AI Drafting Tools Are Fast. Your Commas Still Need a Human.
Today’s tip touched on how an em dash can quietly change who a clause covers or what it requires. An em dash, the long dash that looks like this — and reads like a small dramatic pause dropped mid sentence, is the punctuation mark AI dictation tools reach for most often.
Here’s the fuller picture, starting with how misuse of a comma causes the same kind of trouble even without a dash anywhere in sight.
More California business owners are dictating contract language, emails, and internal policies straight into AI tools, then letting those tools clean up the transcript into something that looks like a finished draft. It is fast, and for a first pass, it can be genuinely useful. The problem is that these tools optimize for how a sentence sounds, not for how a court will later read it, and punctuation is exactly where that gap shows up.
Why a Single Comma Can Change What a Clause Covers
When a sentence places a qualifying word in front of a list of two or more items joined by “and” or “or,” and nothing interrupts that list, the standard rule of construction reads the qualifier as applying to the whole list, not just the item sitting next to it. “Qualified doctors and nurses” is normally understood to mean both have to be qualified, not just the doctors. That is the default reading courts tend to favor. But a default is not a guarantee, and the size of that gap between “usually read this way” and “guaranteed to be read this way” is exactly what can lead into a misunderstanding or even a dispute.
Take a simple real world example. “Incentive available to selected employees and directors.” Read one way, “selected” only modifies employees, and every director qualifies automatically. Read the other way, both employees and directors have to be selected. Both readings are grammatically defensible. That is the trap. A sentence does not need to be poorly written to be ambiguous. It just needs to leave a qualifying word in front of a list without making clear how far it reaches.
The Five Million Dollar Comma, a Real World Warning
It is worth revisiting the missing comma dispute that has become something of a cautionary tale in contract drafting circles, O’Connor v. Oakhurst Dairy. The case involved a Maine overtime law listing a series of activities exempt from overtime pay, where the final two items in that list were joined only by the word “or,” with no comma setting the last one apart from the one before it. That left real uncertainty about whether those final two items described one combined activity or two separate ones, which in turn changed which category of workers the exemption actually covered. The Court determined that this kind of ambiguity, in a provision describing which workers lose a wage protection, should be resolved in the employees’ favor rather than the employer’s. Oakhurst Dairy went on to settle with its delivery drivers in 2018 for five million dollars due to the ambiguity in the statute.
That dispute came down to a missing comma. The punctuation risks showing up in contracts now look a little different, now that AI tools are doing more of the drafting.
The Rise in the Use of Em Dashes
Dashes are turning up everywhere in AI drafted writing these days, often standing in for punctuation that would probably be more appropriate.
Compare these two versions of a deal term.
- With a comma: “The Buyer shall pay the Seller a closing payment of $500,000, a working capital adjustment, and an earnout of up to $250,000, contingent on the Company achieving its 2027 revenue target.”
- With an em dash in place of that last comma, the same sentence instead reads: “The Buyer shall pay the Seller a closing payment of $500,000, a working capital adjustment, and an earnout of up to $250,000 — contingent on the Company achieving its 2027 revenue target.”
Under the convention courts generally apply, a comma set off before a qualifying phrase that follows a list reaches back across the entire list, so the comma version reads as making all three payments, the closing payment and working capital adjustment included, contingent on the revenue target being hit. An em dash carries no equivalent, established convention. Most readers would naturally attach it only to whatever sits directly in front of it, the earnout, and read the closing payment and working capital adjustment as unconditional. So depending purely on which mark ended up in the final draft, the Seller’s guaranteed payday at closing could be five hundred thousand dollars plus working capital, or it could be nothing at all if the target is missed. Same deal terms, same numbers, a real difference in what the Seller can actually count on.
Neither version is grammatically wrong on its face, which is exactly why a transcription tool produces the dash without hesitation, and exactly why a human editor has to catch it before it becomes binding language.
Practice Tip:
If a clause qualifies a list of two or more people, entities, or conditions joined by “and” or “or,” do not rely on a reader’s assumptions about how far the qualifying word reaches. Restate the qualifier for each item, or split the list into numbered subparts.
A Practical Drafting Checklist Before You Hit Send
Read every “and” and “or” list in the document twice, and ask whether the qualifying word in front of it is meant to cover every item or just the first one. Do not let dictation software’s default em dash stand in for the comma, semicolon, or period the sentence actually needs; go back and choose the punctuation that carries the legal meaning you intend. If a qualifier should apply narrowly to only one item in a list, say so directly instead of relying on comma placement alone, for example “selected Employees and all Directors” rather than “selected Employees and Directors.” Treat any AI assisted draft, whether dictated or generated by a chatbot, as a starting point that still needs a lawyer’s eye before it becomes a signed document.
Key Takeaways
AI transcription and dictation tools are efficient, but they optimize for how a sentence sounds, not for how a court will parse it.
A qualifying word placed before a list of two or more items generally applies to the whole list under standard rules of construction, but that default reading is not a guarantee.
The 2017 dispute in O’Connor v. Oakhurst Dairy shows how one missing comma became a genuine, seven figure legal exposure for a business.
Em dashes are a poor substitute for the comma a sentence actually needs. A comma before a qualifying phrase that follows a list generally reaches back across the whole list, an em dash does not carry that same signal, and the gap between the two can quietly change what a clause actually requires.
The fix is not avoiding AI tools, it is treating their output as a draft that still needs review before it becomes binding.
If your business is drafting or transcribing contracts, employment policies, or governance documents with the help of AI tools, BMBR can review that language before a punctuation choice becomes a liability. Contact BMBR to schedule a review.
This post is for informational purposes only and does not constitute legal advice. For advice on your specific situation, consult a qualified attorney.
FAQ
Does a comma actually change the legal meaning of a contract?
Yes. Courts routinely rely on punctuation, including the placement or absence of a comma, to determine what a sentence legally means, particularly in lists joined by “and” or “or.”
What is the Oxford comma case people may have heard about?
O’Connor v. Oakhurst Dairy, a 2017 First Circuit decision in which a missing comma in a Maine overtime law created ambiguity over which workers were exempt from overtime pay, ultimately settling for five million dollars.
Is it safe to use AI dictation or transcription tools to draft contracts?
These tools can speed up a first draft, but they are not a substitute for legal review, and defaults like an em dash standing in for a comma can obscure the precise meaning a legal document needs.
If a sentence qualifies two items in a list, does the qualifier automatically apply to both?
Under the general rule of construction it usually does, unless the sentence is structured to suggest otherwise, but relying on that default in a signed document still carries risk.
Can an em dash replace a comma in a contract without changing its meaning?
Not reliably. A comma in a list, or before a qualifying phrase that follows one, carries an interpretive meaning that courts rely on. An em dash’s meaning is much more flexible, which is exactly why swapping one for the other can recreate the kind of ambiguity a careful drafter was trying to avoid.