United States v. LeCompte , 800 F.3d 1209 ( 2015 )


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  •                                                                                   FILED
    United States Court of Appeals
    PUBLISH                                Tenth Circuit
    UNITED STATES COURT OF APPEALS                        September 1, 2015
    Elisabeth A. Shumaker
    TENTH CIRCUIT                               Clerk of Court
    UNITED STATES OF AMERICA,
    Plaintiff - Appellee,
    v.                                                         No. 14-2200
    PAUL LECOMPTE,
    Defendant - Appellant.
    APPEAL FROM THE UNITED STATES DISTRICT COURT
    FOR THE DISTRICT OF NEW MEXICO
    (D.C. No. 5:13-CR-02677-KG-1)
    Caleb Kruckenberg, Assistant Federal Public Defender, Office of the Federal Public
    Defender for the District of New Mexico, Las Cruces, New Mexico, appearing for
    Appellant.
    David N. Williams, Assistant United States Attorney (Damon P. Martinez, United
    States Attorney, with him on the brief), Office of the United States Attorney for the
    District of New Mexico, Albuquerque, New Mexico, appearing for Appellee.
    Before LUCERO, TYMKOVICH, and MATHESON, Circuit Judges.
    MATHESON, Circuit Judge.
    In 2003, Paul LeCompte pled guilty in state court to a sex offense involving a
    minor female and was required to register as a sex offender. As a result, he was
    required to register as a sex offender. In 2010, after having traveled in interstate
    commerce, Mr. LeCompte failed to register. In 2011, he pled guilty in federal court
    to failing to register under the Sex Offender Registration and Notification Act
    (“SORNA”). As part of the sentence on this conviction, the district court imposed
    several conditions, including one prohibiting any association with minors except in
    the presence of an adult approved by the U.S. Probation Office (“Probation”).
    In 2014, a probation officer visited Mr. LeCompte’s home and found him
    sitting outside with several adults (none of them approved by Probation) and his
    then-girlfriend’s1 three-year-old granddaughter. Because Mr. LeCompte had
    associated with a minor—the granddaughter—in the absence of an approved adult,
    Probation filed a petition to revoke Mr. LeCompte’s supervised release. Mr.
    LeCompte moved to dismiss, challenging the supervised release condition as applied.
    The district court denied his motion, revoked his supervised release, and sentenced
    Mr. LeCompte to a prison term. It also imposed six standard sex offender conditions.
    Mr. LeCompte appeals the district court’s denial of his motion to dismiss. He
    also challenges the procedural and substantive reasonableness of the six sex offender
    conditions imposed. Exercising jurisdiction under 18 U.S.C. § 3742(a), we reverse
    the denial of the motion to dismiss and remand for further proceedings. We do not
    reach his challenges to the six conditions.
    1
    Mr. LeCompte’s then-girlfriend has since become his fiancée.
    -2-
    I. BACKGROUND
    A. Factual and Procedural History
    1. Underlying Sex Offense
    On July 21, 2003, Mr. LeCompte pled guilty to five counts of criminal sexual
    penetration in the fourth degree in violation of New Mexico law. He was 29 years
    old. The offense arose from Mr. LeCompte’s engaging in sexual encounters with a
    minor female approximately 15 times, aware she was 14 years old. He was sentenced
    to 15 months in prison and was required to register as a sex offender.
    2. Failure to Register Conviction and Sentencing
    After traveling from New Mexico to Nevada in 2010, Mr. LeCompte failed to
    register. On May 26, 2011, Mr. LeCompte pled guilty to failing to register as a sex
    offender after having traveled in interstate commerce, in violation of 18 U.S.C.
    § 2250(a), a SORNA provision. Before sentencing, Probation prepared a presentence
    report (“PSR”). The PSR recommended the imposition of several special conditions,
    including one titled “Minor Prohibition”: “You shall not associate with persons
    under the age of eighteen (18), except in the presence of a responsible adult who is
    aware of the nature of your background and current offense, and who has been
    approved by the probation officer.” ROA, Vol. 2 at 42.
