Automate Recurring Invoices

How recurring invoicing works

Start with a saved company and client, add the services you bill regularly, and choose a US or EU VAT format. You can also create a schedule from an existing invoice. Review the next-run preview, set payment due-term days, and save. Recurring invoicing is available on plans that include it; generated invoices count toward your monthly allowance.

Choose a schedule that fits your agreement

Use daily billing, a selected weekday for weekly billing, a day of the month for monthly or quarterly billing, or a month and day for yearly billing. Quarterly means every three months from your schedule’s cycle. Choose Last day for month-end billing; a selected 31st falls back to the final valid day in shorter months without losing your intended day.

Review timezone and due dates

Schedules use 09:00 in your selected timezone. The next-run preview shows the upcoming occurrence before you save. Payment due-term days are separate from the schedule: they set the due date relative to the generated invoice’s issue date.

Generate invoices and optionally email PDF attachments

Due schedules generate a new numbered invoice. If you enable customer email, the generated PDF is attached and sent to the saved recipient. Invoices for the same sender, company, recipient and issue date may be grouped in one message. After sending, review the schedule’s email activity, then continue, edit or pause billing as your agreement changes.

Track recurring invoice email activity

Open Recurring and select Statistics beside a schedule to review its Sending statistics page. The summary distinguishes email batches from transport attempts, including retries, and shows sent batches, failed batches and detected opens. Sent means accepted by the mail transport, not confirmed inbox delivery. Email activity is separate from invoice generation and payment status: an email send or observed open does not mean an invoice has been paid.

Review recurring invoice email history

The schedule’s history lists attempted and sent times, recipient, invoice numbers, status, first and last detected open times, and an Opens count for each email attempt. The summary’s Opens detected counts sent emails with an observed open, while each history row counts tracking-image requests. Times use the schedule’s timezone. History begins when tracking was enabled; an email containing several invoices appears on each included schedule.

Understand observed email opens

An observed open is recorded when the email’s tracking image is requested. It is a useful activity signal, not proof that a human read the message or opened an attached PDF. Blocked images can hide opens; privacy protections, image preloading, caching and email-client proxies can obscure or register activity. Open tracking is not reliable in every email client, and the count is not a count of unique readers.

Repeat freelance services and consulting retainers

A freelancer can schedule a fixed monthly maintenance service; a consultant can bill an agreed retainer with clear line items and payment terms. Review amounts when the agreement changes. These are recurring invoice uses, not a separate timesheet or retainer-balance system.

Keep control when work changes

Edit or pause a schedule when services or fees change. Recurring emails include an unsubscribe link with a confirmation step. Confirming unsubscribe suspends matching active recurring schedules for that sender and recipient, stopping future invoice generation and scheduled email from those schedules. Existing invoices and schedule records remain; this does not disable every application email or affect another sender’s schedules.

Frequently asked questions

Does a recurring invoice automatically charge my client?

No. A schedule generates invoices and can email PDFs. It does not charge a bank account or card. Your customer pays using the instructions or external payment link you provide.

Can I use monthly or last-day billing?

Yes. Monthly and quarterly schedules support a day from 1–31 or Last day. Yearly schedules also include a month selection.

Can I email every invoice I create?

Optional customer email delivery is part of recurring invoicing. Ordinary one-off invoices can be previewed and downloaded; they do not have a direct email action.

Is recurring invoicing included on every plan?

No. Choose a plan that includes recurring invoices and review its current invoice allowance on Pricing.

Can SimpleInvoicePDF email recurring invoices automatically?

Yes. Enable optional customer email on a recurring schedule to send generated PDF attachments to its saved recipient. Invoice generation and email sending are separate steps; recurring invoicing depends on your plan and allowance.

Can I see whether a recurring invoice email was opened?

The schedule’s Statistics page shows Opens detected and first/last observed open times and counts. These signals come from requests for the tracking image. Blocked images, privacy protections and proxies can affect them, so they do not prove human readership, PDF viewing or payment.

Can I see failed recurring invoice emails?

Yes. Sending statistics includes Failed and a history of attempt statuses. Sent means accepted by the mail transport; it does not guarantee delivery to the customer’s inbox.

Can customers unsubscribe from recurring invoice emails?

Yes. A confirmation link in the email lets the recipient unsubscribe from that sender’s recurring emails. Matching active schedules are suspended, stopping future invoice generation and scheduled email from them. Existing invoices and schedules are not deleted, and other senders’ schedules are unaffected.