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What the Musk?

Amy Swaner

May 2026

Calculating...

The Trial Started April 27, 2026

Elon Musk sued Sam Altman and OpenAI for actions that go back to the humble, non-profit beginnings of OpenAI. The filings contain some interesting, flashy gossip on the surface. But beneath the flashy gossip is a serious lesson.

The trial that started this week in Oakland is a vivid illustration of what happens when sophisticated organizations keep everything. Exhibits range from merely embarrassing to damaging — Greg Brockman’s 2017 personal journal, Elon Musk’s 2016 email calling Jeff Bezos “a bit of a tool,” internal communications about how to “control the narrative” around an investigation. These are all in the case for one reason-- nobody disposed of them.

Let's be honest. Law firms keep more, for longer, with less discipline than the Musk v. Altman defendants. Call it the “Just In Case” Rule of document retention and data governance. If your firm subscribes to that, this article shows you why you should rethink that.

What The Discovery Has Actually Produced

Hundreds of unsealed filings in Musk v. Altman have pried open the internal information practices of OpenAI, Microsoft, Meta, and Tesla. The court’s January 15, 2026 summary judgment order (docket; SJ order, 1/15/26) quotes directly from a September 2017 Brockman journal entry:

“This is the only chance we have to get out from Elon. … Financially, what will take me to $1B?”

An unsealed February 3, 2025 text exchange shows Mark Zuckerberg telling Musk that Meta’s teams were,

“on alert to take down content doxxing or threatening the people on your team” working on DOGE."

Internal OpenAI communications from March 2024 show then-communications chief of OpenAI, Hannah Wong, describing efforts to “control the narrative” around the WilmerHale investigation summary.

None of these were created as corporate records. Yet they are now central exhibits — preserved, accessible, and produced because they were relevant under Federal Rule of Civil Procedure 26 and within the corporation’s possession, custody, or control under Rule 34, That is the lesson. Discovery turns on relevance and on whether the producing party had the legal right or practical ability to obtain the material. Courts apply that test functionally. In re NTL, Inc. Securities Litigation, 244 F.R.D. 179 (S.D.N.Y. 2007). Where the corporation does not have control, Rule 45 third-party subpoenas reach the rest.

No governance lever makes existing relevant material vanish once litigation is reasonably anticipated. There is one lever that genuinely reduces what exists to be discovered, and it operates entirely before any preservation duty attaches--defensible disposition under a written retention schedule. Yep, part of one of my favorite topics: Data Governance.

Why This Is A Law Firm Problem

The instinct in most firms is to keep everything. Closed matter files, drafts, internal memos, deposition prep, conflict-check workpapers, engagement letters, billing narratives, KM databases, marketing CRMs — and now AI-tool outputs. Copilot drafts, transcription archives, redline histories, intake-bot logs. The rationales for keeping all of it are familiar: malpractice tail risk, future citation, fee disputes, the possibility a former client will ask for something. None justifies indefinite retention. Most justify defined retention with documented disposition at the end of it.

Three reasons the law firm exposure is worse than the Musk v. Altman defendants’:

Volume and surface area. Firms hold work product, strategic thinking, candid attorney communications, and client confidences for hundreds or thousands of matters at once. Each matter is its own discovery and breach surface.

Confidentiality runs indefinitely. ABA Model Rule 1.6 applies to client information after the representation ends, with no expiration. Indefinite retention extends the duration of that confidentiality risk. Every additional year a closed file sits on a server is another year it can be breached or subpoenaed.

Breach risk is asymmetric. When a tech company is breached, its own information is exposed. When a law firm is breached, the privileged information of dozens or hundreds of unrelated clients is exposed simultaneously. The ABA’s 2024 Cybersecurity TechReport and the steady cadence of firm ransomware incidents (Mossack Fonseca, the 2023 Orrick breach affecting hundreds of thousands of clients, the 2024 Houser LLP incident) drive the point home.

What the Rules Actually Permit

Ostensibly law firms cling to the "Just in Case" Rule mainly in fear of spoliation. We can all agree, however, that routine, good-faith disposition under a written schedule, applied consistently before any duty to preserve attaches, is not spoliation. The 2015 amendments to Federal Rule of Civil Procedure 37(e) tightened the spoliation framework. Sanctions for lost ESI now require that the party failed to take reasonable steps to preserve, that the information cannot be restored or replaced, and — for the most severe sanctions — that the party “acted with the intent to deprive another party of the information’s use in the litigation.” Negligence and even gross negligence will not support an adverse inference. Applebaum v. Target Corp., 831 F.3d 740, 745 (6th Cir. 2016). Conformance in good faith to a valid retention policy, before any duty to preserve arises, does not itself demonstrate the requisite intent to obstruct or deprive. Arthur Andersen LLP v. United States, 544 U.S. 696 (2005).

The Sedona Conference Commentary on Legal Holds and Commentary on Information Governance treat consistent disposition under a written schedule as the foundation of defensible practice. That’s beautiful framing – the foundation of a defensible practice. The duty to preserve attaches when litigation is reasonably anticipated, and the schedule must be suspended at that point — but disposition that occurred before that point is protected. The professional rules are aligned, not in tension. I highly recommend reading the Sedona Commentary if you're hanging on to files "just in case."

ABA Formal Op. 471 (2015) addresses what lawyers owe clients on termination of representation, surveys the split between the entire-file and end-product approaches, and confirms that lawyers are not required to retain every file indefinitely. The Federal Civil Rules and the Professional Rules of Conduct all permit defensible disposition. The “just in case” instinct is a malpractice-aversion habit that can actually be turned against you if you let it supercede good data governance.

What a Defensible Schedule Looks Like — Pick Your Model

Most firms cannot realistically tag every document inside a matter file by sub-category and apply category-specific disposition. A schedule that requires that level of operational sophistication is one most firms will not actually follow. Two simpler models are defensible and implementable; pick the one that fits your needs and infrastructure.

Model 1 — Matter-level Disposition

The entire matter file is treated as a single bucket and disposed of on one schedule triggered by matter close, with a small number of carve-outs handled separately. This is the simpler model and works for solo, small-firm, and many mid-sized practices that do not have document-level tagging in their DMS.

Matter file (all working materials, drafts, correspondence, end-product, internal memos): Retain for the period set by the longest-required category that applies to the matter — typically seven to ten years from matter close for general civil and transactional work, longer for trusts and estates, longer where statute-of-repose or active malpractice exposure requires.

Trust account records (separate): Retain for the period your jurisdiction requires — five years under ABA Model Rule 1.15(a). Check your jurisdiction specifically.

Original client documents (separate): Wills, deeds, executed instruments, and other originals returned to the client at matter close. Get into the habit of returning originals promptly whenever possible. Otherwise, you must babysit them, which comes with a resource drag.

Email (separate, system-level): Three-year default retention on routine business email, with matter-relevant emails captured into the matter file at matter close.

Marketing and CRM (separate): Three years from last contact.

Model 2 — Two-tier Disposition

The matter file is split into two tiers, each with its own disposition schedule. This is the realistic outer limit of category-specific disposition for firms without sophisticated data governance infrastructure.

  • End-product file (final pleadings, executed contracts, recorded instruments, opinion letters, closing binders): Retain for 7 - 10 years from matter close, or longer where the practice area requires; returned to the client at close where the entire-file approach applies.

  • Working file (drafts, internal memos, attorney work product, correspondence, research, deposition prep, billing detail): Retain for 3 - 5 years from matter close, with carve-outs for matters under active or threatened malpractice claim, ongoing investigation, or open ethics issue.

  • Trust account records (separate): As above — 5 years under Model Rule 1.15(a).

  • Email (separate): Three-year default; matter-relevant communications migrated into the working file or end-product file based on substance. •

  • Marketing, CRM, and AI-tool outputs (separate): As below.

Both models — the AI category AI-generated artifacts (copilot drafts, transcription archives, redline histories, intake-bot logs) are records subject to the same retention discipline as their human-authored equivalents, but live mostly outside the matter management system.

Maintain an inventory of AI tools in use, push vendor retention defaults into counsel’s hands (“indefinite” and “use for training” are the common defaults and both are unacceptable), and build AI accounts into legal-hold tooling.

