How to set up recurring invoices

If any part of your income repeats — a monthly retainer, a quarterly support plan, an annual licence — invoicing it by hand every cycle is wasted effort and a recurring chance to forget. Recurring invoices solve this: you define the amount and the rhythm once, and the system raises the invoice on schedule from then on. This guide shows you when recurring billing fits, how to choose a cadence, the one decision that matters most (auto-send versus draft), and how to make the whole thing collect itself.

When recurring invoices make sense

Recurring billing fits any arrangement where the fee is fixed and repeats on a predictable schedule. Classic cases:

• Retainers — a set monthly fee for ongoing availability or a block of hours.

• Subscriptions — access to a product, content, or service on a regular plan.

• Support or maintenance plans — a flat fee for keeping something running.

• Installment arrangements — splitting a large fee into equal scheduled payments.

If the amount changes every cycle based on hours worked, recurring billing still helps — but you'll lean on the draft option below rather than full automation.

The bigger win is psychological: recurring revenue is the difference between starting every month at zero and starting it with a predictable floor. Even a couple of small retainers on autopilot smooth out the feast-or-famine cycle that makes freelance income stressful. That's worth setting up properly once.

Choose the right cadence

Kliently supports weekly, monthly, quarterly, and yearly schedules. Match the cadence to the work and to how your client likes to be billed:

1. Weekly — short, high-frequency engagements or ongoing contractor arrangements.

2. Monthly — the default for most retainers and support plans.

3. Quarterly — heavier plans where a monthly bill would be noise for both sides.

4. Yearly — annual licences or memberships, often with a discount for paying upfront.

Annual cadences are worth nudging clients toward where it suits them — fewer transactions, more predictable cash, and you can pass on a small discount (Kliently's own annual plans give two months free, for example).

Auto-send or save as draft?

This is the decision that defines how hands-off your recurring billing is. Each schedule can either send automatically on its date, or generate a draft you review and send.

• Auto-send when the amount is stable — a flat retainer that's the same every month. Set it and forget it.

• Save as draft when the figure might vary — a retainer plus overage hours, or a plan where you sometimes add a line. You get a pre-built invoice to glance at and tweak before it goes out.

Most freelancers run a mix: flat retainers on auto-send, anything variable on draft. You get the time savings without the risk of mailing a wrong number.

A practical middle path for variable retainers: keep a fixed base on auto-send and add overage hours as a separate one-off invoice each month, pulled straight from your logged time. The predictable part runs itself; the variable part stays a quick, deliberate step. That way one client's messy month never breaks your whole recurring setup.

Set it up in a few steps

1. Build the invoice once with the line items, tax, and any discount you want repeated.

2. Attach a recurring schedule and pick the cadence (weekly, monthly, quarterly, yearly).

3. Choose auto-send or save-as-draft for that schedule.

4. Set the start date — and an end date if it's a fixed-term arrangement.

5. Turn on reminders so follow-up runs without you.

From there the schedule does the lifting. See the full feature in invoicing.

Make collection automatic too

A recurring invoice that still needs manual chasing only solves half the problem. Pair the schedule with two things: a payment method the client can use every cycle without effort, and smart reminders that nudge before due, on the due date, and after — stopping automatically once paid. With your client paying through their preferred rail in their own currency via the client portal, each cycle closes itself.

Keep recurring schedules tidy

• Review active schedules quarterly — cancel any tied to finished engagements.

• Update the amount centrally when a retainer changes, so the next cycle is correct.

• Use draft mode for the first cycle of a new client to sanity-check everything.

• Confirm the end date on fixed-term plans so billing stops on its own.

Set up well, recurring invoices turn your most predictable income into something you genuinely don't think about — which is exactly where billing should sit.