09-1452-cv; 09-1601-cv; 09-2261-cv Doninger v. Niehoff UNITED STATES COURT OF APPEALS 1 FOR THE SECOND CIRCUIT 2 3 August Term 2009 4 5 6 (Argued: January 12, 2010 Decided: April 25, 2011) 7 8 Docket Nos. 09-1452-cv (L), 09-1601-cv (XAP), 09-2261-cv (CON) 9 10

_____________________________________ 11 12 AVERY DONINGER, 13 14 Plaintiff-Appellee-Cross-Appellant , 15 16 -v.- 17 18 KARISSA NIEHOFF, PAULA SCHWARTZ, 19 20 Defendants-Appellants-Cross-Appellees

. 21

_____________________________________ 22 23 Before: KEARSE, CABRANES, and LIVINGSTON, Circuit Judges

. 24 25 Plaintiff-Appellee-Cross-Appellant (“Plainti ff”) appeals from a district court decision 26 granting summary judgment to Defendants-Appellants-Cross-Appellees (“Defendants”) on a claim 27 brought under 42 U.S.C. § 1983 alleging that Defendants, public school officials in Burlington, 28 Connecticut, violated Plaintiff’s rights under the First Amendment of the United States Constitution 29 when they prohibited her from running for Senior Class Secretary in response to her off-campus 30 internet speech. Plaintiff also appeals from the district court judgment granting summary judgment 31 to Defendants on her Equal Protection claim, from the district court’s sua sponte dismissal without 32 prejudice of her claims under the Connecticut Constitution, and from the district court’s 33 determination that she failed properly to assert a claim pursuant to Monell v. Department of Social 342 Services , 436 U.S. 658 (1978). Defendants appeal the di strict court’s denial of their motion for 1 summary judgment on Plaintiff’s claim that Defe ndants violated her First Amendment rights when 2 Defendants prohibited Plaintiff from wearing or otherwise displaying a homemade printed t-shirt 3 in a school assembly. Because we conclude th at Defendants are entitled to qualified immunity on 4 both First Amendment claims, and because we agree withthe district court with regard to Plaintiff’s 5 other claims, the district court’s judgment is affirmed in part and reversed in part. The matter is 6 remanded for the district court to enter judgment for Defendants. 7 Affirmed in part and reversed in part. 8 9 JON L. SCHOENHORN, Jon L. Schoenhorn & Associates, 10 LLC, Hartford, Connecticut (Sara J. Packman, on the 11 brief ), for Plaintiff-Appellee-Cross-Appellant

. 12 13 THOMAS R. GERARDE, Howd & Ludorf, LLC, Hartford, 14 Connecticut (Beatrice S. Jordan, on the brief ), for 15 Defendants-Appellants-Cross-Appellees. 16 17 DEBRA ANN LIVINGSTON, Circuit Judge : 18 We are once again called to consider the circ umstances in which school administrators may 19 discipline students for speech relating directly to the affairs of the schoolwithout running afoul of 20 the First Amendment. More precisely, we must determine if the defendant-school-administrators 21 before us are entitled to qualified immunity on the pl aintiff-student’s claims that they violated her 22 First Amendment rights by (1) preventing her from running for Senior Class Secretary as a direct 23 consequence of her off-campus internet speech, and (2) prohibiting her from wearing a homemade 24 printed t-shirt at a subsequent school assembly. 25 Plaintiff-Appellee-Cross-Appellant Avery Doni nger (“Doninger” or “Plaintiff”) appeals from 26 a January 15, 2009, decision of the United States Di strict Court for the District of Connecticut 271 The grant of partial summary judgment to Defendants from which Doninger appeals is an interlocutory decision not typically appealable prior to a “final decision[ ]” in the case. Myers v. Hertz Corp. , 624 F.3d 537, 552 (2d Cir. 2010) (quoting 28 U.S.C. § 1291). Here, however, we do have jurisdiction over the appeal. On May 14, 2009, the district court certified an interlocutory appeal, pursuant to 28 U.S.C. § 1292(b), from its ruling granting Defendants qualified immunity with respect to Doninger’s blog-related First Amendment claim. See Doninger v. Niehoff , No. 3:07-cv-1129, 2009 WL 1364890, at *2 (D. Conn. May 14, 2009). On July 23, 2009, we granted Doninger’s motion for leave to appeal the interlocutory order of the district court and consolidated her appeal with the appeal that had already been brought by Defendants, discussed infra

. 2 The district court refused to certify these other rulings adverse to Doninger, citing the absence of substantial grounds for difference of opinion on these questions. However, as the court below recognized, “[w]hen a district court certifies, pursuant to 28 U.S.C. § 1292(b), a question of controlling law, the entire order is certified and we may assume jurisdiction over the entire order, not merely over the question as framed by the district court.” City of New York v. Beretta U.S.A. Corp. , 524 F.3d 384, 391-92 (2d Cir. 2008). As a result, we “may address any
3 (Kravitz, J. ) — as well as a March 19, 2009, denial of a motion for reconsideration — granting 1 partial summary judgment to Defendants-Appellants- Cross-Appellees Karissa Niehoff, principal at 2 Lewis S. Mills High School (“LMHS” or “the School”) in Burlington, Connecticut, and Paula 3 Schwartz, superintendent of the school district inwhich LMHS is located (together, “Defendants”), 4 on the claim that Defendants violated Plaintiff’s First Amendment rights when they prohibited her 5 from running for Senior Class Secretary in respons e to a blog entry that Doninger posted from her 6 home during non-school hours. 1 Because we conclude that the asserted First Amendment right at 7 issue was not clearly established, we affirm the district court’s decision on the ground that 8 Defendants were entitled to qualified immunity. Doni nger also appeals the district court’s grant of 9 summary judgment to Defendants on her Equal Protection selective-enforcement claim, its sua 10 sponte dismissal without prejudice of her claims under the Connecticut state constitution, and the 11 court’s determination, on her motion for reconsideration, that she failed prope rly to assert a claim 12 pursuant to Monell v. Department of Social Services , 436 U.S. 658 (1978). 2We affirm the district 13issue fairly included within the certified order.” Yamaha Motor Corp., U.S.A. v. Calhoun , 516 U.S. 199, 205 (1996).

