Letting AI take action: decide by whether you can undo it, not the amount
Decide where a person checks the actions you hand to AI by whether each one can be undone, not by the amount.
Key points
- List by method: cancel now vs. later
- Check expiry, what stays: paused billing
- Can't schedule it? Stop before it runs
- Undoable by cutoff? Check after it runs
Contents
Whether you can undo it depends on how, not on what it is called
A&A perspective
Whether an action can be undone is not settled by its name, such as "cancel" or "delete." Here, "can be undone" means that the connected service's documentation describes a way to reverse the action after it has run. Two actions with the same name can differ: done one way, you can reverse it; done another way, you cannot.
From the sources
Decagon, a company that supplies customer service AI to businesses, has a co-founder describing on a case study page published by Anthropic how its AI is used. Rather than explaining how to get a refund, the AI checks whether the customer qualifies and processes the refund through the payment system itself.
From the sources
The same page says that customers who get in touch usually have their issue resolved without going through a human agent.
A&A perspective
Once AI carries actions through to execution, you have to decide, action by action, where a person steps in. Automate & Augment (A&A), the company writing this article, thinks that drawing that line by amount gets two kinds of action wrong: cheap actions that cannot be undone, and expensive ones that can.
A&A perspective
An email offering a small discount cannot be taken back once it reaches the customer. A large payment that is only scheduled, and will not run before its date, can still be called off. The amount measures something different from whether you can reverse a mistake.
From the sources
Stripe, a payments service widely used for subscription billing, separates cancellations you can reverse from those you cannot on its page about cancelling subscriptions. If you schedule a subscription to cancel at the end of its period, you can withdraw that scheduled cancellation at any time until the period ends. A subscription that has already been canceled, on the other hand, cannot be reactivated.
From the sources
According to Claude Code's official documentation, files changed through Claude's editing tools can be restored with its rewind feature (/rewind). Files that Claude Code deleted or moved by running shell commands cannot be restored by rewinding.
A&A perspective
In both examples, what you want to do is the same: a cancellation, or a change to a file. What differs is the method used to carry it out.
A&A perspective
So when you list the actions you hand to AI, A&A recommends one line per method, not per name. "Cancel" becomes two lines: "cancel at the end of the period" and "cancel now."
Check not only whether you can undo it, but its expiry and what stays
A&A perspective
Each line on the list has three columns to look up and fill in: whether there is a way to undo the action, until when that way works, and what stays behind even after you undo it.
A&A perspective
Even when you find a way to undo an action, fill in the other two columns as well. A plain "yes, it can be undone" leaves them empty.
From the sources
The Stripe and Claude Code documentation mentioned above both state an expiry. Stripe says a scheduled cancellation can be withdrawn only until the period ends. Claude Code's documentation says the records used for rewinding are deleted after about 30 days by default, and that rewinding after that can fail.
A&A perspective
If you decide something is safe because it can be undone, without knowing the expiry, the window may already have closed by the time you notice the mistake. The expiry column matters as much as the column for the way to undo.
A&A perspective
What stays behind means a change that happens alongside the main action and does not necessarily come back when you undo it.
From the sources
Stripe's same page gives an example. When a subscription is canceled, automatic collection is paused for that subscription's invoices that are still open or in draft. Automatic reminder emails stop being sent as well. The page adds that you can still collect payment and send emails manually.
A&A perspective
In other words, a cancellation stops more than the contract. If you let AI cancel subscriptions, A&A thinks the same line should also say who takes over the collection that stopped.
A&A perspective
This is how Stripe works; other services do not necessarily offer the same steps. Fill in the columns for each connected service by reading its own documentation.
A&A perspective
Some actions have no documentation at all, such as manual work inside the company or operations on older systems. In that case, leave the columns blank and treat the action as one that cannot be undone.
A&A perspective
Asking the contractors who used to handle the work by hand whether they have ever reversed it can sometimes fill a blank column.
Hypothetical example
The table below is a fictional example. Suppose the customer inquiries of an online shop, previously handled by a contractor, move to AI. The actions the AI can take are split by method into five lines, and the columns are filled in. The right-hand column is filled in using the approach described in the next two sections.
| Action | Way to undo, expiry, what stays | Where the human check goes |
|---|---|---|
| Write research findings in the order's memo field | Undo: Yes / Expiry: None / What stays: None | Nowhere |
| Move the ship date to the next business day | Undo: Yes / Expiry: The warehouse's same-day cutoff / What stays: The notice sent to the warehouse staff | After it runs, before the cutoff |
| Cancel an order before it ships | Undo: Yes (the order can be restored until the cutoff) / Expiry: The shipping cutoff / What stays: None | After it runs, before the cutoff |
| Issue a refund | Undo: No / Expiry: - / What stays: - | Before it runs |
| Send the buyer an apology email | Undo: No / Expiry: - / What stays: The fact that the buyer read it | The AI drafts, a person sends |
Stop before it runs only what cannot be scheduled or drafted
A&A perspective
When you find an action that cannot be undone, see whether it can be moved into a reversible form before adding an approval. Turn an immediate action into a scheduled one, and a finalized one into a draft. Put outgoing emails and similar messages into an outbox queue that holds them instead of sending at once. If the connected service offers that form, you do not need a check before the action runs.
