Question 1

What is a recurring invoice?

Accepted Answer

A recurring invoice is one you send to the same client on a fixed schedule — weekly, monthly, quarterly, or any other repeating cadence — for the same service. They're the standard billing mechanic for retainers, subscriptions, ongoing maintenance, and any work that repeats on a predictable rhythm. This scheduler doesn't send the invoices for you; it gives you the calendar so you know when to issue each one.

Question 2

Should I bill monthly or quarterly?

Accepted Answer

Monthly is the default for most retainers because it matches how clients budget and how cash flow works for solo freelancers. Quarterly billing makes sense for larger contracts where the per-invoice amount is high and processing fees matter, or for clients who explicitly prefer fewer transactions. Weekly and biweekly cycles are common for time-and-materials sprints. Pick the cadence your contract specifies and let the scheduler handle the dates.

Question 3

Should I bill at the start or end of the billing period?

Accepted Answer

Bill at the start of the period (in advance) for retainers, subscriptions, and any service where you've committed capacity to the client. Bill at the end (in arrears) for time-and-materials work where the amount changes each cycle. Billing in advance protects your cash flow and is the industry default for monthly recurring revenue.

Question 4

How do I handle a price change mid-contract?

Accepted Answer

Finish the current cycle at the old rate and start a new schedule at the new rate from the next issue date. If you need to bill a partial period at the old rate before the change kicks in, use a pro-rata calculator to work out the prorated amount, then create a fresh recurring schedule starting on the change date.

Question 5

What happens at the end of the contract?

Accepted Answer

Set the end condition to "After N invoices" and enter the contracted number of cycles, or "Until date" and enter the contract end date. The schedule will stop generating invoices on that boundary so you don't accidentally bill past the contract. For open-ended retainers, leave it on "Ongoing" — the scheduler shows 12 invoices for planning but keeps going indefinitely.

Question 6

Can I import the schedule into Google Calendar or Outlook?

Accepted Answer

Yes. Click "Download .ics calendar" and you'll get a standard iCalendar file. In Google Calendar, go to Settings → Import & Export → Import. In Outlook, use File → Open & Export → Import/Export. In Apple Calendar, double-click the file. Each invoice becomes an all-day event, and if you set a lead-time reminder, you'll also get a separate prep event a few days before each billing date.

Question 7

iCal vs Google Calendar export — what's the difference?

Accepted Answer

There isn't really a difference for this use case. The .ics file format (RFC 5545) is the universal calendar standard, and Google Calendar, Outlook, Apple Calendar, and most other calendar apps all import it natively. The same file works everywhere — no separate Google Calendar export needed.

Question 8

What if my start date is the 31st of the month?

Accepted Answer

The scheduler clamps to the last day of any month that doesn't have a 31st. So a January 31 start becomes February 28 (or 29 in leap years), March 31, April 30, and so on. If you'd rather lock to the 1st, the 15th, or the last day every month, switch the day-of-month preference instead of using "Same as start date."

#	Issue	Due	Amount
1	Nov 1, 26	Dec 1, 26	$2,000.00
2	Dec 1, 26	Dec 31, 26	$2,000.00
3	Jan 1, 27	Jan 31, 27	$2,000.00
4	Feb 1, 27	Mar 3, 27	$2,000.00
5	Mar 1, 27	Mar 31, 27	$2,000.00
6	Apr 1, 27	May 1, 27	$2,000.00
7	May 1, 27	May 31, 27	$2,000.00
8	Jun 1, 27	Jul 1, 27	$2,000.00
9	Jul 1, 27	Jul 31, 27	$2,000.00
10	Aug 1, 27	Aug 31, 27	$2,000.00
11	Sep 1, 27	Oct 1, 27	$2,000.00
12	Oct 1, 27	Oct 31, 27	$2,000.00

Recurring Invoice Scheduler

Schedule