This case involves allegations that defendant called the personal telephone of a police officer who had previously arrested him, and then told the officer, among other things, "I will fuck up your life, I know where you live, I will take the revenge from you." On March 18, 2025, the People commenced this action by filing a felony complaint charging defendant with Making a Terroristic Threat (Penal Law § 490.20), Harassment in the Second Degree (Penal Law § 240.26[1]), and three counts of Aggravated Harassment in the Second Degree (Penal Law § 240.30[1][A], [1][B], [2]). On June 4, 2025, the court granted the People's application to dismiss the sole felony charge in the complaint. Because at that time fewer than 90 chargeable days had elapsed since the felony action commenced, the People were required to announce their trial readiness on the remaining misdemeanor charges within 90 days of June 4—i.e., by September 2, 2025. See CPL 30.30(7)(c). The People filed a certificate of compliance ("COC") and statement of readiness on July 30, 2025. Defendant now moves to dismiss the action on various grounds and for other relief. The court assumes the parties' familiarity with the facts and arguments raised in the motion. As explained below, the motion is GRANTED IN PART to the extent that the Penal Law § 240.30(2) charge is dismissed and evidence recovered as the result of the warrant to search defendant's cellphone is suppressed under CPL 690.30(1). The motion is otherwise DENIED, and the case should be adjourned for hearings and trial.

The information in this case was sworn by Detective Matthew Mauro based on statements from Police Officer Ekramul Haque, who submitted a supporting deposition adopting the statements attributed to him. The information alleged that Haque issued defendant a desk appearance ticket "one year ago," i.e., in early 2024. Defendant then allegedly called Haque on [*2]March 1, 2025, and said in sum and substance: "I will fuck up your life, I know where you live, I will take the revenge from you, you ruined my life, you arrested me falsely, you arrest people for no reason, I will make your life hell, I will post your poster in the neighborhood." Defendant then posted a recording of the telephone conversation and a photograph of Haque, as well as Haque's family members, on defendant's "social media account."

Based on these allegations, the information charges defendant with three counts of second-degree aggravated harassment, see Penal Law § 240.30(1)(a), (1)(b), (2), and one count of second-degree harassment, see Penal Law § 240.26(1). To be facially sufficient, the information must comply with the requirements of CPL 100.15; it must assert non-hearsay allegations that, if true, establish every element of the charged offenses; and it must assert factual allegations that establish reasonable cause to believe that the defendant committed the charged offenses. See CPL 100.40. The information (or any count thereof) that does not comply with these requirements is defective and may be dismissed, unless the People can cure the defect through amendment and they request leave to amend. See CPL 170.30(1)(a), 170.35(1(a). The People have not requested leave to amend in this case.

The Penal Law § 240.30(2) charge is not facially sufficient. A person is guilty of that offense when, with an intent to "harass or threaten," they make a telephone call "with no purpose of legitimate communication." Penal Law § 240.30(2). A telephone call is not for "legitimate" communication when it is not a "genuine, authentic, or valid" attempt to communicate with the other party. Black's Law Dictionary, "legitimate" (online 2026). In essence, the charge requires allegations of telephone calls made without any intention to initiate actual communication with the receiving party. This interpretation is consistent with the statute's legislative history, which demonstrates that the provision was intended to prohibit "tieing up business phones with repeated calls" and "driving a person to distraction by repeatedly dialing his number." See Temporary Commission on the Revision of the Penal Law and the Criminal Code, Proposed New York Penal Law 390 (1967).

So construed, the Penal Law § 240.30(2) charge is facially insufficient because the People do not allege reasonable cause to believe that defendant called Haque with no purpose of legitimate communication. To the contrary, the information alleges that defendant's call to Haque was a genuine attempt to threaten him. That is, the People allege that defendant's message was the mechanism of his harassment, not that defendant sought to harass Haque by the call itself, apart from its message.

