues the district court usurped the role of a

 jury by resolving all disputed issues regarding administrative exhaustion

 at summary judgment. Arguing by analogy to a breach of contract claim

 decided under state law, Estrada claims that the district court violated Rule

 56 by resolving all disputes. But the CDOC grievance procedures are not a

 contract between two parties, nor are they interpreted based on state law.

 See Ruggiero v. Cnty. of Orange, 

 (2d Cir. 2006) (“There is

 no indication that Congress intended state law to govern [how we interpret

 the PLRA] . . . or that the PLRA’s exhaustion requirement should vary from

 state to state.”).

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        We affirm the district court’s decision to resolve all disputed issues on

  administrative exhaustion, including all disputed facts (if any existed). The

  district court correctly noted that our circuit “has not specifically instructed

  district courts as to how they should resolve factual disputes in the context

  of exhaustion.” Aplt. App’x at 199. We do so now and join “the Second,

  [Third,] Fifth, Seventh, Ninth, and Eleventh Circuits and hold that judges

  may resolve factual disputes relevant to the exhaustion issue without the

  participation of a jury.” Small v. Camden Cnty., 

 (3d Cir.

  2013) (collecting cases).1

        Prisoners “have a right to a jury trial on the merits, but this right does

  not guarantee resolution by a jury of all factual disputes.” 

.

  Ultimately, “[j]uries decide cases, not issues of judicial traffic control.”

  Pavey v. Conley, 

 (7th Cir. 2008). And “[u]ntil the issue of

  exhaustion is resolved, the court cannot know whether it is to decide the

  case or the prison authorities are to.” 

        More fundamentally, “exhaustion is a precondition for bringing suit”

  under the plain language of § 1997e(a). Small, 

. The PLRA

  states: “‘No action shall be brought with respect to prison conditions . . .


        1 This holding contains a caveat: The holding applies “as long as the

  facts are not bound up with the merits of the underlying dispute.” Id. at
  270. In this case, Estrada makes no argument that the merits are
  intertwined with administrative exhaustion.

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  until such administrative remedies as are available are exhausted.’” 42

  U.S.C. § 1997e(a) (emphasis added). The term “shall” is a direct command

  that we must follow. Smith v. Spizzirri, 

, 1177 (2024)

  (Congress’s “use of the word ‘shall’ ‘creates an obligation impervious to

  judicial discretion.’”) (quoting Lexecon Inc. v. Milberg Weiss Bershad Hynes

  & Lerach, 

 (1998)). Thus, to allow a § 1983 claim to reach a

  jury trial before determining the status of administrative exhaustion would

  violate the statute’s plain language.

        Estrada also claims the district court erred by failing to hold an

  evidentiary hearing. Ordinarily, if there are disputed issues of fact, a

  district court should hold an evidentiary hearing before granting summary

  judgment on the defense of failure to exhaust administrative remedies. In

  this case, however, Estrada offered “no evidence to support” his

  “allegation[s]” about the CDOC grievance procedures “beyond the

  allegation[s] [themselves].” May v. Segovia, 

 (10th Cir.

  2019). While Estrada attached a CDOC prison orientation video and inmate

  handbook to his summary judgment response, they stayed inert without

  testimony or a declaration to give them any force. The mere existence of a

  video and an inmate handbook tells us nothing about whether the CDOC

  grievance procedures were available for Estrada to complain about the

  courthouse shooting.

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        To avoid summary judgment, a nonmovant must offer evidence, not

  bare allegations. See Fed. R. Civ. P. 56(c)(1)(A) (setting forth how a party

  introduces summary judgment evidence, including depositions and

  declarations, to support a factual assertion). Applied here, that standard

  means once Smart introduced evidence showing that Estrada had filed

  three other grievances but none about the May 2018 shooting, the burden

  shifted to Estrada to “do more than refer to allegations of counsel contained

  in a brief to withstand summary judgment.” Adams v. Am. Guar. and Liab.

  Ins. Co., 

 (10th Cir. 2000) (quoting Thomas v. Wichita

  Coca–Cola Bottling Co., 

 (10th Cir. 1992)). “Rather,

  sufficient evidence (pertinent to the material issue) must be identified by

  reference to an affidavit [or declaration],2 a deposition transcript or a

  specific exhibit incorporated therein.” 

