What Never Goes in the Chat

The short, hard list

Some things never get pasted into any AI tool, ever, regardless of how convenient it would be:

• Payment details. Card numbers, CVVs, bank account or routing numbers — yours or a customer's.
• Credentials. Passwords, API keys, access tokens, recovery codes. If it grants access to something, it does not go in a chat.
• Government identifiers. Social security numbers, EINs belonging to other parties, driver's licence numbers.
• A customer list. Names with addresses with phone numbers, in bulk. One customer's address to write a scheduling email is ordinary business. Your whole customer database is not.
• Anything under a confidentiality clause. Some commercial and municipal contracts restrict disclosure of terms. Read before you paste.
• Employee records. Pay rates tied to names, disciplinary notes, medical or immigration information.

This is not a list about any particular tool being untrustworthy. It is about a simple principle: information you paste has left your control, and you cannot un-send it.

The redaction habit

You do not need to avoid using real work. You need to strip identifiers first. It takes seconds:

Instead of:

> Draft a follow-up to Margaret Chen, 1847 SW Hillcrest Terrace, Beaverton, 503-555-0147, who we quoted $890 for a roof soft wash on the 3rd.

Paste:

> Draft a follow-up to a homeowner we quoted 12 days ago for a roof soft wash. Quote was in the high hundreds. She hasn't responded. Warm, not pushy, one clear next step.

Then paste the name in yourself when you send it. The AI does not need to know who she is to write a good follow-up. It needs to know the situation.

Once you have done this ten times it becomes automatic, and you stop noticing you are doing it.

Where the real risk is

For most small providers, the realistic risk is not a dramatic breach. It is these three, in order of likelihood:

1. Pasting a whole spreadsheet to ask a quick question about one row.
2. Pasting a contract with confidentiality terms, to summarise it.
3. Pasting a screenshot that has a browser tab, an email preview, or a logged-in dashboard visible in the corner.

That third one catches people constantly. Screenshots capture more than you are looking at. Crop before you paste.

Your system's own secrets

Your system holds keys and connection settings so it can talk to its database and services. You should never need to see, copy, or paste these, and no legitimate task will ask you to.

If you are ever working through a problem — with a support person, a contractor, or an AI — and the path forward involves reading out a key or pasting a configuration file, stop. That is the moment to ask someone you trust. It is also, historically, how most small businesses get compromised: not by an attack, but by a helpful-sounding request.

The one-line test

Before pasting anything, ask:

> If this exact text appeared on a public web page tomorrow, what would happen?

"Nothing" — paste it. "I'd be embarrassed" — probably fine, consider trimming. "I'd have to notify someone, or I'd be in breach of a contract, or someone could spend my money" — do not paste it.

That test takes one second and it is right almost every time.