# Appendix E: Discovery requests for AI conversation data

Paste-ready requests. Renumber to fit your set, conform the definitions to your jurisdiction's local rules, and check the numerical limits on interrogatories before you serve.

Not legal advice. Editable versions at **kovel.io/book/forms**.

## E.1 Definitions

The definitions carry most of the weight. A well-drafted definition of "AI Tool" makes every request below work; a lazy one lets a responding party read the whole set narrowly.

> **"AI Tool"** means any artificial intelligence system, large language model, generative AI application, chatbot, or machine-learning assistant capable of generating text, code, images, audio, or analysis in response to user input, whether accessed through a web interface, desktop or mobile application, browser extension, plug-in, embedded feature of other software, or application programming interface. AI Tool includes without limitation ChatGPT and any other OpenAI product; Claude and any other Anthropic product; Google Gemini, Bard, and NotebookLM; Microsoft Copilot in any form; Meta AI; Perplexity; Grok; DeepSeek; Mistral; and any successor, predecessor, or comparable product, together with any AI feature embedded in productivity, communication, drafting, meeting-notes, or transcription software.
>
> **"AI Conversation"** means any exchange with an AI Tool, including each prompt, query, instruction, or input submitted by a user; each response, completion, or output returned; all files, images, documents, or data uploaded or attached; all associated metadata, including conversation identifiers, message-level timestamps, model identifiers and versions, and the branch or regeneration structure reflecting edited prompts or regenerated responses; and all system prompts, custom instructions, persistent memory entries, saved projects, custom assistants, and knowledge bases associated with the account.
>
> **"Your AI Accounts"** means every account, workspace, organization, team, seat, or API credential with any AI Tool that You, or any of Your officers, directors, employees, agents, or contractors, have used in connection with the subject matter of this action, **including personal accounts**, whether or not the use was authorized and whether or not the account was issued or paid for by You.

The clause on personal accounts is not boilerplate. It is where the material is.

## E.2 Requests for production

> **RFP 1.** All AI Conversations concerning [subject matter of the action].
>
> **RFP 2.** All AI Conversations concerning [the transaction / agreement / termination / incident] at issue, including any in which [the event] was described, analyzed, drafted, summarized, or discussed.
>
> **RFP 3.** All AI Conversations in which You sought analysis of, or commentary upon, Your legal rights, obligations, exposure, or potential claims or defenses relating to the subject matter of this action.
>
> **RFP 4.** All AI Conversations reflecting the drafting, editing, or revision of any communication, document, agreement, policy, or public statement relating to the subject matter of this action, including all intermediate drafts and regenerated variants.
>
> **RFP 5.** All documents, files, images, spreadsheets, or other materials uploaded to or attached within any AI Tool in connection with the subject matter of this action.
>
> **RFP 6.** All persistent memory entries, custom instructions, system prompts, saved projects, custom assistants, and knowledge bases associated with Your AI Accounts that reference the subject matter of this action or any party to it.
>
> **RFP 7.** The complete native data export produced by each AI Tool identified in response to Interrogatory No. 1, in the format made available by the provider, for the period [date] through [date].
>
> **RFP 8.** All documents concerning Your policies, guidelines, training, or instructions governing employee or contractor use of AI Tools, including all versions in effect during the relevant period and all communications announcing or modifying them.
>
> **RFP 9.** For any workspace, team, or enterprise AI deployment, all administrative audit logs, conversation exports, data-retention configurations, and records of changes to retention settings during the relevant period.
>
> **RFP 10.** All documents concerning the deletion, disabling, purging, or export of any AI Conversation, account, or associated data on or after [the date the preservation obligation attached], including deletion logs, timestamps, and any communication concerning such deletion.
>
> **RFP 11.** All litigation hold notices, preservation instructions, and custodian acknowledgments issued in this matter, to the extent they address AI Tools or AI Conversations.
>
> **RFP 12.** All API request and response logs generated by Your programmatic use of any AI Tool in connection with the subject matter of this action.

RFP 10 and RFP 11 are the spoliation pair. Serve them in the first set even if you have no reason to suspect deletion, because the answers are only useful if you asked before anyone had a reason to be careful. RFP 4's "intermediate drafts and regenerated variants" is where the admissions live: the version a person wrote before they decided how it should sound.

## E.3 Interrogatories

> **Rog 1.** Identify every AI Tool used by You, or by any of Your officers, directors, employees, agents, or contractors, in connection with the subject matter of this action. For each, state the product name, the account identifier or email address, the subscription tier, whether the account is personal or organizational, the individuals with access, and the approximate dates of use.
>
> **Rog 2.** For each AI Tool identified above, state whether conversation history was enabled, whether any automatic deletion or data-retention setting was active, the configured retention period, and whether any such setting was changed on or after [date the preservation obligation attached]. If changed, state by whom, when, and why.
>
> **Rog 3.** State whether any AI Conversation relating to the subject matter of this action has been deleted, purged, or rendered inaccessible. If so, identify each such conversation to the extent known, state when and by whom it was deleted, and describe any effort to recover it.
>
> **Rog 4.** Describe Your policies governing the use of AI Tools during the relevant period, including whether personal AI accounts were permitted for work purposes, and identify all individuals responsible for implementing and enforcing those policies.
>
> **Rog 5.** Identify each person who used an AI Tool to draft, revise, analyze, or summarize any document, communication, or public statement relating to the subject matter of this action, and identify the document produced.
>
> **Rog 6.** If You contend that any AI Conversation is protected by the attorney-client privilege or the work-product doctrine, state (a) the date and manner in which the attorney-client relationship was formed; (b) the date of the writing in which counsel directed the use of the AI Tool; (c) the identity and bar admission of the directing attorney; (d) the AI Tool so directed; (e) the terms of service or contractual provisions governing retention and training applicable to that use; and (f) each person other than counsel and client to whom the substance of the conversation was disclosed.

