Does Bonsai Send Automatic Payment Reminders to Clients?

The project wrapped two weeks ago. You sent the invoice from Bonsai the same afternoon, the client replied with a thumbs up, and then the thread went quiet. Now you are staring at an unpaid line item and doing the math on whether it is too soon to say something.

That hesitation is expensive, and it is also extremely common. Bonsai looked at three years of invoice data across 100,000 freelancers and found that 29% of freelance invoices are paid at least a day late. So the question is not whether a client will drift past a due date. It is what happens on the days after, and how much of that follow-up you are expected to do yourself.

The good news is that Bonsai does handle a real chunk of it for you, automatically, without any setup. This post covers the exact reminder schedule Bonsai uses, how to change it, the one date where the automation quietly stops, and what a practical routine looks like for the invoices that outlive it.

The short answer: yes, and it starts before the due date

Bonsai sends automatic payment reminders to your clients, and the feature is on by default on every invoice. You do not have to enable anything for a new invoice to start nudging on your behalf.

What makes Bonsai's version genuinely useful is that it does not wait for an invoice to go bad. According to Bonsai's own documentation, the default schedule sends reminders at four points:

• One week before the due date
• One day before the due date
• One week overdue
• More than two weeks overdue

Two of those four land before the invoice is ever late. That matters more than it sounds. A large share of late payments are not disputes or cash shortages, they are calendar accidents. Somebody filed the invoice, meant to process it Friday, and moved on. A note a week out and a note the day before catch most of those before they become an awkward conversation.

The Activity section of any invoice shows exactly what went out and when, so you are never guessing whether the client has already heard from you.

How to change your reminder preferences

Bonsai lets you set reminder behaviour in two places, depending on how broadly you want the change to apply.

For a whole project, open the project and go to the Settings tab. Scroll to the Reminders section and tick the checkbox there. Every invoice created for that project will then follow the preferences you set, which is the option you want for a retainer client or a long engagement where you have already agreed on a rhythm.

For a single invoice, use the dropdown that appears in the send modal when you email the invoice. That is the right lever for the one client who has asked you to keep email to a minimum, or the one project where a heavier touch is warranted.

It is worth spending five minutes on this per client rather than leaving everything on the default. The right cadence for a corporate client with a formal payment run is not the right cadence for a small studio paying from a personal card. We wrote more about picking a rhythm in our guide to reminder cadence for follow-ups.

What happens 16 days after the due date

Here is the detail most people miss, and it is stated plainly in Bonsai's help documentation: automated reminders stop 16 days after the due date. After that point, any further follow-up has to be sent by hand, using the Send Reminder button on the invoice.

That cutoff is a deliberate and defensible product decision. Nobody wants software emailing their client forever. But look at what it means next to Bonsai's own payment data: over 75% of late invoices are paid within 14 days of the due date, and 90% are paid within a month.

Read those two facts together and the picture gets sharp. The automation runs almost exactly as far as the easy cases go, then switches off. The invoices still open on day 17 are, by definition, the ones that did not resolve on their own — and those are precisely the ones now depending on you to remember them.

That is the gap. Not a flaw in the tool, just the point where the work quietly moves back onto your desk.

Four other places the coverage ends

The 16-day cutoff is the big one, but a few other boundaries are worth knowing before you decide how much to lean on the built-in reminders.

1. Only invoices sent through Bonsai are covered. If a client insisted on a PDF over email, a purchase-order portal, or a deposit agreed in a chat thread, none of that is visible to the automation. It cannot remind on something it never saw.
2. The schedule is a schedule, not a conversation. Reminders fire on fixed dates regardless of context. If a client emailed on Tuesday to say the payment run is the 30th, the day-before reminder still goes out, and it can read as tone-deaf.
3. Reminders go to the invoice contact. In a larger client, the person who approved your work is often not the person who releases the money. If the invoice email address is your day-to-day contact rather than their finance inbox, the nudge may be landing somewhere it cannot act.
4. Escalation is manual. The last automated message sits at the same volume as the first. There is no built-in step that changes the tone or loops in a second contact when a balance ages past a month.