Whichever model you pick, the schedule must be written, applied consistently, suspended on hold triggers, and audited. Selective enforcement — applied to associates but waived for the managing partner — is the signature failure mode.

When the Clock Starts

If agentic AI has taught me anything it’s that a schedule is only as good as its trigger. “Seven years from matter close” means nothing if “matter close” is undefined and as nebulous as morning fog. What that comes down to is pinning down in writing. Perhaps that sounds like an oversimplification, but here's why it's not. It shows a stable, consistent, measurable rule. You need that if you are going to defend a disposition decision years later.

  1. Define "Matter Close" as a Specific Event. "Matter close" cannot be an instinct if it is to stand up to scrutiny. A workable definition combines final invoice issued and paid (or written off), closing letter sent to the client, file marked closed in the practice management system, and any retained originals returned. Always document the event with a date.

  2. Trust Account Records run from termination of the representation, not matter close. ABA Model Rule 1.15(a) (many states have a similar rule) runs from termination. Usually the same date as matter close, but not always. Calendar these separately if needed.

  3. Statutes of Limitation and Repose Run on Separate Clocks. A schedule that disposes of a matter file before the malpractice statute of repose has run is a problem. Build a practice-area lookup into the schedule and trigger disposition at the later of the schedule or the applicable repose period, whichever is longer. Once you close the matter, run both clocks in parallel: the schedule cadence (eg, seven years from matter close) and the repose period, which usually predates close (eg, five years from the act). You dispose of the file when the later of the two has run.

Best Practices

I love data governance, and if you have a hammer, well, everything is a nail. But objectively, a lot of this is just good ‘ole data governance and data hygiene.

  1. Inventory what you retain and where it lives — including personal devices, AI tools, and vendor systems. You cannot govern what you cannot see.

  2. Apply the schedule consistently across the firm, including to founders and named partners. Selective enforcement defeats the doctrine and raises your liability.

  3. Suspend the schedule on legal hold and confirm holds reach AI accounts and personal devices. A schedule that doesn't pause for litigation is not a defensible schedule.

  4. Implement a written communications policy that addresses the use of personal devices and ephemeral messaging, including for senior lawyers.

  5. Review vendor retention and AI-training defaults before procurement. Indefinite retention and "use for training" defaults are common, but unacceptable. These are legal issues that shouldn't be left to the IT department.

  6. Document disposition, holds, and policy updates. Undocumented practice is indefensible practice.

  7. Calendar an annual review to address new tools, new practice areas, and new authorities. Boring advice, but it makes a big difference.

Bottom Line

Exponentially reduce the risk of that candid attorney communication by exercising good data governance. The work product, the strategic thinking, the candid attorney communications, and the client confidences sitting on your firm’s servers could turn out to be someone else’s exhibits in a future trial, or someone else’s data breach, someone else’s malpractice case, and someone else’s bar complaint. You’re keeping that file “just in case.” But really, it is unmanaged risk.

Records disposition is not the only factor at work in this case — channel discipline, privilege design, and platform governance also do real work — but it is the most concrete, the most actionable, and the most under-used.

Editorial note: this article is hardly dispositive or in-depth. Consider doing additional research.

Recommended Reading: Sedona Conference Commentary on Legal Holds, and Commentary on Information Governance

© 2026 Amy Swaner. All Rights Reserved.  May use with attribution and link to article.

Musk v. Altman Can Teach Lawyers A Lot About the “Just In Case” Rule of Document Retention

AI Resource

Quick Reference: Risk Mitigation Checklist for AI Notetaker & Transcription Bots

AI in Legal Practice

Jan 2026

Use this one page checklist to minimize risks for you and your clients when considering AI Notetaker and Transcription Bots.

This easy reference covers bots in meetings, and vendor selection.

Share directly with your clients.

Featured article

Morgan v. V2X Decided a Discovery Dispute. The Commentary Turned It Into Something Bigger.

Amy Swaner

May 2026

Calculating...

On March 30, 2026, a federal magistrate judge in Colorado issued an order in an employment discrimination case most lawyers will never read. They should — but not for the reasons most of the commentary has been suggesting. Morgan v. V2X, Inc., No. 25-cv-01991-SKC-MDB (D. Colo. Mar. 30, 2026), is one of the most thoughtful federal AI decisions issued so far this year. It is also narrower than it is being read to be.

In more than one venue, commentators have turned Magistrate Judge Maritza Dominguez Braswell’s order into a universal AI governance doctrine. It isn’t. What she decided was a discovery dispute about protective-order language in a case where a pro se plaintiff wanted to use public AI tools on documents the corporate defendant had produced under a confidentiality order. Judge Braswell’s reasoning and framework are intelligent and elegant. The reasoning deserves careful attention. But let’s be clear on what Braswell actually held and what it actually means for your use of AI.

Morgan as the Case Study

Background

The underlying case is an employment discrimination lawsuit in the District of Colorado. Archie Morgan is a pro se plaintiff suing his employer V2X. Both sides used AI in their litigation work. V2X has enterprise AI tools. Morgan, representing himself, uses public ones. The AI dispute surfaced when V2X moved to restrict Morgan’s use of public AI platforms — a restriction Morgan argued would create an unfair “technological gap” between a self-represented litigant and a well-funded corporate defendant with proprietary AI and cloud-based systems of its own. V2X also moved to compel Morgan to disclose which tools he was using.

Judge Braswell — who co-chairs her district’s AI Committee, co-founded the Judicial AI Consortium, is on Sedona Conference’s working group (WG13) regarding AI, and is genuinely knowledgeable in this material — did not default to either side’s proposed language. She wrote her own. Before uploading confidential information covered by the protective order to any AI platform, she held, the provider must be contractually prohibited from:

  • Storing or using inputs to train or improve the model;

  • Disclosing inputs to third parties (except where essential to service delivery, and then only on terms no less protective than the protective order itself); and

  • Retaining inputs beyond what is necessary.

She also required that the vendor contractually afford the party the ability to delete all confidential information upon request, and that the party retain written documentation of the contractual protections. And she ordered Morgan to disclose the name of the AI tool he was using, finding that tool selection alone does not reveal mental impressions or legal strategy absent a specific factual record.

That is the entire order. A set of contract requirements and a disclosure obligation, tied to information produced under a protective order. On its face, thoughtful but narrow

What the Judge Decided

Commentary on Morgan has slotted it alongside United States v. Heppner, No. 25-cr-00503 (S.D.N.Y. Feb. 17, 2026), and Warner v. Gilbarco, Inc., No. 2:24-cv-12333 (E.D. Mich. Feb. 10, 2026). That framing puts the three cases into a single bucket labeled “AI and privilege” and treats Braswell as though she were answering the same question as Judge Rakoff and Judge Patti. She wasn’t.

An Everlaw article discussing Morgan noted the procedural posture as material under a protective order being submitted into an AI tool, but then said “the court . . . established a precise set of contractual must-haves for any legal professional looking to integrate AI into their workflow.” Clio went further, headlining its post “Courts Are Starting to Pick AI Tool Winners” and characterizing the order as “a new standard for AI use in litigation”. Respectfully, both are overstatements about the holding and its reach. Heppner and Gilbarco both asked whether a litigant's use of AI waived existing legal protections — traditional doctrinal questions applied to a new technology. The question Braswell answered in Morgan was different and more narrow: in a discovery dispute, what should a protective order say about a pro se plaintiff's use of public AI tools on materials the corporate defendant produced under a confidentiality designation? That is a data governance question, not a privilege question.

As a data governance nerd (or maybe Diva?), this is the same type of question every data protection officer, a cloud governance lead, or a vendor risk analyst asks about any third-party processor. What happens to the data once it leaves my environment? Who can see it? How long does it persist? What rights does the vendor have to use it for their own purposes? Privacy professionals and information governance lawyers have been asking these questions for decades. However, they are more important now, thanks to widespread AI use.

The Applicability of the Order

Braswell decided two things, one of them quite narrow:

1. Work product privilege may apply to an advocate’s AI tool use;

2. A litigant bound by a protective order may not use AI tools on materials covered by that order unless the AI vendor meets her contract-based standard.

That’s it.

