Subpoenas to AI Service Providers Were Partially Approved, With Guardrails

“Contention Interrogatories” Asking for “All” Facts Were Too Broad

October 22, 2026

Published by Michael Berman at October 22, 2026

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In Fontainebleau, Plaintiff served four subpoenas on AI providers and requested A.I. information in an RFP. The court “directed the Parties to submit expedited supplemental briefing addressing whether the requested AI-related information falls within the scope of damages discovery authorized by the District Court, including its relationship, if any, to Defendant’s alleged malice and the statutory limitation on punitive damages under Florida law.” Fontainebleau Florida Hotel, LLC v Shmuley Boteach Jacob, 2026 WL 3151630 (S.D. Fla. Oct.21, 2026). It also applied the work product doctrine.

Defendant raised “blanket objections” to the AI subpoenas. “The Court emphasizes that a party’s communications with and use of AI does not automatically establish either discoverability or protection.” Id. at *10. After analyzing relevance, the court held that each piece of information should be analyzed under a traditional work product framework. It wrote: “The Court must examine the purpose and circumstances of the particular communications rather than presume protection from the medium through which they were created.”

In sum: “The Court emphasizes that a party’s communications with and use of AI does not automatically establish either discoverability or protection. The analysis turns on the ordinary requirements of Rules 26(b)(1), 26(b)(3), and 26(b)(5).”

OVERVIEW

Plaintiff’s subpoenas sought all communications with AI: concerning the hotel, relating to any hotel employee, relating to the litigation, concerning Plaintiff’s counsel, relating to any Court Order in the litigation, or relating to the Judges. The RFP sought: “All of Defendant’s AI Communications regarding Requests 1 through 7 that have, since their creation, been deleted.”

Much of the decision turns on whether the discovery sought information beyond the scope authorized by the court, which was limited to damages. A related issue was whether this was liability discovery that was propounded after the discovery cutoff.

An important issue turned on work product under Heppner, Warner, and their progeny.

Defendant argues that the requests in the subpoenas and the Seventh RFP risk exposing materials protected by the work-product doctrine, including AI-assisted litigation preparation, legal research, draft analyses, and communications concerning defense strategy…. Defendant relies principally on Warner v. Gilbarco, Inc., 820 F. Supp. 3d 629 (E.D. Mich. 2026), for the proposition that litigation-related materials do not automatically lose work-product protection merely because a party used a third-party AI platform to prepare them.

SOME OF THE A.I. COMMUNICATIONS WERE RELEVANT

Plaintiff argued that the requested information was relevant to punitive damages. As a matter of substantive, tort law, the court ruled that “when a defendant’s state of mind bears on a legally cognizable issue, the mere fact that discovery probes the defendant’s thinking, motives, or preparation does not render it impermissible.” It then held:

The same principle applies to Defendant’s AI prompts and communications. To the extent Defendant used AI platforms to generate, revise, or refine statements concerning Plaintiff, its counsel, or its representatives, those communications may reveal not merely the final content of Defendant’s statements but also the purpose for which the statements were created, the instructions Defendant supplied, and the effects he sought to achieve. Such information may provide evidence of the intent underlying Defendant’s conduct that cannot necessarily be discerned from the resulting public statements alone. The Court does not determine that those communications will establish malice or specific intent to harm; it determines only that they bear a sufficient relationship to those disputed damages issues to warrant discovery.

The court wrote: “Here, Plaintiff alleges a continuing course of conduct directed toward the Hotel, its personnel, and its representatives, including conduct involving AI-generated content.” It then added: “That ruling, of course, does not establish that every AI communication is discoverable, but it reinforces the relevance of evidence concerning Defendant’s alleged continuing conduct toward Plaintiff and persons associated with it.” Id. at *5.

In short: “Defendant’s communications with AI platforms concerning the Hotel and the Hotel’s employees, owners, or representatives, including Plaintiff’s counsel, may reveal information relevant to Defendant’s alleged intent to harm Plaintiff, the nature and persistence of the challenged conduct, and the extent to which that conduct allegedly amplified Plaintiff’s injuries. The Court therefore concludes that Request Nos. 1 (seeking AI communications about the Hotel), 3 (seeking AI communications about Plaintiff’s counsel), and 4 (seeking AI communications about any employee, owner, or representative of the Hotel) in the subpoenas to the AI providers and the Seventh RFP fall within the scope of damages discovery authorized by the District Court. Accordingly, Defendant’s blanket scope objection to Request Nos. 1, 3, and 4 is OVERRULED.”