    On September 12, 2011, the district court sentenced Mr. LeCompte to 21
    months in prison and five years of supervised release. The court also imposed 22
    conditions of supervised release, including the minor prohibition condition
    -3-
    recommended by Probation. Mr. LeCompte did not appeal the minor prohibition
    condition.
    3. Revocation of Supervised Release
    On August 28, 2014, Probation Officer Chris Pena visited Mr. LeCompte at his
    residence. Upon arrival, he saw Mr. LeCompte sitting outside with his grandparents,
    his then-girlfriend, her adult daughter, and her three-year-old granddaughter. There
    was no approved adult on the premises. The incident presented a technical violation
    of the minor prohibition condition.
    In response to this incident, Officer Pena administered a polygraph
    examination to Mr. LeCompte. Officer Pena determined he would not petition for a
    violation of supervised release if the polygraph test indicated this incident had been
    Mr. LeCompte’s only contact with a child. During the polygraph examination,
    Officer Pena asked Mr. LeCompte about any other contact with children. He denied
    having any such contact. But when the polygraph examination indicated that Mr.
    LeCompte’s response was deceptive, he revealed having had two other interactions
    with minor children. He explained that earlier in August 2014, he had met his
    girlfriend at her house and her minor granddaughter had been present, but he and his
    girlfriend promptly left the house. Mr. LeCompte also reported that he was at church
    when his “step-brother[’s] kids [came] up to [him] and [gave him] a hug before
    church started.” 
    Id. at 148.2
    2
    Mr. LeCompte provided this information about his church encounter in the
    “Failure of Polygraph Addendum Report Form,” ROA, Vol. 2 at 148, a form that Mr.
    -4-
    On September 18, 2014, Officer Pena filed a “Petition for Revocation of
    Supervised Release,” which alleged that Mr. LeCompte had violated the minor
    prohibition condition based on all three incidents. On October 9, 2014, Mr. LeCompte
    moved to dismiss the petition, challenging the minor prohibition condition as applied to
    the conduct underlying the alleged violation of supervised release. The Government filed
    a response in opposition.
    On November 3, 2014, the district court held a hearing on the motion. Mr.
    LeCompte’s counsel first argued the court was “the proper venue for this motion. . . .
    Certainly, Mr. LeCompte could have appealed these conditions when they were first
    imposed, but now he’s facing violation, and he’s entitled, as I read the cases, to challenge
    the basis for that condition as it applies to his conduct.” ROA, Vol. 5 at 4. The
    Government contended the court could not hear the motion. The district court concluded
    Mr. LeCompte could raise an as-applied challenge to the condition’s validity during the
    revocation proceedings.
    The court then heard testimony from Officer Pena. He testified, in part, that
    “any contact,” even a “chance encounter,” with a child could “potentially” be a
    violation of the minor prohibition condition. 
    Id. at 19,
    25. He described the approval
    process for a “responsible adult” as potentially “lengthy,” 
    id. at 28,
    involving the
    LeCompte had to fill out after he had been found untruthful in the polygraph
    examination, see 
    id. at 7-8.
    The form seems to indicate the incident with his niece
    and nephew occurred only once. See 
    id. at 148.
    But Officer Pena stated that Mr.
    LeCompte admitted this contact occurred each week when he attended church. The
    district court made no finding on the matter and, as explained below, based its
    violation on only the August 28 incident.
    -5-
    adult in individual sessions with Mr. LeCompte in sex-offender treatment and then
    determining “as time goes on” whether to approve the person “based on [his or her]
    willingness to participate [and] based on the defendant’s progress in treatment and
    assessments,” 
    id. at 29-30.
    After hearing this testimony and the parties’ arguments on the merits of the as-
    applied challenge, the district court orally denied Mr. LeCompte’s motion to dismiss
    and revoked his supervised release. The court chose to address Mr. LeCompte’s as-
    applied challenge to the minor prohibition condition on the merits, and concluded the
    condition was “reasonably related to the circumstances that gave rise to the offense
    of conviction and to the history and characteristics of the defendant.” 
    Id. at 39-40.
