Recurring invoices and retainers on autopilot
You already know which clients bill the same amount every month. The problem is remembering to actually send it — on time, every time, without a sticky note on your monitor.
Manual re-billing is easy to forget. You duplicate last month’s invoice, change the date, hope you didn’t miss a line item, and send it — if you remember before the client asks where it is. Miss a cycle and you’ve either billed late or, worse, not billed at all. Multiply that by every retainer client on your books and it turns into a recurring chore that eats a chunk of your month, every month.
SendBilling’s recurring invoicing removes the remembering part. Set a cadence once, and the invoice generates and sends itself on schedule from then on, with the same branding, line items, and tax rules as the invoice you built the first time.
How it works
Three steps, and after the first one you’re not involved again.
Step 1
Set a cadence
Pick weekly, monthly, or a custom interval, a start date, and how many cycles to run — or leave it open-ended.
Step 2
SendBilling generates it
On each due date, a new invoice is created from your template with the right line items, taxes, and invoice number.
Step 3
It sends itself
The invoice can go to the client on schedule. If it remains recorded as unpaid after the due date, configured reminders can follow up automatically.
Example series · Monthly retainer, $1,200
Each generated invoice keeps its own status, so you can see the whole series at a glance in invoice tracking.
Why bill this way
Set-and-forget cadences
Weekly, monthly, quarterly, or a custom interval. Set it once for a client and stop putting a recurring task on your calendar to remember it.
Retainers billed upfront
Retainers work differently from recurring invoices — you bill for the period ahead of time, and SendBilling tracks them separately from one-off jobs so your reports stay accurate.
Automatic send and reminders
Every generated invoice sends itself on schedule, and if a client misses the due date, automatic reminders chase it without you writing another follow-up email.
Edit or pause anytime
A client goes quiet, a project ends, or a rate changes — edit the amount, push the next date out, or pause the whole series in a couple of clicks. Nothing sends while it is paused.
Retainers vs. one-off invoices
A retainer isn’t just a recurring invoice with a different name. You’re billing for a block of work before you do it — a month of support hours, a standing design contract, ongoing maintenance. SendBilling keeps retainers as their own record type, separate from one-off invoices and from pay-as-you-go recurring billing, so your revenue reports show what’s pre-paid retainer income versus what’s billed per project, instead of lumping everything into one number.
And because every invoice in a series still gets its own status — sent, viewed, paid, or overdue — nothing is hidden just because it generated automatically. If payment is not recorded by the due date, that invoice shows up overdue like any other, and automatic payment reminders follow up on it without you having to notice first.
Stop re-sending the same invoice by hand.
Set a cadence once, free and unlimited during early access — no credit card required.
What to review before automating a series
- Confirm the service period, amount, currency, tax, due date, and end condition.
- Choose whether generated invoices send immediately or wait for review.
- Keep the billing contact and external payment instructions current.
- Pause the series when scope, price, tax treatment, or the relationship changes.
- Verify funds outside SendBilling and mark each invoice paid manually.
Recurring generation reduces repetitive document creation; it does not authorize a charge, debit a customer account, or guarantee delivery or payment.
Set up a recurring invoice without repeating mistakes
Recurring generation works best for a stable service with an agreed cadence. Review the parent document carefully because an incorrect contact, amount, date rule, or tax setting can be copied into every future occurrence.
Define the service period
Name what repeats, the frequency, the first run date, the due-date rule, and when the arrangement should be reviewed or stopped.
Separate variable work
Keep usage, expenses, overages, change requests, and one-time setup fees outside the fixed recurring amount unless the agreement defines how they are calculated.
Review generated invoices
Check customer details, currency, taxes, line items, and delivery before relying on automation. Update the parent record when the ongoing agreement changes.
Handle exceptions
Pause or revise the schedule for disputes, service pauses, cancellations, failed delivery, or a changed billing contact rather than allowing incorrect reminders to continue.
Recurring invoices do not debit a customer or prove payment authorization. They generate billing records; the sender still verifies settlement through the bank or external provider.
Browse invoice templatesRecurring invoicing FAQ
What's the difference between a recurring invoice and a retainer?
A recurring invoice bills for work as it happens on a repeating schedule — say, a $500 maintenance invoice every month. A retainer bills upfront for a block of work or time before you do it. Both run on a cadence, but SendBilling tracks them as separate types so your reports don't mix pre-paid retainer income with regular recurring revenue.
Can I change the amount or pause a series without canceling it?
Yes. Open the recurring invoice or retainer and edit the line items, amount, or next send date at any time. Pausing stops future invoices from generating until you resume it — past invoices already sent are untouched either way.
Is recurring invoicing free right now?
Yes. SendBilling is in early access, so recurring invoices and retainers are free and unlimited on every plan, same as the rest of the product. Paid plans launch later with the same features plus priority support and higher usage limits.
Updated August 4, 2026Invoice trackingPayment remindersPricing