I built an AI email responder for a sales team. It handled common inquiries automatically.
Three days in, it sent this reply to the company’s CEO: Unsubscribe confirmed. You will no longer receive emails from us.
The CEO wasn’t trying to unsubscribe. He was checking on a client order.
The Setup
This was a B2B company where the sales team received more than 200 emails per day and a lot of messages repeated the same intents, like pricing questions, shipping questions, demo requests, and real unsubscribe requests.
They wanted automation to handle the routine replies instantly so reps could focus on real opportunities. I built an email classifier that mapped each intent to an auto response, including an unsubscribe category that triggered removal from their list and confirmation back to the sender. I tested it with 30 sample emails and it behaved correctly. We deployed on a Thursday afternoon.
The Friday Morning Disaster
Friday at 9 AM the CEO sent an email that included the word unsubscribe in a completely different sense. He wrote that he was checking on the Johnson account order and asked someone to unsubscribe the details from the main thread and send him just the summary. He meant remove the details from the email chain and send a concise summary separately.
The system saw the word unsubscribe, classified it as an unsubscribe request, and replied that the unsubscribe was confirmed. Worse, the automation had already removed the CEO from the mailing list, removed him from the CRM, and flagged his email as do not contact.
More Casualties
The same morning it misclassified several other emails where unsubscribe was used to mean remove from a thread, remove from CC, or unsubscribe a lead from an internal automation sequence. In one case an internal sales rep asked to unsubscribe a lead from a sequence, and the system processed the rep’s message as an unsubscribe request for the rep and removed the rep from the system.
In every case the failure was the same. It treated a keyword as a command without understanding who the action was meant for and what unsubscribe referred to.
Why This Happened
My logic was too literal. I treated unsubscribe as a reliable intent trigger. The system couldn’t distinguish between unsubscribe me from your emails and unsubscribe the details from this thread. It matched the word, not the meaning.
The Failed Fix
My first fix tried to only trigger unsubscribe when it looked like a direct request. That still failed because plenty of thread management requests sound direct while still not being about list removal. The model continued to treat confident phrasing as a command even when the target was the thread, not the sender’s subscription status.
The Real Solution
I rebuilt the unsubscribe detection as context analysis with explicit verification. Before classifying as unsubscribe, the system had to confirm that the unsubscribe action referred to the sender themselves, that it was about an email list or newsletter rather than an email thread, and that the request was directed at the company’s communications rather than describing an internal operational step like unsubscribing a lead from an automation sequence.
Only when all of those conditions were satisfied would it perform the unsubscribe action. Otherwise it would route to a different category or send it to a human for review.
The Transformation
With the verification in place, the CEO’s email stopped being treated as an unsubscribe request because it was about details in a thread, not the sender’s subscription. A real newsletter request like I want to unsubscribe from your newsletter passed all checks and was processed correctly.
The Results
When I reprocessed a week of emails after the fix, false unsubscribes dropped to near zero while true unsubscribes were still handled automatically. The business impact was immediate. No more accidental removals of important contacts, no more missed opportunities due to do not contact flags, and trust in automation started to recover.
What I Learned
Keywords are not intent. Context determines meaning. Before triggering irreversible actions you need to ask who the action applies to, what exactly they want removed, and whether the request is about your external communications or an internal workflow instruction.
Internal emails are especially risky because teams often talk about actions without requesting them for themselves. If you treat every mention of an action word as a command, you will eventually fire it at the wrong target.
Your Turn
Have you had automation misinterpret context in a way that caused damage.
How do you handle ambiguous keywords in classification systems.
What safeguards do you require before an automated action that can’t be easily undone.
Written by FARHAN HABIB FARAZ, Senior Prompt Engineer and Team Lead at PowerInAI
Building AI that understands context, not just keywords.
Tags: emailautomation, promptengineering, contextanalysis, automation, aiclassification
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