When should I send the first past-due reminder?
Within a few days of the due date. Most invoices that are a few days late were missed, not refused, and a short, friendly reminder usually fixes it. Waiting a month makes the conversation harder and the invoice easier to forget.
How many reminders should I send before a final notice?
Three or four over 30 to 60 days is plenty, as long as each one moves things forward. After the first reminder, ask what's holding the invoice up instead of repeating that it's overdue. The answer tells you what to fix.
What subject line should a payment reminder use?
The invoice number and the due date. It tells the reader what the email is about, and it makes the thread easy to find when their AP team searches for it later.
Should I mention late fees?
Only if your contract or invoice terms include them, and only when you're prepared to apply them. Rules on charging interest on overdue invoices vary by state and country, so check yours before adding a fee to a reminder.
Should I reply in the same thread or start a new email?
Reply in the original thread whenever you can. It keeps the invoice, earlier replies, and any promised dates in one place, which makes it easier for the customer to act on.
Can these be sent automatically?
The first reminder can be. After that, what you send depends on the customer's reply: a missing PO, a new contact, or a short payment each need a different email. That's the part a reminder schedule can't handle.