    The court also said the motion to dismiss could be denied under a heightened scrutiny
    standard, 
    id. at 40,
    presumably because it believed the minor prohibition condition
    implicated Mr. LeCompte’s fundamental right to familial association, as Mr.
    LeCompte had argued.
    The district court rejected Mr. LeCompte’s as-applied challenge to the minor
    prohibition condition, considering only the August 28 incident when he was found
    outside his home with his girlfriend’s granddaughter. The court enumerated three
    similarities between the violation and Mr. LeCompte’s 2003 offense. First, the
    alleged supervised release violation and his prior offense involved females. Second,
    the alleged violation and the prior offense involved minors. Third, the prior offense
    involved “the potential to exploit an adult relationship in order to have access to the
    -6-
    minor female child,” and the condition was intended to prevent that type of behavior.
    Id.3
    For Mr. LeCompte’s violation of his supervised release condition, the district
    court calculated a Guidelines range of 6 to 12 months. The court sentenced Mr.
    LeCompte to six months in prison and five years of supervised release. It imposed
    six sex offender conditions. Mr. LeCompte objected generally to the imposition of
    sex offender conditions and to several of the conditions in particular. The court
    overruled the objections.
    Mr. LeCompte now appeals the denial of his motion to dismiss. He also
    challenges the procedural and substantive reasonableness of the six sex offender
    conditions imposed.
    II. DISCUSSION
    Because we reverse and remand for further consideration on the motion to
    dismiss, we need not reach Mr. LeCompte’s remaining challenges to the conditions
    imposed after his supervised release was revoked.
    3
    As to the church incident, the district court determined Mr. LeCompte did not
    have sufficient notice on how to comply with the condition in church. It held that “in
    order to avoid allegations of unapproved contact in the future, Defendant will need to
    have an adult who has been approved by the probation officer as responsible and who
    is aware of the nature of Defendant’s background and current offense with him when
    he attends church.” ROA, Vol. 3 at 13.
    On appeal, the Government relies only on the August 28 incident to justify the
    district court’s denial of Mr. LeCompte’s motion to dismiss. It does not rely on the
    prior contact with his girlfriend’s minor granddaughter or the church incident.
    -7-
    A. Motion to Dismiss
    The parties agree that the incident at Mr. LeCompte’s residence was a
    violation of the minor prohibition condition. But Mr. LeCompte moved to dismiss
    the revocation petition based on an as-applied challenge to the condition itself. We
    consider (1) whether the district court properly considered Mr. LeCompte’s motion to
    dismiss and, if so, (2) whether the district court properly analyzed the as-applied
    challenge.
    1. The District Court’s Consideration of the Motion to Dismiss
    At the revocation hearing, the district court first determined that it had
    authority to rule on Mr. LeCompte’s motion to dismiss, which challenged the
    supervised release condition as applied:
    On that issue, really, the jurisdictional question, I’m going to, in effect,
    grant the motion . . . for the narrow holding or at least narrow authority
    to raise this issue at the district court level, that the argument is that the
    condition is unconstitutional as applied. . . . It’s a narrow enough issue
    relating to the application of the condition of release to Mr. LeCompte
    specifically, so it is an as-applied kind of question that he’s put forth.
    ROA, Vol. 5 at 5-6, 39.
    The Government disputes this ruling on appeal, contending “a district court
    does not have jurisdiction to consider a motion to dismiss a petition to revoke
    supervised release when the defendant could have, but did not, appeal from the
    sentence that imposed the conditions of supervised release.” Aplee. Br. at 11. It
    notes Mr. LeCompte did not object when the minor prohibition condition was
    originally imposed in 2011, did not appeal the 2011 sentence, did not challenge the
    -8-
    condition in collateral proceedings under 28 U.S.C. § 2255, brought the present
    challenge more than three years after the 2011 sentence was imposed, and “required
    an evidentiary hearing to establish his theory.” 
    Id. at 8.4
    A district court has jurisdiction under 18 U.S.C. § 3231 to hear cases involving
    “offenses against the laws of the United States.” Further, under 18 U.S.C.