SOME OF THE A.I. COMMUNICATIONS WERE BEYOND THE SCOPE OF DISCOVERY

Discovery had been re-opened for a limited purpose. Id. at *8. “The Court agrees with Defendant’s general premise that an order reopening discovery for a limited purpose does not authorize unrestricted additional discovery. The District Court expressly limited the reopening to damages discovery, and that limitation must be enforced.”

“Although the Court finds that certain AI communications are discoverable, it agrees with Defendant that the requests in the subpoenas and Seventh RFP, as drafted, are broader than the damages discovery authorized by the District Court.” Id. at *7.

For example, several were “exceptionally broad.” One “encompasses potentially every AI exchange on matters having no meaningful connection to the amount of damages or Defendant’s alleged intent to harm Plaintiff. Plaintiff has not established that every communication relating to this litigation bears on an issue remaining for the damages trial.” Id.

As to another:

Turning to Request No. 5 in the subpoenas and the Seventh RFP, it seeks all AI communications concerning or relating to any Court Order entered during this litigation.... Such communications may include Defendant’s attempts to understand an Order, research its consequences, consider procedural options, or evaluate the litigation. The fact that Defendant may have expressed disagreement with, frustration about, or hostility toward a Court Order does not, without a sufficient connection to the alleged injury, make the communication relevant to Plaintiff’s damages. Although Plaintiff contends that Defendant’s reactions to Court Orders reflect the depth of his hostility and the reprehensibility of his conduct, that theory is too attenuated to justify discovery of every AI exchange concerning every Order entered in this case. The Court therefore finds that Request No. 5 exceeds the permissible scope of damages discovery.

Id. at *7. “The Court likewise finds that Defendant’s private communications with AI platforms concerning judicial officers, without more, do not bear a sufficient relationship to the damages Plaintiff seeks for the alleged harm to the Hotel.” Id.

THE WORK-PRODUCT DOCTRINE

DOES NOT CATEGORICALLY PROTECT DEFENDANT’S AI COMMUNICATIONS

The court wrote: “Defendant also contends that the requested AI communications may constitute protected work product because they include AI-assisted litigation preparation, research, draft analyses, and other materials concerning the defense of this action.” Id. at *8.

It noted that “Defendant invokes work-product protection over a potentially diverse collection of AI communications without establishing that every communication within the permitted categories was created because of this litigation.” Id.

Heppner & Warner

To set the stage, the Fontainebleau court wrote: “The Parties rely on two recent decisions addressing AI-assisted materials: United States v. Heppner, 820 F. Supp. 3d 292 (S.D.N.Y. 2026) and Warner v. Gilbarco, Inc., 820 F. Supp. 3d 629 (E.D. Mich. 2026).”

“The Court finds Heppner persuasive insofar as it recognizes that independently generated AI communications do not automatically become protected work product merely because counsel represents the user. At the same time, the Court does not read Heppner as establishing that all materials independently prepared by a represented party are categorically unprotected. This is because Rule 26(b)(3)(A) expressly extends to qualifying materials prepared ‘by or for another party or its representative.’ Fed. R. Civ. P. 26(b)(3)(A).”
“In Warner, the court recognized that AI-assisted litigation preparation may qualify for work-product protection and that using a third-party AI tool does not necessarily result in waiver. 820 F. Supp. 3d at 636–37. But Warner does not support Defendant’s blanket objection. The recognition that qualifying AI-assisted litigation preparation may remain protected notwithstanding the use of an AI platform does not establish that all communications with AI concerning an opposing party, its personnel, or its counsel were prepared in anticipation of litigation. The Court must examine the purpose and circumstances of the particular communications rather than presume protection from the medium through which they were created.”