A&A perspective
With a Stripe cancellation, that means scheduling the cancellation for the end of the period instead of cancelling now. A scheduled cancellation can be withdrawn until the period ends.
A&A perspective
For an invoice, it means stopping at a draft instead of finalizing and sending, so that finalizing and sending become separate actions. For an email to a customer, the AI handles drafting and a person does the sending.
A&A perspective
Scheduled and drafted actions still need their own expiry and what-stays columns, because a scheduled action runs once its date arrives.
A&A perspective
Doing these conversions first reduces the number of checks placed before execution. If you start by putting a check on every action and then try to remove some, deciding which ones to drop becomes a judgment call every time.
A&A perspective
If you convert first, each remaining check comes with a one-line reason: the documentation describes no way to undo it. Unlike a check chosen by amount or by feel, its reason is still clear when you look back later.
A&A perspective
Actions that reach people outside the company are handled separately. Even if a system lets you delete the record of a sent email, the fact that the recipient read it cannot be undone. While the email sits in the outbox queue it can be withdrawn, but once it is sent it cannot.
A&A perspective
So the AI handles everything up to the draft, and a person presses send. Only the sending, which cannot be moved into another form, is stopped before it runs.
A&A perspective
Drawing the line by how much the other party loses when a promise is withdrawn is covered in another article, "After-hours inquiries: which promises an auto-reply may confirm."
If you can undo it in time, the check can come after it runs
A&A perspective
Actions that can be undone within their expiry go ahead without being held. Before the expiry arrives, a person looks them over and undoes anything that is wrong. The check sits after execution rather than before it.
A&A perspective
If every action waits for approval before it runs, the AI ends up waiting until the owner is free. With the check placed after, the work proceeds on the spot and a person can review it later in one go. In exchange, between execution and review, the action sits in a state where it can still be undone. Compared with checking first, that stretch of time is the only thing that grows.
A&A perspective
The check placed after does not have to be done by the owner. One option is to keep the contractors who used to run the work as reviewers who check within the expiry. This is A&A's hypothesis; its effect has not been measured.
A&A perspective
This arrangement has one condition: the expiry must be longer than the interval at which the reviewer actually looks at the screen. If the expiry is one hour and the reviewer does not look at night, the check will not come in time. If the expiry is shorter, treat the action like one that cannot be undone and stop it before it runs.
A&A perspective
There is an opposing view: actions that touch money or outside parties should be stopped before execution whether or not they can be undone, because if the expiry passes while nobody is looking, nothing was really checked.
A&A perspective
The argument holds. It is the better fit when the expiry is short, and when you must show business partners or auditors that approval was given before execution.
A&A perspective
In the example table earlier, a person is involved in four of the five lines. By count alone, drawing the line by amount might give about the same number of checks. What differs is the reason attached to each one.
A&A perspective
Here, you can explain that the refund is stopped before execution because the payment side has no way to undo it. You can also explain why the ship date may be reviewed after execution: the deadline is the warehouse's cutoff time.
Summary
A&A perspective
Where a person checks is decided not by the amount but by whether the action can be undone.
A&A perspective
List by method: cancel now vs. later
A&A perspective
Check expiry, what stays: paused billing
A&A perspective
Can't schedule it? Stop before it runs
A&A perspective
Undoable by cutoff? Check after it runs
Where a person checks is decided not by the amount but by whether the action can be undone. That depends on how the action is carried out, not on its name, and the connected service's documentation says which. Stop before execution only the actions that cannot be scheduled or drafted. For actions you can undo within an expiry, place the check after execution, but only when that expiry is longer than the interval at which the reviewer actually looks.
FAQ
If a large action can be undone, is it fine to check it afterward?
Yes, as long as the expiry is longer than the interval at which the reviewer looks. But if you must show business partners or auditors that approval was given before execution, put the check first even when the action can be undone.
Once the work moves to AI, should I end the contract with the contractor right away?
There is no need to end it right away. If they stay on to check results within the expiry, someone is there to undo the AI's mistakes. A&A thinks how much of the role to keep depends on how many actions in your table have the check placed after execution.
Who should look up the three columns?
The person building the system fills them in from the connected services' documentation. The owner looks at the finished table and decides where to stop. When one person fills in the table and another builds the system, a misreading of the documentation is passed along and stays in the build. That is why A&A has one person own the work from the table through implementation.
Sources & editorial note
Primary pages read for this article. Publication dates below belong to the sources; access dates record our research.
- Decagon delivers white-glove customer service at scale with Claude
Anthropic · undated case study page
Accessed 2026-10-21 - Cancel subscriptions
Stripe · undated documentation page
Accessed 2026-10-21 - Checkpointing
Anthropic · undated documentation page
Accessed 2026-10-21