    § 3583(e)(3), a district court may consider whether a defendant’s supervised release
    should be revoked. See United States v. Bailey, 
    259 F.3d 1216
    , 1218-19 (10th Cir.
    2001); see also United States v. Maloney, 
    513 F.3d 350
    , 354 (3d Cir. 2008). The
    Government cites no authority for its assertion that Mr. LeCompte’s failure to appeal
    the condition when it was first imposed would bar the district court from hearing his
    as-applied challenge. Indeed, it appears to concede that Mr. LeCompte could have
    made this as-applied challenge had he appealed the condition when it was first
    imposed. Aplee. Br. at 11 (“No one doubts that a defendant against whom a petition
    for supervised release is filed has the right to raise an as-applied challenge to the
    condition as a defense to the petition.”). But Mr. LeCompte seems to stand in the
    same position in this revocation proceeding as a defendant who had challenged a
    condition on appeal and then lost. That defendant could still bring an as-applied
    challenge in a revocation proceeding, not because he or she had exhausted the right
    to appeal, but because the condition could be applied in a manner that would violate
    4
    We are unsure what the Government’s last contention about the evidentiary
    hearing means. Mr. LeCompte presented his as-applied theory in his motion to
    dismiss as well as during the revocation hearing.
    -9-
    his or her rights. Whether or not the defendant challenged the condition on appeal
    does not change that it could still be applied improperly.
    When Probation files a petition for revocation of supervised release, a
    defendant may move to dismiss that petition because it is legally defective in some
    way, see United States v. Davis, 
    151 F.3d 1304
    , 1305-06 (10th Cir. 1998)
    (considering a defendant’s motion to dismiss a petition for revocation of supervised
    release), including a challenge that the condition at issue is improper as applied to
    him. In an unpublished decision, our court permitted a defendant to make such an as-
    applied challenge to his supervised release condition even when he had failed to
    appeal the condition when it was first imposed. See United States v. Kennedy, 106 F.
    App’x 688, 690 (10th Cir. 2004) (unpublished).5 In Kennedy, the government
    asserted that the defendant had waived an as-applied challenge to the revocation of
    his supervised release by failing to appeal the special condition within ten days after
    the entry of judgment. 
    Id. We disagreed:
    “As Kennedy is not challenging the
    propriety of the special condition on its face, but rather is challenging the special
    condition as applied to his conduct, we conclude we have jurisdiction to hear his
    vagueness as applied argument.” 
    Id. Other circuits
    also have approved of district courts’ considering as-applied
    challenges to supervised release conditions when the defendant had failed to object to
    5
    Although not precedential, we find the reasoning of this unpublished opinion
    instructive. See 10th Cir. R. 32.1 (“Unpublished decisions are not precedential, but
    may be cited for their persuasive value.”); see also Fed. R. App. P. 32.1.
    - 10 -
    or appeal the condition when imposed,6 including as-applied challenges similar to the
    one in this case.7
    6
    See United States v. Brigham, 
    569 F.3d 220
    , 232 (5th Cir. 2009) (“Because
    Brigham did not object to the imposition of these special conditions of supervised
    release at sentencing, the Court considers them only on an ‘as applied’ basis . . . .”);
    United States v. Locke, 
    482 F.3d 764
    , 766 (5th Cir. 2007) (“Locke did not challenge
    the conditions of probation when imposed, only upon revocation. As such, we view
    Locke’s arguments as challenges to the constitutionality of certain conditions of his
    probation as applied to him in the revocation.”); United States v. Johnson, 
    138 F.3d 115
    , 118 n.3 (4th Cir. 1998) (discussing United States v. Taylor, 
    321 F.2d 339
    , 341-
    42 (4th Cir. 1963), in which the court permitted a defendant “to challenge the
    revocation of his probation for non-payment of his fine despite his failure, in an
    earlier appeal, to challenge the fine based on his inability to pay” because “the
    defendant did not challenge the imposition of his fine” and instead “challenged the
    propriety of the revocation based upon his failure to pay a fine he allegedly was
    unable to pay”); United States v. Beech-Nut Nutrition Corp., 
    925 F.2d 604
    , 607 (2d
    Cir. 1991) (“A threshold issue raised by the government is whether appellant lost the
    right to appeal the denial of his request [to travel for business while on probation]
    because he failed to take an appeal from his original sentence. The government
    argues that appellant is, in effect, contesting the conditions of his probation, and not
    having done so at the time he was sentenced should be barred from appealing those
    conditions now. We disagree. Appellant is contesting the district court’s application
    of the conditions of probation, not the conditions themselves.”).
