⚙️Operations & Admin · Step-by-step guide

Every Monday, find unpaid invoices that are overdue and get polite reminder emails drafted for you

A ChatGPT scheduled task (a job ChatGPT runs by itself at a set time) checks your sent invoices every Monday morning, finds any that are past their due date and still unpaid, and drafts a short, polite reminder for each one in Gmail. Nothing goes out until you read and send it.

Created byCorleous Kelly · RVRBN
📰 Read the original: Corleous Kelly: You asked about dots. Here's what they cost and what $20 gets you instead (RVRBN) ↗
⏱️ About 20 minutes🎯 Easy💵 ChatGPT Plus is USD 20/month📋 7 steps
💬 ChatGPT📘 How-to
🎯 What you'll have at the endEvery Monday morning you'll get a list of overdue invoices and a polite reminder already drafted in Gmail for each one, ready for you to check and send.

👀 What you'll get

Example

Here's the kind of thing you'll have at the end:

✅ ListMonday overdue check · 2 November

3 invoices overdue · MYR 7,450 in total

  • INV-1042 · Harbour Lane Cafe · MYR 2,800 · 19 days late · draft ready
  • INV-1047 · Mei Design Studio · MYR 3,150 · 8 days late · draft ready
  • INV-1049 · Tan & Co Florist · MYR 1,500 · 3 days late · no draft: they emailed on Thursday saying payment is on its way

Drafts are in Gmail

  • Open Drafts, check each one and send when you're happy

🧪 Made-up sample to show the kind of result. Your output will vary.

💸 What will this really cost me?

Prices checked 23 Oct 2026
🧪 To try it once
Free: ChatGPT Free can run up to 3 scheduled tasks, once a day in a flexible time window. Whether Gmail can be connected on your plan varies: check the provider's pricing page.
🔁 To keep it running
ChatGPT Plus: USD 20 (MYR 82) a month for exact times (such as Monday 8am), up to 5 active tasks and hourly runs.
⚠️ Watch out for
Corleous Kelly notes QuickBooks isn't on OpenAI's list of apps that work inside ChatGPT tasks, so keep a simple sheet or use Gmail. A task pauses if it needs your approval or its chat is deleted.

🔗 Official pricing: ChatGPT pricing · Scheduled tasks in ChatGPT (plan limits)

Prices change often, so check the links before you pay. Amounts exclude tax. MYR at USD 1 = MYR 4.08 (Bank Negara Malaysia, 19 Oct 2026).

🧾 Which plan do I need?

🪙 Small upgrade · MYR 82/mo

An exact weekly time needs ChatGPT Plus; the free plan only runs tasks once a day in a flexible window.

Tick what you already pay for:

🪙 Small = up to MYR 250 a month more · 💎 Big = over MYR 250 a month more · prices from each provider's pricing page, checked 21 Oct 2026.
ℹ️ How we work this outPrices come from each provider's own pricing page (checked 21 Oct 2026; amounts exclude tax; USD 1 = MYR 4.08, Bank Negara Malaysia 19 Oct 2026). Small upgrade = up to MYR 250 a month more than you pay now. Big upgrade = more than MYR 250 a month more. Check pricing = the provider doesn't publish a price we could confirm. Each guide's needs come from its own "What will this really cost me?" box. Your ticks stay in this browser only (no account, nothing sent to us).
Tick all your plans on the home page →

⏱️ Try it in 10 minutes

✅ Free plan · nothing to connect

What you'll see: a list of overdue invoices worked out from a sample invoice list, with a polite reminder email drafted for each.

Copy the prompt, paste it into one of the free AI apps below and press send. The sample is made up, so swap in your own details if you like.

💬 Your 10-minute test
Today is Monday 26 October 2026. From the invoice list below (swap in your own), find every invoice where Paid is not 'Yes' and the due date is before today.

1. Give me a list: invoice number, client, amount (MYR), days overdue, and the total overdue.
2. For each one, draft a short, polite reminder email: friendly for under 30 days, firmer (but still polite) for over 30 days. Include the invoice number, amount and due date. Don't threaten anything.

Invoices:
INV-301 | Lotus Spa | 1,200 | due 30 Sep | Paid: No
INV-302 | Kopi Lane | 450 | due 15 Oct | Paid: Yes
INV-303 | Sinar Printing | 2,780 | due 10 Oct | Paid: No
INV-304 | Hana Florist | 600 | due 31 Oct | Paid: No
INV-305 | GreenTech | 3,950 | due 5 Sep | Paid: Part (2,000 received)

✅ Works on: ChatGPT Free · Claude Free · Gemini app (free)

Links go to the official plan pages. Free plans have daily limits and can change, so check before you rely on them.

