United States v. Jimenez - Sentencing Appeal

24 - 1661 United States v. Jim enez 1 In the United States Court of Appeals for the Secon d Circuit August Term 202 4 Argued: Apr il 1, 202 5 Decided: February 25, 2026 No. 24-1661 U NITED S TATES OF A MERICA Appellee, v. W ILLIAM J IMENEZ, AK A F LIP, Defendant-Appell a nt. Appeal from the United S tates Dis trict Co urt for the Southern District of New Yor k No. 20- cr -122, De nise L. Cote, District C ourt Ju dge. Before: S ACK, P ÉREZ, and M ERRIAM, Circuit Judges. Defendant- App ellan t Wi llia m Jimen ez p led gu ilty to a charge under 18 U.S.C. § 922(g)(1) of possessing ammunition after a felony con viction. The District Court princip ally sentenced J imenez to 105 months’ imprisonment and three years of supervi sed releas e. The Dist rict Cou rt also i mposed the th ree special conditions of supervised re lease relevant to th is appeal. First, Ji menez must sub mit to searches of his elect ronic devices upon r easonable suspicion of a vio lation of a condition of supervised r elease or unla wful conduct. Second, Jimene z must complete twenty hours of communit y service per week w hen unemployed without excus e. Third, Jimenez must participate in an outpa tient mental hea lth counseling program, which to the extent p racticable and appropriate, is to include c ognitive behavi oral therapy techniques. On appeal, Jimene z challenges these

24 - 1661 United States v. Jim enez 2 special conditions as lacking justification in the relevant senten cing factors, along with other a rguments. Jim enez also challeng es his term of imprison ment, arguing that an intervening change in law regardi ng the calculation of his Guidelines range warranted resentencing on a prior rem and. We conclude that the District Court did not abus e its d isc retion in imp osing the relev ant spe cial c ond itions, and that the appeal waiver in Jimen ez’s plea agreement bars the chal lenge to hi s term of impr isonme nt. As a resul t, for the reasons set fort h be low, we AFFIRM the judgmen t of the D istr ict C ourt. J ACOB R. F IDDELMAN (Daniel le R. S assoon, on the brief), Assistant United S tates Attor neys, for Edward Y. Kim, Acting Unit ed States Attorney for t he Southern Dist rict of New York, Ne w York, NY, for Appellee. S ARAH B AUM GARTEL, Federal Defenders of New York, Inc., Appeals Bur eau, New Yor k, NY, for Defendant- Appellant.

24 - 1661 United States v. Jim enez 3 M YRNA P ÉR EZ, Circuit Judge: Defendant- App ellan t Wi llia m Jimen ez p led gu ilty to a ch arge under 18 U.S.C. § 922(g)(1) of possessing ammun ition after a fe lony conviction. The Distr ict Court pri ncipally sentence d Jimenez t o 105 months’ impris onment and three yea rs of supervi sed relea se. The Distri ct Court also im posed seven special conditions of supervise d release, three of which are at issue in this appea l. First, Jimenez must submit to search es of his e lectronic devices upo n reasonable sus picion of a violation of a condition of supervised r elease or unlawful conduct. Second, Jimenez must complete twenty hours of commu nity servi ce per week when unemploye d without excuse. Thi rd, Jimene z must participate in an outpatient mental health counseling program, which to the extent practicable and appropriate, is to include cognitive beha vioral therapy techniques. On appeal, Jimenez argues these special conditions are “unr easonable” and “were not supported by the rec ord or based on Jimen ez’s individual characterist ics,” along with othe r arg ume nts. Ap pellant’s Br. at 3. Jimenez also chall enges his term of imprisonment, arguing that an intervening change in law regarding the calcu latio n of h is Gu idelin es ra nge warranted resent encing on a prior re mand.

24 - 1661 United States v. Jim enez 4 We conclude that the record adequatel y supports the impo sition of the three challe nge d special conditions, and tha t the appeal waiver in Jimenez’s p lea agreement bars the challenge to his term of imprisonment. As a result, for the reasons set f orth below, w e affirm the judgment o f the Dis trict Court. I. Background In January 2020, Def endant - Appellant W illiam Jimenez sold fe ntanyl - lace d heroin to an undercover New York City P olice Depart ment detect ive on two occasions, using his phone to arrange the transactions. That same month, Jimenez shot an individ ual in the knee a nd was arr ested in his veh icle shortly after. The arresting officers searched Ji menez and hi s vehicle and d iscovered ap proximately twenty small bags of crack cocaine in Jimenez’s left shoe as wel l as approximate ly eight small gl assines of heroin and a bag of marijuana in the vehicle’s ce nter console. Jimenez was ind icted on five co unts. Count one ch arged Jimenez with possessing amm unition after a fe lony conviction, in viola tion of 18 U.S.C. § 922(g)(1). Count two charged Jimenez with discharging a firearm in furtherance of a drug traffickin g crime, in v iolation of 18 U.S.C. § 9 24(c)(1)(A)(i), (ii), and (iii). The final three count s each charged Jimenez with d istributing and possessing with

24 - 1661 United States v. Jim enez 5 intent to distr ibute a control led substance, in violation of 21 U.S.C. § 841(a)(1) and (b)(1)(C). Even tually, Jimenez p led guilty to c ou nt o ne of the indictment pursuant to a plea agreemen t. The plea agreement con tained an express wai ver of ap peal. Jimenez ag reed not to appeal “any s entence within or below the St ipulated Guidelines Range of 84 to 105 months’ imprisonmen t.” App’x at 26. That Stip ula ted Gui delin es Rang e was calculated based on an applicat ion of Section 2K2.1(a)(2) of the Sentencing Guide lines, which establishes a base offense level of 24 where a defendant has two prior “felony convictions of either a crime of violence or a controlled subs tance offense.” U.S. Sent ’ g Gu idelin es Manu al § 2K2.1(a)(2) (U.S. Sen t ’ g Comm ’ n 2021). Prior to the instant of fense, Jimenez had s ix criminal conviction s, inclu ding a 2 011 robbery conviction and a 2015 convic tion for criminal sal e of a controlled substance, which were the basis for apply ing S ect ion 2K2.1(a)(2). The Distr ict Cour t prin cipally sentence d Jimenez to 105 months’ imprisonm ent and three years of sup ervised release. The sentence included seven “special” 1 conditions of supervised re lease, three of wh ich are ch allen ged in th is 1 C onditio ns of sup ervised release a re classif ied as e ither “ mand atory ” or “ discretionar y” condit ions. See U nited S tate s v. Maio rana, 153 F.4th 306, 311 n.4 (2d C ir. 2025). The disc retion ary co nditi ons can be further divide d into “ stand ard” conditi ons, whi ch t he n- ap plicable Se ntencing Guidel ines