The People suggest that the telephone call here was not for any legitimate purpose because it was intended to communicate a threat. Although there is some support for that approach, see People v Shack, 86 NY2d 529, 538 (1995), the court is nevertheless unpersuaded that determining whether a call is for "legitimate communication" can turn on the content of the communication. For one, we are told that Penal Law § 240.30(2) is "limited to conduct" and "does not prohibit speech or expression." Shack, 86 NY2d at 535; see People v Marquan M, 24 NY3d 1, 11 n.4 (2014). That understanding of the statute, however, is inconsistent with a view that statutory liability turns on the content of the communication conveyed by the call. Phrased differently, a statute that prohibits telephone calls that communicate threats but not telephone calls that communicate other messages plainly is a statute that "prohibit[s] speech or expression." Shack, 86 NY2d at 535.

It is also not clear that the Legislature intended Penal Law § 240.30(2) to prohibit threats [*3]made by telephone. The legislative history noted above reveals no intent to prohibit threats. Other provisions in Penal Law article 240 expressly prohibit threats, but Penal Law 240.30(2) does not. See Penal Law §§ 240.26(1), 240.30(1)(a)-(b). This last point is particularly significant, since the Legislature revised one of those prohibitions specifically to address First Amendment concerns. The Legislature's calibrated approach to other speech-restricting provisions counsels against inferring a speech-restriction that the statute's text does not expressly require. Indeed, had the Legislature intended to prohibit threats made by telephone in Penal Law § 240.30(2), it would have been more natural for the Legislature to specify that the provision covers telephone calls not made for a "lawful" purpose, as it did elsewhere. Cf. Penal Law § 240.45(1) (creating criminal nuisance liability for conduct that is "unlawful in itself"). The Legislature's use of "legitimate" rather than "lawful" suggests that it intended a meaning of the word "legitimate" that is distinct from the meaning of the word "lawful."

For these reasons, the Penal Law § 240.30(2) charge is facially insufficient and must be dismissed.

The other second-degree aggravated harassment counts, as well as the second-degree harassment count, are facially sufficient. As is relevant here, a defendant is guilty of second-degree aggravated harassment under Penal Law § 240.30(1)(a) when, with the intent to harass another person, the defendant communicates "a threat to cause physical harm" to that person or to their family, and the defendant knows (or has reason to know) that the threat will cause the other person to fear for their physical safety or the safety of their family. See also Penal Law § 240.30(1)(b) (imposing criminal liability for causing such a communication to be initiated). Similarly, a defendant is guilty of second-degree harassment when, "with intent to harass, annoy or alarm another person," the defendant threatens to "subject[ ] such other person to physical contact." Penal Law § 240.26(1).

Here, giving the information a "fair and not overly restrictive or technical reading," People v Casey, 95 NY2d 354, 360 (2000), it alleges reasonable cause to believe that defendant communicated a threat of physical harm to Haque with the requisite intent. A reasonable person could understand defendant's alleged statement that he was going to "fuck up [ Haque's ] life" and "take the revenge from [ him ]" as communicating a threat to commit acts of physical violence against Haque and his family. And the allegation that defendant posted the threats and other related material to his social media account gave reasonable cause to believe that defendant's threats were serious and not "mere angry words." People v Lagano, 39 NY3d 108, 111-12 (2022) (quoting People v Dietze, 75 NY2d 47, 51 (1989)). These allegations also provided reasonable cause to believe that defendant acted with the requisite intent to harass Haque, i.e., to create an unpleasant or hostile situation for him, especially by uninvited and unwelcome verbal conduct. See Merriam-Webster Dictionary, "harass" (online 2026).

Defendant's facial sufficiency challenges lack merit. First, defendant cites no authority to conclude that Haque's supporting deposition was incapable of converting the complaint to an information, merely because it predated the dismissal of the felony charge in the complaint. Because the statements attributed to Haque in the accusatory instrument were the same both pre- and post-reduction, his supporting deposition effectively removed the hearsay from the accusatory instrument regardless of the charges contained in the instrument. Second, assuming duplicity doctrine applies to misdemeanor accusatory instruments, defendant's duplicity claim fails because the information is susceptible of a non-duplicitous construction: namely, the [*4]information alleged one count each under Penal Law § 240.30(1)(a) and Penal Law § 240.26(1) for the telephone call to Haque, and one count under Penal Law § 240.30(1)(b) for the social media post.^[FN1] Finally, the information adequately alleges reasonable cause to believe that defendant is the person who made the call, as it alleges that Haque previously arrested defendant and that defendant told Haque during the telephone call that Haque had "falsely arrested" him earlier. At this stage of the litigation, these allegations are sufficient to support the People's charges. See People v Dumay, 23 NY3d 518, 525 (2014) (facial sufficiency does not require proof beyond a reasonable doubt).

