Ageing a draft is a way to lie to yourself. The customer has not seen it. Watchtower therefore only evaluates sent unpaid invoices.
That single rule aligns the inbox with how cash actually behaves. Unsent finals do not belong in “overdue.” Neither do invoices you are still arguing internally.
A typical cadence is boring on purpose: a clear reminder, something firmer, a final notice. Automatic email is optional and should stay off until billing contacts are real. Bouncing into nowhere for sixty days is worse than silence.
The sequence stops when the invoice is paid. The failure mode is not “AI too aggressive.” The failure mode is chasing a wire that arrived last Tuesday because nobody matched the deposit.
In a shipment workspace the account is a shipper. Freight invoices without payment terms are due on the invoice date so they still receive a suggested next step instead of sitting in a pile with no due date and no suggestion.
Suggested next steps are for operators. Approve them. Edit them. Send them from a person when the relationship requires a person. The agent is not the relationship.