Your invoice is 60 days past due. Here’s the playbook.

First, the honest picture at day 60

An invoice two months past due is no longer “running a bit late” — something is wrong. Roughly, you’re facing one of four situations: the customer has a cash-flow problem and is quietly triaging vendors; the invoice has a dispute or confusion nobody surfaced; the invoice is genuinely lost in their process (common with larger customers and AP departments); or you’re being strategically slow-paid by someone who’s learned there are no consequences.

The good news: most 60-day invoices are still very collectible. But the approach that works now is different from the approach at day 10 — and continuing to send the same friendly reminder actively hurts, because it confirms there are no consequences.

Step 1 — get your file straight (30 minutes)

Before any escalation, assemble the record. If this account ever reaches collections, an attorney or small-claims court, this file is the difference between recovering and writing off:

• The original invoice, the quote or contract behind it, and proof of delivery or completion (photos, sign-offs, timesheets).
• Every communication about the invoice so far, with dates — emails, texts, call notes.
• Any partial payments or promises to pay, in writing if they exist.
• Confirm the invoice details are actually right — amount, PO number if required, correct billing contact. A surprising share of “deadbeat” invoices are stuck on a wrong PO number.

Step 2 — change the channel and the posture

Sixty days of emails haven’t worked, so stop leading with email. Call. Ask for a specific person, not the info@ inbox. The script is calm and concrete: “Invoice 1042 for $4,250 is now 60 days past due. I need to know when it will be paid.” Then stop talking. You’re not asking whether they intend to pay — you’re asking for a date.

Follow the call with a same-day email that confirms whatever was said (“Per our call today, you’ll be paying invoice 1042 in full by July 30”). Verbal promises evaporate; written confirmations become part of the file. Every promise gets a diary date — and if the date passes unpaid, escalation continues immediately, not two weeks later when you remember.

Step 3 — the statement of account and the deadline letter

If calls don’t produce a date (or the date passes), send a statement of account: a formal summary of everything owed, days past due, and payment instructions. It reads as process, not emotion — which is exactly the signal you want: this business tracks its receivables and escalates on a system.

The next touch sets a specific deadline with a stated consequence: pay by a date, or the account is referred for further action. Only say it if you mean it — a stated consequence that doesn’t happen teaches the customer that none of your deadlines are real. And a hard rule at every step: stay factual, never threaten anything beyond what you’ll actually do, and stop the ladder immediately if they dispute the bill — a disputed invoice is a conversation, not a collection.

Step 4 — the 90-day decision

If a documented, escalating sequence hasn’t produced payment or a kept promise by around 90 days, you’ve reached the handoff decision. The options, roughly in order of cost: a licensed collections partner (contingency fee, but your file does the heavy lifting); small-claims court for amounts within your state’s limit (cheap filing, but your time isn’t free); or an attorney demand letter for larger balances. What you should not do is let the invoice quietly age past a year while you “stay on it” — recovery odds fall with every month, and old anger is expensive to maintain.

This is also the moment to decide about the customer, separately from the invoice: some accounts deserve prepay-only terms going forward; some deserve to be fired. Collecting the money and keeping a serial slow-payer on the same terms just schedules the next 60-day invoice.

The part nobody says out loud

Almost every 60-day invoice was a 5-day invoice once, and most of them reached 60 because follow-up happened in spare moments that a busy month deleted. The playbook above works — but the version of this problem you actually want is the one where a systematic cadence started on day 3, escalated on schedule, documented itself, and made this guide unnecessary. That’s a system, not a resolution — and it’s exactly what JMJ Billings automates, from first courtesy reminder to documented collections handoff at half the standard agency rate.