 (quoting Thomas, 

); accord Fields v. Okla. State Penitentiary, 

 (10th

  Cir. 2007) (emphasizing that “bald allegations cannot preclude summary

  judgment” in a PLRA exhaustion case).

        In sum, in a prisoner case involving the defense of failure to exhaust,

  a district court should, before trial, resolve all disputed issues of law and

  fact that are not intertwined with the merits of the claim. If the plaintiff



        

 (making affidavits and declarations effectively
        2

  synonymous).
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  establishes a disputed issue of material fact, an evidentiary hearing should

  usually be held. If the district court declines to conduct a hearing, it should

  explain why one is unnecessary. But if neither party requests an

  evidentiary hearing, a district court is not obligated to raise the topic sua

  sponte. Here, the district court correctly followed this procedure.

                                        IV

        We now turn to whether Estrada forfeited his challenge to the scope

  of the PLRA. Estrada argues that the PLRA does not apply to a courthouse

  shooting – or any location outside the prison walls. This argument is new

  because Estrada did not make it before the district court when he opposed

  Smart’s motion for summary judgment. Rather, he focused his argument on

  the scope of the CDOC regulation. See Aplt. App’x at 200.

        However, we will consider this argument on appeal because the

  district court thoroughly analyzed the scope of the PLRA in its order

  granting summary judgment. We set aside our general rules on forfeiture

  and waiver when an issue has been “passed upon,” meaning “the district

  court explicitly [has] consider[ed] and resolve[d] an issue of law on the

  merits.” Tesone v. Empire Mktg. Strategies, 

, 991–92 (10th Cir.

  2019) (quoting United States v. Verner, 

 (10th Cir.

  2016)); United States v. Hernandez-Rodriguez, 

 (10th

  Cir. 2003) (“We conclude that when the district court sua sponte raises and

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  explicitly resolves an issue of law on the merits, the appellant may

  challenge that ruling on appeal on the ground addressed by the district

  court even if he failed to raise the issue in district court. In such a case,

  review on appeal is not for ‘plain error,’ but is subject to the same standard

  of appellate review that would be applicable if the appellant had properly

  raised the issue.”). The district court extensively considered the scope of the

  PLRA, along with the CDOC grievance procedure, when it granted

  summary judgment in favor of Smart. Because it “passed upon” the question

  of the scope of the PLRA, we therefore reach Estrada’s PLRA challenge

  raised on appeal.

                                         V

        Next, we must examine the scope of the PLRA. That is, whether and

  how it applies to Estrada’s § 1983 claim for excessive use of force based upon

  a courthouse shooting.

                                         A

        Regarding the applicability of the PLRA, Estrada’s appellate briefing

  centers around a geography-based test. Under his proposed test, the PLRA’s

  exhaustion requirement applies only to a claim for relief “related to the

  conditions of . . . confinement in prison.” Aplt. Br. at 11. In turn, he contends

  that because a courthouse is not a prison, the PLRA does not apply to the

  May 2018 courthouse shooting.

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        In evaluating Estrada’s geography-based test, we start with the text

  of § 1997e(a). Wichita Ctr. for Graduate Med. Educ., Inc. v. United States,

  

 (10th Cir. 2019) (“As always, we start with the plain

  meaning of the text.”). Congress did not define the terms in § 1997e(a). But

  a related provision of the PLRA, 

(g)(2), defines a “civil

  action with respect to prison conditions” broadly as “any civil proceeding . .

  . with respect to the conditions of confinement or the effects of actions

  by government officials on the lives of persons confined in prison[.]”3

  (emphasis added). The district court cited this definition when it concluded

  that the PLRA applied to a courthouse shooting, and it explained that we

  have cited § 3626(g)(2) in support of applying the PLRA to a prisoner case

  regarding activity outside a prison. Aplt. App’x at 201 (discussing

  Dmytryszyn v. Hickox, 

, *1 (10th Cir. 1999) (unpublished)).

