ChatGPT prompts for payment reminder emails, before, on and after the due date

Free reminder generators give you one generic email. The prompts below give you a reminder for each stage, built from your invoice's real facts, in your own tone. Copy one, fill in the brackets and paste it into ChatGPT, Claude or any chat assistant. Then read the result as if the client already had it, because they will.

What to give the model

• The client's first name and your business name.
• The invoice number, the amount with its currency, and the due date.
• How many days late it is, or how many days until it's due.
• How the client can pay: “the Pay button in the invoice email” or “reply for bank details”. Don't paste account numbers into a chatbot.
• Your tone in one line, for example “warm and brief, first names, I sign as Ana”.
• Anything already agreed, word for word from the contract, such as a late fee. If nothing was agreed, say so.

Prompt 1: before the due date

Write a short email to my client [first name] from [my business name].
Purpose: a friendly heads-up that invoice [number] for [amount] is due on [due date]. It is not late.
How they pay: [the Pay button in the invoice email / reply to this email].
Tone: [warm and brief, first names]. Sign as [name].
Rules: 40 to 90 words. Use only the facts above. Don't invent amounts, dates, links, fees or payment details. No guilt, no pressure, no exclamation marks.
Give me a subject line under 60 characters and the body.

A heads-up isn't a reminder, and the prompt says so to stop the model from writing “just a reminder that your payment is due”. Skip this stage for clients who always pay on time; it reads as nagging.

Prompt 2: on the due date

Write a short email to my client [first name] from [my business name].
Purpose: invoice [number] for [amount] is due today, [due date]. Make paying easy and offer help if something about the invoice is wrong.
How they pay: [the Pay button in the invoice email / reply for bank details].
Tone: [warm and direct]. Sign as [name].
Rules: 40 to 90 words. Use only these facts. No threats of any kind: no late fees, interest, collections or legal action. Don't say they opened the invoice unless I tell you they did.
Give me a subject line that includes the invoice number, and the body.

Prompt 3: after the due date

Write a short payment reminder to my client [first name] from [my business name].
Facts: invoice [number] for [amount] was due on [due date], [N] days ago. [Optional: they opened the invoice on [date].] [Optional, only if in the contract: “Our agreement includes a late fee of [exact wording].”]
Purpose: ask for payment and an expected date, and offer to resolve any problem with the invoice.
How they pay: [the Pay button / reply for bank details].
Tone: [friendly and firm]. Sign as [name].
Rules: 50 to 110 words. Use only these facts. Don't add a fee, interest, deadline or consequence I didn't give you. No guilt, no sarcasm.
Give me the subject line and the body.

For the 14-day email, add one line to the purpose: “ask them to reply with the date they'll pay, or who in their company I should contact”. That question gets a reply more often than another polite nudge, and it tells you whether the problem is cash, approval or a lost email.

What to leave out of a reminder

• Threats of legal action, collections, credit reporting or stopping work, unless you've decided to do it and your contract allows it.
• Late fees or interest that aren't in the agreement. Where they are, check your state's limits in late fee limits by state and the amount with the invoice late fee calculator.
• A fake collections department or another name. The FTC has said that a creditor using a different name to suggest a third party is collecting can be covered by the FDCPA.
• Guilt (“I'm sure you understand that I have bills too”) and sarcasm. They put the client on the defensive, and they read badly if the dispute ever reaches small claims court.
• Bank account numbers typed by the model. If you send bank details, paste them yourself and check them twice.

Change the cadence by how the client pays

Payment reminders in SoloWOS

Write your tone once in Settings > General under “How you write to clients” (up to 500 characters, such as “Warm and brief, informal. I sign as Ana.”). On a sent invoice that isn't paid, Draft follow-up with AI opens the assistant with the request ready, and the draft comes back as a card with Confirm and send. In Automations, the “AI payment reminder” template drafts one 14 days after you send an invoice if it's still unpaid, and leaves it in “Ready for your review” on Home with a notification. It never sends by itself.

The AI only gets the invoice's facts (number, amount, due date, days past due, whether the client opened it), the client's first name, your business name and your tone, and it's instructed never to invent amounts, dates, fees, links or threats. The button opens the assistant, so it uses an assistant request (10 a month on Basic, 500 on Solo); the automation uses an AI draft (3 on Basic, 200 on Solo). SoloWOS uses Claude models from Anthropic. Under Anthropic's commercial terms, the data sent for a request isn't used to train their models, and the SoloWOS privacy policy lists what each AI feature sends.

Automatic reminders without AI follow the cadence table above when you send invoices clients pay by card. For the steps after reminders stop working, see what to do when a client won't pay. The SoloWOS AI assistant drafts other follow-ups too, and the AI time savings calculator shows what drafting saves at your volume.