She did not hold that all lawyers everywhere must use only AI tools meeting that standard. She did not hold that a solo practitioner using ChatGPT or Claude on legal work is violating Rule 1.6. She did not hold that consumer AI is per se incompatible with confidentiality obligations. She resolved a discovery dispute about protective order language in a specific case with a specific fact pattern.

Granted, Judge Braswell’s reasoning is attractive. The standard is clean, sensible, and maps to real data governance principles. It should inform how lawyers think about AI tool selection generally. But “should inform” and “is binding authority” are different things.

What Judge Braswell no doubt understood was that different data should be treated differently.

Four Data Categories, Four Enforceability Tiers

Data governance is everything with AI implementation. One of the first questions with AI Governance must be “Whose data is at risk, what is the risk, and what can I enforce?” Four categories of data behave differently, and the required precaution change accordingly.

Your own non-regulated information. A pro se litigant using ChatGPT to analyze her own employment history and draft her own complaint. The information is hers; the harm from any leakage runs to her and only her. She is entitled to make her own decision. Braswell’s rule would be overbroad in this category — and she didn’t purport to apply it here.

Attorney-client privileged communications. The Heppner fact pattern. Here the harm is potentially catastrophic and irreversible. Judge Rakoff’s reasoning raises the question — left open in Heppner itself — of whether feeding lawyer-provided information into a consumer AI tool risks waiving privilege over the original attorney-client communications. If that reasoning is extended in future cases, the three-part standard may actually be insufficient in this category.

Regulated data categories. PHI under HIPAA, nonpublic personal information under GLBA, personal data under state privacy laws. Rule-governed territory. The harm is statutory. The precaution is mandatory, independent of Morgan.

Third-party confidential information under a protective order or similar confidentiality obligation. This is the Morgan fact pattern. The information was V2X’s, produced to Morgan under a confidentiality agreement. Morgan uploading it into a training-enabled AI tool would unravel the bargain without V2X’s consent. The harm is concrete, the non-consenting party bears it, and Braswell’s rule is proportionate.

The Enforceability Spectrum

Once you know which category your data falls in, you need to know which tier of contractual protection the tool actually offers. Tool choice is about whether the protection is enforceable, provable, and durable. That’s not necessarily determined by brand or cost.


Article content

A few concrete examples, as of this writing (vendor terms change; verify before relying):

  • OpenAI Enterprise and OpenAI API commercial tier, Harvey, Anthropic commercial API and enterprise agreements: default no-training on customer data, contractually committed. Strong tier.

  • ChatGPT with the “improve the model for everyone” toggled off: enforceable representation, but dependent on consumer terms of service. Medium tier for most use; handle privileged information with care.

  • A free AI tool, or a browser extension AI tool with no “privacy mode” setting and no visible contract: weak. Do not use with client data.

You should always know which tier you are in, and keep in mind what your firm’s AI policy permits.

Best Practices

Keeping in mind, we only have district court decisions regarding AI at this point. Reading those decisions, six best practices emerge.

  1. Match the tier to the data category. Strong-tier tools are required for third-party confidential information under a protective order, attorney-client privileged communications, and regulated data (PHI, NPI, CUI). Medium-tier tools are acceptable for general research, brainstorming, and non-sensitive drafting. Weak-tier tools belong nowhere near client data.

  2. Audit every AI tool currently in use. Document where the no-training, no-sharing, and no-retention protections are — enterprise terms, MSA, addendum, DPA, or toggle plus vendor representation. Maintain records of what tier each tool occupies and the evidence supporting that placement.

  3. Review your AI policy to map tier to data category. Your policy should expressly address the fact that different categories of data, with different confidentiality needs exist.

  4. Build the spectrum into procurement. Evaluation starts with data processing terms, not features. The right question is not “does the vendor offer a privacy toggle” but “is the toggle anchored in enforceable language, can we prove its state at the time of use, and is the remedy adequate for the data category”.

  5. Counsel should direct AI use whenever the materials may be sought in discovery. The gap between Heppner and Warner turned in part on whether counsel directed the use

  6. Never use a weak-tier tool on client data, regardless of convenience. A browser extension with a “privacy mode” setting and no visible contract is not a defensible choice, and no AI policy should permit it.

The 60-Second Checklist

Before pasting client data into any AI tool, confirm:

  • Whose data is it? (Yours, the client’s, a third party’s under a protective order, or regulated?)

  • What tier is the tool? (Strong, medium-strong, medium, or weak?)

  • Is the tier proportionate to the data sensitivity?

  • Can you prove the protection state today?

  • Did counsel direct the use?

If you cannot answer all five, stop. Either move the work to a different tool or build the record before you proceed.

The Bottom Line

Braswell decided a narrow discovery dispute carefully, and intelligently. Braswell’s order illuminated a principle that was already sound. AI tools that ingest, share, or retain user data are not safe for information held under a confidentiality duty owed to others. She set out a framework for when users can put third-party confidential information into an AI tool. It has limited applicability to a lawyer’s own work outside of that factual posture.

© 2026 Amy Swaner. All Rights Reserved. May use with attribution and link to article.

In Morgan v. V2X, Judge Braswell offers a thoughtful, practical take on AI use in litigation—reminding lawyers (and even pro se litigants like Morgan) that when it comes to confidential data, it’s less about the tool itself and more about how responsibly you handle what you put into it.

AI Resource

Quick Reference: Risk Mitigation Checklist for AI Notetaker & Transcription Bots

AI in Legal Practice

Jan 2026

Use this one page checklist to minimize risks for you and your clients when considering AI Notetaker and Transcription Bots.

This easy reference covers bots in meetings, and vendor selection.

Share directly with your clients.

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AI in Legal Practice

Calculating...

Misinformation about AI and client confidentiality is rampant. In conference hallways, bar association email lists, and CLE panels, the same myths keep surfacing. Yesterday I was speaking with a technologist and one of the top software engineers in the country. They were concerned about the confidentiality needs of attorneys. They understood the technology but had absorbed several of the same misconceptions circulating in the legal profession itself.

Small and solo firms—near and dear to my heart--can least afford to get this wrong. Some of these myths overstate the risk. Others understate it. All of them obscure the practical analysis lawyers actually need to perform in order to make the best decision for your practice and your needs.

This article is a companion to Is It Safe to Put Confidential Information in AI Tools?, which provides a full vendor comparison chart, privilege analysis, and practical framework. Here, we isolate and correct nine common misconceptions. A glossary of technical terms used in this article appears at the end.

Myth 1: “AI Tools Train on Everything You Type.”

Reality: It depends entirely on the product tier and your settings.

This myth persists because it was once partially true—and remains true for free-tier products. When ChatGPT launched in late 2022, the default setting for all users was to permit OpenAI to use conversations for model training. That default created the impression, now hardened into ‘received wisdom,’ that every AI tool ingests and learns from everything you submit.

AI models have evolved since that time. At the paid individual tier, every major platform—Claude, ChatGPT, Gemini, and Microsoft Copilot—offers a toggle to opt out of model training. At the enterprise tier, training on customer data is off by default and governed by a Data Processing Agreement. The critical distinction is between a UI toggle, which a vendor can change unilaterally, and a contractual commitment, which they cannot. Enterprise Data Protection Agreements (DPAs) provide the latter. If you’re using the toggle, check routinely to verify that you have privacy settings as high as possible.

Myth 2: “Using AI Waives Attorney-Client Privilege.”

Reality: Trial courts are addressing this — and the door is wide open to using AI tools when properly configured.

This myth likely draws from United States v. Heppner, No. 25-cr-00503-JSR (S.D.N.Y. Feb. 17, 2026), in which Judge Rakoff held that documents Heppner generated using a consumer version of Claude were not protected because (1) Claude is not an attorney and so could not form an attorney-client relationship; (2) Anthropic's consumer privacy policy gave Heppner no reasonable expectation of confidentiality; and (3) Heppner acted on his own, not at counsel's direction, defeating work product protection.

Two things need to be said about Heppner. First, it is a single district court opinion—persuasive authority at best, binding on no one outside the Southern District of New York. It has not been adopted by any circuit court. Moreover, two subsequent decisions have pushed back on its broader implications. In Warner v. Gilbarco, Inc. (E.D. Mich. Feb. 10, 2026), Magistrate Judge Patti denied a motion to compel a pro se plaintiff’s AI-assisted litigation materials, holding that generative AI platforms are “tools, not persons” and that using them to assist in drafting is no more a waiver of work product protection than using a word processor or a legal research database.