        We agree with the district court’s use of the § 3626(g)(2) definition to

  interpret “prison conditions” in § 1997e(a). Our court has cited § 3626(g)(2) in

  a case concluding that § 1997e(a) reaches a prisoner “challenging the amount




        3 “The PLRA is codified in scattered sections of Titles 11, 18, 28, and

  42 of the United States Code[.]” Green v. Young, 

, 409 n.1 (4th
  Cir. 2006). The PLRA’s exhaustion requirement, § 1997e(a), is in Title 42 of
  the U.S. Code, while § 3626(g)(2) is in Title 18. Both sections were enacted
  at the same time in the same law: the Omnibus Consolidated Recissions and
  Appropriations Act of 1996, PL 104–134, April 26, 1996, 

.

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  of compensation he received for work performed outside the prison.”

  Dmytryszyn, 172 F.3d at *1. In another case, we applied § 1997e(a) to “an

  assault at [a] county courthouse” where the plaintiff was in custody, Forbes v.

  Garcia, 

 (10th Cir. 2017) (unpublished) – a nearly

  identical fact pattern to this case. Thus, although unpublished, we have in two

  prior cases considered these two statutory provisions together to reject the

  strict geographic test proposed by Estrada.

        Estrada counters that the Supreme Court has cast doubt on importing

  the language in § 3626(g)(2) to define the scope of § 1997e(a). We do not

  sense this same doubt. Rather, the Supreme Court “express[ed] no

  definitive opinion on the proper reading of § 3626(g)(2)” as applied to

  § 1997e(a). Porter, 

 n.3.

        Our marrying together of § 3626(g)(2) with § 1997e(a) aligns with

  three other Circuits, who have held it is proper to import the § 3626(g)(2)

  definition to the § 1997e(a) exhaustion requirement. We agree with them

  that both statutes “are part of the same legislation with the same

  overarching objectives,” and “it makes good sense to assume that a

  definition provided by Congress in one statute applies to another related

  statute.” Smith v. Zachary, 

 (7th Cir. 2001); see also

  Ruggerio, 

 (same); Witzke v. Femal, 

, 752–53

  (7th Cir. 2004) (same); Alexander S. v. Boyd, 

 (4th Cir.

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  1997), abrogated on other grounds by Martin v. Hadix, 

 (1999)

  (same).

        Estrada repeatedly cites the Seventh Circuit’s decision in Witzke to

  argue that the phrase “prison conditions” includes only the area inside a

  prison. Aplt. Br. at 22—24. We agree that Witzke is persuasive, but it does

  not help Estrada in this appeal.

        In Witzke, a prisoner alleged that his claim was not “with respect to

  prison conditions” under § 1997e(a) because it involved “his treatment as a

  probationer participating in rehabilitation programs” and in a halfway

  house. 376 F.3d at 749–50; see id. at 750 (“Mr. Witzke contends that he is

  not complaining of prison conditions. Rather, he maintains that the alleged

  events took place while he was a probationer participating in probationary

  programs; therefore, he continues, he is not complaining about prison

  conditions but about his treatment while he was a probationer. Such

  allegations are, in his view, pre-incarceration claims.”). The Seventh Circuit

  rejected the prisoner’s arguments on scope. It first relied on the broad

  definition in § 3626(g)(2) and then observed that the term “prison” is also

  broadly defined in the PLRA as “any Federal, State, or local facility that

  incarcerates or detains juveniles or adults accused of, convicted of,

  sentenced for, or adjudicated delinquent for, violations of criminal law.” Id.

  at 752 (quoting 

(g)(5)); see also Jackson v. Johnson, 475

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 (5th Cir. 2007) (favorably discussing Witzke). Like the court

  in Witzke, we conclude the § 3626(g)(2) definition applies to the PLRA and

  aids in our decision to reject Estrada’s strict geography test.

                                        B

        For Estrada, on the day of the May 2018 courthouse shooting, the

  Logan County courthouse functioned as a “prison.” It was a “local facility”

  that “detains” inmates, like Estrada, “accused” or “convicted” of “violations

  of criminal law[.]” 

(g)(5). Estrada was a prisoner in CDOC

  custody at the time he was shot; he was fully restrained, shackled, and

  under the control of armed CDOC officers inside the courthouse. He was

  only at the courthouse temporarily and only for a hearing in another

  Colorado state criminal case. Likewise, he was transported there (and also

  shot) by a CDOC officer. And, finally, but-for the shooting, he would have

  been transported back to the Logan County jail from the courthouse in

  CDOC custody.