24 - 1661 United States v. Jim enez 6 appe al. First, Jimene z must “submit [his] per son, and an y property, residence, vehicle, papers, com puter, other electroni c communication, da ta storage devices, cloud storage or media, and effects to a search by any United States Probation Officer ” upon “re asonable susp icion” that Jimenez v iolated “a cond ition of supervision or [engaged in] unlawful conduct” (the “search co ndition”). App’x at 91. Second, J imenez mu st “complete 20 hours of community service per week in a program approved b y the Probation Officer” if he is “not emp loyed [or] exc used from emp loy ment” (the “commun ity service condition”). Id. Thir d, the D istric t Court included a c ondition re quiring a “ cognitive behaviora l treatment progr am under the gu idance and superv ision of t he probation off icer, until such time as [Jimenez] [is] re leased from the program by the probation offi cer” (the “menta l health treatmen t condition”). I d. Jimenez previous ly appealed several of h is supervision cond itions, and by order dated Mar ch 18, 2024, we va cated, in par t, the thr ee conditions listed above due to the District C ourt’s failure to provide suff icient explanations. See United recomme nd ed in m ost cases, and “s pecial ” condi tions, which t he Guideline s sugg est ed for “appropriate” cases. Id.; see also U.S. S ent’g Guidel ines Manual § 5D1. 3 (U.S. Sent’ g Comm ’n 2021). This case deals with the last category. N otably, the 2 025 S entencing Guid elines no longe r incl ude la nguage recom mendi ng either th e “standard” or “special” conditions. See U.S. Sent’g Guidel ines Manual § 5D1.3(b)(2) – (3) (U.S. Sent’g Comm ’n 202 5); U nited Sta tes v. Mc Adam, 165 F. 4th 688, 694 (2d Cir. 2 026).

24 - 1661 United States v. Jim enez 7 States v. Jime nez, No. 22 -1022-cr, 2024 WL 1152535 (2d Cir. Mar. 18, 2024) (sum mary order). In doing so, we remanded with instructions for th e District Court to “determine whether each of the special conditions that wer e imposed without specific justificat ion is reason abl y related to the fa ctors set forth in the Sentencing Guide lines § 5D1.3(b) and, if so, to e xplain the reasons for imposing the condition.” Id. at *4. On remand, t he District Court resent enced Jime nez and reimposed t he rele vant sp ecia l cond itions, with some modifica tions. 2 In doing so, the Dis trict Court elaborated on its re asons for imposing the contested condit ions. This second appeal followed. II. Discussion Jimenez ma kes two overarching chal lenges on appeal. First, he asks this Court to vacate three of the special conditions of su pervised re lease. Second, he seeks a rema nd so that the Distri ct Court can reconsider his t erm of imprisonment. 2 In particul ar, the District Court altered the mental h ealth treatment condit ion, wh ich no w requ ires that Jimenez “partic ipate in an outpa tient mental he alth coun seling progra m” whic h “shall includ e regular therapy sessions that, to the extent practicable and as determ ined to be appropri ate by the th erapy provider, include co gniti ve beh avioral th erapy t echni ques.” Ap p’x at 141.

24 - 1661 United States v. Jim enez 8 A. Challenges to Sp ecial Conditions of Supervised Releas e We generally review challenges to specia l conditio ns of supervised release for procedura l and substantive reasonablene ss under an abuse of discret ion standard. See U nited States v. Sims, 92 F.4th 115, 1 22 (2d Cir. 20 24); United States v. Boles, 914 F.3d 95, 111 (2d Cir. 2019). “When a challenge to a condition of supervise d release presen ts an is sue of la w,” our rev iew is de novo because “any error of law necessar ily constitutes an abuse of discret ion. ” Boles, 914 F.3d at 111 (quoting Unite d States v. McLaurin, 7 31 F.3d 258, 261 (2d Cir. 2013)). When a district court imposes s pecial conditions, procedural rea sonableness requires tha t the cour t “ mus t ‘ make an individua lized assessme nt ’ ” of the nee d for each condition, and “make findings specific to the defendant, connecting those findings to the applic able § 3553(a) factors that wo uld jus tify i nclud ing the sp ecia l condition.” Sims, 92 F.4 th at 123 (quoting United States v. Eag lin, 913 F.3d 88, 94 (2d Cir. 2019)). “ The failure to articulat e this reasoning on the record is error,” but “ we m ay sti ll upho ld a condition if the d istrict court ’ s r eason ing is self - evid ent in the record. . . and the condition meets the purposes o f supervised release.” United States v. Robinson, 13 4 F.4th 104, 111 (2d Cir. 2025) (cit ation modified).

24 - 1661 United States v. Jim enez 9 Substan tively, d istrict c ourts have discr etion to impos e c onditions of supervise d release, so long as those co nditions are reaso nably related to certai n statutor y sentencing factors, including: (A) the nature an d circumstances of the offens e and the histor y and characteristics of the defe ndant; (B) the ne ed for the sentence i mposed to afford adequate deterr ence to crimin al conduct; (C) th e need to protect t he public from further crim es of the def endant; and (D) the need to provide the d efendant with neede d educational or voc ational traini ng, medical care, or other co rrection al treatm ent in t he most effecti ve manner. United States v. Carlineo, 998 F.3d 533, 5 36 (2d Cir. 2021) (quoting U.S. Se nt ’ g Guide lines Man ual § 5D1.3(b) (U.S. Sent ’g Comm’n 20 18)); see also 18 U.S.C. § 3583(d)(1); Unite d States v. Lawrence, 139 F.4th 115, 125 (2d Cir. 2025) (assessing a condition’s connection to the sentencing factors as part of its substantive reasonableness analysis). Add itiona lly, dis trict co urts “must als o consider how a spec ial cond ition wil l impact any cog niz able lib erty inter ests, ” and a condition “ affec ting a cogn iza ble l ib erty inte rest must be ‘ sup ported by particu larized findings that it does not constitute a greater deprivation of liberty than re asonably necessary to accomp lish the goals of sent encing. ’” Sims, 92 F. 4th at 12 5 (quoting United States v. M atta, 777 F.3d 116, 122 (2d Cir. 2015)); see also Robinson, 134 F.4th at 1 11. Finally, speci al conditions must be “consis tent with pertinent Sentencing

24 - 1661 United States v. Jim enez 10 Commission policy s tatements.” United States v. F arooq, 58 F.4t h 687, 694 (2d Cir. 2023) (quoting Eaglin, 913 F.3d a t 94). 1. Electronic Search Co ndition T he District Court acted within the bounds of its discretion in i mposing the electron ic search con dition, spec ifically, its requirement s related to his electro nic devices. On remand, t he Distr ict Court explained that the electronic sear ch condition is “customary in this district” and that “ if the defend ant return s to drug deal ing or other unlawful conduct, ther e may be reasonab le suspicion that evidence of that behavior can be found on s ome electron ic device.” A pp’x at 12 6 – 27. The reference to customary practic e, even if true, is plainly inadequate to ful fill the procedural duty to provi de an “indiv idualized assess ment. . . on the re cord.” United States v. Betts, 886 F.3d 198, 202 (2d Cir. 2018). And t he Dis tric t Co urt ’s explanation regarding the risk of Jimenez returning to drug crime s was phr ased in a way that might mislea ding ly sugg est it was applicab le to any defendant convicte d of drug crimes. However, the transcript reveal s that the District Court conduc t ed an appropriately indiv idualized assessmen t. The District Court commented and relied o n Jimenez ’s lengthy crim inal record, including crimes of violence and