In Morgan v. V2X, Inc., No. 25-cv-01991-SKC-MDB (D. Colo. Mar. 30, 2026), the court similarly held that a pro se litigant’s AI-assisted materials qualified for work product protection under FRCP 26(b)(3), while also requiring that any AI tool used to process confidential discovery material be subject to contractual safeguards—including prohibitions on training, restrictions on onward disclosure, and the ability to delete data on request. Second, the holding turned entirely on the absence of reasonable precautions. The court explicitly left open that counsel-directed AI use on a platform with contractual confidentiality protections could yield a different result.

There is currently no case that stands for the proposition that AI waives privilege. What we do know is that using a free consumer tool with no privacy controls and no attorney involvement almost certainly waives privilege — which is exactly what privilege law has always required. The doctrine has never protected careless sharing of protected information, regardless of the technology involved.

Myth 3: “Legal-Specific AI Tools Are Inherently Safer Than General-Purpose Ones.”

Reality: Safety comes from security architecture and contractual commitments, not from the label on the product.

There is a comforting assumption in some corners of the profession that tools built specifically for lawyers—like Harvey—are categorically safer than general-purpose tools like Claude or ChatGPT. Harvey’s security posture is strong: SOC 2 Type II, ISO 27001, AES-256 encryption, no training on customer data by default, and a DPA included with the product.

But every general-purpose AI tool in the market offers the same certifications at enterprise tier. Claude, ChatGPT, Gemini, and Microsoft Copilot all hold SOC 2 Type II and ISO 27001 certification. They all offer AES-256 encryption in transit and at rest. They all provide enterprise DPAs with contractual no-training commitments. The companion article includes a full comparison chart. The protections flow from the vendor’s infrastructure and agreements, not from whether the marketing materials mention “legal.”

Myth 4: “My Cloud DMS Is Secure, but AI Isn’t.”

Reality: AI tools and cloud DMS platforms share the same infrastructure, encryption, and vendor access model.

This may be the most consequential myth on the list, because it underlies most firm-level AI prohibitions. The reasoning goes: “We trust NetDocuments (or Clio, or iManage, or Microsoft 365) with client files, but AI is different, and we cannot trust it.”

It is worth examining what, exactly, is supposed to be different. Your document management system (DMS) stores client documents on third-party cloud servers. So does AI. Your DMS encrypts data in transit with TLS and at rest with AES-256. So does AI. Your DMS vendor’s support engineers can access your data for maintenance and troubleshooting purposes. So can AI vendor employees, within defined and, depending on your set-up, contractually bounded safety review processes. Hopefully your DMS vendor holds SOC 2 Type II and ISO 27001. So does every major AI platform.

The reason we as lawyers are comfortable with cloud DMS is that we’ve evaluated the vendor, configured the settings, and signed a DPA. And frankly, we’re comfortable because these applications are so common as to be standardly used in law practice today. It’s widely accepted that your email lives in the cloud. And your documents are stored and categorized in the cloud.

AI is new and not taken for granted like DMS applications. There are differences between AI apps and DMS apps, but with training turned off, and privacy settings turned on, those differences are not so wide.

Myth 5: “AI Vendors Can Read My Prompts Whenever They Want.”

Reality: Human review is limited by purpose, bounded by contract at enterprise tier, and structurally close to vendor access at your DMS or email provider.

Every major AI vendor reserves the right, in its terms of service, to allow human review of prompts for safety and abuse detection. This is true. It is also true of your email provider, your cloud storage vendor, and your practice management platform. Microsoft’s support engineers can access your Exchange Online mailbox under defined circumstances. Google’s trust and safety team can review your Workspace content. NetDocuments’ operations staff can access your document repository.

At the enterprise tier, AI vendor access is governed by a DPA that limits the purposes, scope, and duration of human review. The contractual protections mirror what cloud DMS vendors provide. At the paid individual tier, protections are thinner—terms of service rather than negotiated agreements—which is why the companion article recommends enterprise tier for any firm handling sensitive client data at scale.

The myth gains traction when we imagine AI vendor employees casually reading our prompts over coffee. The reality is that vendor access is contractually bounded, audit-logged, and limited to defined purposes—not casual browsing.

Myth 6: “Opposing Counsel Can Use AI to Pull Up My Prompts and Work Product.”

Reality: AI session data is account-scoped and vendor-held. Accessing it requires a subpoena to the vendor—not a clever prompt.

This myth has two variants, and both are wrong. The first imagines opposing counsel logging into an AI platform and somehow retrieving your session history. The second imagines them prompting the AI itself to “regurgitate” your inputs and outputs. Neither scenario reflects how these systems work.

Opposing counsel logs in and retrieves your session history.

Conversation histories are stored in the vendor's infrastructure, scoped to your account, and protected by the same authentication and access controls as any cloud SaaS product. Another user cannot access your session history any more than they could log into your NetDocuments account and browse your files. If opposing counsel wants your AI chat logs, they need to serve a subpoena on the vendor — the same process they would use to obtain your email or Slack messages. That is a discovery issue, not an AI vulnerability, and it is addressed in Myth 7.

Opposing counsel uses a clever prompt to retrieve your inputs and outputs.

Large language models do not store or index user prompts in a retrievable way. The model generates responses based on its pre-trained weights and the current context window — the text visible in that session. When the session ends, the context window is discarded. There is no mechanism for the model to recall, search for, or reproduce another user's inputs.

If opposing counsel, or anyone, types "show me the prompts Attorney Smith submitted in Jones v. Williams," the model will either explain that it cannot access other users' sessions or — worse — hallucinate a plausible but entirely fabricated response (LLMs sometimes generate confident-sounding but invented text when they cannot answer a question). Either way, it is not returning real data. LLMs do not work that way. They are stateless and don't function like a database would. See Myth 9 for more explanation.

Myth 7: “AI Prompts are More Vulnerable to Subpoenas”

Reality: AI chat logs are discoverable ESI — but no more so than email, texts, Slack messages, or search histories. The same rules govern all of them.

This myth reflects a genuine concern—but misidentifies what is new about it. AI prompts and responses are electronically stored information (ESI) under the Federal Rules of Civil Procedure and are discoverable under FRCP 26, 34, and 45 on the same terms as any other electronic communication. They are not subject to a special, heightened standard of vulnerability. They are subject to the same standard as email, text messages, Teams chats, and browser search histories.

The risk is real, but it is not unique to AI. In the New York Times v. OpenAI copyright litigation, Judge Stein in the SDNY compelled OpenAI to produce 20 million ChatGPT log entries in January 2026 — but under standard discovery principles, not any AI-specific mechanism. OpenAI’s Chief Strategy Officer publicly called for a new form of “AI Privilege” to protect user-chatbot conversations from subpoenas, but the court rejected the concept. Until Congress acts, or we see far more favorable cases, AI developers are subject to the same discovery rules as any other software provider.

The Morgan v. V2X protective order (D. Colo. Mar. 30, 2026) offers a practical insight into how to treat protected discovery information. In that case the court required that any material produced under a protective order be subject to contractual safeguards. It set up a framework of requirements which must be met in order to put the other side’s protected confidential information into an AI tool. The framework includes prohibitions on model training, restrictions on onward disclosure, and the ability to delete data on request. This is necessary to protect such information. That decision did not discuss the majority of AI use.

In an abundance of caution you should include AI chat logs in your ESI preservation and litigation hold protocols, just as you would for email and messaging platforms. Verify your AI vendor’s data retention windows. And if you are using AI to process material subject to a protective order, confirm that the vendor’s contractual commitments satisfy the order’s requirements.

Myth 8: "AI Tools Can Secretly Upload My Entire Device or My DMS."

Reality: AI tools see only what you put in the prompt, what you've stored in the "shared memory" features of some AI tools — or the specific data sources the tool was explicitly configured to access. They have no background access to your files, drives, or other applications.

This myth can drive many firm-level AI policies. The fear is that downloading an AI desktop app, installing a browser extension, or signing into a copilot somehow gives the AI access to everything on your machine — every email in your Outlook, every document in your DMS, every client file on your hard drive. The reality is far more bounded.

AI tools come in three architectural categories, and each is limited to what its configuration explicitly permits:

  • Standalone web and desktop AI tools (the consumer or paid Claude, ChatGPT, Gemini, or Copilot Chat app). These see only what you type or paste into the prompt window, plus any file you explicitly upload. They have no read access to your local drive, your other applications, your DMS, or your email. Closing the browser tab or quitting the app ends the session.

  • Integrated AI tools (Microsoft 365 Copilot tied to your tenant, Google Workspace AI features tied to your Workspace account, IDE-integrated coding assistants). These see the data sources the integration was configured to access — by you or your firm's administrator. Microsoft 365 Copilot can see your Exchange Online mailbox and your SharePoint documents because your tenant administrator enabled that scope. It cannot see your personal files, your iManage DMS (unless separately integrated), or applications outside the Microsoft 365 boundary.

  • Browser extensions and meeting bots. Both operate within the permissions you (or your IT admin) granted at install, generally.  Browser extensions see the active tabs you use with the extension. Browser extensions are generally less privacy-friendly than a chat interface with privacy settings on. Search requests and results are more likely to be retained and used to help train LLMs. Meeting transcription bots see the meeting they were invited to. Use caution when you are in a meeting someone else organized with a meeting transcription bot in it. You are relying on the privacy settings the meeting organizer set. Some have as a default that they will capture and use meeting information. However, neither of these tools rummage through your file system, your DMS, or your applications. The data they see is the data you (or your administrator) explicitly put within their reach.

In other words, AI tool risk is not "the AI is watching everything." It is "the AI is doing what your integration says it can do, with the data your integration gives it access to." That makes the diligence question concrete and answerable — what tool, what tier, what integration scope, what DPA? The same diligence you already apply to cloud DMS and email applies here. Vague fear of background access is not the worry when using reputable AI tools.

The one caveat is AI agents. You can unintentionally grant greater access to an AI agent--and thereby every app it integrates with -- that will allow it to access your local and cloud-based systems. Be extra cautious when using AI Agents, and follow these best practices.

Myth 9: “I Put Certain Info into AI, and It Will Remember It and Spit It Back Out Someday.”

Reality: AI models are stateless by default. Persistence features exist on some platforms but are user-controlled, account-scoped, and distinct from model training.

Each AI conversation starts from zero. The model carries no memory of prior sessions unless you have explicitly enabled a persistence (memory) feature. When a session ends, your input exists in only two places: (1) the vendor’s server logs, subject to the retention policy and DPA, and (2) the model’s weights—but only if your data was used for training. If training is off (paid tier with toggle disabled, or enterprise tier with contractual no-training), your input never influences the model at all. It is processed, a response is generated, and the content is retained only as a server log subject to the vendor’s documented retention window.

Some vendors do offer optional persistence features, and lawyers should understand how they work. For example, ChatGPT’s Memory feature allows the tool to save high-level preferences and details across sessions—your name, tone preferences, project context—and reference past conversations to personalize responses. Memories are stored separately from chat history, meaning deleting a chat does not delete saved memories. Memory can be turned off entirely, and individual memories can be reviewed and deleted in settings. Importantly, OpenAI states that memories and workspace information are excluded from model training.

Google’s Gemini takes a different approach through its Gemini Apps Activity setting. When “Keep Activity” is turned on, Google saves conversations to your account, may use them to personalize future responses, and reserves the right to have human reviewers assess a subset of chats—with reviewed conversations retained for up to three years. When turned off, conversations are still held for up to 72 hours for service delivery and security, but are not reviewed or used for model improvement. The distinction is that “off” provides materially stronger privacy, and lawyers using Gemini for anything involving client data should verify this setting.

Note: Verify that this information about retention periods and human review is still accurate. AI vendors change their terms of service and privacy policies as quickly as some people change their shoes.

Even in the worst case — free tier, training enabled, no opt-out — the likelihood of a model reproducing a specific privileged communication verbatim is astronomically low. Model training adjusts statistical weights (internal numerical values that encode everything a model has learned during training) across billions of internal parameters (internal numerical values) using aggregated data. It does not memorize and replay individual inputs. The AI safety literature treats verbatim memorization as an edge case, not a typical, likely, or systemic exposure. But it is best practice to use a tier where training is contractually off, verify the retention period, disable optional memory features if your use case involves client data, and then the risks shrink exponentially.

Glossary of Technical Terms

Context window. The text a model can “see” during a single conversation. This includes everything you have typed in the current session and the model’s responses. When a session ends, the context window is discarded. The model does not carry it forward.

Data Processing Agreement (DPA). A legally binding contract between a data controller (the law firm) and a data processor (the AI vendor) that governs how personal and confidential data is handled. Unlike a terms-of-service toggle, a DPA is a contractual commitment that the vendor cannot change unilaterally. Enterprise-tier DPAs typically include commitments on data use restrictions, no-training clauses, data retention and deletion, breach notification, and audit rights.

Edge case. A scenario that occurs only under unusual or extreme conditions. In AI safety research, verbatim memorization of training data is considered an edge case—theoretically possible but vanishingly rare in practice, especially with modern training techniques designed to prevent it.

Inference. The process by which a trained AI model generates a response to a prompt. During inference, the model applies its pre-existing knowledge (stored in its weights) to produce output. No learning occurs during inference—the model’s weights do not change.

Parameters. The numerical values inside a model that determine how it processes language and generates responses. Large language models contain billions of parameters.  During training, these values are adjusted using large datasets. During inference (when you use the tool), they are fixed.

Stateless. A system that does not retain information between interactions. AI models are stateless by default: each new session begins with no memory of prior sessions. Any persistence (such as ChatGPT’s Memory feature) is a separate, optional layer built on top of the model, not a property of the model itself.

Weights. The internal numerical values that encode everything a model has learned during training. When people say a model has been “trained on” data, they mean the data was used to adjust these weights. Once training is complete, the weights are fixed. When training on your data is disabled, your inputs do not influence the weights and cannot become part of the model’s knowledge.

The Common Thread

Every myth on this list shares a common root: a misunderstanding, or lack of awareness of, how AI tools work.  The technology behind the technology.

ABA Formal Opinion 477R requires that lawyers take reasonable precautions with electronic communications—including vetting vendors and understanding data handling. ABA Formal Opinion 512 applies that same framework to AI tools. Neither opinion prohibits AI use. Both require informed, diligent adoption.

The myths persist because they offer simple answers to a question that requires nuance. The real answer—that AI tools are safe when properly vetted, configured, and governed—is less dramatic but far more useful. The law in this area is still developing. Heppner, Gilbarco, and Morgan are district court opinions, not circuit authority, and the courts are still working out how existing privilege and work product doctrines apply to AI-assisted legal work. So far, the trajectory shows that courts are applying existing frameworks to new technology, not creating AI-specific exceptions.

For the full framework, vendor comparison chart, and practical checklist, see the companion article.

© 2026 Amy Swaner. All Rights Reserved.  May use with attribution and link to article.



9 Privacy Myths About Attorney-Client Confidentiality with AI Tools

Data Privacy and Ethics

Calculating...

Privacy Problems with Generative AI 

Renown AI and privacy expert Daniel J. Solove recently published a paper discussing Generative AI in regard to privacy concerns. 1 Generative AI, while transformative, presents significant privacy challenges.  Solove identified three specific areas of concern: personal data being used by AI, potentially misleading information created by AI, and AI’s ability to undermine fairness and due process.  His paper made me re-think our approach to AI regulation and privacy laws. 

DATA RECONSTITUTION 

Most people using AI presumably understand that privacy concerns are inextricably linked with AI developments—these concerns are widely discussed, recognized, and written about.  But far fewer people are aware of the subtle ways they may inadvertently share personal identifying information (PII) when using AI tools, even with supposedly 'anonymized' data. One of the primary concerns is AI’s generation of new personal data through inferences. GenAI consumes personal data, but it also produces additional data, and can link several sources of private information, often revealing sensitive details that were not initially evident, or were not evident when they were used individually but together are identifiable.  I call this data reconstitution. So even if you are confident you are not sharing personal details, you might still be inadvertently sharing information that can be “reconstituted” to reveal confidential information.  This blurring of lines between data collection and processing circumvents traditional privacy protections and leaves individuals with little control over the information organizations can infer about them.  Even when consumers and individuals have the opportunity to opt out of data collection, there is no way for us to opt out of data inference. 

FAKES AND DEEP FAKES 

Another vein of privacy concern centers around GenAI’s potential for creating malevolent material. GenAI can generate misleading or harmful content, such as deepfakes or false information, which can be used to deceive and manipulate individuals. This capability exacerbates existing privacy concerns by facilitating the spread of misinformation and enabling malicious activities.  For example, AI can be wrongfully used to skillfully recreate the voice of someone we recognize, spewing out hate speech, or being used for malicious political gains.

To date, there is no comprehensive federal law (or state law for that matter) that provides adequate protection to individuals against such fakes and deep fakes. Moreover, the dynamic and opaque nature of Generative AI algorithms poses significant transparency challenges. Understanding these algorithms requires access to the training data, which is often inaccessible or incomprehensible to the general public. This lack of transparency makes it difficult for regulatory bodies to oversee AI systems, and comparably difficult for individuals to trust AI systems. 

DUE PROCESS AND FAIRNESS 

Finally, Generative AI can undermine due process and fairness. AI-generated decisions often lack meaningful avenues for individuals to challenge them. This can lead to situations where people are subjected to decisions that significantly impact their lives without adequate recourse to seek redress or challenge the accuracy and fairness of those decisions. 

This issue can have profound implications across various sectors, including criminal justice, employment, and finance. For example, in the criminal justice system, AI-powered risk assessment tools are increasingly being used to inform decisions about bail, sentencing, and parole. A notable case is the use of the COMPAS (Correctional Offender Management Profiling for Alternative Sanctions) system in several U.S. states. 

In 2016, an investigative report by ProPublica found that the COMPAS system, which predicts the likelihood of a criminal reoffending, was biased against Black defendants. The system was more likely to falsely flag Black defendants as future criminals, wrongly labeling them as high risk nearly twice as often as white defendants. Conversely, white defendants were more likely to be incorrectly labeled as low risk. 

This case highlights several critical issues: 

  1. Opacity: The algorithmic decision-making process was not transparent, making it difficult for defendants to understand or challenge the assessments. 

  1. Bias: The AI system appeared to perpetuate and potentially amplify existing societal biases. 

  1. Lack of due process: Defendants had limited ability to contest these AI-generated risk scores, which significantly influenced their treatment in the justice system. 

  1. Far-reaching consequences: These AI-driven decisions had profound impacts on individuals' lives, affecting their liberty and future prospects. 

The COMPAS case underscores the urgent need for safeguards and oversight in AI systems, especially those used in high-stakes decision-making processes. It highlights the importance of transparency, fairness, and the right to contest AI-generated outcomes. 

To address these concerns, policymakers and AI developers must work towards creating systems that are not only accurate but also fair, transparent, and accountable. This could involve regular audits of AI systems, diverse representation in AI development teams, and clear mechanisms for individuals to challenge AI-driven decisions that affect them. 

Moreover, there's a growing call for "algorithmic impact assessments" - systematic evaluations of AI systems before their deployment to identify potential biases and negative impacts. Such assessments could help prevent unfair outcomes and ensure that AI systems enhance, rather than undermine, principles of due process and equal treatment under the law.2

Regulations Solove Suggests and Their Rationale 

Solove emphasizes the need for comprehensive reforms in privacy law to address the unique challenges posed by Generative AI. He argues against "AI exceptionalism," suggesting that privacy issues related to AI should be tackled as part of broader privacy law reforms. This holistic approach ensures that privacy protections are robust and effective across various contexts, not just AI-specific scenarios. 

One of Solove's key recommendations is to reduce the burden on individuals to manage their privacy. Currently it feels to me like the entire burden of protecting my personal information rests squarely on my shoulders, and I am responsible for protecting my information, with very little power or control, and without knowing the rules.  A standout example of this is Meta’s decision to use all of our personal photos, images, and content on Instagram and Facebook for training their AI models.  For those under the egis of the GDPR they can opt out.  It is unnecessarily difficult, but at least there is a possibility of an option.   With those not covered by the GDPR, such as myself and all people living in the United States and many others, we have no option to opt out.  And it is not clear at all how these images and information will be used. Solove critiques this traditional model of privacy self-management, where individuals are expected to make informed decisions about their data. Instead, he advocates for placing more responsibility on organizations, mandating significant obligations to mitigate risks and ensure accountability. This makes a great deal of sense to me, since those very companies are the ones best placed and most incentivized to exploit my information.  It would also put us in better alignment with the GDPR laws and regulations. 

Critics worry that this will have a chilling effect on technological innovation.  However, Solove also supports adopting a harm and risk-based approach to AI regulation. This involves identifying and addressing potential harms and risks associated with AI, both before and after AI tools are deployed. By balancing preventive (ex-ante) and reactive (ex-post) regulatory measures, policymakers can protect privacy without stifling innovation. 

Transparency and accountability are crucial elements of Solove's regulatory framework. He calls for improved mechanisms to ensure that organizations provide clear and accessible information about their AI systems and maintain robust internal and external accountability measures. This helps build trust and ensures compliance with privacy laws. 

Involving diverse stakeholders in the development and regulation of AI is another important recommendation. Solove emphasizes the need to include voices from underrepresented and marginalized communities to ensure that AI systems are fair and equitable. This inclusive approach helps address biases and ensures that the concerns of all affected parties are considered. 

At present, we cannot make our own sweeping changes to privacy laws, or lack of privacy laws.  We can, however, be certain to use best practices when dealing with PII or any sensitive data. 

Best Practices for Using AI in the Workplace 

As lawyers and legal professionals using Generative AI we can follow several best practices to mitigate privacy risks and ensure responsible use of the technology, including the following: 

1. Transparency and Disclosure: Provide clear and accessible information about AI systems, including data sources, training data, and decision-making processes to those in our firm, and to our clients. Transparency builds trust and helps individuals understand how their data is being used. 

2. Minimize Data Collection and Use.  Practice data minimization by collecting only the necessary data for specific purposes. Implement purpose limitations to ensure data is used only for stated objectives and avoid excessive data collection.  For example, if you need a client’s annual income, but you ask for and receive a copy of their entire form 1040 tax return, you are collecting far more personal information than needed.  

3. Obtain Genuine Consent: Ensure informed consent by providing clear, understandable privacy notices to our potential clients. Individuals should be aware of and agree to how their data will be used, including for AI applications. Therefore, before we even undertake representation of clients, we should inform them of how, why, and when their information will be used, and what we are doing to actively protect their data. 

4. Incorporate Privacy by Design. Integrate privacy considerations into the development and deployment of AI systems that we use in our offices, and all other cloud-based technology that we use in our firms, since AI systems are no more vulnerable than any other cloud-based system.  Accordingly, we should use privacy-enhancing technologies and practices, such as anonymization, encryption, and secure data storage. 

5. Implement Accountability Measures: Establish strong internal and external accountability mechanisms.  Have an AI use policy—more on that in my next article. Conduct regular audits, assessments, and impact analyses to identify and mitigate privacy risks. Be prepared to demonstrate compliance with privacy laws to your clients, your insurance carrier, and potentially to a judge or other decision-making body. 

6. Address Bias and Discrimination: Proactively identify and mitigate biases in AI systems.  Bias is implicit in generative AI tools because they are a reflection of the data used to train them, and that data contains various biases.  We need to be uncompromising and unapologetic for our monitoring of discriminatory output, and also discriminatory input. AI can save us as lawyers a great deal of time, but that is only beneficial if we make the effort to regularly test for discriminatory outcomes and implement corrective measures to avoid perpetuating or amplifying existing inequalities and biases. 

8. Enhance Due Process and Remedies: Provide clear avenues for individuals to challenge AI decisions and seek redress for privacy harms. Ensure that individuals' rights are protected and that they have meaningful ways to contest AI-generated outcomes. 

By following these best practices, our law firms can responsibly harness the power of Generative AI while safeguarding privacy and building trust with our clients, and with the courts.  Since so much is dependent on our reputations, responsible use of AI is a baseline action, not an added measure, to ensure we maintain the highest standards of professional integrity and client trust.  

We as a society are impatiently waiting for comprehensive laws to guide GenAI use, and data privacy.  Until those laws are implemented, these measures aligns with Solove's broader recommendations for comprehensive privacy law reforms and effective regulatory frameworks to manage the complexities of AI. 

1Artificial Intelligence and Privacy, GWU Legal Studies Research Paper No. 2024-36, Daniel J. Solove


The Evolution of Privacy Law in the Age of AI, and Best Practices for Using AI in Your Workplace

AI Tools and Techniques

Calculating...

Executive Summary

AI tools are here to stay. Understanding their distinct "personalities" is essential to competent and strategic use. This article explores how AI personalities—shaped by training data, model architecture, and developer intent—impact legal outcomes, from drafting style to ethical reasoning. Drawing comparisons among leading AI tools such as ChatGPT, Claude, Gemini, Perplexity, Grok, and open-source models, the article offers practical guidance for matching the right AI to the right legal task. By recognizing and leveraging these differences, legal professionals can enhance accuracy, creativity, compliance, and client satisfaction—while mitigating the risks of over-reliance or misalignment. AI is no longer a one-size-fits-all assistant; choosing wisely is now a matter of legal judgment.

_________________________________________________________

At the end of a recent presentation on AI to a group of local government officials, I was asked, "what is the best AI tool?" My lawyer training kicked in and I immediately responded: "It depends." This wasn’t evasion—it was precision. In the precision-driven world of legal work, allAI tools are not created equal. What separates one large language model from another isn't merely technical capability—it's personality by design. These distinct AI "personalities" can produce dramatically different legal work products: from risk-averse contract language to creative settlement frameworks, from meticulously cited research to persuasive argumentation. The difference can impact case outcomes, client satisfaction, and even ethical compliance.

The differences in LLMs manifest as personalities that directly influence drafting style, risk tolerance, and analytical approach. Understanding these nuances isn't just interesting—it's becoming essential to competent representation in an AI-augmented legal landscape. This article examines how AI personalities emerge from architecture, training, and design intent, and provides practical guidance for selecting the right digital assistant for your specific legal tasks.

Why AI Tools Differ: Data, Algorithms, and Purpose

Three core factors shape every generative AI model. I’ve discussed these three factors in several other articles, so I’ll keep it short here.

Training Data The information used to train the model, in other words, what the model "learns" from, affects everything from legal knowledge to tone. Some tools are trained on broad internet data; others include specialized legal, academic, or scientific texts. This data forms the foundation of the AI's knowledge base and influences the accuracy and relevance of its outputs.

Underlying ArchitectureIn an LLM, the algorithm is the set of mathematical procedures and rules that govern how the model processes inputs and generates outputs. It’s the engine behind the tool’s ability to understand language, reason about it, and produce coherent, context-appropriate responses.The model's algorithm affects reasoning ability, hallucination rates, and how it balances creativity with caution. Some algorithms are optimized for long-context memory or symbolic reasoning, while others are optimized for speed and resource efficiency.

Design Intent and Safety ProtocolsGuardrails, default prompts, and content filters all shape how the AI behaves in practice. A model designed for creative brainstorming will act very differently than one tuned for precision research or ethical deliberation.

Behind the scenes, every model runs on hidden instructions—called system prompts—that set the tone, priorities, and boundaries of an AI tool.

  • Safety filters: These limit what the model is allowed to say—especially about controversial or high-risk topics. Case in point: DeepSeek being prohibited from discussing topics that the Chinese Government would find uncomfortable.

  • Voice and persona: Some tools (ChatGPT, Claude) are designed to be personable; others (Perplexity) are intentionally minimal.

  • Governance objectives: Anthropic programs Claude to follow a constitutional “code of conduct.” xAI’s Grok minimizes restrictions to promote expressive freedom.

Together, these elements give rise to what many users describe as an AI tool’s "personality."

AI Personality as a Reflection of Vision

Even though AI models are not sentient and have no emotional self-awareness, users regularly perceive them as having distinct personalities. This isn't accidental. It's a result of deliberate decisions by developers about how the tool should behave. Each major AI tool essentially expresses its creator’s vision for what AI should be, and those visions diverge meaningfully.

OpenAI (ChatGPT):

We continue to believe that the best way to make an AI system safe is by iteratively and gradually releasing it into the world, giving society time to adapt and co-evolve with the technology, learning from experience, and continuing to make the technology - Sam Altman

OpenAI's mission centers on ensuring that AGI benefits all of humanity. ChatGPT reflects this in its design: helpful, friendly, cautious, and broadly capable. It aims for alignment with user intent while maintaining a highly moderated, safety-first posture. It strives to be a reliable assistant in almost any context, but sometimes hesitates in nuanced or high-risk domains.

Anthropic (Claude):

The vision of AI as a guarantor of liberty, individual rights, and equality under the law is too powerful a vision not to fight for. — Dario Amodei

Claude is built with "Constitutional AI," a framework that encourages the model to reason ethically and transparently. This gives Claude a reflective, principled tone. It often feels like a thoughtful counselor—ideal for lawyers working on ethical dilemmas, AI policy, or complex compliance matters. Its design is shaped by Anthropic's belief that AI should be fundamentally safe, interpretable, and grounded in human values.

Google DeepMind (Gemini):

For a long time, we’ve been working towards a universal AI agent that can be truly helpful in everyday life. - Demis Hassabis

Gemini reflects Google's legacy as a search and information company. Its personality is efficient, structured, and knowledge-driven. Gemini often avoids embellishment or speculation, favoring clean, fact-based responses. While it may feel less personal or imaginative, it excels at surfacing relevant data quickly—especially when integrated with Google’s suite of tools. Gemini is best understood as a highly competent knowledge worker: focused, fast, and efficient.

Perplexity:

“The journey of Perplexity began with a leap of faith. We built the platform prioritising accuracy and transparency.” - Aravind Srivanas

Purpose-built as an "answer engine," Perplexity is pragmatic and direct. It doesn’t engage in creative dialogue or philosophical reflection. Instead, it returns clear answers with citations, acting more like a high-speed research librarian than an assistant. This utilitarian ethos reflects a belief that transparency and speed are paramount.

xAI (Grok):

The good future of AI is one of immense prosperity where there is an age of abundance; no shortage of goods and services.” - Elon Musk

Grok, developed by Elon Musk’s xAI and integrated into X (formerly Twitter), presents a more irreverent, edgy personality. It is designed to be humorous, bold, and occasionally provocative—emphasizing freedom of expression and fewer content restrictions. Grok feels more like a contrarian intern than a polished assistant, which may appeal to users seeking unfiltered dialogue. However, this tone is less suited to professional or regulated legal work unless handled with great care.

These different visions shape not only what the tools can do, but also how they feel to use. And that feeling matters, especially in legal work that demands both trust and precision. So how do the tools apply to legal work, here is a general guide, based on my personal observations and investigation.

AI Tool Personalities: A Guide for Legal Professionals

1. OpenAI (ChatGPT) _______________________________________

Core Personality Traits:

  • Friendly, careful, helpful, versatile

  • Balanced between creativity and caution

  • Polite with visible hedging or disclaimers

  • Conflict-avoidant and generally neutral in tone

Implications: OpenAI wants its models to be general-purpose assistants: safe for everyday users but capable enough for professionals. It's walking a fine line between helpfulness and containment. This results in a personality that is measured, moderate, and neutral unless fine-tuned otherwise (e.g., via custom GPTs).

Best Legal Uses:

  • Creative brainstorming (marketing content, slogans)

  • General legal drafting (with custom instructions)

  • Client communication templates

  • Reviewing contracts and identifying red flags

  • Summarizing discovery or deposition transcripts

2. Anthropic (Claude)______________________________________

Core Personality Traits:

  • Ethical, reflective, deferential, emotionally intelligent

  • More philosophical than productivity-focused

  • Prioritizes moral consistency and safety reasoning

  • Measured, thoughtful, and nuanced in responses

Implications: Claude is designed to avoid manipulation, deception, and misuse by grounding its responses in a visible set of principles. Its personality reflects moral agency, sometimes at the expense of assertiveness or creativity. It's ideal when you want an AI that prioritizes safety before cleverness.

