How to chase overdue invoices without burning the relationship

Before the invoice is even late

The best way to chase fewer invoices is to prevent lateness in the first place:

• Agree payment terms in writing up front (e.g. “due within 14 days”).
• Make paying frictionless — send a one-click payment link, not bank details in an email footer.
• Send a friendly heads-up a few days before the due date, not just after.

The escalation ladder

The key idea: match the firmness to how late the invoice is. A predictable, escalating sequence gets you paid faster than sending the same soft nudge forever.

Always stop the moment they pay, and keep every message polite and factual — the goal is to get paid and keep the client.

Copy-paste templates

Day 0 — friendly email (on the due date)

Subject: Invoice {{invoice_number}} — due today

Hi {{first_name}},

Just a quick reminder that invoice {{invoice_number}} for {{amount}} is due today.
You can pay it in one click here: {{payment_link}}

Thanks so much!
{{your_name}}

Day 5 — firmer email

Subject: Invoice {{invoice_number}} is now 5 days overdue

Hi {{first_name}},

Following up on invoice {{invoice_number}} for {{amount}}, which was due on {{due_date}}
and is now 5 days overdue. Our agreed terms are payment within {{terms}} days.

Please settle it here: {{payment_link}}
If there's a problem or you need anything from us, just reply and let me know.

Thanks,
{{your_name}}

Day 10 — SMS

Worth doing by hand today: SMS escalation inside UntilPaid is coming soon while we complete carrier registration. Everything else on this ladder is automated now.

Hi {{first_name}}, invoice {{invoice_number}} ({{amount}}) is now 10 days overdue.
You can pay here: {{payment_link}} — thanks, {{your_name}}. Reply STOP to opt out.

Day 14 — final notice before access is paused

Subject: Action needed — invoice {{invoice_number}} 14 days overdue

Hi {{first_name}},

Invoice {{invoice_number}} for {{amount}} is now 14 days overdue. To keep things fair,
access to {{deliverable}} will be paused until the invoice is settled.

You can pay and restore access immediately here: {{payment_link}}
Happy to jump on a quick call if something's holding this up.

Thanks,
{{your_name}}

Staying on the right side of the rules

A few basics keep your chasing professional and compliant:

• Only contact people you have a genuine business relationship with about their own invoice.
• Give an easy opt-out — a one-click unsubscribe on emails and honouring SMS STOP replies.
• Keep messages honest and stick to the facts of the invoice.
• Send during business hours in the recipient’s timezone.

How to automate the whole ladder

Doing this by hand for every late invoice eats your week. If you invoice through Stripe, UntilPaid runs this ladder automatically: it reads your overdue invoices (read-only), sends the escalating emails on your schedule and timezone, and — if a client still hasn’t paid by day 14 — fires a signed webhook so your app can revoke their access until Stripe marks the invoice paid. It stops the instant they pay, and every email carries a one-click unsubscribe.