Defendant's as-applied constitutional challenge also lacks merit. To be sure, by prohibiting threats, the second-degree harassment and aggravated harassment statutes regulate speech and must comply with the First Amendment. That is, the statutes may punish only "constitutionally proscribable expression." Lagano, 39 NY3d at 111. But "true threats" are not protected speech, since "everyone agrees [ that they ] lie outside the bounds of the First Amendment's protection." Counterman v Colorado, 600 US 66, 72 (2023). At a minimum, the true-threats doctrine encompasses threats of physical violence—that is, threats "to commit an act of unlawful violence to a particular individual." Virginia v Black, 538 US 343, 359 (2003). Therefore, because defendant is alleged to have made a threat of physical harm to Haque not in jest or passing, the First Amendment is not violated by applying a criminal sanction for those threats.^[FN2]

In sum, the charges under Penal Law § 240.30(1)(a), Penal Law § 240.30(1)(b), and Penal Law § 240.26(1) are facially sufficient, while the charge under Penal Law 240.30(2) is not.

As indicated, the People were required to announce their trial readiness by September 2, 2025. See CPL 30.30(7)(c). To validly declare ready, the People must first file a COC certifying that, "after exercising due diligence and making reasonable inquiries and efforts to ascertain the existence of, obtain, and disclose material and information subject to discovery, the prosecution has disclosed and made available all known material and information it has obtained subject to discovery." CPL 245.50(1), (3). In determining whether a COC is valid, the "key question" is whether the People made "reasonable efforts to comply with statutory directives." People v Bay, 41 NY3d 200, 211 (2023) (cleaned up); see CPL 245.50(6). This "fundamentally case-specific" inquiry turns on a variety of factors, including a list of factors set out in the discovery statute. Bay, 41 NY3d at 212; see CPL 245.50(5)(a). Where the People did not make reasonable efforts, the court must strike their COC. See Bay, 41 NY3d at 213.

The People's brief articulates their efforts to comply with their discovery obligations in adequate detail. The court has also considered the arguments of the defense. Based on the People's documented efforts to comply with their discovery obligations, the volume of discovery provided and outstanding, the complexity of the case and its discovery, the People's explanation for alleged discovery lapses and their response when apprised of those lapses, as well as any prejudice to the defense, the court concludes that the People properly certified that they had exercised due diligence and made reasonable efforts to obtain and disclose discoverable material, and that their COC is thus valid.

Defendant's COC challenge spans 193 paragraphs across 32 pages and raises a variety of grievances. The argument appears to be that the People could not have been trial ready when they certified their discovery compliance because, at the time, the People had not obtained or reviewed "core documents" related to the case. But the People have provided explanations for each of the alleged failures identified by the defense, and the court is not persuaded that any one of them or all of them collectively demonstrate that the People failed to exercise reasonable diligence before filing their COC.

For instance, the People's belated disclosure of search warrant material does not demonstrate a lack of diligence. The People obtained a warrant to search defendant's cellphone on April 18, 2025, and disclosed materials related to the warrant with their COC on July 30, 2025, with 34 days of speedy trial time remaining. In a conferral on September 2, 2025, counsel asserted for the first time that the search warrant disclosures were incomplete, and the prosecutor confirmed that he had neglected to turn over warrant materials that he had obtained in July 2025. The prosecutor promptly disclosed those materials on September 2 and filed a supplemental COC the next day. The People's inadvertent failure to turn over materials that were timely obtained, and their immediate disclosure of those materials upon learning that they were [*5]outstanding, does not show a lack of diligence.

