# Appendix D: Litigation hold and preservation letters

Three letters. The internal hold you send to your own client and custodians, the external preservation demand you send to the other side, and the short version you send when you have twenty minutes and a real risk that history is being cleared tonight.

The AI-specific value in all three is the same: name the products, kill the auto-deletion, and reach the surfaces people forget.

Templates are starting points, not legal advice. Adapt them and have counsel review before sending. Editable versions at **kovel.io/book/forms**.

## D.1 Internal litigation hold notice

Sent by counsel to the client organization and its custodians.

> **PRIVILEGED AND CONFIDENTIAL — ATTORNEY-CLIENT COMMUNICATION**
>
> **To:** [Custodians]  
> **From:** [Attorney / General Counsel]  
> **Date:** [Date]  
> **Re:** LITIGATION HOLD — Preservation of documents and data, including AI assistant conversations
>
> **Action required. Do not delete anything described below. This notice supersedes all routine deletion and retention policies until it is lifted in writing.**
>
> **1. Why you are receiving this.** [Describe the dispute, claim, investigation, or anticipated litigation.] The law requires us to preserve potentially relevant information from this point forward. Failure to do so can result in court sanctions against the company, adverse instructions to a jury, and personal consequences for individuals who destroy records.
>
> **2. What must be preserved.** All documents and electronically stored information relating to [subject matter], including but not limited to email, text and instant messages, chat platform messages, documents, drafts, notes, calendars, voicemails, photographs, databases, and metadata.
>
> **3. AI assistant conversations are expressly included.** This is not a routine category and requires your attention. You must preserve all conversations, prompts, responses, uploads, and outputs involving any artificial intelligence assistant or large language model relating to the subject matter, including:
>
> > (a) Consumer and professional AI assistants, including ChatGPT and any OpenAI product, Claude, Google Gemini, Microsoft Copilot, Meta AI, Perplexity, Grok, DeepSeek, and any comparable tool;
> >
> > (b) AI features embedded in other software, including drafting, summarization, meeting-notes, and transcription assistants;
> >
> > (c) Conversations in **personal accounts** where the subject matter was discussed, whether or not the account is company-issued and whether or not the use was authorized;
> >
> > (d) Saved projects, custom GPTs or assistants, **persistent memory**, custom instructions, system prompts, and uploaded files or knowledge bases;
> >
> > (e) Locally cached conversation data in desktop and mobile applications, and copies in personal or company cloud backups;
> >
> > (f) API request and response logs, where the tool was accessed programmatically;
> >
> > (g) Workspace, team, or enterprise administrative records, including audit logs, retention settings, and conversation exports available to administrators.
>
> **4. Specific instructions.** You must, immediately:
>
> > (i) **Disable any automatic deletion or data-retention setting** in every AI tool you use. In most products this is under Settings, in a section named Data Controls, Privacy, or Personalization.
> >
> > (ii) **Stop using temporary, incognito, or ephemeral chat modes** for anything touching the subject matter. These modes do not write to history and defeat preservation.
> >
> > (iii) **Do not delete conversations**, projects, memory entries, custom instructions, or accounts.
> >
> > (iv) **Do not close or cancel** any AI subscription or account, which may trigger deletion of the underlying data.
> >
> > (v) **Run the tool's data export** and retain the archive. [IT / counsel] will provide instructions and a collection location.
> >
> > (vi) Preserve devices. Do not wipe, reset, trade in, or reimage any device that has been used with these tools.
>
> **5. Do not attempt to determine relevance yourself.** Preserve broadly. Questions about scope go to [contact], not to your own judgment about what matters.
>
> **6. Certification.** Reply to this notice confirming you have read it, disabled auto-deletion in each AI tool you use, and preserved the categories above. Identify by name each AI tool you have used in connection with the subject matter, including personal accounts.
>
> **7. Duration.** This hold remains in effect until you receive written notice from [attorney] that it has been lifted.
>
> Questions: [name, phone, email]. Ask before you delete anything, not after.

The certification in paragraph 6 is the part people cut for brevity. Keep it. A signed acknowledgment naming the tools each custodian used is a collection map and a defensibility record in one document, and it converts "we sent a hold" into "we sent a hold and here is what each custodian confirmed."

## D.2 Preservation demand to an opposing party

Sent as early as litigation is reasonably anticipated. Send it before the complaint if you can.

