How a Weekly Dry-Run Caught Our freee OAuth Token Expiry Before Month-End

Nothing is worse than discovering your automation script is broken on the day of the month-end deadline. Here's how I built a weekly dry-run to prevent exactly that. Background: Our Month-End Automation Stack At TechsFree, we automate a series of tasks at the end of every month: Time Task 17:00 Hajimari timesheet auto-entry (Playwright) 18:00 Identity work report + invoice Google Forms auto-submit (CDP) 19:00 Edge-tech invoice email preview These directly impact company revenue and payments. What used to take 2–3 hours of manual work every month is now fully automated. Tech stack: Playwright + Chrome CDP → browser automation for web services freee API → receipt OCR, transaction registration, invoice data Python / Node.js → 9 automation scripts SSH → remote execution on internal servers OpenClaw cron jobs → auto-trigger on the last business day of each month The Problem: Breakage Stays Hidden Until Month-End There's a critical flaw in this setup: each component only runs once a month .