Likewise, the People's post-COC warrant for defendant's social media information does not render their COC invalid. In this case, the People originally obtained a warrant for defendant's social media information on June 23, 2025, before they filed their COC. As the People explain, the warrant was not timely executed due to an oversight by a non-attorney member of the district attorney's office. The assigned prosecutor learned about the warrant's non-execution on September 3 and obtained a new warrant on September 12; he received responsive materials on September 18 and disclosed those (and other) materials on September 22. Under the circumstances, the People's failure to timely obtain the social media information does not demonstrate a lack of diligence.

Defendant also complains about the People's failure to promptly disclose the prosecution file for CR-015822-24KN—the earlier case in which Haque issued a DAT to defendant and which was dismissed and sealed pursuant to CPL 30.30. The People maintain that the material is not discoverable under CPL 245.20, and defendant does not identify which provision of that statute requires disclosure in this case. Indeed, defendant refers to the CR-015822-24KN prosecution file as Rosario or Brady information, suggesting his view that its discoverability derives from outside CPL 245.20. In any event, the defense made a demand for the material on or about September 8, and the People submitted an unsealing order to Supreme Court on September 10 to allow the material's disclosure. Supreme Court denied that request, apparently for procedural noncompliance, and the People resubmitted it to Criminal Court on September 12, where it was approved that day. The People then disclosed the prosecution file in CR-015822-24KN on October 1, 2025. On this record, the People's failure to turn over the requested materials sooner does not demonstrate a lack of diligence, and the People's prompt action to facilitate the disclosure of that material—notwithstanding the dispute as to its discoverability—demonstrates good faith.

The court has considered defendant's other arguments and finds them to be without merit. The COC challenge is therefore denied.

Supreme Court issued two warrants in this case: one dated April 18, 2025, which authorized a search of the cellphone seized from defendant incident to his arrest; and a second dated September 15, 2025, which authorized a search of defendant's Instagram and Facebook accounts. Defendant moves to controvert the warrants and suppress evidence pursuant to CPL 710.20.

As defendant correctly points out, the People failed to timely execute the search warrant for defendant's cellphone. The following facts are undisputed: police seized defendant's phone incident to his arrest on March 17, 2025; Supreme Court issued the warrant to search the phone on April 18, 2025; a detective delivered the phone to the digital evidence laboratory on May 1, 2025; the laboratory began attempting to extract information from the phone on May 8 or May 9, 2025; and the laboratory completed its extraction on or about July 2, 2025.

CPL 690.30(1) provides that a search warrant "must be executed not more than ten days after the date of issuance." This provision "assures reasonableness by providing a ten day time limit check against stale search warrants for validity from issuance to execution, irrespective of continuing existence of probable cause." Peter Preiser, Practice Commentaries to CPL 690.30, [*6]11A McKinney's Consol. Laws of New York 146 (2009). The CPL does not define execution, and the term should be given a practical interpretation to avoid "unreasonable or absurd" results. People v Schneider, 37 NY3d 187, 196 (2021).

Courts have articulated a range of views about when execution occurs for a cellphone warrant. Although results vary, those views share a central tenet that execution occurs when investigators take a substantial step toward carrying out the search authorized by the warrant. That approach make sense. It is consistent with the definition of "execute," which is "to perform or complete" some function. Black's Law Dictionary 369 (10th ed.). Especially for a multi-step search like the search of a cellphone, "performing" the search fairly encompasses completing a step of that process. The approach also advances the statutory purpose of promoting prompt investigative action, because it ensures that investigators take some substantial step toward completing the search within the ten-day window.

Determining what initial step constitutes execution is straightforward in cases where the cellphone is not in police custody when the warrant is issued. The "prevailing view" in those cases is that a substantial preliminary step toward carrying out the search is achieved—and thus the warrant is executed—when investigators seize the phone. See Commonwealth v Bowens, 265 A3d 730, 751 (Pa Super Ct 2021) (en banc); Fed R Crim P 41(e)(2)(B); cf. People v. DeProspero, 20 NY3d 527, 529, 531 (2013). The rule becomes somewhat more complicated in cases like this one, where investigators already have custody of the cellphone when the warrant issues.