24 - 1661 United States v. Jim enez 11 extensive invo lvement with dr ug trafficking, see App’x 106, 12 2, and his disciplinary record w hile in federal custod y, including violation s involving phone use, see App’x 107. The record also reveals that Jimenez used his phone to conduct the drug transa ctions at issue in th is case, see App’x 120, an d thus, the Dis tric t Court ’s comments regarding the poss ibility of finding evidence of future wrongdoing on Jimenez’s devices were rooted in the record. Over all, th e Dis tric t Court’s assessm ent was sufficientl y individua lized and the b asis for the elec tronic search condition was sufficiently articulat ed. See United States v. Corsey, 7 23 F.3d 366, 374 (2d Cir. 2013) (requiring t hat the sentencing judge “explain enough a bout the sentence for a re viewing court both to unde rstand it and to assure itself that the judge consi dered the principles enunci ated in federal statutes and the Guide lines ”). We turn to whether the electronic searc h condition was, substantively, reasonably related to the relevant s entencin g factors. As the pa rties’ a rguments suggest, this ana lysis is complex and cannot be satisfied by mere all usion to the appropriate factors. Left unchecked, t he sentencing factors, including the need to deter criminal conduct and pr otect the public, can imperm issib ly an d superfici ally be stretched to wrongly support imp osing electronic search conditions in almost

24 - 1661 United States v. Jim enez 12 any case. O ur own decisio ns have sometimes been less than ri gorous in avoiding such generalized co nsiderations; we have recently no ted in dicta that such conditions “can be an impor tant tool for probation officers to carry out” effective supervision. Unit ed States v. Thompso n, 143 F.4th 169, 180 (2d Cir. 2025). W e must be war y whe re such high - level, generaliz ed concerns are involved and reli ed upon by distri ct courts a nd the governm ent. “Exclusive r eliance on . . . generalized considera tions is inconsi stent with th e requirement that the district court make an ‘ind ividualized as sessment’ as to eac h defendant when determining whethe r to impose a special condition.” United States v. Olive ras, 96 F.4th 298, 314 (2d C ir. 2024) (quo ting Eaglin, 913 F.3d at 94). Moreover, special conditions must be re asonably related to the releva nt sentencin g factors, not merely related. See Si ms, 92 F.4th at 126. And more specifically, the relevant sentencing factors ask whether a condition is likely to protect the public from a specific defendant’s cr imes, as opposed to criminality more general ly. See U.S. Sent ’ g Guidelines Manual § 5D1.3(b) (U.S. S ent’g Co mm’n 2025) (l istin g “ the need to protect t he public from further crim es of the defendant ” a s an appropriate consideration (e mphasis added)).

24 - 1661 United States v. Jim enez 13 T here is reason to he sitate in imposing electronic search cond itions in man y cases. To start with the obvious, e lectronic search conditions are not part of the “mandatory” conditions of s upervised re lease. See 18 U.S.C. § 3583(d). Nor are they included in the Guid eline s list of “standard” d iscretionary condit ions. See U.S. Sent’g Guide lines Manual § 5D1.3(b) (2) (U.S. Sent’g C omm’n 2025). Therefore, el ectronic search co ndition s have not been determined to be appropriate or advisable in every case by the relevant s tatutes, nor are they im plicated so regularly as to be characterized as “standard” by th e Gu idelin es. And as we ha ve noted, such conditions poten tially pose enormous conseq uences to criminal defendants’ lives. See United States v. Gr iffin, 839 F. App’x 660, 661 n.5 (2d Cir. 2021) (summary order) (notin g “the sear ch condition’s language appe ars to be unclear as to whether it is intende d to apply to an employe r’s computer equipment or electro nic device s furnished. . . for use in the emp loyer’s business, which c ould impact [a defendant ’s] future employm ent prospects”). D is trict c ourts m ust rigorously e nsure th at e lectronic search conditions are reasonably r elated to the sentencing factors as applied to the specific defendant before the m. Of course, the par ties dispu te how th at case - specif ic inq uiry ap plies to t his case. O ur C ircu it has clarif ied in recent months the circumstances under which an

24 - 1661 United States v. Jim enez 14 electronic search condition is substantively reasonab le. Most obviously, electroni c search conditions w ill ofte n be reasonably related to the sentenci ng factors where a defendant’s “convi ctions involved sex o ffenses,” beca use nearly all such offenses prosecuted under fe deral law involve th e use of electronic devices. See Robi nson, 134 F.4th at 112 (citin g U.S. Sent ’ g Guidel ine s Manua l § 5D1.3(d)(7)(C) (U.S. Sent’g Comm’n 2024)). In other cases, our precedents demo nstrate that we t olerate such conditions in two limited scenar ios. First, if the record demonst rates that the defendant instrumen talized an electronic device in the commission of the instan t offense conduct and surrounding circumstances, we are likely to find that the condition is reason able. Secon d, and more rarely, where the defendant presents an unusually high r isk of reoffending, w e may find the condition is reason able. Jimenez falls squa rely within t hese categori es, and we conclud e, based on this record, that the electronic condit ion is substantive ly reasonable. First, where electronic devi ces were instrumentali zed in the commission of the instant offense conduct and s urrounding circums tances, 3 w e have regular ly 3 T his case do es not requi re us to ascert ain under w hat circum stances the us e of an el ectronic device in a previous offense ma y justify a si milar cond ition. But there is reas on to believe that w here an elect ronic device wa s instrume ntalize d in the com mission of a previou s offense, rat her than the instant offe nse, the rela tionship betwee n an e lectr onic se arch c onditi on an d the se ntenc ing fa ctors i s much weake r because the condit ion lo ses an enti re pi llar of support in the sente ncing f actors: the nat ure a nd circum stance s of the instant off ense. Thou gh w e have s uggeste d, in n on - pre cedential d ecisions, th at “[w]e have frequently

24 - 1661 United States v. Jim enez 15 held that an electronic search condi tion is permissible. See, e.g., Lawrence, 139 F.4th at 125 (defendant “used only a cellphone to sell drugs”); United States v. Lewis, 125 F.4th 69, 76 (2d Cir. 2 025) (defendant “r epeatedly used e lectronic devices to carry out the t hree fraudulent s chemes cha rged”); Robinson, 134 F.4t h at 11 2 (noting the condition “would be even more apparent if [defendant’s] conv ictions involved . . . the use of e lectronics”); United States v. Arg uedas, 134 F.4th 54, 70 (2d Cir. 2025) (“[T]he record reveal s that Arguedas used electroni c devices to document a number of his assaults an d to commission v iolent acts against r ival gang members.”). In such cases, an electronic search condition connects directly to the nature and circumstances of the offense at issue. See Carlineo, 99 8 F.3d at 536. Therefore, where the sentencing court determines that an electronic device w as instrumentalized in the commission of the instant offens e conduct, or the appr oved of su ch conditi ons wher e the cond uct und erly ing a c onviction or prior convicti on has inv olved the use o f computers or other electro nic devices,” we have never squarely addr essed th e issue. See, e.g., United States v. Th omas, 82 7 F. A pp’x 72, 75 (2d Ci r. 20 20) (sum mary order); United States v. Franco, 733 F. App’x 13, 16 (2d Cir. 2018) (summary order). I n Thomas, the defendant inst rumentalized electroni c devices in the “c onduct leading up to his i nstant convi ction,” so it is n ot particula rly usefu l in determinin g how to approac h a case wh ere th at fact or is absen t. 827 F. App’ x at 75 (em phasis added). And i n Franco, the challe nge to the electr onic searc h conditi on was rejected at least in part because t he defendant fail ed to challenge a substant ially similar conditi on that he was alrea dy subject to. 733 F. App’x at 16.

