Best Invoice Reminder Schedule: When to Send

If you are wondering when to send an invoice reminder, the answer is not “when it feels awkward enough.” The best approach is a calm, predictable invoice reminder schedule that looks like a standard accounts payable process.

This guide gives you a reliable default schedule (7 days before, due date, 3/7/14 days after), plus variations for different payment terms and client types. If you also want ready-to-copy email wording, pair this with your templates post:

Invoice Reminder Email Templates (+ Subject Lines for Due and Overdue): Here

Set rules once. Reminders run automatically.

Start here: https://canyoupaythat.com/

Why timing matters more than tone

Most late payments are not personal. They happen because:

The invoice is buried.
The invoice is waiting for approval.
The payer needs a link, reference, or PO number.
The reminder never arrived at the right moment in their workflow.

A good schedule fixes this by putting the invoice back in front of the client before it becomes overdue, and then following up on a consistent cadence until it is paid.

The best default invoice reminder schedule

This is the schedule that works for the majority of service businesses:

7 days before due date
On the due date
3 days after due date
7 days after due date
14 days after due date (final)

One table you can copy into your billing process

If you want subject lines and full email copy, link this schedule to your templates post:

https://canyoupaythat.com/blog/invoice-reminder-email-templates-7-days-before-due-date-overdue-subject-lines

The exact send times that usually perform best

Pick a consistent time so reminders feel routine:

Weekdays: 9:00 to 11:00 in the client’s timezone
Avoid: Friday late afternoon, weekends, and public holidays
If your client is global: set organization timezone in your app and schedule based on that

If your reminders hit inboxes when accounting teams are triaging payments, you get paid faster.

Adjust the schedule based on payment terms (Net 7, Net 15, Net 30)

The default schedule assumes a typical due date, but your reminder cadence should match the terms you set.

If your invoice is “due upon receipt”

Use a tighter cadence because the due date is immediate:

Same day: send invoice
2 days later: reminder
5 days later: reminder
10 days later: final

Add a clear due date anyway (even if it is “today”) so the reminders have a reference point.

If your terms are Net 7

3 days before due
Due date
3 days overdue
7 days overdue (final)

If your terms are Net 15

7 days before due
Due date
3 days overdue
7 days overdue
14 days overdue (final)

If your terms are Net 30

Add an earlier “soft touch” because the cycle is longer:

14 days before due (optional)
7 days before due
Due date
7 days overdue
14 days overdue (final)

Adjust the schedule based on invoice size and client type

High-ticket invoices (large projects)

Large invoices often require approvals. Your goal is to start the approval conversation early.

Recommended schedule:

14 days before due (status check)
7 days before due
Due date
3 days overdue
7 days overdue
14 days overdue (final)

Also include a line that asks who owns the approval step.

Retainers

Retainers get paid fastest when they feel like rent. Make them routine:

Send invoice on the same day each month
Reminder 3 days before due (optional)
Due date
3 days overdue
7 days overdue (final)

If you want a deeper breakdown of retainers vs milestones vs deposits, connect this schedule to your billing model post once published.

First-time clients

For first invoices, increase clarity, not pressure:

7 days before due
Due date
3 days overdue
7 days overdue
14 days overdue (final)

Include “Vendor setup” and “PO needed” as common blockers.

What each reminder should include (to eliminate back and forth)

Every reminder should contain:

Invoice number
Amount
Due date
One link to view/download invoice
Optional pay link (if supported)

The biggest unlock: invoice right after milestones

If you do milestone billing, timing is everything. The fastest payments happen when the invoice is sent:

within 60 minutes of milestone delivery, or
immediately after written approval

That is why “when to send invoice reminder” starts earlier than overdue reminders. The earliest reminder is the invoice itself, triggered by delivery.

Recommended automation rules you can set once and reuse

If you are building this into your app, a great default ruleset for agencies looks like:

Reminder 1: 7 days before due
Reminder 2: Due date
Reminder 3: 3 days after due
Reminder 4: 7 days after due
Reminder 5: 14 days after due (final)

Optional toggles (good for paid tiers):

Skip weekends
Skip holidays (by org locale)
Stop reminders instantly on “Paid”
Escalation option: at 14 days overdue, include “work pause” language

Common scenarios and how the schedule changes

“We already paid”

Do not change the schedule. Instead:

Ask for payment date/reference so you can mark it paid.
Stop reminders once paid status is confirmed.

“Invoice is in approvals”

Add a status touch earlier:

7 days before due: ask who owns approvals
Due date: ask expected payment date

“Please resend the invoice”

Resend instantly and keep the schedule running. The problem is usually discoverability.

“We need a PO number”

This is not a reminder problem. It is a procurement requirement.

Pause escalation tone, get the PO info, then continue reminders.

FAQ

When should I send the first invoice reminder?

For most agencies, the first reminder should be 7 days before the due date. It prevents late payments by catching invoices before they get buried.

What is the best invoice reminder schedule?

A proven default is: 7 days before due, due date, then 3, 7, and 14 days after. Adjust for Net 7 or Net 30 by tightening or extending the cadence.

How many overdue reminders should I send?

Most agencies see results with 3 to 4 follow ups after the due date: 3 days overdue, 7 days overdue, and 14 days overdue as a final touch.

The best invoice reminder schedule is predictable, short, and easy to act on. Send a gentle heads up before the due date, follow up on the due date, then escalate in a calm cadence (3, 7, 14 days after).