Recurring Invoice Schedule: Frequency, Billing Day, Due Date

A recurring invoice schedule is the set of decisions behind a repeating recurring invoice: how often it goes out, which day it is dated, when it falls due, and which period of work it covers. Get them right once and the invoices arrive when the client can pay them. Get them wrong and every cycle lands just after the client's payment run, falls on a day that does not exist in February, or bills a period nobody can identify.

This guide covers those decisions with worked examples. For what recurring invoices are and how to set one up in your software, start with the recurring invoices guide.

How often should recurring invoices go out?

Match the frequency to how the client thinks about the cost, then check the admin load. Monthly is the default for retainers because most businesses budget and pay suppliers monthly.

The every-two-weeks pricing trap

Worked example with stated inputs: a contractor agrees $48,000 a year of work. Billed monthly, that is 12 invoices of $4,000. Billed twice a month, it is 24 invoices of $2,000. Billed every two weeks, it is 26 invoices of about $1,846.15, not $2,000.

If the contractor quotes "$2,000 every two weeks" thinking it equals "$4,000 a month", the client pays 26 × $2,000 = $52,000 a year, which is $4,000 (8.3%) more than intended. Some clients will spot it; their finance team certainly will. Quote fortnightly work as a fortnightly price, or use twice-monthly billing if you want a monthly equivalent.

Should you bill in advance or in arrears?

Bill in advance for fixed retainers and in arrears for work you cannot price until it is done. The choice moves your cash by a full cycle.

Worked example: a $2,000 monthly retainer for March 2027, on net 15 terms.

Billing in advance gets the same $2,000 about 30 days sooner every month and means a client who stops paying owes you for at most one cycle. Billing in arrears suits hourly or usage-based retainers, where the March amount is only known on March 31. Many retainers combine the two: a fixed base billed in advance, plus overage hours billed in arrears on the next invoice. See retainer invoicing for the agreement side.

Which day of the month should a recurring invoice go out?

Pick a day between the 1st and the 28th that every month has, and that gives the client's accounts team time to approve the invoice before their payment run. The 1st is the obvious choice and works for most clients; a later day can be better when it lines up with a client's payment calendar.

Avoid the 29th, 30th and 31st

Seven months have 31 days, four have 30, and February has 28 (29 in a leap year). A schedule anchored on the 31st has to do something in the other five months, and tools differ:

• Stripe Billing documents the behaviour: a monthly subscription anchored on January 31 bills on the last day of each shorter month, so February 28, then March 31, April 30 and so on.
• Other tools may shift the date, skip it or roll it into the next month, and not all document which. Unless your tool's documentation says how it handles month-end, choose a day from the 1st to the 28th.

If you genuinely need end-of-month billing (for example, billing in arrears for the month just finished), use the 1st of the following month and label the service period as the previous month.

Busy days and time zones

FreshBooks' help center notes that recurring templates start generating around 1 AM Eastern time and that templates set for the 1st of the month can take longer because of a larger queue, suggesting the 2nd or another day instead. Stripe's billing anchors are in UTC. If you schedule a run late in the evening in your own time zone, the invoice may be dated the next day; schedule morning runs to keep the invoice date you expect.

How do you line up the due date with the client's payment run?

Ask the client when they pay suppliers, then choose terms so the due date falls just before a run. Many accounts payable teams pay on fixed days, such as weekly on a Thursday or on the 15th and the last business day of the month, and approve invoices a few days ahead.

Worked example: the client pays suppliers on the 15th and on the last business day of each month. Your $2,000 invoice goes out on Monday, March 1, 2027.

Net 10 is paid two weeks earlier than net 15, though only five days shorter on paper. The same logic applies to any payment calendar: once you know the run dates, work backwards. Your invoice payment terms and the net 30 guide cover term choices in general (see also the net 30 definition). A due date only helps if paying is easy, so put a payment link or bank details on the template; invoice payment methods compares the options.

How do you handle partial months?

Prorate the first or last cycle, and agree the method in the contract. There are two common methods, and they give different answers.

Worked example: a $3,000 monthly retainer starts on Monday, March 15, 2027. March has 31 days, so the client is billed for 17 days (March 15 to 31 inclusive).

The $200 spread between methods is small once, but it is exactly the kind of difference that starts a dispute when it was never agreed. After the first partial invoice, move the schedule onto your normal billing day. Stripe Billing prorates automatically between subscription creation and the first full invoice date; most invoice-based tools leave the first invoice to you, so create it as a one-off and start the recurring schedule on the next full cycle.