24 - 1661 United States v. Jim enez 16 surrounding circumstances, the re is less concern that the court reli ed on the general notion that searches can help ide ntify and deter criminal conduct. Second, we have held that an electronic search condition may b e appropriate – in rare circumstances where certai n unusual factors are p resent – even if the underly ing crime did not i nvolve the instrum entalization of an electron ic device. Indeed, “we ha ve never held that a n electronic search term would only b e appropriate. . . if [a defendant’s] convictions i nvolved . . . the use of electronics.” La wrence, 139 F.4th at 125 (alter ation s in origin al) (quoting Robinson, 134 F.4th a t 112). Importantly though, this is a high bar th at will not be reache d in the vast majority of cases. F or example, in U nited States v. Robins on, we relied o n three specific facts to jus tify the condition: 1) the defendant’s “pr olific” crimina l history including “nine cr iminal convictions before the age of 30,” 2) the fac t that the defendant “com mitted the instant offense whi le under post - r elease supervis ion,” and 3) the fact that the defendant “lied to police in his post - arrest statement. ” 134 F.4th at 111. Giv en the conflu ence of the se considerati ons, the Court determi ned that the recor d supported a finding that the electronic sear ch condition was reasonably related to the defendant’s h istory and character istics. Id. But we als o

24 - 1661 United States v. Jim enez 17 noted that our holding was consistent with cases in which we had vaca ted electronic search conditions imposed o n somewhat s imilar defendants with signif ican t crimina l his tories bec ause in Robinson, the defendant “ ha [d] accumulated more prior adult cr iminal convictions than either of th [e] defendants [in other cases] an d lied to law enforce ment following his arres t, which disti nguis he [d] his case.” 134 F.4th at 112 n.5. Si milar ly, in T hompson we observed that a n extensive “hi story of recidivis m and the na ture of [the de fendant’s] past crimes” in clud ing a crime “c ommi tt ed while [the defendan t] was on parole supe rvision ” and multiple sex offe nses, justified the condition. 143 F.4th at 179. Likew ise, in Arguedas, we op ined that al though the defendant “used electronic devices,” the “seve rity of [his] conduct and his penchant for re -offending” c ould have provided an independently sufficient rea son to impose an electronic search condition. 13 4 F.4th at 70. In that c ase, the defe ndant had a lengthy history of “murder, atte mpted murder, and other ‘re ally appalling acts of violence’” including “offenses c ommitted wh ile on parole or pr obation.” Id. at 62 –63. T aken togeth er, our precedent s d ictate th at t o jus tify impos ing a n elect ron ic search condition when an elec tronic device was not used in commission of the offense, the defendant’s criminal history must be extremely lengthy and mus t

24 - 1661 United States v. Jim enez 18 contain s pecif ic indicators – beyond the m ere number o f prior offenses – that th e defendant is unusual ly likely to co mmit new offenses whil e on supervised release. As in Robinson, this is likely to require a record of un lawful con duct during a previous term of super vision, or eviden ce that the defendant has be en dece itful toward supervisin g or law enforce ment officers in the past. The comb ination of these factors can, in some circumstances, demonstr ate an extrem e risk of reoffend ing th at sup pl ies the nece ssary r easonab le re lation shi p to the sentencing factors. Turning to this case, the electronic search condition is reasonably related t o the sentencing factors because Jimenez used his phon e to facilitate the drug transactions w ith an undercover New Yor k Police Depart ment detective, and the initial indictment included charges r elating to those tran sactions. Tha t Jim enez pled guilty on ly to th e possession of a mmunition after a fe lony conviction ch arge is no matter. T he sentencing factors incorporate not only the formal elements of the convicted crime, b ut also, the nature and circumstances of that offense. See Farooq, 58 F.4th at 695 (consi dering both “the charged conduct and the conduct to which [the de fendant] pled guilty” in discussing the nature a nd circumstances of the offense). Jimene z used an electronic device in the commission of the charged

24 - 1661 United States v. Jim enez 19 conduct, and therefore, t he electro nic search cond ition i s justified. See Lawrence, 139 F.4th at 125. Because t he Gover nment als o po ints t o the r isk of re - offending as justification for the electronic search condition, we conclude th at Jimenez’s sp ecific criminal history wo uld not be e nough to j ustify the electronic search condition on its own. As noted above, i n Robinson, we expressly distinguished our decision not to vacate the electronic search condition in that case fro m othe r cases involving less severe reco rds. One of those cases was Jimenez’s first appeal. In Robi nson, we noted that “Rob inson ha[d] accumu lated more prior adul t criminal convictions tha n [Jimenez] and lied to law enforcement fol lowing his ar rest.” 134 F.4t h at 112 n.5. Therefore, e ven if we were in clined to conclu de that Jim e nez’s seven total convictions were enough to justify the condition on their own (which we are not), Robinson a t least sug gests th at the y are not. Furthermore, the record do es not suggest that Jimene z had a history of committing new off enses while under supe rvision. 4 4 Jimenez’s asserti on that the electronic search condition “is broader than necess ary” to achieve the relev ant sente nci ng goals, see Ap pellant’s B r. at 35, is unavailin g. See U nit ed Stat es v. Law renc e, 139 F.4t h 115, 125 (2d Ci r. 2025); see also U nited S tates v. Oliv eras, 96 F.4th 298, 315 (2d Ci r. 202 4) (appr oving home searches r equiring rea sona ble suspicion, noting “th ose conditi ons do not c onstitute a greater deprivation than reaso nably neces sary because t hey requ ire reason able suspici on” (emp hasis in orig inal)).

