Automatic Invoice Reminders (How to Get Paid Without Chasing)

If you are a freelancer or a digital agency, you already know the real cost of late payments: broken focus, awkward follow-ups, and cash flow anxiety that shows up right when you need momentum.

Automatic invoice reminders solve that by turning “chasing” into a simple system. You set rules once, your client gets polite nudges at the right moments, and reminders stop when the invoice is paid.

If you want the fastest path to implementation, start with Can You Pay That automatic invoice reminders and build your follow-up flow around a client portal link and scheduled nudges.

Key takeaways

1. The best reminder systems are proactive: before due date, on due date, then a small overdue sequence.
2. Every reminder should include invoice details plus a clear payment path (link/portal).
3. Automation feels less awkward because it is consistent and “process-driven”, not emotional.
4. Reminders should only run for invoices that are actually sent, and they should stop once paid.
5. Track what was sent, to whom, and when, so you do not double-nudge or miss a reply.

What are automatic invoice reminders?

Automatic invoice reminders are scheduled messages (usually email, sometimes SMS) that go out based on invoice timing, for example a few days before the due date, on the due date, and after the invoice becomes overdue.

The difference vs manual follow-up is not just convenience. Automation creates consistency:

1. The reminder always goes out.
2. The wording stays professional.
3. The timing is predictable.
4. You stop losing time scanning spreadsheets and inbox threads.

Many accounting tools implement this as simple rules: turn reminders on, choose “days before/after due date”, and customize the subject/body.

Why automatic reminders work (and why they feel less awkward)

Most late invoices are not malicious. They are stuck in “busy”: approval queues, inbox overload, missing PO numbers, or a client who meant to pay “tomorrow”.

Automatic reminders work because they:

1. Reduce forgetfulness. A nudge at the right time brings the invoice back to the top of the stack.
2. Depersonalize the follow-up. Clients interpret it as process, not pressure.
3. Increase clarity. Repeating due date + amount + payment method removes friction.
4. Create a paper trail. You can see what was sent and when, which matters if you ever need to escalate.

Stripe’s guidance on reminders is basically “timing + clarity + convenience”: remind before due date, on due date, and shortly after, and make paying easy with a link or clear payment instructions.

The “Clean Follow-Up” framework (Clarity, Convenience, Consistency)

A reminder sequence only needs three things to perform well.

1) Clarity

Your invoice and your reminder should make it obvious:

1. what is due (amount)
2. what it is for (invoice number, project, period)
3. when it is due (date, time zone if relevant)
4. what happens next (late fee terms if you use them, escalation step if needed)

2) Convenience

If the client has to hunt for a PDF or ask “how do I pay?”, payment gets delayed.

Aim for:

1. a direct payment link when possible
2. a client portal link that shows the invoice and payment options
3. bank details included in a consistent, copyable format (for wire transfers)

3) Consistency

Consistency is what removes awkwardness. You are not deciding whether to follow up based on mood, you are following your process.

The best consistency rule: reminders only run on invoices that are marked as sent, and they stop once paid.

The best schedule for automatic invoice reminders

Here is a practical schedule that matches what many authoritative guides recommend: a pre-due nudge, a due-date reminder, then a short overdue sequence.

This mirrors Stripe’s timing guidance (pre-due 3–7 days, due date, then 1–7 days overdue, then escalating intervals).

For a deeper timing breakdown (including 3/7/14-day variations and what to do with Net-7 vs Net-30), use this guide: best invoice reminder schedule.

When to pause reminders

Pause or switch to a human follow-up when:

1. the client replies with a dispute or billing question
2. the invoice needs a PO number or vendor onboarding step
3. the client asks for a revised invoice
4. the invoice is partially paid and needs reconciliation

Automation is great, but escalation should still be intentional.

What every invoice reminder should include

Use this as your minimum checklist. It prevents “reply friction”, which is one of the biggest hidden causes of delayed payments.

Must-have fields

1. Client name (or billing contact name)
2. Invoice number/reference
3. Amount due and currency
4. Due date
5. Payment method instructions
6. A payment link or portal link (if available)
7. A short “If you already paid, please ignore this” line

Nice-to-have fields (agency-friendly)

1. Project name + delivery period (e.g., “December maintenance”)
2. PO number or vendor ID (if the client uses procurement)
3. PDF attached (some tools support attaching PDFs to reminder emails)

Templates (short, customizable examples)

These are intentionally short so you can adapt them to your voice.

1) Pre-due reminder (3–7 days before)

Subject: Invoice #[123] due on [date]

Body:

Hi [Name], quick heads-up that Invoice #[123] for [amount] is due on [date]. You can pay here: [link]. If you have any questions, reply to this email.

2) Due date reminder

Subject: Invoice #[123] is due today

Body:

Hi [Name], reminder that Invoice #[123] for [amount] is due today. Payment link: [link]. If you already paid, thank you, and please ignore this message.