    Courts have consistently said that a defendant cannot challenge the condition
    on its face at a revocation hearing. See, e.g., United States v. Helton, No. 14-7070,
    
    2015 WL 2342881
    , at *2 (10th Cir. May 18, 2015) (unpublished); United States v.
    Preacely, 
    702 F.3d 373
    , 376 (7th Cir. 2012). But the challenge here is as-applied. In
    Helton, we cited to Beech-Nut Nutrition Corp. for its distinction between “facial
    challenges to conditions” and “challenges to their specific application” and its
    holding that district courts could hear the latter. 
    2015 WL 2342881
    at *2.
    7
    See 
    Brigham, 569 F.3d at 232-33
    (considering the appellant’s arguments that
    the special conditions, as applied, violated the § 3583(d) factors); 
    Locke, 482 F.3d at 768
    (considering and rejecting an as-applied challenge to a “probation condition
    denying [the defendant’s] access to the Internet” on the basis that it “imposed a
    greater deprivation of his First Amendment rights than was reasonably necessary”);
    United States v. Friedberg, 
    78 F.3d 94
    , 96-97 (2d Cir. 1996) (considering whether
    the district court’s denial of the defendant’s request to travel, which would have been
    an exception to a probation condition, met the Federal Probation Act goals of
    rehabilitating the defendant and protecting the public); Beech-Nut Nutrition Corp.,
    - 11 -
    The rationale for permitting an as-applied challenge is sound. When a court
    imposes a particular condition of supervised release, a defendant may not be able to
    anticipate that Probation will consider particular conduct prohibited. In fact, courts
    have dismissed challenges to conditions when first imposed based on a defendant’s
    fear of hypothetical applications of the condition. See United States v. Rhodes, 
    552 F.3d 624
    , 628 (7th Cir. 2009) (rejecting as unripe the defendant’s challenge to a
    condition that said he could be subject to penile plethysmograph testing because such
    testing would not necessarily be imposed after his release from prison); United States
    v. Schoenborn, 
    4 F.3d 1424
    , 1434 (7th Cir. 1993) (rejecting as unripe the defendant’s
    argument that any violation of his supervised release, “say for missing an
    appointment with his probation officer or for drinking a beer,” could result in
    additional jail time exceeding the statutory maximum because a court cannot render a
    decision in “hypothetical cases”).
    Thus, allowing as-applied challenges to the condition accounts for
    unanticipated applications. See United States v. Mickelson, 
    433 F.3d 1050
    , 1057 (8th
    Cir. 2006) (rejecting a facial challenge that a condition was unreasonable, but 
    adding 925 F.2d at 608
    (considering whether the application of a condition served the
    Federal Probation Act goals of rehabilitating the defendant and protecting the
    public); see also United States v. Roberts, 229 F. App’x 172, 178 (3d Cir. 2007)
    (unpublished) (remanding the case with instructions to consider the defendants’
    argument, made in a request for a modification or clarification of their supervised
    release conditions, that a “condition, as applied by the probation office, does not
    meet the requirements of 18 U.S.C. § 3583(d) and that the probation office’s refusal
    of permission for defendants to associate renders an otherwise permissible condition
    of release unconstitutional”).
    - 12 -
    that “if such permission is arbitrarily or unfairly denied, [the defendant] is free to
    seek relief from the district court under § 3583(e)”). To hold otherwise would place
    courts and defendants in a double bind: conditions may be unreviewable when
    initially imposed as unripe or too abstract but also unreviewable later on when
    applied to a particular factual scenario.
    For these reasons, we reject the Government’s arguments and review the
    district court’s analysis of the motion to dismiss.
    2. The As-Applied Challenge
    We must determine whether the district court erred by denying Mr.