24 - 1661 United States v. Jim enez 20 2. Communi ty Service Condit ion W e a lso affirm th e imposition of the spe cial condition requiring Jimenez to perform co mmunity servic e for twent y hours a week w hile u nemployed (and not excused from emplo yment). On reman d, the Distri ct Cour t explain ed that it imposed the comm unity service condit ion because it did n ot “want [Jimenez] hanging around the neighborhood or hanging out at home d oing nothing,” an d because the conditio n serves as “hopefully a motiva tor to the defen da nt to get a job and earn money legitima tely.” App ’x at 128 – 29. I n doing so, the District Court referenced Ji menez’s “chec kered work history. ” Id. at 128. In li ght of o ther aspects of the record discuss ed below, the District Court’s e xplanation p asses muster. Before we reach the substan tive rea sonableness of the condition, howe ver, we must exami ne whether the issue s raised are ripe for review. “Ripeness is a cons titut iona l prer equisit e to [th e ] exe rcise of jurisdic tion by federal courts.” United States v. Traficante, 966 F.3 d 99, 106 (2d Cir. 2020) (a ltera tion in or igin al) (quoting United States v. Fell, 360 F.3d 135, 139 (2d Cir. 202 4)). And we have “lon g recognized that ‘[a] claim is not ri pe if it depends upon contingent future events that may not oc cur as anticipated, or indeed may not occur at all. ’ ” Id. (alter ation in or igina l) (q uotin g Nat’l Org. fo r Marriag e, Inc. v. Walsh, 714 F.3d 682, 687 (2d Cir.

24 - 1661 United States v. Jim enez 21 2013)). In contrast, “a p ure ly legal question” is “em inently fit for judicial review. ” United States v. Quin ones, 313 F.3d 49, 59 (2d Cir. 200 2) (quoting Nutriti onal Health All. v. Shalala, 144 F. 3d 220, 22 7 (2d Cir. 1998)). Here, t he community servic e provisi on requires twenty hours of communit y service per week if Jimenez is not employed and not ex cused from employm ent. The Government sugge sts that fact ends the inquiry, and that Ji menez’s argument is unripe. B ut the contingent nature of the community service is n ot determi native. I ns tead, we look to the specif ic legal i ssues rai sed by challenge s to a condition to assess ripeness. If those challe nge s solely rel y on questio ns of law, they are rip e. Our decision in United States v. Villafane- Lozada is instru ctiv e. 9 73 F.3d 147 (2d Cir. 2020). There, the defe ndant chal lenged a “ver ification testing con dition” on several grounds, includin g “that it (i) permits the use of compu terized voice stress analysi s, which [the defendant] sa [i d] is not scientif ically proven to be reliable, and (i i) improperly de legates [author ity] to the pr obation officer.” Id. at 151. Facing thes e two separate cha llenges to the same cond ition, we re cognized that “[t] hough b oth challenges concern the same condition o f supervision, the ripeness of each may differ depending on th e issues they raise.” Id. Th e relia bil ity challenge, we concluded, was not ripe b ecause it was impossible to te ll whether

24 - 1661 United States v. Jim enez 22 the technolog y used at the time of the defendant’s f uture super vised release would be reliabl e. Id. On the other hand, we fo und that the delegation challenge was ripe becau se the defendant argued “the already realized delegation of j udicial power to a probation officer” was imper missible. Id. Clearly then, ri peness is a n issue - specif ic inq uiry. Like t he de lega tion c halle nge in Villafane- Lozada, Jimenez’s challenges to the community service c ondition permit reso lution now. Villafane - Lozada directs our attention to whether a challenge hinges o n a “hypothetical” situation th at may or may not occur, or on the plain terms of the condition itse lf. Id. Jimenez asserts that the co mmunity service condition is vague becaus e it la cks c larify ing ter ms, affords the Probation Office with too much d iscret ion to d ecide when emp loyment is excused, is based on a p unitive purpose, and may result in Jimenez servi ng more than 400 hours of co mmunity service. Despite the Governme nt’s arguments to t he contrary, t hese challenges focus on aspects of the c ommunity service condition that ar e “ already reali zed.” Id. D etermining whether the c ond ition, as wri tten, is vague, delegates too much au thority, is punitive, or may require more t han 400 hours of com munity service, does not require th e Court to consider the poss ibil ity of hypothetical futur e events. Each of t hese inquirie s is conce rned only with the

24 - 1661 United States v. Jim enez 23 nature of the cond ition as it stands. See id. (holding challenge based on delegat ion to probation officer was ripe because it targeted “the probation officer’s a lready - granted authori ty”); see also United S tates v. Kunz, 68 F.4th 748, 76 9 –70 (2d Cir. 2023) (same); United States v. Reeves, 591 F.3d 77, 81 (2d Cir. 2010) (a ddressing vag ueness challenge). We pause to clar ify two points. F irst, o ur d ecis ion in United States v. Traficante does not alter our conclusion that the challenge s based on vagueness and delegation to probat ion are ripe for review. 966 F.3d at 105 – 07. Our de cisi on in Traficante was pitche d towards a peculiar proce dural posture, where the district court had effective ly replaced a condition original ly imposed with a standing order. Id. at 104. In effect, t he standing order “m erely rei terate[d] t he existing procedures for addi ng conditions if and whe n they become necessary during terms of s upervised release.” Id. Theref ore, we reason ed that t he standi ng order did “‘not impose. . . any new obligations’ b eyond what the law already allow s.” Id. at 105 (alter ation in orig inal) (quo ting United States v. Jacques, 321 F.3d 255, 265 – 66 (2d Cir. 2 003)). In this context, the C ourt de termined that a ch allen ge to the standing order based on vag ueness was unrip e because it rel ied on the di strict court first making a particular find ing for its terms to have any legal force. Id. at

24 - 1661 United States v. Jim enez 24 106. We conclude d that the over lapping deleg ation chal lenge was unr ipe for simila r reas ons: because the de legation itself was “cond itioned on the district court” making a particular finding during the defendan t’s term of superv ised release. Id. at 10 6–07; see also United States v. Birkedahl, 973 F.3d 49, 57 (2d C ir. 2020) (same); United States v. Bryant, 976 F.3d 165, 182 (2d Cir. 20 20) (same). These holdin gs do n ot ap pl y here. We expressly distinguished Traficante in Villafane- Lozada, r ecogn izin g that a “delegation [that] has a lready occurred and is no t contingent on future judicial action” is ripe for review. 973 F.3d at 151. The sa me holds true here, for both the vag ueness and de legation chal lenges, as there is no question that the ch allenged condition imposes new obligat ions “beyond wha t the law already allows.” Traficante, 966 F.3d at 105. Second, Jimenez’s challenge bas ed on the 400 - hour threshold is focused on the le galit y of the con dition ’s curre nt terms and is fit for re view. Contra Traficante, 966 F.3d at 106. A quick g lance at the argument might suggest the opposite, given the uncert ainty over whet her the threshold will ever be reac hed. But Jimenez

