How do you decide when to send physical letters for serious overdue invoices?

Overdue invoices are always a headache. I’m facing a client who is 90 days late on payment, and my emails are falling on deaf ears.

Considering sending a physical letter to their office. It feels more serious, but is it really the best way to handle this?

90 days? They’re definitely playing games. Skip the letter and call them now. Don’t talk to your usual contact; ask for whoever handles payments. If they blow you off, then send a letter with a hard deadline and make it clear you’ll take action. Phone calls work way better than letters for getting paid.

Physical letters work when they ignore your emails. It shows you mean business about getting paid.

I send one after 60 days of no response. Make it clear this is their last chance before you escalate. Getting actual mail makes it clear you are not going away.

I wait 60 days before sending letters, but only if they’ve gone completely silent. At 90 days, you can’t just rely on mail anymore.

Certified mail worked for me - forces them to sign for it. I include the original invoice and give them just 10 days to pay. Spell out exactly what happens if they don’t.

Honestly though, you should be digging into their business by now. Are they still open? Cash flow issues? Sometimes your letter hits their desk right as they’re shutting down.

And start charging late fees if you aren’t already. Learned that one the hard way.

I go over to see them if it’s bad.

At 90 days, a letter won’t magically fix this. They know they owe you money.

Here’s what I’d do first:

  • Check if they’re still in business - search their website, social media, anything recent
  • Find who actually cuts the checks - not your project contact
  • Send one final email with a clear deadline before escalating

If you still want to send a letter after that, fine. But don’t expect it to be some magic bullet.

The real question is what you’ll do when they ignore the letter too. Have a plan ready - collections, small claims court, whatever makes sense for the amount.

Next time, ask for payment terms upfront and stick to them. 90 days is way too long to let this slide.

Sending a letter might get their attention. Just make sure to keep it professional.