5 Things to Do Before Sending a Sensitive File

Most data leaks are not the result of sophisticated attacks. They are the result of someone in a hurry pasting the wrong file into the wrong window. This is a short pre-flight checklist you can run in under a minute before you hit send.

1. Re-open the file and look at the first page

When you exported the PDF, did the bank statement show your full account number? Are the redactions actually flattened, or just black rectangles drawn on top of selectable text? Open the final file in the same viewer the recipient will use and scroll through it. A surprising number of leaks are 'redactions' that turned out to be visual only.

2. Verify the recipient one more time

Type the recipient's name out, then look at the avatar. If you are using Gmail, the autocomplete sometimes picks a contact you have not talked to in five years who happens to share a first name. The 30 seconds you spend confirming the recipient is the cheapest insurance available.

3. Set a hard expiry

If your tool offers expiration, pick the shortest window the recipient can realistically meet. Two hours is often enough. The recipient will not be mad about the deadline — they will be mildly impressed by the discipline.

4. Add a password if the file is unique to that person

A payslip, a passport scan, or a signed contract is irreplaceable. Layer a password and send it through a different channel. The friction is the point — it forces a deliberate handoff.

5. Send to yourself first

Before sending a high-stakes file, send it to a personal address or a second device. Open it there. Make sure it renders correctly, the expiry works, the password gate works. Five minutes of self-testing beats hours of damage control.

If a file is important enough to password-protect, it is important enough to test before sending.

Bonus: write down what you sent and when

Keep a one-line note in your notes app: 'Sent passport scan to [Name] on [date], expires [time].' This is your future-self insurance. When the recipient says 'I never got it' three weeks from now, you have the answer.

The whole checklist takes 60 seconds. It will save you an afternoon at least once a year.