4 court’s determination on these claims as well. 1 Defendants appeal the district court’s partial denial of their motion for summary judgment, 2 asserting that they are entitled to qualified immunity on Doninger’s remaining First Amendment 3 claim — a claim alleging that her rights were viol ated when Niehoff prohib ited her from displaying 4 in a school assembly a homemade t-shirt emblaz oned with “Team Avery” on the front and “Support 5 LSM Freedom of Speech” on the back. We reverse the district court on the basis that Defendants 6 are entitled to qualified immunity on this claim as well, since, given the legal framework and the 7 particular factual circumstances of this case, the rights at issue were not clearly established. 8 BACKGROUND 9 I. Factual Background 10 At the time of the events relevant to the instant dispute, Doninger was both on the Student 11 Council and serving as the Junior Class Secretary at LMHS, a public high school in Burlington. The 12 school district had in place a policy regarding elig ibility to represent its schools in such positions. 13 The district’s policy stated: 14 All students elected to student offices, or who represent their schools in extracurricu15 lar activities, shall have and maintain good citizenship records. Any student who 16 does not maintain a good citizenship record shall not be allowed to represent fellow 17 students nor the schools for a period of time recommended by the student's principal, 18 but in no case, except when approved by the board of education, shall the time 19 exceed twelve calendar months. 20 21 Joint Appendix (“J.A.”) 251. LMHS’s student handbook — which D oninger, as an LMHS student, 22 signed, attesting that she had reviewed it with he r family — specified, further, that the objectives 23 of the School’s Student Council include: (1) “[m] aintain[ing] a continuous communication channel 245 from students to both faculty and administration, as well as among the students within the school,” 1 and (2) “[d]irect[ing] students inthe duties and responsibilities of good citizenship, using the school 2 environment as the primary training ground.” Id. at 253. 3 The dispute at the heart of this case arose over the scheduling of an event called “Jamfest,” 4 an annual battle-of-the-bands concert that Doni nger and other Student Council members had helped 5 to plan. Jamfest was scheduled to take place inthe School’s new auditorium on Saturday, April 28, 6 2007, but shortly before the date of the event, the School’s administrators learned that the LMHS 7 teacher responsible for operating the auditorium’s sound and lighting equipment, David Miller, 8 would be unable to attend on that date. As a re sult, at an April 24 Student Council meeting, which 9 occurred prior to the start of the school day, the students were informed that Jamfest could not be 10 held in the auditorium without Miller, and that th ey had the option either to keep the scheduled date 11 and hold the event in the cafeteria, or to find a new date. This announcement upset Doninger and 12 her fellow organizers, who wanted to hold the even t in the auditorium that weekend, as planned. 13 Jennifer Hill, the Student Council’ s faculty advisor, recommended that they discuss the situation 14 with Niehoff, the School’s principal, and she acco mpanied them to Niehoff’s office. They were 15 unable to see Niehoff immediately, but Doninger volunteered to return to the principal’s office 16 during her study hall to help schedule a meeting for later in the day. 17 Thereafter, however, four Student Council members, including Doninger, decided to take 18 immediate action. From LMHS’s computer lab, theygained access to the email account of the father 19 of one of the students. Using that account, the students sent a mass email alerting various LMHS 20 parents, students, and others that “the Central Office [had] decided that the Student Council could 21 not hold its annual Jamfest/battle of the bands in the auditorium” and urging them to “contact [the] 223 The policy also restricted use of school computers to “school-related purposes” and use of student email accounts to “communication only w ith identifiable individuals or organizations with a recognized role in the school-related activity.” J.A. 275. Doninger executed the Regional School District # 10 Acceptable Use Agreement on September 6, 2006, agreeing to abide by this use policy.
6 central office and ask that we be let [sic] to use our auditorium.” J.A. 219. They did so in spite of 1 a school email policy that specifically restricted “[a]ccess of the Internet or e-mail using accounts 2 other than those provided by the district for school purposes.” 3 Id. at 275. The mass email included 3 the district office’s phone number and urged recipients to call that office and forward the email “to 4 as many people as you can.” Id. at 219. Another email, sent later that same day, included 5 Superintendent Schwartz’s email address and a corrected phone number. Both Schwartz and 6 Niehoff received an influx of telephone calls and emails regarding Jamfest. As a result, Niehoff was 7 called back to her office from a planned in-service training day. 8 Later that day, Niehoff, who by this time had in her possession a copy of the students’ first 9 email, encountered Doninger in the hallway at sc hool. The parties differ in their accounts of the 10 ensuing conversation, which took place in Niehoff’s office. Doninger states that Niehoff informed 11 her about the calls and emails that had been received that day and told her that because Schwartz 12 was upset, “Jamfest was cancelled on [April] 28th.” Prelim. Inj. Hearing Tr. (“P.I. Hearing Tr.”) 13 at 262:4. Doninger testified that Niehoff left open the possibility of Jamfest happening at a later date 14 “if [the students] play [their] cards right,” but not “until after [the] talent show.” Id. at 261:22-23. 15 In contrast, Niehoff asserts that she never told Doninger that Jamfest was cancelled, but rather 16
stressed that the information included in the mass em ail (to the effect that the auditorium could not 17 be used) was incorrect, as “the option of rescheduli ng was always there if they did not want to use 18 the cafeteria on the 28th.” Id. at 492:3-4. Niehoff contends that she then had a discussion with 194Peter Bogen, an assistant principal at LMHS, was present during the conversation and also recalls generally that Niehoff advised Doninger regarding her obligation to engage in appropriate communications in the resolution of conflict and to be a role model for others.
7 Doninger in which she told Doninger that her conduct — sending a mass email from the computer 1 lab that contained inaccurate information, rather th an working with the administration to resolve the 2 problem — was unbecoming of a class officer. 4Doninger, however, denies that Niehoff said 3 anything regarding her responsibilities as a class offi cer. Finally, Niehoff st ates that she requested 4 that Doninger, with the other senders of the email, compose a new email to correct the misinforma5 tion in the first one. Niehoff contends that Doninge r agreed to do so, while Doninger denies that this 6 conversation took place. 7 That night, from her home, Doninger posted a message on her publicly accessible blog 8 hosted by livejournal.com, a website unaffiliated with LMHS. The blog post began as follows: 9 jamfest is cancelled due to douchebags in centr al office. here is an email that we sent 10 out to a ton of people and asked them to forward to everyone in their address book 11 to help get support for jamfest. basically, because we sent it out, Paula Schwartz is 12 getting a TON of phone calls and emails and such. we have so much support and we 13 really appriciate [sic] it. however, she got pissed off and decide d to just cancel the 14 whole thing all together. anddd [sic] so basically we aren't going to have it at all, but 15 in the slightest chance we do it is going to be after the talent show on may 18th. 16 anddd.. [sic] here is the letter we sent out to parents. 17 18 J.A. at 167. Doninger reproduced the email thatshe and the other Student Council members had 19 sent that morning and then continued: 20 And here is a letter my mom sent to Paula [Schwartz] and cc’d Karissa [Niehoff] to 21 get an idea of what to write if you want to write somethi ng or call her to piss her off 22 more. im down.-- 23 24 Id. Doninger next reproduced an email that her mother had sent to Schwartz earlier in the day 25 concerning the dispute. Doninger testified that her use of the word “douchebags” in the blog post 268 “referr[ed] to anyone involved in the cancellation of Jamfest,” including Schwartz. P.I. Hearing Tr. 1 at 379:6-7. The purpose of her blog posting, she testified, was to encourage more people to contact 2 the administration in an effort to change its positi on that Jamfest could not be held in the auditorium 3 on April 28. Several LMHS students posted comme nts to the blog, including one that referred to 4 Superintendent Schwartz as a “dirty whore.” J.A. at 168. 5 The following morning, April 25, 2007, Schwartzand Niehoff continued to receive phone 6 calls and emails regarding Jamfest, as well as personal visits from students. In addition, during the 7 day, a group of students gathered outside the administration office. A student later testified that the 8 assembled students were “pretty upset” and “fired up,” although he also stated that he “d[idn’t] think 9 they were going to do anything threatening.” P. I. Hearing Tr. at 80:23-81:7. Doninger testified that 10 the students were “all riled up,” id. at 434:13, believing that Jamfest had been cancelled, and that 11 they planned “to go and sit in the office until they got an answer,” id. at 435:1-2. She did however 12 claim that the students left after she spoke to them . Niehoff and Schwartz te stified that on both April 13 24 and 25, they were forced to miss or arrived late to several school-related activities as a result of 14 the controversy, including a health seminar, an observation of a non-tenured teacher, and a 15 superintendents’ meeting. Doninger contends that these claims are “self-serving” and that some of 16 this supposed disruption was a product of Defendant s’ own choosing to devote time to resolving the 17 Jamfest controversy. 18 That same morning of April 25, Doninger and the three other Student Council members who 19 sent the mass email were called out of class to meet with Schwartz, Niehoff, Hill, Miller, and David 20 Fortin, LMHS’s Director of Building and Grounds, regarding Jamfest. The four Student Council 21 members were again advised that the auditorium would not be available on April 28, and told that 225 Jamfest was successfully held as scheduled on this date, with all but one of the scheduled bands participating.
9 Jamfest could be held in the cafeteria on that date or in the auditorium on a later date. It was agreed 1 that Jamfest would take place in the new auditorium on June 8, 2007. 5 During this meeting, 2 Schwartz suggested to Doninger and the other student s that they should have come to her to resolve 3 the controversy rather than sending a mass email. Schwartz asked the stude nts to send out another 4 email explaining that the situation had been resolved, which they did. 5 Doninger’s blog post did not come to the attention of school officials until May 7, 2007, 6 about two weeks later. Niehoff testified that on viewing the blog post, she was disappointed by the 7 fact that Doninger had republished the mass email and inaccurately reported that Jamfest had been 8 cancelled, despite the fact that Niehoff had spoken with her about the email and had worked with 9 her to clear up any confusion as to Jamfest’s sche duling. She also testified that she was disappointed 10 by the language used in the posting, and by the fact that it “continue[d] to encourage people to incite 11 confrontation” with Schwartz, P.I. Hearing Tr . at 508:11-12, when Niehoff had met with Doninger 12 and had suggested that such behavior was inappropriate for a class officer. Niehoff testified that 13 because she knew that Doninger had advanced placement exams around the time Niehoff was made 14 aware of the blog post, she did not immediately bri ng the fact that she, Niehoff, and others were 15 aware of the post to Doninger’s attention. She did consult with other administrators at the School, 16 seeking advice as to an appropriate response. 17 On May 17, 2007, Doninger went to Niehoff’s office to accept her nomination for Senior 18 Class Secretary. At that time, Niehoff confronted Doninger regarding the post and requested that 19 Doninger apologize to Schwartz, show the blog entry to her mother, and withdraw her candidacy 206It is uncontested that, as Niehoff asserted, class officers are automatically members at large of the Student Council.
10 for Senior Class Secretary. Doninger agreed to comply with the firs t two requests, but did not agree 1 to the third. In response, Niehoff refused to allo w Doninger to run for a senior class officer position, 2 although Doninger was permitted to retain her current position as Junior Class Secretary. Niehoff 3 testified at the preliminary injunction hearing that she took this action because, inter alia , she felt 4 that the blog post failed to demonstrate good citi zenship, which was significant because Doninger 5 was “acting as a class officer at the time that she created the blog,” P.I. H earing Tr. at 559:7-8, and 6 because it violated the principles governing stude nt officers set out in the student handbook that 7 Doninger had signed. 6 Niehoff determined that Doninger’s name would not appear on the election 8 ballot nor would she be permitted to give a campaign speech at a May 25 school assembly regarding 9 the election. Doninger was not otherwise disciplined for her blog post. 10 On May 24, 2007, the day before the student el ection, Doninger and her mother visited a 11 local television news station where newscasters taped an interview with them regarding Doninger’s 12 blog post and Niehoff’s decision not to let her participate in the class election. Doninger requested 13 the opportunity to make an announcement about the program in civics class later that same day, but 14 as she was explaining this request to her teach er, an apparent supporter yelled out, “[E]veryone 15 watch the news at six.” Id. at 292:13-14. This disruption resu lted in the student being sent to 16 Niehoff’s office. 17 Some time before the start of school the next day, when elections were scheduled to be held, 18 Niehoff learned that an undetermined number of students planned to wear “Vote for Avery” t-shirts 19 to that day’s assembly, where candidates were to give speeches before approximately 600 of their 207Plaintiff claims that the t-shirts were to beworn in silent protest, an account of the students’ intentions that the district court seemed to accept below, see Doninger v. Niehoff , 594 F. Supp. 2d 211, 225 (D. Conn. 2009). We are pointed to no evidence, however, and find none in our own search of the record, regarding the students’ plans. There is also no evidence that any intentions they may have had were in any way communicated to Niehoff.