The Fontainebleau Analysis

The Fontainebleau court wrote:

Neither decision establishes a categorical rule governing all AI communications. Rather, they underscore that the applicability of work-product protection depends on the nature, purpose, and circumstances of the particular materials. Here, communications independently generated by Defendant to create, revise, or disseminate content concerning the Hotel, its personnel, or Plaintiff’s counsel are not transformed into attorney work product merely because Defendant is a litigant or because the resulting content may bear on this action. To the extent such communications were created for the purpose of producing public-facing statements or pursuing Defendant’s independent activities, rather than preparing the defense of this litigation, they ordinarily would not satisfy Rule 26(b)(3)(A). The Court therefore rejects Defendant’s blanket work-product objection to Request Nos. 1, 3, 4, and 7. However, that conclusion does not foreclose a properly supported, document-specific claim of protection. If a particular communication was prepared because of this litigation and otherwise satisfies Rule 26(b)(3), Defendant may assert the protection in accordance with the Federal Rules. Defendant must, however, identify the withheld material and describe the nature of the asserted protection sufficiently to permit Plaintiff to assess the claim without revealing the protected information itself. See Fed. R. Civ. P. 26(b)(5)(A).

The Court emphasizes that a party’s communications with and use of AI does not automatically establish either discoverability or protection. The analysis turns on the ordinary requirements of Rules 26(b)(1), 26(b)(3), and 26(b)(5). Defendant may not withhold all communications within the permitted categories based on a generalized assertion that they concern litigation, and Plaintiff may not obtain genuinely protected litigation-preparation materials merely by describing them as AI communications.

Id. at *10 (emphasis added).

DEFENDANT WAS NOT COMPELLED TO CONSENT TO THE SUBPOENAS

The court also addressed an oral motion based on an alleged failure to preserve AI communications. Id. at *10. Plaintiff contended that third-party subpoenas were proper based on this assertion and Plaintiff asked for an order compelling Defendant to consent to the subpoenas.

The court denied the motion: “Although Plaintiff may pursue appropriately limited subpoenas, the Court declines to compel Defendant to execute consents or authorizations permitting the AI providers to disclose responsive communications. Rule 34 permits a party to request documents and electronically stored information within another party’s possession, custody, or control. See Fed. R. Civ. P. 34(a)(1). The Rule requires a responding party to produce responsive, nonprivileged materials within that party’s control, but it does not expressly require a party to execute an authorization allowing a third party to disclose records directly to an adversary.”

The court wrote that no rule “establishes that a litigant must execute a blanket authorization permitting a third-party service provider to disclose the litigant’s private records merely because an opposing party seeks relevant information. And Plaintiff cites to no authorities to support its request.”

The court stated two caveats:

“[T]he Court will not compel Defendant to execute prospective authorizations based solely on the possibility that such consent might facilitate Plaintiff’s third-party discovery.’
“The Court further emphasizes that permitting the issuance of subpoenas does not establish their enforceability. Rule 45 provides procedures for objections and motions to quash or modify subpoenas by nonparties. Accordingly, the Court’s ruling preserves Plaintiff’s ability to seek authorized third-party discovery consistent with this Order without prematurely adjudicating the obligations of nonparties that have not appeared before the Court.” [emphasis added].

PARTIES MUST DISCUSS LOGISTICS

Lastly, the court added:

But there is one additional wrinkle. The Court recognizes that Defendant may, consistent with this Order, assert that certain responsive AI communications within the possession of the AI providers are subject to work-product protection. And if Plaintiff serves the subpoenas on the AI providers and requires them to produce the document directly to Plaintiff’s counsel, Defendant will be deprived of the opportunity to determine whether there are any work-product protected documents within the production that should otherwise be withheld and identified on a privilege log. For that reason, the Parties are DIRECTED to meet and confer to discuss the logistics of how the AI providers, to the extent they have responsive materials, will be instructed to produce such materials. If the Parties cannot agree on a procedure, the Court will hear the Parties’ respective positions on this issue at the follow-up discovery hearing that is tentatively set for October 26, 2026 at 1 p.m.

Id. at *12 (emphasis added).

Resolving that wrinkle should not be a problem. There is plenty of guidance on that issue. Maryland Appellate Decision Permitting Limited Forensic Search of Non-Parties’ Cell Phones (Mar. 24, 2022).

For more on Heppner, Warner, and their progeny, please visit: