Is Doctorow’s Enshittification Phenomenon coming to Legal IT? Is Now the Moment to Act?
Introduction
As many of you will know, enshittification is a phenomenon coined by author and digital rights activist Cory Doctorow to describe the predictable and troubling behaviour of online platforms as they mature. While the neologism may raise an eyebrow in polite company, the concept it describes is entirely serious - and increasingly relevant to those of us working in legal technology procurement and strategy.
At its core, enshittification describes the process by which online platforms and services gradually degrade in quality in order to maximise short-term profits. The cycle, as Doctorow describes it, follows a remarkably consistent three-stage trajectory:
Stage 1: Attracting Users: The platform operates at a loss or offers extraordinary utility in order to attract a massive user base. At this stage, the focus is purely on growth, convenience, and an excellent user experience. Think of the early days of many of the legal SaaS platforms that came to market promising to revolutionise how law firms and legal departments operate.
Stage 2: Squeezing Business Customers: Once users are sufficiently "locked in" meaning the cost and complexity of leaving has become prohibitive, the platform pivots. It begins to monetise its business customers more aggressively. They also make it harder for vendors, creators, or partners to access the user base without paying significantly more for the privilege.
Stage 3: Maximising Shareholder Value: Finally, the platform turns on both its end users and its business customers simultaneously. The overall experience degrades: excessive price increases, changing modes, hidden fees, restrictive contractual terms, and a product roadmap that prioritises shareholder returns over genuine innovation. The result is that everyone, users and business customers alike, is left with a markedly inferior product or commercial deal compared to what originally attracted them to the platform.
Whilst this concept was originally applied to Big Tech platforms, the logic extends to any service heavily reliant on network effects or subscription lock-in. As economist Paul Krugman and others have noted, this so-called "earnings inflection strategy" is arguably a natural life cycle for platforms once they achieve a position of market dominance.
The Legal Tech Dimension
It is becoming increasingly apparent from the behaviour of SaaS vendors and from some of the structural changes we are observing in the AI market that legal technology may too be experiencing its own enshittification moment. The question I want to pose, therefore, is this: is now the moment at which we need to attempt to tackle this, before it becomes entrenched? I believe the answer is yes, and for the following reasons.
Why We Must Act Now
1. Law Firms and In-House Clients Cannot Function Under Chronic Instability
If this phenomenon is allowed to run to its logical extreme, law firms and in-house legal clients will simply not be able to cope or function effectively. Many organisations want, and indeed need, to enter into long-term technology partnerships. Stable systems, embedded workflows, and trained teams are not built overnight. If enshittification continues unchecked, the result will be a market in which clients are perpetually chopping and changing between systems, incurring significant cost, disruption, and loss of institutional knowledge in the process. This gives no benefit to anybody, not clients, their clients and ultimately not the vendors themselves.
2. The Window of Opportunity Is Now - and It May Not Stay Open
We are currently going through a period of real growth of private equity-backed groups (please refer to our M&A Tracker for further details), alongside the exponential rise of AI-driven legal tools. These twin forces are reshaping the vendor landscape at pace. If we do not begin to tackle the structural conditions that enable enshittification now, whilst the market is still forming, it will become considerably harder to do so once consolidation has occurred and the dominant players are entrenched. The time to set standards, negotiating norms, and procurement expectations is before market power concentrates, not after.
3. A Plethora of Competing Systems Creates Real Leverage - But Only If We Use It
On a more positive note, there is currently a genuine abundance of systems in the marketplace. This is not a permanent state of affairs, but whilst it exists, it represents a real opportunity. Competition between vendors means that effective procurement, including the negotiation of long-term deals with robust price protections and contractual commitments, is entirely achievable. We have competitive leverage right now. We should be using it deliberately and strategically, rather than allowing it to dissipate through inertia or fragmented purchasing decisions.
4. Platform Consolidation Could Work in Our Favour - If We Plan for It
We are also seeing an increasing number of broader platforms emerge - solutions that seek to do more across the legal workflow rather than serving a single narrow function. This consolidation dynamic, whilst carrying its own risks, also presents an opportunity. If clients are working with fewer suppliers that cover more ground, there is a compelling case for investing significantly more effort in the procurement and negotiation of those relationships. The stakes are higher, and so the due diligence and contractual rigor should be correspondingly greater.
5. The Rise of Collective Experience - A Resource We Should Not Squander
Finally, and perhaps most importantly, we are fortunate to work with a great many highly experienced professionals in this space. What is becoming increasingly apparent is that, collectively, we have accumulated an enormous depth of knowledge from years of dealing with the SaaS market, its rhythms, its tactics, its pressure points, and its pitfalls. That knowledge, properly harnessed, represents a genuine and powerful resource. We now have a fantastic opportunity to apply it constructively to shape our long-term future, rather than allowing each new generation of procurement decisions to repeat the same hard-learned lessons from scratch. We now need to stand back and take stock of what we have learnt before putting these learnings into action.
Conclusion: Rebalancing, Not Retribution
I want to be absolutely clear about what I am, and am not, advocating here. This is not a call to be harsh with technology suppliers or to adopt any form of collective action. Far from it. The vast majority of practitioners and clients in this space simply want long-term, collaborative partnerships with their vendors. Good suppliers want the same. Sustainable relationships, built on trust and mutual benefit, are in everyone's interest.
However, the lack of balance in the current model does need to be addressed. As I have previously explored in my article, Is There a Silver Lining in Cloud Software?, the pendulum has swung considerably. The old on-premise software model, perpetual licenses with annual support and maintenance fees, was arguably too favourable to the customer. But the modern SaaS arrangement has overcorrected in the opposite direction. Once your data and workflows are embedded in a system, the structural reality is that vendors have the potential to charge more or less what they choose. Budget certainty, which is fundamental to any properly run legal business or in-house department, becomes a fiction.
We need to readdress this balance, not in a spirit of adversarialism, but in a spirit of long-term thinking. Neither law firms nor in-house clients can operate effectively without clarity over their technology costs. Nor, ultimately, can vendors build genuinely great products if their business model is premised on extraction rather than value creation.
Now could be a genuine window of opportunity, a moment to reset expectations, renegotiate norms, and establish a healthier equilibrium for the long-term benefit of the entire market. That opportunity will not remain open indefinitely. The question is whether we have the will to take it.
For further reading on enshittification, see Cory Doctorow's original essays at pluralistic.net and the Wikipedia entry on Enshittification.
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