8 She also required another student, who was w earing a different t-shirt bearing the legend “Vote for Avery,” to remove it.

11 fellow students. It was also ru mored that supporters of Doninger were planning a write-in campaign 1 on her behalf. Niehoff relayed this informati on to Schwartz and Vice-Principal Bogen by email 2 early on the morning of May 25. 3 Niehoff’s information proved largely accurate as, indeed, a group of students had planned 4 to wear t-shirts into the assembly bearing “Team Avery” on the front and “Support LSM Freedom 5 of Speech” on the back. At least two of these students were themselves running for office and 6 originally intended to wear the t-shirts during their speeches, although there is nothing in the record 7 to suggest that Niehoff was aware of this. 7 That morning, Niehoff stationed herself outside the 8 auditorium as several hundred students made th eir way in through two entrances to hear the 9 candidate speeches. A few students wearing “Team Avery” shirts attempted to enter the auditorium 10 prior to the beginning of the assembly. Niehoff instructed them to remove their shirts. 8 One student 11 testified that, in asking him to remove the shirt, Niehoff stated that it was “disruptive” and “set[] a 12 bad example.” P.I. Hearing Tr. at 213:19. Niehoff herself testified that she was acting to prevent 13 the wearing of “any shirt that [she] felt would cause disruption” at the assembly, id. at 590:12-13, 14 and that it was her opinion that the shirts at issue would have caused disruption. There is no 15 evidence in the record that Niehoff (or any other sc hool official) made any effort to prevent students 16 from wearing the t-shirts other than at the election assembly. 17 At the time of the assembly, Doninger was not wearing a “Team Avery” shirt, but was 1812 carrying one with her. She testified that she was going to “put it on after,” id. at 293:21, but instead 1 put it in a backpack when Niehoff told her the shirts were not permitted in the assembly. Doninger 2 was permitted to enter the auditorium wearing th e t-shirt she had on, which read “RIP Democracy.” 3 Even though Doninger was not a candidate and was not permitted to give a speech at the assembly, 4 students there shouted “Vote for Avery.” (In th e words of one student who was present, “there 5 wasn’t screaming or anything, it’s not like there was a riot, but people were yelling Avery’s name, 6 vote for Avery.” Id. at 117:23-25.) Niehoff warned these students to be respectful. 7 Among the students who gave speeches before th e assembled crowd were the two candidates 8 who were in fact listed on the ballot for the positi on of Senior Class Secretary, including the student 9 who ultimately was awarded the position, “A.K.” Even though not on the ballot, Doninger 10 nevertheless received a plurality of the votes for the position as a write-in candidate. Niehoff, 11 however, in accordance with her earlier decision, awarded the position of Senior Class Secretary to 12 A.K., who received the next highest number of votes. 13 II. Procedural History 14 In 2007, prior to Avery Doninger’s reaching the age of majority, her mother, Lauren 15 Doninger, filed a complaint on her behalf in Connecticut Superior Court asserting claims under 42 16 U.S.C. § 1983 and state law. Doninger v. Niehoff (“Doninger II ”), 527 F.3d 41, 46-47 (2d Cir. 17 2008), aff’g Doninger v. Niehoff (“Doninger I ”), 514 F. Supp. 2d 199 (D. Conn. 2007). Defendants 18 removed the action to the United States District Court for the District of Connecticut. Lauren 19 Doninger subsequently filed a motion for a preliminary injunction asking the court, inter alia , to 20 void the election for Senior Class Secretary, to strip the title from the student to whom it had been 21 awarded, and to require a new electi on in which her daughter could run. Id. at 47; see also Doninger 2213 I, 514 F. Supp. 2d at 202. In the alternative, she asked that the School be enjoined to grant her 1 daughter “the same title, honors, and obligations as the student elected to the position, including the 2 privilege of speaking as a class officer at graduation.” Doninger II, 527 F.3d at 43. After extensive 3 development of the factual record, the district c ourt denied the request for an injunction based on 4 Doninger’s failure to show like lihood of success on the merits. See Doninger I, 514 F. Supp. 2d at 5 218. On appeal, this Court affirmed. Doninger II, 527 F.3d 41. 6 After Avery Doninger graduated from high sc hool, she was substituted for her mother as 7 plaintiff. Although her request for an injuncti on has been mooted by her graduation, Doninger now 8 seeks damages for the alleged violation of her cons titutional rights. The district court entertained 9 cross-motions for summary judgment, and on January 15, 2009, denied Doninger’s motion and 10 granted Defendants’ motion in part and denied it in part. See Doninger v. Niehoff (“Doninger III ”), 11 594 F. Supp. 2d 211 (D. Conn. 2009). It subsequen tly denied motions for reconsideration. 12 Doninger v. Niehoff , No. 3:07-cv-1129, 2009 WL 763492 (D. Conn. Mar. 19, 2009). Defendants 13 appealed the partial denial of qualified immunityand, as previously noted, Doninger was granted 14 leave to appeal the district court’s order partially granting summary judgment to Defendants. 15 DISCUSSION 16 The standard of review in these appeals from a partial grant and partial denial of summary 17 judgment is de novo