        It is important to our holding that every case fact fits under CDOC’s

  umbrella. When the shooting happened, Estrada was in CDOC custody and

  Smart was acting as a CDOC officer. This posture distinguishes this case

  from the Second Circuit case Estrada relies on, Hubbs v. Suffolk Cnty.

  Sheriff’s Dep’t, 

 (2d Cir. 2015).



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        In Hubbs, the plaintiff sued the sheriff’s deputies under § 1983 for

  beating him in a holding cell inside a courthouse. Id. at 57. The Second

  Circuit reversed summary judgment, but not because of the geographic

  location of the courthouse. Rather, the sheriff’s deputies (defendants) did

  not adduce sufficient evidence to establish the exhaustion affirmative

  defense at the summary judgment stage. Id. at 56–57. The available

  grievance procedure in that case stated it did not apply to issues and events

  outside of the warden’s control, and the defendants’ summary judgment

  filings failed to establish that the deputies fell within the warden’s chain of

  command. Id. at 59–61. As a result, the Second Circuit determined, on the

  limited record before it, “no administrative remedies were available to

  [plaintiff], and there was thus nothing for him to exhaust.” Id. at 61. Here,

  in contrast, Estrada was a CDOC inmate and Smart was a CDOC officer.

  As a result, CDOC’s grievance procedures applied.

        Again, whether the PLRA applies is not dependent strictly and solely

  upon geography but on whether a prisoner is confined in any jail, prison, or

  other correctional facility. Congress used the term “any” in § 1997e(a). “The

  term ‘any’ ensures that the definition has a wide reach[.]” United States v.

  Hutchinson, 

 (10th Cir. 2009) (quoting Boyle v. United

  States, 

 (2009)); see also Nelson v. United States, 

 (10th Cir. 2022) (holding that “the word ‘any’ has an expansive

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  meaning, that is, ‘one or some indiscriminately of whatever kind’”) (quoting

  United States v. Gonzales, 

 (1997)). Here, the word “any”

  expands a list of three nouns already listed disjunctively, i.e., “any jail,

  prison, or other correctional facility[.]” § 1997e(a). “Equally broad is the

  phrase ‘with respect to.’” Pharm. Care Mgmt. Ass’n v. Mulready, 

, 1205 (10th Cir. 2023). The phrase “with respect to prison conditions”

  is therefore “unmistakably broad[.]” 

        “Time and again,” the Supreme Court has “refus[ed] to add unwritten

  limits onto [the PLRA’s] rigorous textual requirements” and “reject[ed]

  every attempt to” narrow the PLRA. Ross v. Blake, 

 (2016).

  In fact, Ҥ 1997e(a) mandates initial recourse to the prison grievance process

  even when a prisoner seeks . . . a remedy not available in that process[.]”

  Porter, 

 n.4 (describing the holding in Booth v. Churner, 

 (2001)).

        We are bound to adhere to this clear guidance. No federal Circuit has

  adopted Estrada’s narrow reading of the PLRA; instead, our sister Circuits

  have all determined the scope of the PLRA is broadly construed, as we do

  again in this case. See, e.g., Ruggiero, 

 (joining “[t]wo other

  courts of appeals” in reading the phrase “any jail, prison, or other

  correctional facility” within § 1997e “expansively”) (first citing Witzke, 

; and then citing Alexander S. v. Boyd, 

 (4th Cir.

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  1997), abrogated on other grounds by Martin v. Hadix, 

 (1999));

  id. at 175 (“By referring to ‘prisoners,’ Congress placed a constraint on suits

  filed by all litigants who could be characterized as prisoners, regardless of

  the type of facility in which they are imprisoned.”).

        In Porter, the Supreme Court addressed the phrase “prison

  conditions” in § 1997e(a) and determined that it “applies to all inmate suits

  about prison life, whether they involve general circumstances or particular

  episodes, and whether they allege excessive force or some other wrong.” 

. Porter did not provide a geographical dimension to this holding

  and did not cabin its reach. Rather, Porter held: “We here read the term

  ‘prison conditions’ not in isolation, but ‘in its proper context.’ The PLRA

  exhaustion provision is captioned ‘Suits by prisoners’; this unqualified

  heading scarcely aids the argument that Congress meant to bi-sect the

  universe of prisoner suits.” 

 at 527–28 (citations omitted).

