25 Before: CALABRESI, PÉREZ, and NATHAN, Circuit Judges. 26 On appeal from a sentencing judgment entered in the United States District 27 Court for the Northern District of New York (D’Agostino, J.). 28 29 Defendant-Appellant Dewey K. Sims pleaded guilty to possessing a firearm 30 after a prior felony conviction, in violation of 18 U.S.C. § 922(g). The district court 31 imposed a term of imprisonment followed by a term of supervised release, subject 32 to, as relevant here, a special condition that prohibited Sims from associating with 33 “any member, associate, or prospect of the Jungle Junkies, or any other criminal 34 gang, club, or organization.” Appellant’s App’x at 92. On appeal, Sims challenges 1 the condition as: (1) lacking support for its imposition from the district court or the 2 record itself; and (2) impermissibly overbroad and vague. We agree that neither 3 the district court’s comments during the sentencing hearing nor the record show 4 that it fulfilled the requirements necessary to impose the special condition of 5 supervised release in question. For that reason, we vacate the condition and 6 remand for the limited purpose of permitting the district court to further explain 7 its reasoning or develop the record as needed. 8 9 VACATED IN PART AND REMANDED. 10 11 12 James P. Egan, Assistant Federal Public Defender, 13 Federal Public Defender’s Office, Northern District of 14 New York, Syracuse, NY, for Defendant-Appellant. 15 16 Emmet O’Hanlon, Assistant United States Attorney for 17 Carla B. Freedman, United States Attorney for the 18 Northern District of New York, Albany, NY, for Appellee. 19 20 21 MYRNA PÉREZ, Circuit Judge: 22 In this appeal, Defendant-Appellant Dewey K. Sims challenges the district 23 court’s imposition of a “special condition” 1 of supervised release prohibiting him

1 In this decision, we use the term “special conditions” to refer to the discretionary conditions imposed by sentencing courts that are not specifically required or recommended in 18 U.S.C. § 3583 (concerning the imposition of a term of supervised release after imprisonment) or the United States Sentencing Guidelines (the “Guidelines”). While the Guidelines technically describe a category of “recommended” conditions as “special” because their appropriateness is contingent on whether certain circumstances are present, we consider those recommended conditions to be “as necessary to the administration of supervised release as the standard conditions,” which “are presumed suitable in all cases.” United States v. Thomas, 299 F.3d 150, 153–54 (2d Cir. 2002) (quoting United States v. Asuncion-Pimental, 290 F.3d 91, 94 (2d Cir. 2002)); see also Asuncion-Pimental, 290 F.3d at 94 (“[T]he suitability of the conditions provided in § 5D1.3(d) may be contingent on the presence of specific factors in each case. Where these factors 2 1 from “associat[ing] with any member, associate, or prospect” of any “criminal 2 gang, club, or organization.” Appellant’s App’x (“App’x”) at 92. 3 When imposing a sentence that includes a term of supervised release, 4 sentencing courts are given broad discretion to attach “special conditions,” which 5 constrain the defendant’s behavior. But the court’s authority to impose such 6 conditions is not boundless. One limitation is that the sentencing court’s 7 explanation of its decision to impose the special condition must be supported by 8 the record. In this case, the sentencing court’s reason for imposing the special 9 condition was neither adequately explained nor supported by the record, and 10