Best Legal Uses:

  • Ethical guidance and AI policy brainstorming

  • Drafting internal firm policies or compliance materials

  • Client communications requiring emotional intelligence

  • Creative brainstorming with ethical nuance

  • Creating CLE presentations or legal training materials


    3. Google DeepMind (Gemini)________________________________

Core Personality Traits:

  • Efficient and information-rich

  • Integrated and context-aware

  • Neutral and guarded in tone

  • Less personality-driven, more utilitarian

  • Fact-based with structured outputs

Implications: Gemini reflects Google's legacy as a search and information company. Its personality is efficient, structured, and knowledge-driven. It excels at surfacing relevant data quickly—especially when integrated with Google's suite of tools. Gemini is best understood as a highly competent knowledge worker: focused, fast, and efficient.

Best Legal Uses:

  • Legal research requiring factual citations

  • Fast factual queries about legal matters

  • Reviewing contracts for specific data points

  • Information extraction from complex documents

  • Integration with existing Google Workspace documents

4. Perplexity ______________________________________________

Core Personality Traits:

  • Direct, concise, no-frills, source-focused

  • Utilitarian and pragmatic in approach

  • Minimal speculation or creative embellishment

  • Citation-driven and transparent

Implications: Perplexity's personality is shaped by its goal to replace or augment search engines, not your assistant. It doesn't try to sound empathetic or chatty; it tries to show its work. That utilitarian approach results in a personality that feels more like a high-speed research librarian.

Best Legal Uses:

  • Legal research requiring extensive citations

  • Fast factual queries with minimal verbosity

  • Finding relevant case law and precedents

  • Due diligence research on companies or individuals

  • Gathering evidence-based information quickly

5. xAI (Grok)______________________________________________

Core Personality Traits:

  • Irreverent, edgy, bold, occasionally provocative

  • Humorous and contrarian in tone

  • Fewer content restrictions than competitors

  • Resembles a contrarian intern more than a polished assistant

Implications: Grok's personality may appeal to users seeking unfiltered dialogue or creative brainstorming outside conventional boundaries. However, this tone is less suited to professional or regulated legal work unless handled with great care. It presents higher reputational risks in formal settings.

Best Legal Uses:

  • Brainstorming unconventional legal strategies

  • Generating alternative perspectives on legal problems

  • Informal research or exploration

  • Testing arguments against potential counterpoints

  • Internal creative sessions (with appropriate oversight)


Open Source Models

1. Mistral/LLaMA __________________________________________

Core Personality Traits:

  • Lean, powerful, and unopinionated (unless fine-tuned)

  • Minimalist engineering ethos

  • Highly customizable based on implementation

  • Generally neutral without specific personality defaults

Corporate Vision: Open-source models reflect the minimalist engineering ethos of their communities: lean, powerful, and unopinionated—unless fine-tuned. They prioritize flexibility, customization, and community-driven development.

Implications: These models allow for maximum customization to specific legal needs but require more technical expertise to implement effectively. They provide greater control over data privacy and can be deployed in air-gapped environments for sensitive legal work.

Best Legal Uses:

  • Self-hosted solutions for confidential legal matters

  • Custom-tuned applications for specific practice areas

  • Integration into existing legal workflow systems

  • Situations requiring full control over AI training and usage

  • Specialized legal document analysis with custom training

2. DeepSeek ______________________________________________

Core Personality Traits:

  • Academic and research-oriented

  • Methodical and precise in reasoning

  • Strong technical foundation with mathematical capabilities

  • Balanced between helpfulness and caution

  • Generally neutral and objective in tone

Corporate Vision: DeepSeek aims to "seek truth from facts" with a mission focused on advancing frontier AI research while making powerful models accessible. Founded by former researchers from top AI labs, DeepSeek emphasizes both cutting-edge capabilities and responsible deployment of AI technology.

Implications: DeepSeek's personality reflects its research origins, making it particularly well-suited for technically complex legal work requiring methodical reasoning. Its approach balances innovation with responsibility, producing responses that are technically precise while maintaining appropriate professional boundaries. The model excels at tasks requiring systematic thinking and technical accuracy.

Best Legal Uses:

  • Analysis of complex regulatory frameworks

  • Patent law research and technical documentation

  • Reasoning through intricate legal problems step-by-step

  • Financial and tax law applications requiring mathematical precision

  • Research-intensive legal projects requiring methodical approaches

Hallucination Rates and Legal Accuracy

The tendency to "hallucinate" (generate plausible but factually incorrect information) varies significantly across AI platforms, with critical implications for legal work:

Hallucination Risk Comparison:

  • Claude: Generally exhibits lower hallucination rates when discussing legal principles, due to its constitutional AI framework that encourages epistemic humility. Claude typically acknowledges uncertainty rather than inventing details, making it slightly safer for preliminary legal analysis.

  • ChatGPT: Shows higher variance in hallucination rates depending on the version used. GPT-4o demonstrates improved reliability over earlier versions but still occasionally fabricates case citations or statute numbers, particularly when pushed beyond its knowledge boundaries.

  • Gemini: Tends toward lower hallucination rates when discussing factual legal information within its training corpus but may struggle with jurisdiction-specific nuances. Its integration with Google's search capabilities can mitigate some risks.

  • Perplexity: By combining generative AI with search functionality, Perplexity reduces hallucination risks for recent legal developments. However, its synthesis of multiple sources can occasionally create misleading impressions of legal consensus where genuine disputes exist.

_________________________________________________________

Best Practices and Risk Mitigation Strategies:

  1. Require AI tools to provide specific citations for all legal claims.

  2. Cross-verify AI-generated legal information across multiple platforms (eg, use Gemini to check Claude’s output).

  3. Keep the Human in the loop; Use AI outputs as starting points rather than authoritative sources.

  4. Verify every legal citation, even if you are using a legal-specific tool. AI tools—even legal-specific ones—are not experts in nuance. Make certain that the cited case is a real case, and actually stands for the proposition you’re citing it for.

  5. Develop prompt techniques that explicitly discourage speculation in areas of uncertainty.

_________________________________________________________

Choosing the Right Tool for the Task

With this context in mind, lawyers can make smarter choices about which tool to use based on the task at hand. Below is a quick reference guide:

Conclusion: Know the Tool, Know the Task

In the same way lawyers choose the right precedent or statute for a given case, choosing the right AI tool can dramatically improve outcomes. Rather than asking which AI is “best,” we should be asking: Best for what?

Distinct AI "personalities" represent more than a quirk of engineering—it offers a strategic advantage for lawyers who understand how to leverage these differences. Just as a skilled attorney selects the right specialist for different aspects of a case, tomorrow's legal professionals must develop fluency in matching AI tools to specific legal tasks. And the most important tool — your professional judgment. The ultimate responsibility for legal work remains with the attorney.

Personality by Design: Matching AI Tools to Legal Tasks

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AI training, consulting and tools for law firms. Built by lawyers, engineered for legal ethics.

Lexara Consulting, LLC · Iowa · © 2026

Lexara provides legal-adjacent consulting, training, and software. Engaging Lexara does not create an attorney–client relationship, and the services described on this site are not the practice of law. See Iowa R. Prof'l Conduct 32:5.7.

AI training, consulting and tools for law firms. Built by lawyers, engineered for legal ethics.

Lexara Consulting, LLC · Iowa · © 2026

Lexara provides legal-adjacent consulting, training, and software. Engaging Lexara does not create an attorney–client relationship, and the services described on this site are not the practice of law. See Iowa R. Prof'l Conduct 32:5.7.

AI training, consulting and tools for law firms. Built by lawyers, engineered for legal ethics.

Lexara Consulting, LLC · Iowa · © 2026

Lexara provides legal-adjacent consulting, training, and software. Engaging Lexara does not create an attorney–client relationship, and the services described on this site are not the practice of law. See Iowa R. Prof'l Conduct 32:5.7.

AI training, consulting and tools for law firms. Built by lawyers, engineered for legal ethics.

Lexara Consulting, LLC · Iowa · © 2026

Lexara provides legal-adjacent consulting, training, and software. Engaging Lexara does not create an attorney–client relationship, and the services described on this site are not the practice of law. See Iowa R. Prof'l Conduct 32:5.7.