None of this makes Bonsai a poor choice. It is a strong, well-integrated system and its pre-due reminders are better than what a lot of competing tools offer. If you are comparing options in this category, our breakdown of how HoneyBook handles automatic reminders is a useful side-by-side, and the rest of our invoice reminder and follow-up guides cover the other major platforms.

Late fees are a separate lever, and a blunt one

Bonsai can also apply late fees automatically, which people sometimes assume is part of the reminder system. It is not. It is configured separately under Settings, then Defaults, then Invoices.

According to Bonsai's documentation on invoice defaults, you set a default late fee as a percentage. The fee is applied the day after the due date and recurs monthly until the invoice is paid. You can also set your default Days Until Due there; Bonsai ships with one month.

Two practical notes. First, defaults only apply to invoices created after you save them, so changing the setting today does nothing for the invoice you are worrying about now. Second, a late fee is a policy, not a nudge. It works best when it was written into the agreement before the work started and the client already knows it exists. Bolting one on mid-dispute usually buys a harder conversation rather than a faster payment.

A simple routine for the invoices that outlive the automation

You do not need a new system for this. You need a defined answer to one question: what happens on day 17? Here is a routine that works without much overhead.

1. Set a recurring calendar block, fifteen minutes, once a week. Open Bonsai's invoice list filtered to unpaid and sort by oldest. This is the entire administrative cost of the habit.
2. For anything past 16 days, send one manual reminder from the invoice and change something about it. Reply on the original email thread rather than starting a new one, or address it to the finance contact instead. A message that looks different gets read differently.
3. At the one-month mark, switch channels. A two-line message on the platform where you normally talk to that client, or a short call, resolves more stuck invoices than a fifth email will.
4. Log the outcome somewhere you will see it at renewal. A client who always needs three reminders is telling you something useful about your deposit terms next time.

If keeping that habit alive is the part that keeps slipping, a dedicated follow-up tool such as DueDrop can carry the reminder schedule past the point where your invoicing app stops, working alongside Bonsai rather than replacing it. Either way, the principle is the same: the follow-up after day 16 should be a decision you made once, not a decision you make every time.

And it is worth saying clearly, because a lot of freelancers carry this quietly: following up on money you have already earned is not rude. You delivered the work. A short, friendly, factual note is a normal part of running a business, and most clients are relieved to be reminded rather than annoyed by it.

Frequently Asked Questions

Does Bonsai send payment reminders automatically without me setting it up?

Yes. Automated email reminders are enabled by default on every invoice, so a new invoice will start reminding your client without any configuration. You can adjust the behaviour per project under the project's Settings tab, or per invoice using the dropdown in the send modal.

When exactly does Bonsai send invoice reminders?

The default schedule sends four reminders: one week before the due date, one day before the due date, one week overdue, and again once the invoice is more than two weeks overdue. You can review everything that was sent in the Activity section of the invoice.

Do Bonsai reminders ever stop?

Yes. Automated reminders stop 16 days after the due date. Beyond that point you have to send any further follow-up manually with the Send Reminder button on the invoice, which is why it helps to have a weekly habit for reviewing anything still open past that window.

Can Bonsai charge a late fee automatically?

It can, but it is configured separately from reminders under Settings, Defaults, Invoices. You set a percentage, and the fee applies the day after the due date and recurs monthly until the invoice is paid. Defaults only affect invoices created after you save the change.

Will Bonsai remind clients about invoices I sent from another tool?

No. The automation only covers invoices that exist inside Bonsai. Anything you billed by PDF, through a client's procurement portal, or agreed informally sits outside the system and needs to be tracked separately.

The takeaway

Bonsai answers the headline question well. Reminders are automatic, they start before the due date, and they are easy to tune. The useful work is knowing the edges.

• Bonsai sends automatic reminders by default: one week before due, one day before due, one week overdue, and past two weeks overdue.
• Automated reminders stop 16 days after the due date, and everything after that is manual.
• Bonsai's own research shows 75% of late invoices clear within 14 days, so the cutoff lands right where the difficult cases begin.
• Only invoices created inside Bonsai are covered, and reminders go to the invoice contact, who may not be the person who releases payment.
• Late fees are configured separately and only apply to invoices created after you save the setting.
• Decide in advance what happens on day 17, and the awkward part of getting paid stops being a decision you make invoice by invoice.