        Estrada’s appeal also runs contrary to another holding in Porter. In

  his Reply Brief, he claims that “construing the text to impose a temporal

  limit (rather than a geographical limit) does not withstand scrutiny.” Reply

  Br. at 10. But Porter held that it is “plausible that Congress inserted ‘prison

  conditions’ into the exhaustion provision simply to make it clear that

  preincarceration claims fall outside § 1997e(a), for example, a § 1983 claim

  against the prisoner’s arresting officer.” 

. Although the

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  temporal test may limit the statute’s reach, nothing indicates that Congress

  intended courts to add a geographic limitation.

                                        C

        Another reason we determine the PLRA’s scope broadly is because

  narrowing it to only apply within the prison walls would subvert a major

  purpose of the PLRA: to improve the overall conditions of confinement by

  drawing immediate attention to prisoner treatment issues as they occur.

  Rapid reporting allows corrections officers and officials to address problems

  quickly, not months or years later following the outcome of a lawsuit.

        For example, in this case, if Estrada had timely pursued the three-

  step grievance process regarding the courthouse shooting, he would have

  alerted prison officials that CDOC officers perhaps need additional training

  on the appropriate tactics and means to prevent prisoners in custody from

  escaping a courthouse. Or, at the very least, his grievances would have

  drawn CDOC’s attention to Smart, who shot a fully restrained prisoner

  three times without any attempt to use a taser or other lesser force.

  Estrada’s unwarranted shooting “by a corrections officer may be reflective

  of a systemic problem traceable to poor hiring practices, inadequate

  training, or insufficient supervision.” 

; see also Ruggerio, 

 (explaining the importance of the “larger interests at stake under the

  PLRA” beyond the prisoner’s federal lawsuit).

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        Carving out a wide exception for all incidents that happen anywhere

  beyond the boundary of a prison would unravel the PLRA’s blanket

  coverage. As oral argument in this case demonstrated, these gaps in

  coverage would cover far more than courthouse shootings. When pressed,

  Estrada’s counsel could not defend an objective test based on geography

  (and, in fact, disclaimed proposing a geographic test for the PLRA, at one

  point) or refute that if we adopted Estrada’s interpretation of the PLRA, all

  transportation of all prisoners to or from prisons would be deemed outside

  the zone of the PLRA. Such gaps would be significant; prisoners routinely

  are transported from prison to other correctional facilities, medical

  appointments, or courthouses.

        Estrada’s geography-based test is also contrary to the history and

  statutory context of the PLRA. See Ross, 

 (“So too, the history

  of the PLRA underscores the mandatory nature of its exhaustion regime.”).

  Congress passed the PLRA for a variety of reasons, including to “reduce the

  ‘disruptive tide of frivolous prisoner litigation.’” Tuckel, 

  (quoting Woodford v. Ngo, 

 (2006)). The goal was “fewer and

  better prisoner suits.” Jones, 

. Congress also sought “to

  eliminate unwarranted federal-court interference with the administration

  of prisons,” Woodford, 

, and “to . . . afford[ ] corrections



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  officials time and opportunity to address complaints internally before

  allowing the initiation of a federal case.” Porter, 

.

        Requiring a prisoner to file a grievance is not a technicality; instead,

  it is mandatory to ensure prison “efficiency” and “administrative agency

  authority” by allowing prison officials to promptly review incidents and

  gather evidence, as well as maintain control over the flow of prison life.

  Woodford, 

 (quoting McCarthy v. Madigan, 

  (1992)). Administrative exhaustion alerts prison officials to problems as

  they occur, avoiding delays and the loss or destruction of evidence.

  Exhaustion also gives an agency the “‘opportunity to correct its own

  mistakes with respect to the programs it administers before it is haled into

  federal court,’ and it discourages ‘disregard of [the agency’s] procedures.’”

  

 (quoting McCarthy, 

).