24 - 1661 United States v. Jim enez 25 argues that the condit ion is improper because it does not contain an express maximum of 400 hou rs. 5 Although they are ripe for rev iew, Jim enez’s chall enges nevertheless fa il on the meri ts. Firs t, th e comm unity servic e co nditio n is not impe rmissib ly va gue. The condition w ould b e “unconstitutional if it is so vague that ‘men of co mmon intellig ence must necessarily gu ess at its meaning and differ as to its application.’” United States v. Mac Millen, 544 F.3 d 71, 76 (2d Cir. 2008) (quo ting United States v. Simmons, 343 F.3d 72, 81 (2d Cir. 2003)). But “[o]n the other h and, a good deal of flexib ility is af f orded district cour ts.” Ree ves, 591 F.3d at 81. “[C]onditions need not be cas t in le tters s ix feet hi gh, or. .. describe ev ery possible pe rmutation, 5 S everal non - precedentia l decisio ns reach a different conclusion, but those decis ions rest on an error of law; as such, they have been undermined or exp ressly refuted already. In Unit ed Sta tes v. B urdic k, the Court he ld a defendant’s “overbreadth and vagueness ” challenges were unripe. 789 F. App ’x 886, 888 – 89 (2d Cir. 2019) (summary order). But th at deci sion was pr emised on the not ion tha t the distr ict cou rt retained the ability to r emedy pote ntial lega l issues with the conditi on at a later date, through m odific ation under 18 U.S.C. § 3583(e). Id. at 8 89. As we have since re cognized, “ ‘the illegality of a condition of supervised rel ease is not a proper ground for modificatio n under’ 18 U.S.C. § 3583(e)(2),” and therefore, a district co urt’s abil ity to modif y conditi ons cannot j ustify d elaying our r eview of the legal is sues that t he conditio n raises. Se e Villafane - Lozada, 973 F.3d at 152 (quo ting United States v. Lus sier, 104 F.3d 32, 34 (2d Cir. 1997)). Indeed, we have al ready expressly dispose d of that a spect of Bu rdick. See i d. at 152 n.3 (no ting “we do n ot break fro m that panel’s de cision l ightly”). In U nited St ates v. Leo ne, w e primarily dismissed a vagueness cha llenge be cause it wa s meritles s, not beca use it was unripe. 813 F. App’x 6 65, 669 (2d C ir. 2020) (summary o rder). Regar dless, the Cour t’s disc ussion of r ipeness re lied o n Burdick. Id. Finally, in United States v. Mor rishow, we rejected a chall enge to a similar communit y service provision based on the notion that it was unclear whether the defendant would ever have to engag e in community service, let alone d o more tha n 400 hours of it. No. 23 - 7622, 2024 W L 46905 24, at * 3 (2d Cir. No v. 6, 2024) (summary order). Again, th at decis ion appeared to rely, at least in part, o n the incorrect n otion tha t the def endant was “free to return to the di strict court to req uest a modifica tion.” Id.

24 - 1661 United States v. Jim enez 26 or . . . spell out ev ery last, sel f - evident deta il.” Id. (alter ation s in o rigina l) (quo ting United States v. Johnson, 446 F.3d 272, 280 (2d C ir. 2006)). Jimenez points to se veral purporte dly cruc ial deta ils that th e Distr ict Court d id not eluc idate, in cludin g “when Jimenez’s co mmunity service obligat ion would start, how the hours he owed would accrue (or not) from wee k to week, and under what c ircumstances the Probat ion Departm ent could ex cuse Jimenez from this com munity servi ce requirement.” Appel lant’s Br. at 38–39. As the Distric t Court expressl y noted, “[t]here are known and identified reasons why the probatio n office excuses people from emp loy ment ” i ncluding disability, s chooling, and job train ing. App’x at 130. Reading those “kn own and ident ified” bases for excus al into the condit ion renders the condi tion sufficiently def inite. And though there are m eaningful diff erences in a court’s discretion to impose employment and c ommunity service condit ions, discussed below, th e fact that Jimenez’s unchallenged e mployment condition simila rly lacks seve ral of t he terms purportedly missi ng from his challenged community service condition unde rmines Jimenez’s argu ment. Next, the commun ity service condition is not pun itive. Of course, punish men t is no t a pe rmissib le ju stif icat ion fo r a spe cial c ond ition. See U.S. Sent ’ g Guidelines Manual § 5D1.3(b) (U.S. Sent ’ g Comm ’ n 2025); 18 U.S.C. § 3583(c).

24 - 1661 United States v. Jim enez 27 C ontrary to Ji menez’s assertion s on appeal, however, th e mere fact that a Distr ict Court imposed a c ondition to incentivize c ertain beha vior s like main tainin g employment does not make i t punitive. I f it were i mpermissibl e to impo se a condition that is des igned to “motivate J imenez to ‘get a job,’” district courts could never impose any condition requiring employment. Appellant’s Br. at 42. Instead, such conditions are directly relevant to t he pertinent sentencing factors s uch as Jimenez’s rehab ilitation. Third, the community servi ce condition does no t impermissibl y delegat e authority to the prob ation office. “[A] district court may not delegate to the Probation Depart ment decision making author ity which wou ld make a defendant’s l iberty itself contingen t on a probation off icer’s exercise of discret ion.” Matta, 777 F.3d a t 1 22. “In othe r words, th e Probation Office may supervise an d execute a sen tence but may not fashion a sentence’s t erms.” Carlineo, 998 F.3d at 538. The community s ervice condition here indispu tably vests some decision - making author ity with the proba tion office. They determine whet her Jim enez is excused from his employ ment obligations, and by e xtension, from his community service obligations. But these decisions do not amount to placin g Jimenez’s “liberty” in the pro bation office’s hands. Matta, 777 F.3d a t 122. Instea d, the

24 - 1661 United States v. Jim enez 28 special conditions merely permit the pro bation office to afford Jimenez g reater liber ty, by exercising it s discreti on to excuse hi m from emp loyment. T he discretion afforded t o the probation office is additive, not sub tractive, to Jimenez’s liber ty, and th erefore, does not cons titute an imprope r delegation. See United States v. Floyd, 840 F. App’x 625, 627 – 28 (2d Cir. 2021) (sum mary order) (r ejecting delegation challenge where “ the Probation Office cannot decide whether to impos e the curfew in the firs t in stance; it can only adjust the cur few times to accommodate [the d efendant]”). Fourth, the comm unity service conditi on is reasonably related to the relevant sentencing factors. A s the District Court expl ained, such conditions are pertinent to deterring further criminal conduct b y ensuring the defendant stays engaged in lega l endeavors. See A pp’x at 129. Additional ly, the District Court appropriately tied the condition to Jimen ez’s specific h istory and character istics, noting his “checke red work history.” Id. at 128. Indeed, J imenez himsel f has pointed out that emp loyment and community service have he lped rehabilitate him in the past, and that certain pe riods of his criminal h istory overlapped wi th periods of unproduc tivity. These con nections a dequate ly justify a communi ty service condition tha t is tied to a lack of e mployment.