3) Overdue reminder (1–7 days late)

Subject: Invoice #[123] is overdue

Body:

Hi [Name], Invoice #[123] for [amount] was due on [date] and is now overdue. Can you confirm payment timing? You can pay here: [link]. If something is blocking payment, tell me what you need and I will help.

Want a bigger set of templates plus subject lines (including softer and firmer versions)? Use invoice reminder email templates and subject lines.

How to set up automatic invoice reminders in any workflow

You do not need a complex system. You need clean inputs and clear rules.

Step 1: Standardize your payment terms

Pick defaults you can defend:

1. Net-7 or Net-14 for small freelance projects
2. Net-14 or Net-30 for larger clients with procurement

Whatever you choose, put it on the invoice and align the reminder schedule to it.

Step 2: Ensure invoices have the right “status”

Many tools only send reminders after the invoice is marked as sent (not draft).

This sounds obvious, but it is a common reason automation “doesn’t work”.

Step 3: Create a reminder rule set

At minimum:

1. Pre-due reminder (3–7 days before)
2. Due date reminder
3. Overdue reminder (3–7 days after)

Some tools let you set multiple reminders, for example Zoho Books mentions enabling many reminders and configuring both automatic and manual reminder options.

(Authoritative reference: Zoho Books invoice reminders)

Step 4: Customize subject lines and body text

Avoid robotic copy. Keep it short, clear, and consistent with your brand voice.

QuickBooks, for example, explicitly supports editing subject lines and the email message for reminder templates.

(Authoritative reference: QuickBooks automatic invoice reminders setup)

Step 5: Make paying ridiculously easy

If a payment link or portal can be included, do it. Stripe explicitly calls out including a payment link and clear payment instructions as part of effective reminders.

Step 6: Add stop rules and tracking

Two requirements:

1. reminders stop once paid
2. you can see whether a reminder was sent (or at least have a log)

Step 7: Handle exceptions without breaking the system

Create a simple exception list:

1. VIP clients who pay on a fixed schedule
2. clients with procurement rules (they need PO, vendor setup)
3. clients in dispute (switch to human handling)

For agencies: reduce reminders with better billing structure

The fastest way to send fewer reminders is to make invoices easier to approve.

For agencies, that usually means one of these:

1. deposit upfront
2. milestone-based billing
3. monthly retainers

If you want a practical breakdown of which model gets agencies paid faster (and how to invoice each one), read 50% upfront vs milestones vs monthly retainers.

Then apply automation on top. Good billing structure reduces friction, automation reduces manual effort.

Manual reminders vs accounting tools vs dedicated reminder tools

Different setups work for different teams. Here is a quick decision table.

If you want the dedicated workflow approach (without changing how you create invoices), start here: check Can You Pay That.

Common mistakes (and how to fix them)

Mistake 1: Waiting until the invoice is overdue

Fix: add a pre-due reminder. Stripe recommends sending upcoming payment reminders 3–7 days before the due date.

Mistake 2: No payment link, no clear “how to pay”

Fix: include a payment link or explicit payment instructions every time.

Mistake 3: Reminders firing on drafts

Fix: ensure reminders only run after “sent”. FreeAgent explicitly notes reminders only send when an invoice has been marked sent (not draft).

Mistake 4: Over-reminding and annoying good clients

Fix: cap your sequence, and use exceptions for clients who pay on predictable cycles. Stripe warns against overwhelming recipients with too many messages.

Mistake 5: Not knowing what was sent or whether the client replied

Fix: log reminders, keep email history tied to the invoice, and pause automation when a human conversation starts.

Conclusion: automate the awkward part, keep the relationship

Automatic invoice reminders are not about being pushy. They are about being consistent, clear, and easy to pay.

If you do three things well, you will feel the impact immediately:

1. Set a proactive schedule.
2. Include the details and a payment path every time.
3. Track reminders and stop them when paid.

For more practical invoicing guides, visit the invoice automation blog.

And if you want a simple system that sends professional follow-ups for you, try Can You Pay That for invoice reminders.

FAQ

Do automatic invoice reminders work for freelancers and small agencies?

Yes. They are especially effective when you invoice repeatedly and need consistent follow-up without spending time writing emails.

When should I send an invoice reminder?

A strong default is 3–7 days before due date, on the due date, then 1–7 days after if unpaid.

How many reminders is too many?

For most client relationships, 2–4 reminders total is enough (pre-due, due, then 1–2 overdue touches). Adjust based on your payment terms and relationship.

Should reminders go out before the due date or only after?

Before is better. A pre-due nudge prevents late payment, which is easier than fixing late payment.

Do reminders stop automatically when someone pays?

They should. Some tools explicitly stop reminders after an invoice is paid, which is a key automation requirement.

What should I write in an invoice reminder email?

Keep it short: invoice reference, amount, due date, and a payment link or clear instructions, plus a line that they can ignore it if already paid.

Can I automate reminders without changing how I create invoices?

Yes. You can keep your invoice creation workflow and automate follow-up around invoice status, due date, and a portal or payment link.

If you want help mapping your exact flow, contact the Can You Pay That team.