Under those circumstances, the court is not persuaded that execution happens immediately when the warrant issues, as some courts have held. See People v Ruffin, 178 AD3d 455, 455 (1st Dept 2019); see also State v Nadeau, 1 A3d 445, 463 (Me 2010); United States v Carrington, 700 Fed Appx 224, 232 (4th Cir 2017). For one thing, that approach does not fit comfortably with the plain meaning of the word "execute," because it means that investigators could execute a warrant before the warrant exists. That doesn't make much sense. Moreover, under the execution-upon-issuance approach, investigators could indefinitely delay taking any action to search a defendant's cellphone after the warrant's issuance, subject only to the existing constitutional requirement that they act reasonably. Cf. United States v Smith, 967 F3d 198, 205 (2d Cir 2020). This would undermine the statute's purpose of promoting prompt investigative action, and it would make the statute's protections redundant of the protections provided by the Fourth Amendment.^[FN3] The Legislature cannot have intended CPL 690.30(1) to provide no [*7]protection distinct from the Constitution, especially since CPL 690.30(1) was meant to operate independently of constitutional requirements. See Preiser, supra, Practice Commentaries to CPL 690.30; see also People v Badji, 36 NY3d 393, 398 (2021) (noting that the primary consideration of statutory interpretation is "to ascertain and give effect to the intention of the legislature").

The court is equally not persuaded that execution happens only once the search of the cellphone is complete, as defendant suggests. This approach fails to account for the practical reality that cellphone searches are often delayed significantly by technical challenges associated with modern encryption. See United States v Cleveland, 907 F3d 423, 430-31 (6th Cir 2018). Given that reality, courts have uniformly held that execution does not require a completed search. See State v Sanchez, 476 P3d 889, 893 (NM 2020) ("Such an interpretation of the rule—that a search warrant for an electronic device is not executed until the information on that device is extracted—does not account for the practical realities of searching electronic devices."); see also Carrington, 700 Fed Appx at 232; United States v Gerber, 994 F2d 1556, 1559 (11th Cir 1993). That reasoning is persuasive.

Whatever act may constitute execution between these two points, the People failed to do it within ten days of the warrant's issuance in this case. The warrant issued on April 18, meaning that some substantial step was required on or before April 28. The next step documented by investigators was the May 1 delivery of defendant's cellphone to the laboratory for forensic examination.^[FN4] This action was probably sufficient to constitute execution, but it occurred outside the ten-day window in violation of CPL 690.30(1). The fruits of the search should therefore be suppressed in this case.^[FN5]

Defendant's motion to controvert the social media warrant is denied.^[FN6] The allegations of the warrant affidavit gave the issuing judge a sufficient basis to conclude that there was probable cause to believe that crimes or evidence of crimes might be found on defendant's social media [*8]accounts. Among other things, Detective Maura's affidavit alleged: that Haque recounted to him the content of the telephone call Haque received from defendant; that Maura viewed a recording of the telephone call on defendant's social media account; that Maura interviewed another member of NYPD, who had also arrested defendant in the past and had similarly been the subject of social media posts by defendant; and that defendant's social media accounts were accessible through his cellphone, which was in the People's custody (although the People could not access those accounts without defendant's password). These allegations easily gave the issuing judge a sufficient basis to conclude that probable cause existed to issue the social media warrant.

Contrary to defendant's contention, the warrants were not overbroad merely because they sought information from defendant's social media accounts for the roughly three-month period from January 28 to May 6, 2025. Although the warrant application did not articulate a justification for that temporal restriction, and the People do not provide a justification in their papers, the court concludes that the chosen three-month period is not unreasonable. Importantly, the warrant affidavit arguably gave probable cause to believe that defendant may have created relevant social media posts at any time after his arrest in early 2024. The warrant did not seek information from before that time. There is thus no concern in this case that the warrant authorized a search of defendant's social media for posts made during a time when there was no probable cause to believe evidence of a crime may exist. Cf United States v Zelaya-Veliz, 94 F4th 321, 340 (4th Cir 2024) (Wilkinson, J.) (discussing Fourth Amendment considerations implicated by temporal restrictions in social media search warrants).

The court has considered defendant's remaining arguments and finds them to be meritless.

The foregoing constitutes the order of the court.