    LeCompte’s motion to dismiss after determining the minor prohibition condition
    itself is proper as applied to the facts underlying the violation.
    a. Standard of review
    The district court concluded the condition is proper as applied because “the
    special condition is reasonably related to the circumstances that gave rise to the
    offense of conviction and to the history and characteristics of the defendant.” ROA,
    Vol. 5 at 39-40.
    We review the “district court’s decision to revoke supervised release for abuse
    of discretion. Legal questions relating to the revocation of supervised release are
    reviewed de novo. A district court necessarily abuses its discretion when it makes an
    error of law.” United States v. Disney, 
    253 F.3d 1211
    , 1213 (10th Cir. 2001)
    (quotations and citations omitted); see also United States v. Brigham, 
    569 F.3d 220
    ,
    232-34 (5th Cir. 2009) (stating “[w]hile revocation decisions are reviewed for abuse
    - 13 -
    of discretion, the legal and constitutional bases of the challenges thereto are reviewed
    de novo” and then analyzing the as-applied challenge seemingly under de novo
    review); United States v. Locke, 
    482 F.3d 764
    , 766-68 (5th Cir. 2007) (same); United
    States v. Roberts, 229 F. App’x 172, 175 (3d Cir. 2007) (unpublished) (noting its
    consideration of the district court’s denial of the defendants’ motion to reconsider,
    which was based on an as-applied challenge, “is plenary where the denial was based
    on the interpretation and application of a legal precept” (quotations omitted)).8
    b. Merits
    Mr. LeCompte argues the minor prohibition condition is unreasonable under
    18 U.S.C. § 3583(d) as applied to his conduct. We remand for further proceedings
    consistent with this opinion.
    18 U.S.C. § 3583(d) provides that conditions of supervised release must:
    (1) [be] reasonably related to the factors set forth in section 3553(a)(1),
    (a)(2)(B), (a)(2)(C), and (a)(2)(D);
    (2) involve[] no greater deprivation of liberty than is reasonably
    necessary for the purposes set forth in section 3553(a)(2)(B), (a)(2)(C),
    and (a)(2)(D); and
    (3) [be] consistent with any pertinent policy statements issued by the
    Sentencing Commission pursuant to 28 U.S.C. 994(a).
    8
    We base our analysis only on the August 28 incident. The condition, as
    applied, restricted Mr. LeCompte’s association with his girlfriend’s granddaughter,
    not a child or grandchild of his own. Mr. LeCompte argues a heightened standard of
    review applies because of an alleged restriction on his right to familial association
    and his First Amendment associational right. This circuit has not squarely addressed
    what standard of review applies under these circumstances, and we need not address
    this issue here given that we reverse under the abuse-of-discretion standard.
    - 14 -
    18 U.S.C. § 3583(d). The relevant § 3553 factors for § 3583(d)(1) are (i) the nature
    and circumstances of the offense and the defendant’s history and characteristics,
    (ii) the deterrence of criminal conduct, (iii) the protection of the public from further
    crimes of the defendant, and (iv) the defendant’s educational, vocational, medical, or
    other correctional needs. 
    Id. §§ 3553(a)(1),
    (a)(2)(B), (a)(2)(C), and (a)(2)(D). The
    relevant § 3553 factors for § 3583(d)(2) are the same (ii) through (iv) factors. 
    Id. §§ 3553(a)(2)(B),
    (a)(2)(C), and (a)(2)(D). We consider § 3583(d)(1) and
    § 3583(d)(2) in turn.
    i. § 3583(d)(1) factor—reasonably related to the nature and circumstances
    of the offense and the defendant’s history and characteristics
    The relevant offense is the failure-to-register offense. The “nature and
    circumstances” of the offense and Mr. LeCompte’s “history and characteristics”
    include his prior sex offense, which was the basis for the registration requirement.