What should each recurring invoice say about the period?

Every recurring invoice should name the exact period it covers, in a form the client's bookkeeper can match without asking: "Website maintenance, service period March 1 to 31, 2027" or "Q2 2027 bookkeeping retainer (April to June)".

• If your tool fills in dates automatically, use its period placeholders (some tools offer month, quarter or year variables for line descriptions). Check that they cover your frequency; weekly periods are the ones most often missing.
• If it does not, either write a description that is true every cycle ("monthly maintenance plan") and put the period in the notes when you review the draft, or keep the schedule on drafts so you can add it.
• Keep the numbering continuous. Each generated invoice takes the next number in your sequence; the period goes in the description, not the invoice number.

The rest of the invoice follows the usual rules in how to write an invoice.

Example: a year of one monthly schedule

Worked example: a $1,500 monthly support plan for a client who pays on the 15th and the last business day, billed in advance on the 1st with net 10 terms, starting January 1, 2027, with a price change to $1,600 from July after written notice in May.

Twelve invoices, one change, no month-end problems, and every due date falls before the client's mid-month run. Keep the May notice and the July change in your invoice audit trail so the price change is easy to evidence later.

Which schedule options does InvoiceQuickly offer?

InvoiceQuickly's recurring schedules are on the Pro plan ($9/month). You choose weekly, monthly, quarterly or yearly and set the first run date. Each invoice is dated on its run date and uses the saved due-in days (30 by default); you can save due-in days, currency, tax, discount, notes and terms. The form does not offer every-two-weeks or twice-monthly frequencies. Invoices are created as drafts for review by default, or emailed automatically if you choose. Schedules can be paused, resumed or archived but not edited, so a price change means archiving the old schedule and creating a new one from the change date.

Practical fit: InvoiceQuickly suits a monthly, quarterly or yearly fixed fee. New schedules retain their original billing day, use the last day of a shorter month, and return to the original day when it exists. Save tax, discount and payment terms on the schedule. For fortnightly billing or variable lines, adjust a draft or use a tool whose templates support that workflow. Tax rules for repeated supplies vary by jurisdiction; the invoice tax compliance guide covers the basics. The recurring invoices guide compares tools.

When a fixed schedule is the wrong approach

• Work that starts and stops unpredictably. Bill on milestones or with progress billing as work completes.
• Amounts that depend on usage every month. Either invoice in arrears from actual usage or use a billing system built for metered pricing.
• Clients who must raise a purchase order each cycle. Each invoice needs a new PO reference; schedule drafts, not automatic sends.
• Annual plans where renewal is uncertain. Send a renewal notice and confirm before the yearly invoice is created rather than letting it generate on its own.

Frequently asked questions

What is the best day of the month to send recurring invoices?

The 1st works for most monthly retainers billed in advance, as long as the due date lands before the client's next payment run. Avoid the 29th to 31st unless your tool documents how it handles short months; any day from the 1st to the 28th exists in every month.

Is it better to invoice monthly or every two weeks?

Monthly suits most retainers and is what most clients budget for. Every two weeks suits work priced per fortnight. Remember that every-two-weeks billing produces 26 invoices a year, not 24, so a fortnightly price is not half of a monthly price.

Should recurring invoices be sent before or after the work?

Send fixed-fee recurring invoices before the period (in advance) and variable or hourly ones after it (in arrears). Billing in advance brings cash in about one cycle earlier and limits how much a non-paying client can owe.

How do I prorate the first recurring invoice?

Multiply the monthly fee by the days of service and divide by the days in the month (or by 30, if your contract says so). A $3,000 retainer starting March 15 is $1,645.16 using actual days or $1,700 using a 30-day month. State the method in your contract.

What payment terms should I use for a recurring invoice schedule?

Work backwards from the client's payment run. If they pay on the 15th and you invoice on the 1st, net 10 is paid on the 15th; net 15 slips to the month-end run. Shorter terms are reasonable for recurring work because the client already expects the invoice.

Can I change a recurring invoice schedule later?

Yes, but give the client written notice before the new amount or date takes effect, and make the change before the next run date. Some tools let you edit the template; others require you to end the schedule and create a new one.

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Last reviewed: October 27, 2026. Tool behaviour is summarized from Stripe and FreshBooks documentation as of that date. Dates in the examples use the 2027 calendar.

Set up the schedule once and review the first invoice. Start free, then upgrade to Pro for recurring schedules, email delivery and automatic payment reminders. For follow-up wording, the free payment reminder templates work with any tool.