24 - 1661 United States v. Jim enez 29 Fina lly, t o the extent Jimenez argues tha t the condition could result in m ore than 400 ho ur s of community se rvice a s a standalone basis for vacating, the argument is un availin g. Jimenez’s argument is based on our decision in United States v. Parkins, in which we vacated a sp ecial condition that imposed 6 95 hours of community servic e. 935 F.3d 63, 66, 68 (2d Cir. 2019). T here, because con ditions of supervised release must be “consistent with any pertinent policy s tatements issued by the Senten cing Commiss ion,” 18 U.S.C. § 3583(d), we were guided by the Sentenci ng Guidelin es, which sug gest that “[c]ommunity servic e generall y should not be imposed in ex cess of 400 hours.” U.S. Sent ’ g Guidel ines Manual § 5F1.3 cmt. n. 1 (U.S. Sent ’ g Co mm ’ n 202 5). Cruc ially though, w e have never held that a condition is pe r se impermissible because it cou ld lead to over 400 hours of community se rvice. Our decision in Parkins establishes no bright line rule. W e merely h eld that courts shoul d “generally r efrain” from impos ing conditions tha t exceed the 40 0 - hour thr eshold, and that w hen they do, the re must be a compe lling justifica tion that d istinguishes the defe ndant “from the ge nerality of cases.” Parkins, 935 F.3d a t 66, 67– 68 (premising its holding on the district court’s “inadequate, ind ividualized justif ication for a higher amount ”); United S tates v. Kim, 790 F. App ’x 321, 324 (2d Cir. 20 19) (summary order) (conclud ing th at Parkins

24 - 1661 United States v. Jim enez 30 demands “a more co mprehensive justifica tion” where a conditi on exceeds the 400 - hour threshold). Here, the specific co ndition imposed is un iquely justif ied and withs tand s comparison to P arkins. There, we note d that “the d istrict cour t did not find that Parkins was in ne ed of any of the training that co mmunity ser vice might provide, and there is no reason on this recor d to believe tha t 695 hours of community service i s required for Parki ns to achieve the benefi t such service offers.” Parkins, 935 F.3d at 67. We also expr essed concern that the justification of keeping the defendant pro ductive “lack[ed] a limiting pr inciple that would allow an evaluation of how much com munity service is ‘greater than necessary’ to keep [the defendant] off the str eet” and that the condition migh t actually “disrupt[]” his productive occupat ion. Id. The conditi on here does not present th o se concerns because it is contin gent on Jimene z’s lack of employ ment (or excuse from emplo yment). There fore, the condition incorporate s its own limitin g pr incip le an d ensures that community servic e will not int erfere with prod uctive empl oyment. And a s discussed ab ove, the District Cou rt did not rely solely on general ideas about the benefi ts of productiv ity. Jimenez himse lf attested to the benefits o f remaining product ive and the tendency to revert to criminality when

24 - 1661 United States v. Jim enez 31 unemployed. See Dkt. No. 59 at 4 – 8 (not ing Jimenez “reverte d to selling drugs” and “returned to poor decisi on - making” dur ing periods of u nemploymen t). On this record, and wi th these limitat ions, the community ser vice condition is just ified despite the possibi lity of exceeding 400 hours. 3. Mental Health Treatment Cond ition Finally, we affirm th e imposition of the menta l health treatment condition. The Distr ict Cour t explained that it imposed the mental health treatment con dit ion because it “believe[d] [Jimenez] could benefit enormously,” sp ecifically in the employment context, by helping him “w ork[] out problems at home, pr oblems with [his] emp loyer, problems with [his] cowor kers.” App’x at 12 4–25. Additionally, th e District Court ass erted th at “one of the r isks of recid ivism is not being able to change your mind - set in a way that is helpful to ree ntry in society.” Id. Such explanations, on their own, would likely be insufficient because they rely on generalized ideas about the be nefit of th erapy rather than J imenez’s individual circumstances. But the District Court proceeded to explain that it thought “mental health treat ment would, hope fully, assist Mr. Jimenez in dea ling with h is past and present dem ons that have preven ted him from achieving the goals that he legitimately has to support hi mself and his family and n ot r eturn ing to a life of

24 - 1661 United States v. Jim enez 32 crime. ” Id. at 131 –32. And finally, the Di strict Co urt sta ted th at “look ing at Mr. Jimenez ’s personal history he re, he needs [mental health treatm ent].” Id. at 132. These s tatements demons trate tha t the Dis trict Cour t prop erly impos ed the condition based on Jimenez’s individua l characteristics. Additionally, the co ndition is substant ively reasonable as it is reasonably related to t he relevant sentencing factors. Jimenez expressed feel ings of loneli ness, grief, sel f - destruction, and stress in his sub missions t o the District Court, expressly connecting such feelings to his involvement in criminal activity. In o ther portions of the record, Jimenez sugg ests that previous interact ions with mental health services w ere helpful. And at his or iginal sentencing, Ji menez told the Court: “ I was not in the right mi ndset when I made this mista ke,” and expressed a desi re “to use the resources availab le to [him] to get the support [he needs].” App’x at 83. Thus, the mental health treatment condition does not rely on the general notion that therapy is he lpful for everyone, b ut instead, is reasonably rela ted to both Jimenez’s history an d characteristics an d the need to deter cr iminal conduct. Jimenez’s challenges do not alter th is conclusion. Second, the condit ion is not vag ue. Jimenez contends t hat the condition “ has no clear conten t, purpose, or goal,” and therefore, lacks clarity on “wha t

24 - 1661 United States v. Jim enez 33 ‘successful part icipation’ requ ires,” in pa rt because he has not been d iagnosed with an y specific me ntal health condition. Reply Br. at 16. In doing so, Jimenez relie s on our decis ion in Carlineo, where we vacated a condition wh ich required the defendant “t o participate in [a] progra m. . . [which] could include a sentencing circle and a listening circle” and which might re quire the defendant to “ listen to stories a bout Muslim refu gees or people who su ffered from violence f or being Muslim.” 998 F.3d at 5 36–3 7. The con dition in Carlineo lack ed spe cific ity regarding what activities wou ld actually take place in the sente ncing and listening circles, and therefor e, did not provide the defe ndant with notice of what “co uld trigger a charge of v iolating the cond ition.” Id. at 5 37. In contra st, the me ntal health treatment co ndition here merely requires pa rtici pation in a counseling program, in cludin g regular ther apy s essio ns, the deta ils o f which will b e determi ned by service providers and pro bation officers. As such, there is no notice issue. I t is clear “what conduc t could trigger a charge of vio lat i ng the condit ion,” id.: failing to p articipate in the program and the sess ions. I ndeed, we expressly

24 - 1661 United States v. Jim enez 34 distinguished the condition at issue in Carlineo from “special conditions such as substance abuse and mental heal th treatment.” Id. 6 Third, the con dition does n ot impermissi bly delegate au thority to p robation officers. It does n ot entitle probat ion officers to impose a dditional burdens on Jimenez, such as gi ving them the a uthority to deci de whether Jim enez particip ates in treatmen t at all. Contra United St ates v. Harris, 164 F. 4 th 181, 197 (2d C ir. 2026). Instead, it merely affords probation office rs the authori ty to ha ndle certain deta ils of the treat ment, a d ynamic that is plainly pe rmissible. See Villafane- Lo zada, 973 F.3d at 1 53 (“ [T] he choice between va rious outpatient therapy options. .. is routinely delegated t o probation officers.”); Matta, 777 F.3d a t 122 (“[A] district court may delegate t o a probation officer decisionmaking aut hority over certain minor details of su pervised release — fo r example, the selection of a therap y provider o r treatm ent schedule. ”); contra United States v. Peterson, 248 F.3d 79, 85 (2d Cir. 2001) (vaca ting a similar con dition where defen dant was “required to 6 Defend ant’s c ontent ion tha t his lack of a speci fic me ntal he alth dia gnos is muddie s the water s on what “s uccessf ul partic ipation” looks like, Reply Br. at 16, is contradicted by the terms of the condit ion, which specif ically requires cognitive beh avioral therapy “to the ext ent practicable and as determ ined to b e appropriate by th e therapy provider. ” App ’x at 141. As discus sed below, we have frequentl y affirmed similar c onditions t hat are not e xpressly ta ilored t o a specific d iagnosis. If a nything, the condit ion imposed in this case provides more clar ity, not less, by p rioritizi ng a specif ic kind of tre atment.