    On the § 3583(d)(1) requirement, the district court made three findings. First,
    the supervised release violation and his prior offense involved females. Second, the
    violation and the prior offense involved minors. Third, the prior offense involved
    “the potential to exploit an adult relationship in order to have access to the minor
    female child,” and the condition was intended to prevent that type of behavior. As
    we discuss below, the district court’s reasoning does not show how application of the
    condition to the facts underlying the violation was “reasonably related” to the prior
    offense. Further, the district court failed to discuss key facts about the prior sex
    offense and the defendant’s history and characteristics.
    - 15 -
    1) The district court’s three comparisons9
    The district court’s main reason for applying the minor prohibition condition
    to the facts underlying the violation involved surface comparisons to Mr. LeCompte’s
    prior sex offense. Our recent decision in United States v. Martinez-Torres, No. 14-
    2084, 
    2015 WL 4590987
    , at *1 (10th Cir. July 31, 2015), suggests this alone may not
    suffice:
    The district court’s sole expressed reason for the condition was that
    Defendant had been convicted of a sex offense—intentionally causing
    the penetration of the sexual organ of a child younger than 14 years of
    age. But that is not enough. Before imposing the special condition, the
    district court needed to make an individualized assessment of whether it
    was appropriate for Defendant.
    No such individualized assessment was made here. Moreover, the district court’s
    three comparisons fall short.
    The first two comparisons—the prior offense and the revocation violation both
    involved a female and a minor—are superficial. Beyond these general similarities,
    the prior sex offense differed significantly from what happened here. Mr.
    LeCompte’s prior offense involved sexual conduct with a teenager. By contrast, the
    revocation offense involved no apparent inappropriate conduct and consisted of
    sitting with Mr. LeCompte’s girlfriend’s three-year-old granddaughter in the
    9
    Case law on how to consider as-applied challenges based on § 3583(d) is
    virtually nonexistent. The cases discussed in the next sections involved the
    imposition of sex offender conditions, not the application of an already-imposed
    condition to a violation of supervised release. In each one, the court doubted the
    reasonableness of a sex offender condition imposed in the first instance because the
    record lacked support to justify the condition. These decisions inform our review of
    the district court’s as-applied analysis.
    - 16 -
    presence of other adults, including his grandparents, his girlfriend, and her adult
    daughter.
    We also question whether the district court supported its equating the prior sex
    offense and the revocation violation as both involving “the potential to exploit an
    adult relationship in order to have access to the minor female child.” The court failed
    to explain how Mr. LeCompte’s sitting with his girlfriend and her granddaughter
    outside his residence in the presence of other adults established this concern.
    2) What the district court failed to discuss
    The district court failed to discuss relevant aspects of the prior sex offense and
    Mr. LeCompte’s history and characteristics. In particular, it did not discuss the
    absence of any sex offenses or offenses against minors since Mr. LeCompte’s prior
    sex offense and the age of the prior sex offense.10
    First, Mr. LeCompte showed he has engaged in only age-appropriate
    relationships and has not had any inappropriate incidents involving minors since his
    prior sex offense.11 In this respect, we find persuasive United States v. Goodwin, 
    717 F.3d 511
    , 513-14 (7th Cir. 2013), which concerned a similar condition imposed for a
    failure-to-register conviction. The Seventh Circuit vacated the condition, holding
    10
    “Although we are not hypertechnical in requiring the court to explain why it
    imposed a special condition of release—a statement of ‘generalized reasons’
    suffices—the explanation must be sufficient for this court to conduct a proper
    review.” Martinez-Torres, 
    2015 WL 4590987
    , at *4 (citation omitted). The district
    court’s as-applied analysis fell short of the “necessary individualized assessment”
    that would be required and makes our review difficult. 
    Id. 11 Mr.
    LeCompte was convicted for attempted burglary in 2010.
    - 17 -
    such a “sweeping condition” could not be reasonably related to the appellant’s prior
    sex offense involving a minor “particularly since there is no evidence in the record of
    any incidents involving minors in the almost two decades since [the appellant’s] 1994
    conviction.” 
    Id. at 523.