. McBride v. BIC Consumer Prods. Mfg. Co. , 583 F.3d 92, 96 (2d Cir. 2009). 18 Summary judgment is proper only when, construing the evidence in the light most favorable to the 19 non-movant, “there is no genuine dispute as to any material fact and the movant is entitled to 20 judgment as a matter of law.” Fed. R. Civ. P. 56(a); see also McBride , 583 F.3d at 96. 21 I. First Amendment Claims 2214 As we did in Doninger II, we begin with some basic prin ciples of First Amendment law. 1 While students do not “shed their constitutional rights to freedom of speech or expression at the 2 schoolhouse gate,” Tinker v. Des Moines Indep. Cmty. Sch. Dist. , 393 U.S. 503, 506 (1969), the 3 constitutional rights of students in public school “are not automatically coextensive with the rights 4 of adults in other settings,” Bethel Sch. Dist. No. 403 v. Fraser , 478 U.S. 675, 682 (1986). Instead, 5 these rights must be applied in a manner consistent with the “special characteristics of the school 6 environment.” Tinker , 393 U.S. at 506. Thus, school administrators may prohibit student 7 expression that will “materially and substantially disrupt the work and discipline of the school.” Id. 8 at 513. Because schools have a responsibility fo r “teaching students the boundaries of socially 9 appropriate behavior,” Fraser , 478 U.S. at 681, offensive speech that would receive full 10 constitutional protection if used by an adult in public discourse may, consistent with the First 11 Amendment, give rise to disciplinary action by a school, id. at 682. Additionally, educators are 12 permitted to exercise editorial control over “sc hool-sponsored expressive activities such as school 13 publications or theatrical productions,” Doninger II, 527 F.3d at 48, so long as their actions are 14 “reasonably related to legitimate pedagogical concerns,” Hazelwood Sch. Dist. v. Kuhlmeier , 484 15 U.S. 260, 273 (1988). Finally, and most recently, the Supreme Court has determined that public 16 schools may “take steps to safeguard those entruste d to their care from speech that can reasonably 17 be regarded as encouraging illegal drug use,” Morse v. Frederick , 551 U.S. 393, 397 (2007), 18 because of the special nature of the school envi ronment and the dangers posed by student drug use, 19 id. at 408. 20 Our analysis of the two First Amendment claims at issue in this case is further guided by the 21 doctrine of qualified immunity. In deciding whether to grant a government official’s motion for 2215 summary judgment on qualified immunity grounds, a c ourt conducts a two-part inquiry. The court 1 asks whether “the facts, viewed in the light most favorable to the plaintiff, show that the [official’s] 2 conduct violated a constitutional right.” Gilles v. Repicky , 511 F.3d 239, 244 (2d Cir. 2007) 3 (quoting Walczyk v. Rio , 496 F.3d 139, 154 (2d Cir. 2007)); see also Saucier v. Katz , 533 U.S. 194, 4 201 (2001), abrogated on other grounds by Pearson v. Callahan , 129 S. Ct. 808, 818 (2009). “[I]f 5 the plaintiff has satisfied th[at part], the court must decide whether the right at issue was ‘clearly 6 established’ at the time of [the] defendant’s alleged misconduct.” Pearson , 129 S. Ct. at 816; see 7 also Gilles , 511 F.3d at 243. “If the conduct did not violate a clearly established constitutional right, 8 or if it was objectively reasonable for the [official ] to believe that his conduct did not violate such 9 a right, then the [official] is protected by qualified immunity.” Gilles , 511 F.3d at 244; see also 10 DeFabio v. E. Hampton Union Free Sch. Dist. , 623 F.3d 71, 77 (2d Cir. 2010). Until recently, 11 courts were required to perform the two-part qualified immunity inquiry in order, first asking 12 whether the defendant violated a constitutional right and, if it was determined that a right was 13 violated, only then asking whether that right was “clearly established.” See Saucier , 533 U.S. at 14 201. Following the Supreme Court’s decision in Pearson v. Callahan , however, we may now 15 exercise our discretion in deciding the order in which to conduct the qualified immunity analysis. 16 129 S. Ct. at 821. 17 In determining if a right is clearly establishe d, this Court looks to whether (1) it was defined 18 with reasonable clarity, (2) the Supreme Court or the Second Circuit has confirmed the existence 19 of the right, and (3) a reasonable defendant w ould have understood that his conduct was unlawful. 20 Young v. Cnty. of Fulton , 160 F.3d 899, 903 (2d Cir. 1998). “The question is not what a lawyer 21 would learn or intuit from researching case law, but what a reasonable person in [the] defendant’s 2216 position should know about the constitutionality of the conduct.” Id. Moreover, when faced with 1 a qualified immunity defense, a court should consid er the specific scope and nature of a defendant’s 2 qualified immunity claim. That is, a determination of whether the right at issue was “clearly 3 established” “must be undertaken in light of the sp ecific context of the case, not as a broad general 4 proposition.” Saucier , 533 U.S. at 201. Thus, the qualified immunity analysis must be “‘particular5 ized’” in the sense that “‘[t]he contours of the right must be sufficiently clear that a reasonable 6 official would understand that what heis doing violates that right. This is not to say that an official 7 action is protected by qualified immunity unless the very action in question has previously been held 8 unlawful; but it is to say that in the light of pre-existing law the unlawfulness must be apparent.’” 9 Zieper v. Metzinger , 474 F.3d 60, 68 (2d Cir. 2007) (quoting Anderson v. Creighton , 483 U.S. 635, 10 640 (1987)); see also Pena v. DePrisco , 432 F.3d 98, 114-15 (2d Cir. 2005). 11 A. Discipline for the Blog Post 12 We begin with Doninger’s claim that her First Amendment rights were violated when 13 Niehoff prohibited her from running for Senior Cl ass Secretary in response to Doninger’s blog post. 14 Citing Fraser, the district court concluded that “Doninger’s First Amendment rights were not 15 violated when she was told that she could not run for class secretary because of an offensive blog 16 entry that was clearly designed to come on to campus and influence fellow students.” Doninger III, 17 594 F. Supp. 2d at 221. Alternatively, the court determined in its qualified immunity analysis that 18 any First Amendment right claimed by Doninger “not to be prohibited from participating in a 19 voluntary, extracurricular activity because of offe nsive off-campus speech when it was reasonably 20 foreseeable that the speech would come on to campus and thus come to the attention of school 21 authorities” was not clearly established. Id. at 222. 2217 We do not reach the question whether school o fficials violated Doninger’s First Amendment 1 rights by preventing her from running for Senior Cl ass Secretary. We see no need to decide this 2 question. We agree with the district court that any First Amendment right allegedly violated here 3 was not clearly established, such that “it would [h ave been] clear to a reasonable [school official] 4 that [her] conduct was unlawful in th e situation [she] confronted.” Saucier , 533 U.S. at 202. 5 Accordingly, Defendants were properly afforded qualified immunity as to this claim. 6 Doninger’s principal argument to the contrary is that under Supreme Court precedent and 7 this Court’s decision in Thomas v. Board of Education , 607 F.2d 1043 (2d Cir. 1979), “it wasclearly 8 established at the time [of the ev ents in this case] that off campus speech could not be the subject 9 of school discipline,” Plaintiff-Appellee-Cross-Appellant Reply Br. at 12 (emphasis added). But 10 as we explained in Doninger II, the “Supreme Court has yet to speak on the scope of a school’s 11 authority to regulate expression that, like Avery’s, does not occur on school grounds or at a 12 school-sponsored event.” 527 F.3d at 48. It is thus incorrect to urge, as Doninger does, that 13 Supreme Court precedent necessarily insulates students from discipline for speech-related activity 14 occurring away from school property, no matter its relation to school affairs or its likelihood of 15 having effects — even substantial and disruptive effects — in school. 16 This Court’s 1979 decision in Thomassimilarly fails to establish that off-campus speech may 17 never properly be disciplined. In Thomas , public school students were punished for publishing and 18 distributing to their peers a lewd, satiricalnewspaper. 607 F.2d at 1045-46. The production, 19 publication, and distribution of the paper occurre d almost entirely off campus, although some copies 20 eventually found their way to school grounds and drew the attention of school officials. Id. This 21 Court concluded that because the students’ activ ities were deliberately designed to take place away 2218 from school, such that “any activity within the school itself was de minimis ,” the school, in 1 punishing them, had “ventured out of the school yard and into the general community,” and the 2 punishment imposed could not “withstand the proscription of the First Amendment.” Id . at 1050. 3
The Thomas Court noted, however, that it could “envision a case in which a group of students incites 4 substantial disruption within the school from some remote locale,” suggesting that such behavior, 5 simply not present in the case before it, might appropriately be disciplined. Id. at 1052 n.17. Judge 6 Newman, moreover, concurring in the result in Thomas , explicitly noted that “[s]chool authorities 7 ought to be accorded some latitude to regulate stude nt activity that affects matters of legitimate 8 concern to the school community, and territoriality is not necessarily a useful concept in determining 9 the limit of their authority.” Id. at 1058 n.13 (Newman, J. , concurring). 10 It is therefore not the case that, in this Circuit, Thomasclearly established that off-campus 11 speech-related conduct may never be the basis for disc ipline by school officials. Indeed, this Court 12 expressly held that it could in Wisniewski v. Board of Education , 494 F.3d 34 (2d Cir. 2007), a case 13 decided only a few months after the events in question here. In Wisniewski , a public school student 14 used an instant messaging (“IM”) program to communicate with fellow students from his home 15 computer. For a three-week period, whenever hesent an IM, the message was accompanied by a 16 crudely drawn icon depicting one of his teachers be ing shot in the head, with text below reading 17 “Kill Mr. VanderMolen.” Id. at 35-36. When the icon came to th e attention of school officials, it 18 caused a disturbance, leading to a criminal inves tigation and also requiring the special attention of 19 school officials, the replacement of VanderMolen (w ho asked to be relieved of teaching the student’s 20 class), and interviews of pupils during class time. Id. at 35. Citing Tinker and Thomas , we 21 determined that “[t]he fact that [the] creation and transmission of the IM icon occurred away from 2219 school property does not necessarily insulate [the student] from sc hool discipline.” Id . at 39. 1 Where the icon’s off-campus display “pose[d] a reas onably foreseeable risk that [it] would come to 2 the attention of school authorities and . . . ‘mat erially and substantially disrupt the work and 3 discipline of the school,’” the student’s suspension for this display did not run afoul of the First 4 Amendment. See id. at 38-39 (quoting Morse , 551 U.S. at 403). 5 Doninger next contends that even if off-cam pus expression may in some circumstances be 6 regulated by school officials, any reasonable schooladministrator would know that such regulation 7 is permissible onlywhen speech-related activity satisfies the so-called Tinker test employed in 8 Wisniewski— i.e., when it poses a reasonably foreseeablerisk of coming to the attention of school 9 authorities and materially and substantially disrupting the work and discipline of the school. See 10 id. at 38-39 (applying Tinker standard to off-campus speech). Doninger urges that no reasonable 11 school administrator could have deemed that standardsatisfied here or, at a minimum, that disputed 12
issues of material fact exist as to the reasonableness of any suchconclusion. We disagree with all 13 these propositions. 14 At the start, it would gravely distort the doctrine of qualified immunityto hold that a school 15 official should “fairly be said to ‘know’ that th e law forb[ids] conduct not previously identified as 16 unlawful.” Harlow v. Fitzgerald , 457 U.S. 800, 818 (1982). Doninge r has identified no case — and 17 we are aware of none — that enunciates her supposedly bright-line principle strictly limiting the 18 regulation of off-campus speech to Tinker-style circumstances or otherwise demonstrating a clearly 19 established rule applicable to the sp ecific circumstances of this case. See Gilles , 511 F.3d at 244 20 (noting that “[t]he inquiry into whether a right at issue was clearly established is tied to the specific 21 facts and context of the case”). I ndeed, in the previous iteration of this case before this Court, we 2220 specifically noted that the applicability of Fraser to plainly offensive off-campus student speech is 1 uncertain, Doninger II, 527 F.3d at 49-50, reinforcing the absence of a clearly established right 2 under the circumstances of this case. 3 To the extent Doninger concedes that courts have upheld as consistent with First Amendment 4 principles the regulation of off-campus expression satisfying the Tinker standard, moreover, Tinker 5 itself provides “substantial grounds” for the School o fficials here “to have concluded [they] had 6 legitimate justification under the law for acting as [they] did.” Saucier , 533 U.S. at 208. The 7 undisputed facts — that Doninger’s blog post directly pertained to an event at LMHS, that it invited 8 other students to read and respond to it by contacting school officials, that students did in fact post 9 comments on the post, and that school administrato rs eventually became aw are of it — demonstrate 10 that it was reasonably foreseeable that Doni nger’s post would reach school property and have 11 disruptive consequences there. See Doninger II, 527 F.3d at 50; Wisniewski , 494 F.3d at 39-40. In 12 Doninger II, we relied primarily on two additional facts to conclude that Doninger’s blog post 13 portended foreseeable disruption to the school’s wo rk and discipline: namely, (1) that the language 14 Doninger employed (asking others to call the “douchebags” in the central office to “piss [them] off 15 more”) was “potentially disruptive of effort s to resolve the ongoing controversy,” 527 F.3d at 50-51; 16 and (2) that in the midst of this controversy, D oninger’s blog post conveyed the “‘at best misleading 17 and at wors[t] false’ information that Jamfest had been cancelled in [Doninger’s] effort to solicit 18 more calls and emails to Schwartz,” id. at 51 (first alteration in original) (quoting Doninger I, 514 19 F. Supp. 2d at 202). 20 Doninger argues that in light of further development of the record since Doninger II and the 21 procedural posture of our review of a grant of summary judgment, di sputed issues of fact now exist 229The district court credited Niehoff’s testimony regarding her April 24 conversation with Doninger in ruling on Doninger’s motion for a preliminary injunction, see Doninger II, 527 F.3d at 45, but Doninger’s recollection of that convers ation is different and must now be assumed to be true in reviewing a grant of summary judgment against her on her blog-post-related claim.