> [Date]
>
> [Opposing party / counsel]
>
> **Re: [Matter] — Demand for preservation of evidence, including AI assistant conversations**
>
> Dear [Counsel]:
>
> This firm represents [Client] in connection with [description]. Litigation is reasonably anticipated. This letter provides notice of your client's obligation to preserve relevant evidence and identifies categories requiring specific attention.
>
> **1. Preservation obligation.** Your client is obligated to preserve all documents and electronically stored information relevant to this dispute and to suspend any routine destruction or automatic deletion affecting such material. That obligation attached no later than the date of this letter and may have attached earlier.
>
> **2. Categories.** Without limiting the general obligation, preserve all material relating to [subject matter], including email, messaging, documents and drafts, calendars, and associated metadata.
>
> **3. AI assistant conversations.** We specifically identify, and demand preservation of, all conversations, prompts, responses, uploads, and generated outputs involving any AI assistant or large language model concerning the subject matter of this dispute, including without limitation ChatGPT and other OpenAI products, Claude, Google Gemini, Microsoft Copilot, Meta AI, Perplexity, Grok, and comparable tools; AI features embedded within other applications; conversations occurring in **personal accounts**; saved projects, custom assistants, **persistent memory entries**, custom instructions, and uploaded files; locally cached application data and cloud backups; API logs; and workspace or enterprise administrative exports, audit logs, and retention configurations.
>
> **4. Specific steps.** We demand that your client immediately (a) disable automatic deletion and data-retention limits in all such tools; (b) cease use of temporary, incognito, or ephemeral chat modes for matters relating to this dispute; (c) refrain from deleting conversations, memory entries, projects, or accounts; (d) refrain from cancelling subscriptions that would trigger deletion; (e) preserve devices without wiping or reimaging; and (f) execute and retain the native data export offered by each such tool.
>
> **5. Note on retention windows.** Several of these products delete conversation data within a short period following user deletion, in some cases thirty days. Because that window is materially shorter than typical email retention, we ask that these steps be taken now rather than in the ordinary course of discovery planning.
>
> **6. Consequences.** Failure to preserve may result in a motion for sanctions under Federal Rule of Civil Procedure 37(e) or the applicable state analogue, including an adverse-inference instruction. This letter is intended to establish that your client was on specific notice of these categories.
>
> **7. Confirmation.** Please confirm in writing within [14] days that a litigation hold has issued, that it names AI assistant data, and that automatic deletion has been suspended. We are prepared to meet and confer regarding scope and format.
>
> Very truly yours,
>
> [Counsel]

Paragraph 6 is doing the real work. It is not there to be aggressive. It is there so that a later deletion cannot be characterized as an innocent failure to appreciate that these categories were in scope.

## D.3 The short version

For when you have twenty minutes and a live risk. Email it now, follow with D.2.

> **Re: [Matter] — preservation notice**
>
> Litigation is reasonably anticipated regarding [subject]. Your client must preserve all relevant documents and electronically stored information and suspend routine and automatic deletion.
>
> We specifically identify AI assistant data as within scope: all conversations, prompts, outputs, uploaded files, persistent memory, and custom instructions in ChatGPT, Claude, Gemini, Copilot, Perplexity, and comparable tools, in both business and personal accounts, together with application caches, cloud backups, API logs, and enterprise audit and export records.
>
> Because several of these products purge deleted conversations within approximately thirty days, we ask that automatic deletion be disabled and ephemeral chat modes discontinued today. Please confirm.
>
> [Counsel]

## D.4 Meet-and-confer script

For the Rule 26(f) conference, or the first call after your preservation letter.

**Open with the concession.** "We are producing our client's AI conversation data and we are asking for yours. This is reciprocal."

That sentence removes most of the fight. A demand that runs one direction gets litigated. A reciprocal one gets negotiated.

**Then work the four questions.**

1. *Which tools, and which accounts?* Get a custodian-by-custodian list, and press on personal accounts used for work. The answer "we only use the enterprise deployment" is very often incomplete, and it is better to establish that now than at a deposition.

2. *What does your hold say?* Ask whether their hold notice names AI tools specifically and whether it instructed custodians to disable auto-deletion. If it does not, say so on the call and follow up in writing. You have just created the record.

3. *What format?* Ask for the provider's native export, in JSON, with conversation identifiers, message timestamps, model identifiers, and branch structure intact. Refuse PDF screenshots. The stated reason is that screenshots strip metadata and cannot be authenticated or deduplicated.

4. *Where does privilege land?* If they intend to assert a Kovel arrangement, ask now for the date of the engagement provision and the date of the direction. Two dates. You will learn immediately whether this is a real framework or one assembled after the demand letter.

**Close by putting it in the protocol.** Anything agreed on this call goes into the ESI protocol by name. A generic reference to "electronic communications" will not survive a later dispute about whether AI chats were covered.