    Second, the district court failed to address the remoteness of Mr. LeCompte’s
    prior sex offense. In United States v. Dougan, 
    684 F.3d 1030
    , 1034 (10th Cir. 2012),
    we held the district court had abused its discretion when it imposed sex offender
    conditions for a robbery conviction based on a 17-year-old offense that involved
    sexual conduct. Although we did not establish a bright-line rule for when a sex
    offense becomes too remote in time, we determined this 17-year-old conviction was
    too remote in time to be reasonably related to the imposition of sex-offender
    conditions: “The government presented no evidence that Dougan has a propensity to
    commit any future sexual offenses or that Dougan has committed any sexual offense
    since [his prior sex offense], at the latest. Dougan has shown no proclivity toward
    sexual violence over the last seventeen years.” 
    Id. at 1037.12
    This court held as such
    12
    Other circuits have similarly held that old offenses can be too remote in time
    to justify the imposition of certain conditions. See, e.g., United States v. Sharp, 469
    F. App’x 523, 525-26 (9th Cir. 2012) (unpublished) (vacating sex offender conditions
    imposed for a felon in possession of a firearm conviction because the 10-year-old sex
    offense was too old and the conditions were not “reasonably related to his past
    violations of court-ordered conditions, none of which involved sexual behavior”);
    United States v. Kent, 
    209 F.3d 1073
    , 1074, 1077 (8th Cir. 2000) (vacating a
    condition prohibiting contact with the defendant’s wife imposed for a white-collar
    conviction when the physical, mental, and emotional abuse of the wife occurred 13
    years earlier, there had been no abuse since then, and there was no evidence on the
    defendant’s current mental condition). Indeed, the Ninth Circuit held that a 10-year-
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    even though the defendant failed to register as a sex offender on two occasions. 
    Id. at 1034,
    1037.13
    ii. § 3583(d)(2) factor—no greater deprivation of liberty than reasonably
    necessary for deterrence, protection of the public, and rehabilitation
    There is no indication the district court considered whether applying the minor
    prohibition condition to the facts underlying the violation would “involve[] no
    greater deprivation of liberty than is reasonably necessary,” 18 U.S.C. § 3583(d)(2),
    to achieve the purposes of deterring criminal activity, protecting the public, and
    promoting the defendant’s rehabilitation, see 
    id. §§ 3553
    (a)(2)(B), (a)(2)(C), and
    (a)(2)(D).14
    The district court did not explain how applying the minor prohibition condition
    to the conduct here would achieve the purposes of deterring criminal activity,
    protecting the public, and promoting the defendant’s rehabilitation. The court also
    old sex offense was too remote to be reasonably related to special sex offender
    conditions.
    13
    We also note that the “failure to register is a fundamentally different kind of
    crime than a sex offense.” 
    Dougan, 684 F.3d at 1037
    . Even though
    it is permissible to impose special sex-offender-related conditions of
    supervised release even where the crime of conviction is not a sex
    crime, in such cases we would require a stronger nexus than we have
    here between the defendant’s history and characteristics and the sex-
    offender-related conditions before we could conclude that the latter
    were ‘reasonably related’ to the former.
    
    Id. at 1036
    (citation omitted).
    14
    See supra, note 11.
    - 19 -
    did not discuss that since his release from prison, Mr. LeCompte moved to New
    Mexico to live with his grandparents and, according to him, is “actively engaging in
    church and other positive social activities.” ROA, Vol. 2 at 19; see United States v.
    Windless, 
    719 F.3d 415
    , 418-19, 422 (5th Cir. 2013) (holding a similar condition
    imposed for a failure-to-register offense involved a greater deprivation of liberty than
    necessary in part because the prior sex offense was 18 or 19 years old and the
    defendant had committed no crimes against minors since then). Finally, finding a
    violation based on the sitting incident may hamper Mr. LeCompte from developing a
    meaningful, future, family relationship. See United States v. Johnson, 
    529 U.S. 53
    ,
    59 (2000) (noting supervised release conditions are meant to “fulfill[] rehabilitative
    ends, distinct from those served by incarceration”).
    III. CONCLUSION
    For the foregoing reasons, we conclude the district court’s as-applied analysis
    was inadequate and incomplete. We reverse the district court’s denial of the motion
    to dismiss and remand for further consideration consistent with this opinion.
    - 20 -