21 as to the reasonableness of any conclusion that her post was potentially disruptive. We agree with 1 Doninger that, when the record is viewed in the li ght most favorable to her, it no longer supports the 2 conclusion that on April 24 Niehoff informed Doninge r both that her behavior was inappropriate for 3
a class officer and that the students’ mass email contained inaccurate information (because Niehoff 4 was amenable to rescheduling Jamfest so it could be held in the auditorium). There similarly exists 5 a factual dispute as to whether Niehoff obtained Doninger’s word th at the email would be corrected, 6 only subsequently to learn that Doninger republishe d it that very night, and as to whether Doninger’s 7 blog post, claiming that Jamfest had been cancelled, was in fact false. 9 8 Even taking the facts presented in the reco rd in the light most favorable to Doninger, 9 however, there remains no triable issue here as to whether it was objectively reasonable for school 10 administrators to conclude that Doninger’s posting was potentially disruptive to the degree required 11 by Tinker . According to the undisputed facts in this case, the controversy over Jamfest’s scheduling 12 had already resulted in a deluge of phone calls and emails, several disrupted schedules, and many 13 upset students even before Doninger posted her comments on livejournal.com. This disruption 14 continued the next day, as calls poured in for both Principal Niehoff and S uperintendent Schwartz, 15 a group of upset students gathered outside Nieho ff’s office, and Doninger and three other students 16 were called out of class to meet with Schwartz, Niehoff, Hill, Miller, and Fortin (themselves pulled 17 away from other duties) in an effort to resolve the controversy. Perhaps a school official in these 18 circumstances might err in concluding that Doni nger’s blog post — disseminated amidst circulating 1922 rumors that Jamfest had been arbitrarily cancelled, calling the responsible school administrators 1 “douchebags,” and urging fellow students to take ac tion to “piss [them] off more” — was of the sort 2 to stoke disruption and frustrate the School ’s ongoing efforts at conflict resolution. See Doninger 3
II, 527 F.3d at 51 (noting that “[t]he question is not whether there has been actual disruption, but 4 whether school officials ‘might reasonably portend disruption’ from the student expression at issue” 5 (quoting LaVine v. Blaine Sch. Dist. , 257 F.3d 981, 989 (9th Cir. 2001))). But even viewing the 6 evidence in the light most favorable to Doninger, there is simply nothing in the record creating a 7 disputed issue of fact as to the objective reasonablenessof any such judgment. See Lennon v. 8 Miller , 66 F.3d 416, 420-21 (2d Cir. 1995) (“An [official’s] actions are objectively unreasonable 9 when no [official] of reasonable competence coul d have made the same choice in similar 10 circumstances. Thus, if the court determines that the only conclusion a rational jury could reach is 11 that reasonable [officials] would disagree about the legality of the defendants’ conduct under the 12 circumstances, summary judgement for the [officials] is appropriate.” (citation omitted))