Rog 6 is the one to draft carefully. It asks for the two dates in subparts (a) and (b) that separate a real Kovel framework from a retrofitted one, and subpart (f) opens the waiver inquiry. A responding party with a genuine arrangement answers it easily. A party without one takes an extension.

## E.4 Rule 30(b)(6) deposition topics

> **Topic 1.** The identity, procurement, deployment, and configuration of all AI Tools used by the organization during the relevant period, including subscription tiers, administrative controls, and data-retention settings.
>
> **Topic 2.** The organization's policies, training, and enforcement regarding employee use of AI Tools, including the use of personal AI accounts for work purposes.
>
> **Topic 3.** The organization's efforts to identify, preserve, collect, and produce AI Conversations in this action, including the content and distribution of any litigation hold, the custodian acknowledgments received, and the steps taken to suspend automatic deletion.
>
> **Topic 4.** The technical capabilities available to the organization to export, search, and produce AI Conversation data, including administrative export tools, audit logs, and compliance integrations.
>
> **Topic 5.** Any deletion, purge, or loss of AI Conversation data on or after [date], and the circumstances of each.
>
> **Topic 6.** The organization's use of AI Tools in connection with [the specific transaction, decision, or event at issue].

Topic 4 is the burden-killer. Once a designee testifies that the admin console exports conversations, the objection that production would be burdensome is gone.

## E.5 Subpoena to an AI provider

Read chapter 11 before serving one of these. The Stored Communications Act will block a civil subpoena for the *contents* of stored communications, and a major provider will send you a well-practiced objection rather than a production. Serve it for non-content records only, and treat the party as your source for content.

> **Attachment A — Documents Requested**
>
> 1. Documents sufficient to identify all accounts associated with the email address(es) [list], including account creation date, subscription tier and history, and current status.
>
> 2. Documents sufficient to show the data-retention settings applicable to each such account during the period [dates], and any changes to those settings.
>
> 3. Documents sufficient to show whether any deletion request was received for each such account during the period [dates], and the date of each.
>
> 4. Non-content connection or access logs for each such account for the period [dates], to the extent retained.
>
> 5. Documents sufficient to show the terms of service and data-usage policies in effect for each such account during the period [dates].
>
> 6. Documents sufficient to show whether any account is subject to a litigation hold, preservation order, or legal-process obligation that has suspended deletion.
>
> **Note:** This subpoena does not seek the contents of any stored communication. Requests are limited to non-content records, subscriber information, and policy documents.

That closing note is worth including. It narrows the objection to something the provider can actually respond to, and Request 6 is quietly the most interesting one, because a provider under an unrelated preservation order may still be holding conversations your opponent believes are gone.

## E.6 ESI protocol language

Insert into the negotiated protocol. This is more durable than any single request.

> **§ __. AI assistant data.** The parties agree that "electronically stored information" as used in this Protocol includes AI Conversations, defined as exchanges with any artificial intelligence assistant or large language model, including all prompts, responses, uploaded files, system prompts, custom instructions, persistent memory entries, saved projects, and associated metadata.
>
> **(a) Sources.** Each party shall identify, for each custodian, all AI Tools used in connection with the subject matter of this action, including tools accessed through personal accounts, and shall include such tools in its data-source inventory.
>
> **(b) Preservation.** Each party shall instruct its custodians to disable automatic deletion and data-retention limits in all identified AI Tools and to discontinue the use of temporary, incognito, or ephemeral chat modes for matters relating to this action.
>
> **(c) Format.** AI Conversations shall be produced in the native export format made available by the provider, in JSON where offered, preserving conversation identifiers, message-level timestamps, model identifiers, role designations, and branch or regeneration structure. Production as static images or PDF is not sufficient absent agreement.
>
> **(d) Enterprise deployments.** A party operating a workspace, team, or enterprise AI deployment shall produce from its administrative export and audit facilities and shall not assert burden on the basis that individual custodian collection would be required where an administrative export exists.
>
> **(e) Privilege.** A party asserting privilege over any AI Conversation shall log the assertion at the conversation level and shall identify the directing attorney, the date of the writing establishing direction, and the date the attorney-client relationship was formed.

Subsection (e) is the one they will push back on. Hold the line: a party asserting Kovel protection is claiming a specific factual predicate, and the two dates are the predicate. Agreeing to log them costs an honest party nothing.