24 - 1661 United States v. Jim enez 35 participate in a mental hea lth intervention only if directed to do so by his probation officer”). B. Challenge to Term of Impris onment W e affirm the District Co urt’s refusal to revi sit Jimenez’s sentence o f impr isonme nt on re mand, wh ich we review de novo as a question of law. Jimenez’s chief con tention is that a deve lopment in our precedent on the application of certain Guidelines provisions just ifies a reduction in his sentence. Indeed, pursuant to United States v. Gibson, a case we dec ided after Ji menez’s origi nal sentence bu t before our order rem anding for resentenc ing, his Guide lines range m ight be lower if he were sentenced for t he f irst time today. 55 F.4th 153 (2d Cir. 2022). In Gibson, we determin ed that crimes u nder New York Pen al Law § 220.39(1) do no t categorically q ualify as cri mes of a “co ntrolled subst ance offense” under U.S.S.G. § 4B1.1. Id. at 167. And here, Jimenez’s prior convict ion under § 220.39(1) was used as a predicate “contro lled substance offense” to determi ne his base offense le vel, albeit under a separate Guideli nes provisio n, U.S.S.G. § 2K2.1(a)(2). S uch changes in the law may justify a district court ’s ven turing beyond t he scope of a limite d remand for resentencing in some cases. “In general, when we

24 - 1661 United States v. Jim enez 36 remand to a district court for re sentencing, that remand is ‘for limited, and not de novo sentencing.’” United States v. Valente, 915 F.3d 916, 924 (2d C ir. 2019) (quoting United States v. Malki, 718 F.3d 178, 182 (2d Cir. 2013)). 7 But there is an excep tion to the general rule. W here there are “compelling circumstances,” includ ing b ut not limite d to “an i ntervening change in controlling law,” a distr ict court can exceed the co nfines of its limited revi ew on remand and reconsider aspects of its previous decision. Id. (quot ing United Stat es v. Carr, 557 F.3d 93, 102 (2d Cir. 2009)). Jimenez assert s that th is case fal ls with in this except ion. A fter all, our decision in Gibson is an interve ning change in the controlling law on an issue key to the calculation of his sen tence. Crucially though, th is case involves a plainly applicable ap peal wa iv er. Jimenez expressly a greed that he would “not file a direct appeal. . . of any sentence within or below the Stipulated Gu idelines Range of 84 to 105 mon ths’ imprisonment.” A pp’x at 26. Jimenez was sen tenced to 105 months’ impr isonme n t, and t hus, the appeal wa iver app lies. 7 In his r eply, Jime nez cites V alente for the prop ositi on that “‘an inte rveni ng chan ge in contr olling law’ allo ws a defend ant to r aise issue s that were ‘prev iously waived.’” Reply B r. 2 0 (quoting Va lente, 915 F.3d at 924). But Valent e and the ca ses it cites d o not de al with a binding a ppeal wa iver. Instea d, the y stand for the separate pro posit ion that a district court, on limited reman d, can consider issu es that were n ot previous ly raised before the district court if there is a compe lling reason t o do so.

24 - 1661 United States v. Jim enez 37 “W e have lon g enforced wai vers of direct appeal ri ghts in plea agreem ents, even though the gro und s for appeal aro se after the plea agreement was ent ered into.” Garcia- Santos v. United Stat es, 273 F.3d 506, 509 (2d C ir. 2001). That remains true even when the grounds for appeal rel ate to a subsequent change in our precedent re garding the calculation of the defen dant’s sentence. See United States v. Morgan, 406 F.3d 1 3 5, 137 (2d Cir. 2005) (A defendant’s “i nability to fores ee that subsequently de cided cases would crea te new appeal issues does not supply a basis for failing to enforce an appeal waiver.”); see also Sanford v. United States, 84 1 F.3d 578, 580 (2d Cir. 2016) (holding c hange in law governing a defendant’s sentence did not j ustify putting aside a waiver). Here, t hough Gibson was decided prior to our or der remanding this case for resentencing (and th us, could have been raised for this Court’s consideration on Jimenez ’s first app eal), Jimenez fi rst raised the a rgument that his t erm of imprisonm ent should be reduced be fore the Di strict Court at resentenci ng. Had Jimenez raised his ar gument based on Gib son to this Court on h is first appeal, there would have been l ittle doubt that such a challen ge to his sentence was barred by the appeal w aiver. See Morgan, 40 6 F.3d at 137. The question, t hen, is whether the

24 - 1661 United States v. Jim enez 38 fact that Jimenez w aited to ra ise the i ssue until rem and before the Di strict Court changes that result. We hold that it does not. Though the posture of this ca se enables Jimenez to avail himself of the law permitt ing district courts to reach issues outside th e scope of their limited remand based on subsequent changes in the law, his appea l waiver neverth eless preclud es his argument. To hold otherwis e would create an unwarrant ed exception to an otherwi se enforceable appeal w aiver wh enever a case is remand ed for resentencing. T hough an intervening change in controlling law may constitute a compelling reason for a distr ict court to venture b eyond the scope of its limited remand i n some cases, we hold that an intervening change in contr olling law is not a compelling reason whe re the defenda nt is boun d by an appeal waiver that would have fore closed the sentencing argument were it raised on appeal. III. Conclusion In summa ry, we hold that the three sp ecial conditi ons were procedurally and substantive ly reasonable. In doing so, we reiterate that special condi tions must be reasonab ly related to the appropr iate sentencing fac tors as they app ly to the specific defenda nt before the court. We also clarify that a challenge to a special

24 - 1661 United States v. Jim enez 39 condition is not unripe merely because the conditi on itself imp licate s the occurrence o f future event s. Instead, co urts mus t engage in a n issue - specif ic analysis. Fi nally, whe re a defendant ha s pled guil ty and ag reed to an appe al waiver, the defenda nt may not attemp t to circumvent the for ce of that waiver by asking a distric t court on re mand to con sider arguments that would have b een foreclosed had they been raised on appeal. For the foregoi ng reasons, the Di strict Court’s jud gment is A FFIRMED.