        As a result, if a prisoner later files a federal lawsuit, the parties and

  the court will have a developed factual record. See id. at 95 (explaining that

  “proper exhaustion often results in the creation of an administrative record

  that is helpful to the court [because] [w]hen a grievance is filed shortly after

  the event giving rise to the grievance, witnesses can be identified and

  questioned while memories are still fresh, and evidence can be gathered and

  preserved”). From a prisoner’s perspective, administrative exhaustion plays

  a critical role in gathering and preserving critical evidence.

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        We also must consider the statutory evolution of administrative

  exhaustion. The PLRA “differs markedly from its predecessor.” Porter, 

. In passing the PLRA, Congress “invigorated” the exhaustion

  requirement. Woodford, 

 (quoting Porter, 

).

  Prior to 1980, prisoners faced “no obligation to exhaust administrative

  remedies.” 

 Congress then initially “enacted a weak exhaustion

  provision” that was “in large part discretionary” and “authorized district

  courts to stay actions . . . for a limited time while a prisoner exhausted ‘such

  plain, speedy, and effective administrative remedies as are available.’” 

  (quoting § 1997e(a)(1) (1994 ed.)).

        “[T]he new § 1997e(a) removed the conditions that administrative

  remedies be ‘plain, speedy, and effective’ and that they satisfy minimum

  standards.” Ross, 

 (quoting Porter, 

). We must

  acknowledge that “[w]hen Congress amends legislation, courts must

  ‘presume it intends [the change] to have real and substantial effect.’” 

 at

  641–42 (quoting Stone v. INS, 

 (1995)). Thus, because

  Congress’ intent in passing the PLRA was to broaden and strengthen

  administrative exhaustion, we decline to exclude the courthouse shooting

  from the reach of the PLRA.




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        For all these reasons, we hold that the PLRA’s exhaustion

  requirement applies to the May 2018 courthouse shooting of a CDOC inmate

  by a CDOC officer.

                                       VI

        We now turn to the scope of the CDOC grievance procedures.

  Ultimately, we must decide whether AR 850-04 applies to a courthouse

  shooting, because “it is the prison’s requirements, and not the PLRA, that

  define the boundaries of proper exhaustion.” Jones, 

.

        The district court ruled that to plead a federal lawsuit based on the

  courthouse shooting, Estrada was first required to file Steps 1, 2, and 3

  grievances about the shooting, as set forth in CDOC’s AR 850-04. In this

  case, like in Jones, which analyzed administrative exhaustion within the

  Michigan Department of Corrections, AR 850-04 “describes what issues are

  grievable[.]” Jones, 549 U.S. at 206–07. Thus, AR 850-04 defines the scope

  of the CDOC grievance procedures.

        Here is the language in AR 850-04 that determines whether the three-

  step grievance procedures applied to Estrada’s courthouse shooting:




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  Aplt. App’x at 123 (highlight added).

        In analyzing this language, the district court provided four reasons

  why the courthouse shooting is within the scope of AR 850-04. The first

  three reasons are based on the highlighted language above, and the fourth

  is based on nearby language in AR 850-04:


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     1. Including But Not Limited To. First, “AR 850-04 explicitly states that
        the grievance procedure includes issues that occur within the facility,
        but is not limited to them.”

     2. Employees’ Actions. Second, “the phrase ‘actions by employees and
        offenders’ is not placed within the previous portion of the paragraph
        which describes incidents within the facility, indicating that employees’
        actions need not necessarily occur within the facility to be covered by AR
        850-04.”

     3. Not Listed as an Exclusion. Third, the list of exclusions included in
        AR 850-04 “notably does not include incidents occurring outside the
        prison, quite clearly implying that the procedure is available for such
        incidents.”

     4. Covers Offenders Outside the Facility. Fourth, “[Smart] points out
        that CDOC policy does mention covering incidents outside the facility in
        the context of who the grievance procedure is made available to in AR
        850-04(IV)(A)(2). To wit, the AR provides that ‘[t]he grievance procedure
        is available only to offenders sentenced to the [C]DOC. This includes
        [C]DOC offenders housed in private facilities and offenders who have
        been released to parole, community, or ISP supervision.’” (citation
        omitted).

  Aplt. App’x at 197, 204.

        We conclude that the district court’s analysis of the scope of the CDOC

  regulations is reasonable. The fourth point, on its own, disproves Estrada’s

  repeated assertion that nothing suggests the CDOC procedures apply

  outside the prison walls.

        The Supreme Court has advised that “[w]hen an administrative

  process is susceptible of multiple reasonable interpretations, Congress has

  determined that the inmate should err on the side of exhaustion.” Ross, 

. In Ross, the Supreme Court expressly held that “new § 1997e(a)

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  removed the conditions that administrative remedies be ‘plain, speedy, and

  effective’ and that they satisfy minimum standards.” Id. at 641 (quoting

  Porter, 

). As a result, a prisoner is not excused from the duty

  to exhaust all administrative remedies by pointing to a “reasonable mistake

  about the meaning of a prison’s grievance procedures.” Id.; see also Porter,

  

 n.4 (“[T]he PLRA establishes a different regime. For

  litigation within § 1997e(a)’s compass, Congress has replaced the ‘general

  rule of non-exhaustion’ with a general rule of exhaustion.”).

        Applied to this case, the Supreme Court’s dual guidance in Ross and

  Porter is dispositive. The district court’s inquiry was not to choose who, as

  between Estrada and Smart, offered a better interpretation of AR 850-04.

  Instead, under controlling Supreme Court law, Estrada was required to

  show that it would be unreasonable to apply CDOC’s three-step grievance

  procedures to the courthouse shooting. Ross, 

. This is a

  more difficult showing, and Estrada failed to make it. The district court

  pointed to four reasons why it is reasonable to apply AR 850-04 to the

  courthouse shooting, and we affirm this “reasonable interpretation of the

  grievance requirements.” Thomas v. Parker, 

 (10th Cir.

  2010).

        Ultimately, we affirm the district court’s entry of summary judgment.

  We agree that, because Estrada failed to exhaust his § 1983 claim regarding

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  the courthouse shooting by following CDOC’s three-step grievance process,

  his claim was barred.

                                       VII

        Estrada makes a final argument that we decline to reach. Trying to

  expand what he argued in response to the summary judgment motion,

  Estrada argues on appeal that his claim was not subject to the PLRA based

  on an exception. He did not make this argument below. We acknowledge a

  “built-in exception to the exhaustion requirement: A prisoner need not

  exhaust remedies if they are not ‘available.’” Ross, 578 U.S. at 635–36. This

  “unavailability” of administrative remedies exception can take three forms:

     1. Dead end: if the administrative process “operates as a simple
        dead end—with officers unable or consistently unwilling to provide
        any relief to aggrieved inmates”;

     2. Opaqueness: if it is so “opaque that it becomes, practically
        speaking, incapable of use”; and

     3. Threats or Intimidation: if prison administrators “thwart
        inmates from taking advantage of a grievance process through
        machination, misrepresentation, or intimidation.”


  Id. at 643–44; see also May, 

 (same).

        Estrada claims on appeal that the opaqueness exception applies here,

  because no prisoner, including him, could determine that AR 850-04 applied

  to a courthouse shooting. But this new argument was never presented to

  the district court, and we decline to reach it. As we have repeatedly held,

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  we “deem arguments that litigants fail to present before the district court

  but then subsequently urge on appeal to be forfeited.” Havens v. Colo. Dep’t

  of Corr., 

 (10th Cir. 2018). The district court specifically

  noted that it did not analyze opaqueness because Estrada did not argue it.

  Aplt. App’x at 208.

        In addition, failure to argue plain error on appeal waives the issue.

  United States v. Leffler, 

 (10th Cir. 2019) (“When an

  appellant fails to preserve an issue and also fails to make a plain-error

  argument on appeal, we ordinarily deem the issue waived (rather than

  merely forfeited) and decline to review the issue at all—for plain error or

  otherwise.”). In this case, Estrada argued plain error on appeal, but he

  waited until the reply brief, affording Smart no opportunity to respond. We

  “need not decide whether” raising plain error for the first time in a reply

  “avoids waiver because [Estrada’s] argument is insufficient.” Hayes v.

  SkyWest Airlines, Inc., 

, 1201 (10th Cir. 2021). Estrada fails

  to show it is “clear or obvious that the district court should have” applied

  the opaqueness exception when he “did not present” this argument – or any

  probative evidence supporting it – at summary judgment. 

                                       VIII

        The district court’s entry of summary judgment against Estrada is

  AFFIRMED.

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