. And this 13 is the concern of qualified immunity doctrine. See Gilles , 511 F.3d at 244. 14 Doninger urges in reply that there isa disputed issue of fact as to whether Niehoff disciplined 15 her because her posting was potentially disruptive, or simply because it was offensive, and that this 16 factual dispute renders the district court’s grant of summary judgment erroneous. Indeed, it was on 17
this basis that the district court concluded that it could not grant summary judgment solely on the 18
basis of a Tinker analysis of the disruptive potential of Doninger’s speech. See Doninger III, 594 19 F. Supp. 2d at 219-20. Even assuming the existence of such a factual dispute, however, the Supreme 20 Court has stated that “a defense of qualified immunity may not be rebutted by evidence that the 21 defendant’s conduct was . . . improperly motivated.” Crawford-El v. Britton , 523 U.S. 574, 588 2223 (1998). Evidence of subjective intent “is si mply irrelevant to [this] defense.” Id . Granted, this rule 1 does not apply when intent is an element of a First Amendment claim or defense “ as defined by 2 clearly established law ” and a factual dispute as to intent precludes the conclusion that a government 3 official’s conduct was objectively reasonable. Locurto v. Safir , 264 F.3d 154, 169 (2d Cir. 2001) 4 (emphasis added). But such is not the case here. 5
The district court concluded that under Tinker a defendant must show “not only a potential 6 for disruption, but also that ‘the concern for di sruption, rather than some other, impermissible 7 motive, was the actual reason for’ the punishment imposed.” Doninger III, 594 F. Supp. 2d at 219 8 (quoting Locurto v. Giuliani , 447 F.3d 159, 180 (2d Cir. 2006)). Inso ruling, however, it relied not 9 on our school speech cases but rather on our case law addressing the different context of alleged 10 retaliation against government employees for the ex ercise of First Amendment rights. In that 11 setting, retaliatory intent is a necessary element of the First Amendment claim. See Johnson v. 12
Ganim , 342 F.3d 105, 112 (2d Cir. 2003). Moreover, it is an established element of the so-called 13 Pickering balancing test defense that a government official establish that an adverse employment 14 action was taken “not in retaliation for the em ployee’s speech, but because of [a] potential for 15 disruption.” Id. at 114. 16 In contrast, the Supreme Court in Tinker did not clearly establish in tent as an element of any 17 claim or defense, nor has our case law pursuant to Tinker . As a result, even assuming a factual 18 dispute exists as to Niehoff’s motivation, qualif ied immunity is still proper where Defendants were 19 objectively reasonable in their judgment that they“might reasonably portend disruption from the 20 student expression at issue.” Doninger II, 527 F.3d at 51 (internal quotation marks omitted). 21 Moreover, even if this were not the case — even if intent constituted a clearly established element 2224 of a Tinker defense — the supposed factual dispute as to whether Niehoff was motivated by the 1 offensiveness of Doninger’s speech or by its disrup tive potential would still not matter here. As the 2 district court recognized, it was also not clearly esta blished at the time of these events that Doninger 3 had any First Amendment right not to be prohibite d from running for Senior Class Secretary because 4 of offensive off-campus speech, at least when such sp eech pertained to a school event, invited 5 students to read and respond to it by contacting school administrators, and it was reasonably 6 foreseeable “that the speech would come on to campus and thus come to the attention of school 7 authorities.” Doninger III, 594 F. Supp. 2d. at 222. 8 Finally, our conclusion that whatever ri ght Doninger may have had was not clearly 9 established is buttressed by the similarities between this case and the Sixth Circuit’s decision in 10 Lowery v. Euverard , 497 F.3d 584 (6th Cir. 2007), decided only s hortly after the events at issue here. 11
In Lowery , a group of high school football players signe d a petition expressing their hatred of the 12 coach and their desire not to play for him. When the coach became aw are of this activity, he 13 dismissed those players who refuse d to apologize from the team. Id. at 585-86. The Sixth Circuit, 14 conducting an analysis under Tinker , concluded that the school did not violate the players’ First 15 Amendment rights by deeming them unfit to serve on th e football team so long as they were actively 16 working to undermine the coach. Id. at 587-96. In determining that the students’ First Amendment 17 rights had not been violated, the Sixth Circuit notedthat “Plaintiffs’ regular education has not been 18 impeded, and, significantly, they are free to continue their campaign to have [the coach] fired. What 19 they are not free to do is continue to play football for him while actively working to undermine his 20 authority.” Id. at 600 (emphasis omitted). 21 Similarly, Doninger’s discipline extended only to her role as a student government 2225 representative: she was not suspended from cl asses or punished in any other way. Given that 1 Doninger, in serving in such a position, was to help maintain a “continuous communication channel 2 from students to both faculty and administration,” it was not unreasonable for Niehoff to conclude 3 that Doninger, by posting an incendiary blog post inthe midst of an ongoing school controversy, had 4 demonstrated her unwillingness properly to carry out this role. To be clear, we do not conclude in 5 any way that school administrators are immune fr om First Amendment scrutiny when they react to 6 student speech by limiting students’ participation in extracurricular activities. Here, however, 7 pursuant to Tinker and its progeny, it was objectively reasonabl e for school officials to conclude that 8 Doninger’s behavior was potentially disruptive of student government functions (such as the 9 organization of Jamfest) and that Doninger was not free to engage in such behavior while serving 10 as a class representative — a representative charged with working with these very same school 11 officials to carry out her responsibilities. 12 Qualified immunity “balances two important interests — the need to hold public officials 13 accountable when they exercise power irresponsibly and the need to shield officials from 14 harassment, distraction, and liability when they perform their duties reasonably.” Pearson , 129 S. 15 Ct. at 815. Under the qualified immunity doctrine, government officials such as the school 16 administrators here “are shielded from liability for civil damages insofar as their conduct does not 17 violate clearly established statutory or constitutional rights of which a reasonable person would have 18 known.” Harlow , 457 U.S. at 818. They are entitled to the protection of qualified immunity unless 19 the unlawfulness of their actions was apparent in light of preexisting law. See Anderson , 483 U.S. 20 at 639-40. There was no such apparent unlawfuln ess here. Instead, it was objectively reasonable 21 for Niehoff and Schwartz to believe they coul d prohibit Doninger from running for Senior Class 2210We note that Defendants rely not only on Tinker to assert qualified immunity as to thisclaim, but also on the argument that the t-shirts were prohibited as part of a general, viewpointneutral restriction on electioneering materials at the school assembly. Because we conclude that Defendants are entitled to qualified immunity on the ground that their actions, even if mistaken, were objectively reasonable in light of Tinker, we do not consider this argument.
26 Secretary without violating her First Amendment right s, given the “specific facts and context of the 1
case.” Gilles , 511 F.3d at 244. We thus conclude that Ni ehoff and Schwartz were properly afforded 2 qualified immunity as to Doninger’s blog post claim. 3 B. The T-Shirt Controversy 4 We turn next to Defendants’ argument that th e district court erred in denying them qualified 5 immunity on Doninger’s claim that they violated her First Amendment rights when they prohibited 6 her from displaying a “Team Avery” t-shirt in the election assembly. Applying Tinker and viewing 7 the facts in the light most favorableto Doninger, the district court concluded: (1) that a reasonable 8 jury could find that permitting students to wear the t-shirts into the assembly would not have 9 materially and substantially interfered with the election process; and (2) that Doninger’s right to 10 display her t-shirt in the auditorium wasclearly established. See Doninger III, 594 F. Supp. 2d at 11 225-27. We agree that a reasonable fact-finder c ould conclude that Defendants were mistaken in 12 assessing the likely impact of the t-shirts and thus the permissibility of prohibiting them pursuant 13