➡️ Like it? The full setup adds: The full setup makes this a ChatGPT scheduled task every Monday that checks your sheet or Gmail and leaves the reminders as drafts for you. Go to the steps ↓

⚡ One-click install

Checked install pages (app stores, official sites and template pages): tap to get it straight away.

⬇️ Get ChatGPT on iPhoneApp Store⬇️ Get ChatGPT on AndroidGoogle Play

🧰 Before you start

⏱️ Time neededAbout 20 minutes
💵 Rough costChatGPT Plus is USD 20/month

🪜 Step by step

🐣 Beginner mode: showing the 6 essential steps only. Extra steps are hidden; tap 🚀 Advanced at the top to see all 7.
✅ 0 of 7 steps done 📄 Printable page
  1. 1
    ☐

    Make your invoice list

    If you don't have one, start a Google Sheet with columns: Invoice number, Client, Client email, Amount, Due date, Paid (Yes/No). Mark paid ones as you get paid.

  2. 2
    ☐

    Connect Gmail

    In ChatGPT, go to Settings, then Apps, and connect Gmail (and Google Drive if your sheet is there). Read what each permission allows.

  3. 3
    ☐

    Create the task

    Open a new chat (not inside a Project, because tasks in Projects can't read Project files) and paste the 'Monday overdue check' prompt below, filled in.

  4. 4
    ☐

    Confirm the schedule

    ChatGPT shows a confirmation with the schedule. Check it says every Monday at your time and in your time zone. You can edit it later under Scheduled.

  5. 5
    ☐

    Turn on notifications

    In Settings, then Notifications, choose push or email so you're told when the list is ready.

  6. 6
    ☐

    Check and send

    On Monday, read the list, open each draft in Gmail, fix anything (a client may have paid another way) and send it yourself.

  7. 7
    ☐

    Optional: firmer second reminder

    Add a line to the task: for invoices over 30 days late, draft a firmer second reminder for you to review.

    ➕ Extra step: hidden in 🐣 Beginner mode

💬 Copy-paste prompts

Tap Copy prompt, paste it into your AI (Grok, ChatGPT, Claude or Gemini), then replace the [yellow bits] with your own details.

💬 Monday overdue check
Every Monday at [8:00am], [time zone]:
1. Open my invoice list [Google Sheet name] (or search my Gmail sent mail for invoices from the last 90 days).
2. Find every invoice where Paid is not 'Yes' and the due date is before today.
3. Give me a list: invoice number, client, amount in [currency], days overdue, total overdue.
4. For each one, create a Gmail draft (do NOT send) to the client: subject 'Friendly reminder: invoice [number]', under 90 words, polite, with the amount, due date, how to pay ([bank transfer details / payment link]) and 'please ignore this if you've already paid'. Sign it [your name, business].
5. If a client has replied about this invoice in the last 14 days, don't draft a reminder; tell me instead.
Never send, mark as paid or change my sheet. Only read and draft.

⚠️ Tips & common mistakes

🌟 Why it's worth it

💡 Why it mattersLate payments hurt small businesses more than lost sales, and chasing them is the job everyone puts off. A weekly list with reminders already drafted turns it into five minutes of reading and clicking send.
🏷️ Real exampleCorleous Kelly, founder of RVRBN (a small-business automation studio in Saint Johns, Florida), wrote on 7 Oct 2026 that you don't need a USD 100 dot for this: 'A Monday check for overdue invoices, with reminders drafted for you, fits a scheduled task' on the USD 20 ChatGPT Plus plan, which can keep five tasks running as often as hourly and use connected apps like Gmail. He recommends letting it read and draft, and asking before anything goes out.
🔌 Connects to:GmailA Google Sheet or list of invoicesChatGPT scheduled tasks
📘 Proof level: How-toA how-to guide, template or new feature from the maker or a guide site. It shows what you can set up and claims no particular results.
📰 Found via Newsletter · RVRBN: Corleous Kelly: You asked about dots. Here's what they cost and what $20 gets you instead (RVRBN) ↗

🔗 Helpful links

🔗 Corleous Kelly's article (source) ↗🔗 OpenAI Help: Scheduled tasks in ChatGPT ↗🔗 OpenAI Help: Connected apps in ChatGPT ↗

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