Before a demand letter gets sent, the plaintiff's attorney has already done the math. They know the claim amount, your likely defense costs, and whether you're the type of company that fights back. That's not a legal strategy — it's a business model.
I recently spoke with John Magliery, a defense attorney with extensive ADA Title III experience, to get his take on how these claims actually work. This post covers what he shared. Not every plaintiff firm operates this way — many are genuinely focused on improving access — but a significant share of the activity we're seeing is driven by economics, not access. How Plaintiff Firms Decide Who to Target
Most large companies have taken meaningful steps toward accessibility. That's partly why mid-market and smaller organizations are absorbing a growing share of claim activity.
What attracts attention? Errors that show up on freely available scan tools — WebAIM WAVE, Google Lighthouse, SortSite. If your site has obvious, unfixed issues that anyone can find in thirty seconds, you're an easier target than a company that's visibly working on it.
The other factor is settlement math. Plaintiff firms focused on fee-shifting look for defendants unlikely to litigate small-value claims where defense costs exceed what it would cost to settle. If you'd rather pay $5,000 than spend $25,000 defending, they've found the right number.
Key takeaway: A single investment in accessibility is preferable to multiple settlements that are individually too small to fight but cumulatively damaging.
Watch John explain which companies are most likely to be targeted — and why.
John's first move when a new client comes to him with a demand letter isn't to panic — it's to investigate. Questions regarding public accommodation status, personal jurisdiction, and the commercial nature of the site remain live in some courts. There may be more defensibility than it initially looks like.
What he tells clients not to do: stop working on accessibility while the claim is pending. The ADA is a remedial statute. If you fix the issues identified in the lawsuit, you can moot the claim. His analogy is simple — if you're sued because your building has stairs and you build a compliant ramp, the lawsuit goes away. The same principle applies to your website.
Key takeaway: Investigating legal defenses and improving accessibility are not competing priorities. Remediation is a legitimate path to resolving the claim itself.
Watch John walk through what he tells clients to do — and not do — the day a demand letter arrives.
Most of the companies John works with aren't starting from zero — they're aware of their obligations and have taken some steps. The dispute is usually about whether those steps were enough.
His guidance centers on two things: address what automated scan tools flag, and make sure core functionality actually works for disabled users. If your site sells products, users with disabilities need to be able to view them, add them to a cart, and check out. That's the bar.
Highly technical issues that don't impact the site's core function are lower priority than barriers that prevent someone from completing a transaction. Internal resources are finite, which is why having a vendor that helps you rank and prioritize issues matters — you can't fix everything at once, and fixing the wrong things first doesn't protect you.
Key takeaway: Having a plan and executing against it is what separates companies that see repeat claims from those that don’t.
Watch John share what actually reduces the risk of a second or third claim.
Plaintiff firms in this space are good at finding the number that makes fighting uncomfortable for everyone except the largest companies. Unless you're prepared to absorb recurring settlements as a cost of doing business — and some companies do make that call — the math tends to favor getting ahead of it.
The legal standard is still unsettled. DOJ guidance is non-binding, and their statements in various cases have pointed in slightly different directions. That ambiguity cuts both ways, but it means you can't assume you're covered based on any single interpretation.
Key takeaway: Once a demand letter is in hand, every path to resolution, settlement, or litigation costs more than remediation would have.
Watch John explain why proactive accessibility costs less than resolving a claim after the fact.
These cases are not primarily legal disputes — they're economic ones. The claim amount, the defense cost, and the likelihood you'll fight back are all factored in before the demand letter is sent. Knowing that changes what the right response looks like, both when a claim arrives and long before one does.
Explore more insights in my Notes from the Field series.
If you’re evaluating how to move from reactive fixes to a more sustainable approach, we’re happy to share what that looks like in practice
This post is based on a conversation with John Magliery, Partner at Davis Wright Tremaine LLP, as part of the Notes from the Field series. Content reflects his professional perspective. It does not constitute legal advice.