to Tinker . At the same time, however, we conclude that any such mistake was reasonable. 14 Accordingly, Defendants are entitled to qualified immunity on this claim as well. 10 15 i. Jurisdiction to Review the Denial of Qualified Immunity on the “T-Shirt” Claim 16 We address a preliminary matter at the st art. Doninger argues that we do not have 17 jurisdiction over the district court’s denial of qualif ied immunity as to the so-called “t-shirt” claim. 18 Generally, “a district court’s denial of a claim of qualified immunity, to the extent that it turns on 1911 We note that Doninger again argues that a factual dispute regarding Niehoff’s motive, which Doninger urges was “to quash speech supporting her” rather than to avoid disruption, precludes the grant of qualified immunity. As we have already stated, however, our case law has not clearly established motive as an element of any Tinker-related claim or defense. As a result, any factual dispute as to Niehoff’s motive doe s not preclude the conclusion that Niehoff’s conduct was objectively reasonable and entitled to qualified immunity. See Crawford-El , 523 U.S. at 588.
27 an issue of law, is an appealable ‘final decision’ within the meaning of 28 U.S.C. § 1291 1 notwithstanding the absence of a final judgment.” Tierney v. Davidson , 133 F.3d 189, 194 (2d Cir. 2 1998) (internal quotation marks omitted) (quoting Mitchell v. Forsyth , 472 U.S. 511, 530 (1985)). 3 We do not, however, have jurisdiction to review a denial of qualified immun ity to the extent it is 4 based on a district court’s finding that there is enough evidence in the record to create a genuine 5 issue as to factual questions that are, in fact, material to resolution of the qualified immunity claim. 6 Salim v. Proulx , 93 F.3d 86, 89-90 (2d Cir. 1996) (citing Johnson v. Jones , 515 U.S. 304 (1995), and 7 Behrens v. Pelletier , 516 U.S. 299 (1996)). 8 Here, we may exercise interlocutory jurisdic tion to determine whether, assuming Doninger’s 9 version of the facts is true, Defendants are entitled to qualified immunity as a matter of law. 10 Tierney , 133 F.3d at 194. To the extent we base our decision on undisputed facts and Doninger’s 11 version of any material disputed facts, we have jurisdiction to consider whether, as a matter of law, 12
the district court erred in determini ng that this case is sufficiently like Tinker so that school officials 13 of reasonable competence could not disagree that the actions taken here, in their particular factual 14 context, were illegal. 11 See Malley v. Briggs , 475 U.S. 335, 341 (1986); see also Anderson , 483 U.S. 15 at 638 (noting that qualified immunity shields govern ment officials from liability “as long as their 16 actions could reasonably have been thought consistent with the rights they are alleged to have 17 violated”). 1828 ii. Defendants’ Entitlement to Qualified Immunity 1 We turn now to the merits of Defendants' qualified immunity claim. Unlike the blog post, 2
the t-shirts at issue in this case constitute d student speech on, not be yond, school grounds. The t3 shirts were not vulgar, see Fraser , 478 U.S. at 683, did notpromote drug use, see Morse , 551 U.S. 4 at 409, and were not student speech that could reasonably be perceived to “bear the imprimatur of 5 the school,” Hazelwood , 484 U.S. at 271. Defendants assert that the t-shirts were banned to prevent 6 two kinds of disruption to school activities: (1) vo cal outbursts or other disruptions in the assembly 7 to which the students were reporting; and (2) a possible write-in campaign to elect Doninger as 8 Senior Class Secretary even though she had been removed from the ballot. 9 We note that the district court, in denying Defendants’ motion for reconsideration, asserted 10 that Defendants failed to make these arguments in their motion for summary judgment, although the 11 court nonetheless proceeded to consider their merits. See Doninger , 2009 WL 763492, at *1-*2. 12 Our review of the parties’ submissions on summary judgment, however, demonstrates that 13 Defendants sufficiently highlighted the indicia of disruption in the record so as to preserve the claim 14 that they acted in an objectively reasonable manner pursuant to Tinker . At oral argument on the 15 summary judgment motion, Defendants’ counsel urged that there was a risk of disruption arising 16 from the prospect that students might drown out the candidates’ speeches during the election 17 assembly with cheers of support for Doninger. In c ounsel’s words, “What if . . . the principal says, 18 quiet everybody and they say no and then the T-shirts come out . . . that’s absolutely disruptive.” 19 Oral Argument Tr. at 80:7-14. We conclude that Defendants’ arguments regarding both (1) the 20 threatened disruption of the election assembly and (2) the possibility of a write-in campaign were 21 raised with “sufficient particul arity” so as to be preserved. See McCardle v. Haddad , 131 F.3d 43, 2229 51 (2d Cir. 1997). Indeed, Doninger does not argue to the contrary. Because we conclude that the 1 threat of disruption to the school assembly al one provided school officials with “substantial 2 grounds” for their actions, however, such that “[i]t cannot be said there wa s a clearly established 3 rule” as to the illegality of their conduct, see Saucier , 533 U.S. at 208-09, we need address only the 4 first of Defendants’ arguments. 5 We again focus on the second prong of the qualified immunity inquiry — whether, assuming 6 that Doninger had a First Amendment right to wear he r t-shirt at the assembly, this right was clearly 7 established. Cf. Pearson , 129 S. Ct. at 818-19. “The relevant, dispositive inquiry in determining 8 whether a right is clearly established is whether it would be clear to a reasonable [official] that his 9 conduct was unlawful in the situation he confronted.” Saucier , 533 U.S. at 202. If “‘[officials] of 10 reasonable competence could disagree’ on the legality of the action at issue in its particular factual 11 context,” then the defendant is entitled to qualified i mmunity, “[e]ven if the right at issue was clearly 12 established in certain respects.” Walczyk , 496 F.3d at 154 (quoting Malley , 475 U.S. at 341). 13 Qualified immunity analysis, moreover, is “objective” rather than “subjective.” See, e.g., Anderson , 14 483 U.S. at 641. Thus, qualified immunity protects government officials when they make 15 “reasonable mistakes” about the legality of their actions, Saucier , 533 U.S. at 206, and “applies 16 regardless of whether the government official’s erro r is a mistake of law, a mistake of fact, or a 17 mistake based on mixed questions of law and fact,” Pearson , 129 S. Ct. at 815 (internal quotation 18 marks omitted). “In this respect, the Supreme C ourt has observed that qualified immunity protects 19 ‘all but the plainly incompetent or those who knowingly violate the law.’” Walczyk , 496 F.3d at 154 20 (quoting Malley , 475 U.S. at 341); see also Saucier , 533 U.S. at 202. 21 The law governing restrictions on student sp eech can be difficult and confusing, even for 2230 lawyers, law professors, and judges. The relevantSupreme Court cases can be hard to reconcile, 1 and courts often struggle to determine which standard applies in any particular case. See, e.g. , 2
Morse , 551 U.S. at 430 (Breyer, J. , concurring in the judgment in part and dissenting in part) (noting 3 that the law regarding student speech is often unclear, with various courts describing the governing 4 standards as “complex and often difficult to apply”). We conclude, for instance, that Tinker governs 5 here — that because the t-shirts were not vulgar, see Fraser , 478 U.S. at 683, could not reasonably 6 be perceived to bear the School’s imprimatur, see Hazelwood , 484 U.S. at 271, and did not 7 encourage drug use, see Morse , 551 U.S. at 409, they could be s ubject to regulation different from 8 that permissible for adults in non-school settings only if they threatened substantial disruption to the 9 work and discipline of the School. But as we have suggested in the past, it is not entirely clear 10 whether Tinker ’s rule (as opposed to other potential standards) applies to all student speech not 11 falling within the holdings of Fraser , Hazelwood , or Morse

. See Guiles ex rel. Guiles v. Marineau , 12 461 F.3d 320, 326 (2d Cir. 2006); see also Morse , 551 U.S. at 405 (“ Fraser established that the 13 mode of analysis set forth in Tinker is not absolute.”). In Morse , the Supreme Court’s most recent 14 pronouncement on student speech, the C ourt noted that “the rule of Tinker is not the only basis for 15 restricting student speech.” Id . at 406. Granted, two Justices who helped constitute the Morse 16 majority joined only on the understanding that Morse does not hold that the special characteristics 17
of schools necessarilyjustify any additional speech restrictions. Id . at 423 (Alito, J., concurring). 18 But this qualification does not rule out the possi bility that some such hitherto unrecognized grounds 19 of regulation may exist. 20 To be clear, we neither r ecognize any such grounds, nor express a view as to their 21 desirability. As the Supreme Court stated in Tinker , “[t]he Nation’s future depends upon leaders 2231 trained through wide exposure to [the] robust exchange of ideas,” and students “may not be confined 1 to the expression of those sentiments that are officially approved.” 393 U.S. at 511-12. 2 That said, a reasonable school official could well note salient differences between the 3
circumstances here and those in Tinker . In Tinker , school officials prohib ited high school students 4 from wearing black armbands to school in protest of the Vietnam War. They sought to punish with 5 suspension individual students who engaged in “a s ilent, passive expression” of dissenting political 6 opinion in circumstances in which the rights of other students were not implicated and the wearing 7 of the armbands “was entirely divorced from . . . [even] potentially disruptive conduct.” Id . at 505, 8 508. Here, in contrast, some undetermined numbe r of students, agitated by the actions of school 9 officials, wished jointly to affirm support for a student they believed had been improperly 10 disciplined by being prohibited from running for cla ss office. They wished to do so specifically in 11 the context of a school election assembly at whic h the candidates for various offices, also students, 12 were scheduled to speak. In lightof these significant differences in the two scenarios (not the least 13 of which involves the interests of other student s), an official in De fendants’ position who thought 14 that a less demanding standard of potential disrup tion might apply could not be said to have an 15 unreasonable understanding of what the law requires. See Malley , 475 U.S. at 341 (stating that 16 qualified immunity is designed to protect “all but the plainly incompetent or those who knowingly 17 violate the law”). And as the Supreme Court has repeatedly affirmed, “[i ]f the [official’s] mistake 18 as to what the law requires is reasonable . . . [she] is entitled to the immunity defense.” Saucier , 533 19
U.S. at 205. 20 Further, even assuming, arguendo , that it would be clear to a reasonable official that the 21 Tinker standard applied in the circumstances presented, Defendants are still entitled to qualified 2232 immunity if such an official could have reasonably erred in determining whether the potential for 1 disruption at the assembly was sufficient to satisfy that standard. Even viewing the evidence in the 2 light most favorable to Doninger, we conclude that such is the case here. 3 To be clear, to prohibit student speech on the ground that it will result in disruption, 4 “administrators . . . must be able to show that [their] action ‘was caused by something more than a 5 mere desire to avoid the discomfort and unpleasantness that always accompany an unpopular 6 viewpoint.’” DeFabio , 623 F.3d at 78 (quoting Tinker , 393 U.S. at 508). As we explained the 7 standard in our review of the district court’s order denying a preliminary injunction in this case, 8 “[t]he question is . . . whether school official s ‘might reasonably portend disruption’ from the 9 student expression at issue.” Doninger II, 527 F.3d at 51 (quoting LaVine , 257 F.3d at 989). The 10 line between the potential for “substantial disrup tion of or material interference with school 11 activities,” Tinker , 393 U.S. at 514, however, and the potential for less significant interference is 12 similar to the “hazy border” that the Supreme C ourt has recognized to exist between acceptable and 13 excessive uses of force. See Saucier , 533 U.S. at 206 (quoting Priester v. Riviera Beach , 208 F.3d 14 919, 926-927 (11th Cir. 2000)). The Court has ma de clear that qualified immunity operates to 15 protect officials in such areas of indeterminacy and “to ensure that before they are subjected to suit, 16 [they] are on notice their conduct is unlawful.” Id

