Recurring Invoices: The Complete Guide for Subscription Businesses

What Are Recurring Invoices?

Recurring invoices are automated invoices that are generated and sent to clients on a regular schedule—weekly, monthly, quarterly, or annually. Instead of manually creating the same invoice every month, you set it up once and let the system handle the rest.

Who Needs Recurring Invoices?

Recurring invoices are essential for businesses with predictable, repeating revenue streams:

• Freelancers with retainer clients: Monthly design, development, or consulting retainers
• SaaS companies: Monthly or annual software subscriptions
• Service providers: Bookkeeping, maintenance, hosting services
• Membership sites: Gym memberships, online courses, coaching programs
• Property managers: Monthly rent or lease payments
• Agencies: Ongoing marketing, SEO, or social media management

Benefits of Recurring Invoices

1. Save Massive Amounts of Time

Imagine you have 10 monthly retainer clients. Without recurring invoices, you spend 10-15 minutes per invoice = 100-150 minutes per month = 20 hours per year just on repetitive invoicing tasks. Recurring invoices reduce this to zero.

2. Never Miss an Invoice

Forgetting to send an invoice means delayed payment. Automated recurring invoices ensure every client is billed on time, every time.

3. Improve Cash Flow Predictability

When invoices go out automatically on the 1st of every month, you can predict your income more accurately and plan your business finances better.

4. Reduce Human Error

No more typos, wrong amounts, or calculation mistakes. Set it up once correctly, and every invoice will be perfect.

5. Professional Client Experience

Clients appreciate consistency. Receiving their invoice on the same day every month builds trust and makes payment planning easier for them too.

How to Set Up Recurring Invoices

Step 1: Choose Your Invoicing Software

Not all invoice tools support recurring invoices. InvoiceKit makes it easy with a dedicated recurring invoice feature that lets you:

• Set custom frequencies (weekly, monthly, quarterly, yearly)
• Choose specific billing dates (1st of month, 15th, last day, etc.)
• Auto-send emails when invoices are generated
• Pause or resume recurring invoices anytime
• Set start and end dates for fixed-term contracts

Step 2: Create Your Invoice Template

Set up the recurring invoice with all the details that will stay the same:

• Client information
• Service description (e.g., "Monthly Retainer - January 2025")
• Amount and tax rate
• Payment terms (e.g., "Due within 15 days")

Step 3: Configure the Schedule

Choose your billing frequency and settings:

• Frequency: Weekly, bi-weekly, monthly, quarterly, or yearly
• Start date: When should the first invoice be generated?
• End date: Leave blank for ongoing subscriptions, or set an end date for fixed contracts
• Day of month: For monthly invoices, choose which day (1st, 15th, last day, etc.)
• Auto-send: Enable to automatically email invoices to clients

Step 4: Set Payment Terms

Define when payment is due relative to the invoice date:

• Due immediately (0 days)
• Net 15 (15 days)
• Net 30 (30 days)
• Custom (any number of days)

Best Practices for Recurring Invoices

1. Communicate with Clients First

Before setting up recurring invoices, let your client know:

• What day they'll receive invoices
• The amount and what it covers
• Payment terms and methods
• How long the recurring billing will continue

2. Use Clear Descriptions

Make it obvious what the invoice is for. Instead of "Services," use "Monthly Website Maintenance - February 2025" or "Q1 2025 Retainer (January-March)."

3. Review Generated Invoices

Even with automation, periodically check that invoices are generating correctly. Verify amounts, dates, and client information.

4. Handle Scope Changes Promptly

If your retainer rate changes or services are adjusted, update the recurring invoice template immediately to avoid confusion.

5. Pause Instead of Delete

If a client is on vacation or taking a break, pause the recurring invoice rather than deleting it. You can easily resume when they're ready.

Common Recurring Invoice Scenarios

Monthly Retainer ($2,000/month)

Setup: Frequency = Monthly, Day = 1st, Due in = 15 days, Auto-send = Yes

Result: Invoice automatically generated and emailed on the 1st of every month, due on the 15th.

Quarterly Subscription ($1,500/quarter)

Setup: Frequency = Quarterly, Start = Jan 1, Due in = 30 days

Result: Invoices generated Jan 1, Apr 1, Jul 1, Oct 1 each year.

Weekly Service ($500/week)

Setup: Frequency = Weekly, Day = Monday, Due in = 7 days

Result: Invoice generated every Monday, due the following Monday.

Annual Membership ($1,200/year)

Setup: Frequency = Yearly, Start = Member join date, Due in = 15 days

Result: Invoice generated once per year on anniversary date.

Troubleshooting Recurring Invoices

Problem: Client Didn't Receive Invoice

Solutions:

• Check spam/junk folders
• Verify email address is correct
• Manually resend from your invoice dashboard
• Add your sending email to client's contacts

Problem: Wrong Amount Charged

Solutions:

• Update the recurring invoice template immediately
• Send a corrected invoice or credit note
• Communicate the change to your client

Problem: Need to Skip One Month

Solutions:

• Pause the recurring invoice temporarily
• Resume after the skip period
• Or adjust the next run date manually

Recurring Invoices vs. Subscription Payments

It's important to understand the difference:

• Recurring Invoices: Generate invoices automatically, but clients still need to pay manually (bank transfer, check, etc.)
• Subscription Payments: Automatically charge the client's credit card on file (requires payment processor integration like Stripe)

Many businesses use recurring invoices first, then upgrade to automatic subscription payments as they grow.

Start Automating Your Billing Today

Recurring invoices are one of the best time-saving features for any business with predictable revenue. Stop wasting hours on repetitive invoicing and start focusing on growing your business.

Ready to automate your billing? Try InvoiceKit's recurring invoices free and save hours every month. Set up your first recurring invoice in under 5 minutes!