. 17 According to the undisputed facts in this case, Doninger and her supporters were clearly 18 upset about the decision to remove her from the ballot, and were eager to speak out publicly 19 concerning their views. Doninger had appeared on a local news show with her mother to talk about 20 her blog posting and her resulting punishment. She atte mpted to discuss the news interview in class 21 on the day preceding the election assembly, provoking another student to shout out apparent support 2233 in sufficiently disruptive terms that the student was sent to Niehoff’s office. By at least the early 1 morning hours of the day of the election, Niehoff was aware of a plan by students specifically to 2 bring t-shirts supportive of Doninger into an elec tion assembly at which other students, including 3 the two candidates for Senior Class Secretary, we re scheduled to speak. Niehoff may not have 4 known with certainty that permitting the t-shirts into the assembly would cause students to disrupt 5 those speeches. But she could not responsibly have ignored the fact that Doninger herself, in her 6 blog post of the previous month, ha d already demonstrated some willingness to incite confrontation 7 with school officials. And we note further that Niehoff’s concern about the potential disruption of 8 the assembly was partially borne out even in the absence of the t-shirts, when students shouted “Vote 9 for Avery” and had to be warned to be respectful. 10 “School principals,” as the Supreme Court has recently noted, “have a difficult job.” Morse , 11 551 U.S. at 409. Given Niehoff’s responsibility for ensuring an orderly election process, enforcing 12 the punishment against Doninger, and safeguarding the interests of those students who were to speak 13 at the assembly, she faced a difficult task in a ssessing whether the threat of disruption was severe 14 enough to justify preventing Doninger from wearing her t-shirt into the assembly. A reasonable jury 15 could find that a school official who believed the threatened disruption here was sufficiently 16 substantial was, under the circumstances, mistaken. We cannot conclude, however, that such a 17 mistake was anything but reasonable – the very so rt of mistake for which the qualified immunity 18 doctrine exists to shield officials against unwarranted liability. 19 “The concern of the immunity inquiry is to acknowledge that reasonable mistakes can be 20 made[.]” Saucier , 533 U.S. at 205. To be clear, the need to make difficult choices cannot protect 21 principals or other school officials when they make unreasonable judgments regarding the legality 2234 of their actions. “In our system, state-operate d schools may not be enclaves of totalitarianism. 1 School officials do not possess absolute authority over their students.” Tinker , 393 U.S. at 511. But 2 the record here does not suggest, much less show, the Lewis S. Mills High School to be anything 3 remotely resembling an “enclave[] of totalitarianism,” or that the defendant school officials acted 4 in a way that suggested a claim to “absolute authority over their students.” We conclude that, in the 5 circumstances here, reasonable school officials c ould disagree about the potential for a substantial 6 disruption of the assembly as a result of permitting students to wear the t-shirts inside. Accordingly, 7 Defendants are entitled to qualified immunity. 8 C. Monell Liability 9 In addition to her claims against Defendants in their individual capacities, Doninger asserts 10 on appeal that she also brought a claim under Monell v. Department of Social Services , 436 U.S. 658 11 (1978), for money damages against them in their o fficial capacities, based on a “final policymaker” 12 theory of municipal liability. See Jeffes v. Barnes , 208 F.3d 49, 57 (2d Cir. 2000) . The district court 13 rejected this claim, first raised in Plaintiff’s motion for reconsideration at the summary judgment 14 stage, for a number of reasons, including: (1) th e express statement by Plaintiff’s counsel at an 15 earlier stage that the sole action being brought agai nst Defendants in their official capacities was for 16 injunctive relief and, to the extent this statement was in error, counsel’s tardiness in correcting it; 17 (2) Plaintiff’s failure to mention a Monellclaim throughout briefing and oral argument on the 18 parties’ summary judgment motions; and (3) to the extent Doninger relied on her second amended 19 complaint to put Defendants on notice of her supposed Monell claim, that this pleading was 20 insufficient to provide such notice and was, in any event, filed several months after Defendants’ 21 motion for summary judgment and permitted solelyfor the limited purpose of substituting Avery 2235 Doninger as a party in place of her mother. Doninger , 2009 WL 763492, at *4-*5. 1 Plaintiff argues on appeal that Defe ndants were on notice of her alleged Monell claim based 2 on the fact that her second amended complaint referred to a suit against Defendants in their 3 individual and official capacities and because the burden was on Defendants to obtain clarification 4 of what claims were being asserted at the time they moved for summary judgment. We disagree. 5 Plaintiff’s counsel unequivocally declared at a deposition conducted on February 25, 2008, that the 6 only claim being brought against De fendants in their official capac ities was one for injunctive relief. 7 The second amended complaint, moreover, was permitted solely to substitute Avery Doninger as 8 a plaintiff in place of her mother. See Doninger , 2009 WL 763492, at *5; cf. Port Dock & Stone 9 Corp. v. Oldcastle Ne., Inc. , 507 F.3d 117, 121 (2d Cir. 2007) (noting that the factual allegations in 10 a complaint must be sufficient “to give the defendant fair notice of what the claim is and the grounds 11 upon which it rests”). Although Plaintiff finally raised the question of municipal liability in her 12 motion for reconsideration, albeit without specify ing on what basis she was claiming this liability 13 existed, Defendants were nevertheless not on notice of any Monell claim at the time they filed their 14 motion for summary judgment, nor did the filing of the second amended complaint put them on such 15 notice given the limited purpose for which it was allowed. As a result, the district court’s grant of 16 summary judgment to them on the blog post claim was not in error. 17
To the extent Plaintiff’s motion for reconsideration might be viewed as an attempt to amend 18 the complaint to add a Monell claim, the district court — whic h stated that it was “inclined to 19 believe either that counsel intentionally hid the ball in the hope of sneaking past summary judgment 20 unchallenged or that he never even thought of pressing a Monell claim against the school district 21 until the Court issued its decision granting summary judgment on the blog entry claim,” Doninger , 2236 2009 WL 763492, at *4 — did not abuse its discretion inrefusing permission to add a claim at that 1 late stage, see Holmes v. Grubman , 568 F.3d 329, 334 (2d Cir. 2009) (“Ge nerally, ‘[a] district court 2 has discretion to deny leave [to amend a complaint] for good reason, including futility, bad faith, 3 undue delay, or undue prejudice to the opposing party.’” (quoting McCarthy v. Dun & Bradstreet 4 Corp. , 482 F.3d 184, 200 (2d Cir. 2007))). Thus, the districtcourt did not err in finding that Plaintiff 5 had not properly asserted a Monell claim against the school district. 6 II. Other Claims 7 Finally, in addition to her First Amendment claims, Doninger also argues on appeal that the 8 district court erred in granting summary judgmen t to Defendants on her Equal Protection claim and 9 dismissing sua sponte her claims under the Connecticut Constitution. See Doninger III, 594 F. 10 Supp. 2d at 227-29. With regard to her Equal Protection claim, Doninger purports to make a 11 “selective enforcement” argument pursuant to LeClair v. Saunders , 627 F.2d 606, 609-10 (2d Cir. 12 1980), on the theory that she was treated differently from the other Student Council officers who 13 sent the mass email, based on her exercise of Fi rst Amendment rights. In order to succeed on a 14 selective enforcement theory, Doninger must show both “(1) that [she was] treated differently from 15 other similarly situated individuals, and (2) that such differential treatment was based on 16 impermissible considerations such as race, relig ion, intent to inhibit or punish the exercise of 17 constitutional rights, or malicious or ba d faith intent to injure a person.” Harlen Assocs. v. Inc. Vill. 18 of Mineola , 273 F.3d 494, 499 (2d Cir. 2001) (internal quotation marks omitted). Here, it is 19 undisputed that Doninger was disqualified for runni ng for Senior Class Secretary because of her 20 April 24 posting on livejournal.com. She has not shown that any other Student Council member 21 went unpunished after engaging in similarly offens ive speech in circumstances that were potentially 2237 disruptive to resolution of an ongoing dispute between students and the School’s administration. 1 We therefore affirm the district court’s grant of summary judgment in favor of Defendants on 2 Doninger’s Equal Protection claim. 3 We similarly affirm the judgment of the district court dismissing Doninger’s claims based 4 on the Connecticut Constitution. We agree with the district court that Doninger has failed to 5 “identif[y] a single Connecticut decision that s uggests that free speech protections for public school 6 students are broader under the Connecticut Constitution than under the U.S. Constitution.” 7 Doninger III, 594 F. Supp. 2d at 228. In any event, the dismi ssal was without prejudice. The 8 decision not to exercise supplemental jurisdiction was not an abuse of discretion. 9 CONCLUSION 10 We have considered all of Doninger’s contentions on appeal and have found them to be 11 without merit. For the foregoing reasons, the judgment of the district court is AFFIRMED IN 12
PART and REVERSED IN PART : This matter is remanded for the district court to enter judgment 13
for Defendants. The dismissal of Doni nger’s state claims without prejudice is AFFIRMED

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