Clippy performs “Microsoft Outage” in interpretive Dance
Look! Someone wrote a screenplay!
INT. REDMOND, BUILDING 34. 3:47 AM. A conference room that smells like cold pizza and regret.
Office 365 EVP: Talk to me. Why is Exchange still down?
MID-LEVEL MANAGER (Dave): So, good news and bad news.
EVP: Give me the good news.
DAVE: We found the service that’s failing.
EVP: Great. Who owns it?
DAVE: That’s the bad news. It’s called auth-bridge-final-v2-REAL. The commit history says it was written by “Copilot” and approved by “Copilot.”
EVP: Then get the engineer who prompted it.
DAVE: That was Priya. She was in the Q2 “efficiency realignment.”
EVP: Her backup?
DAVE: Also realigned. So was her backup’s backup. The whole team is a Slack channel now, and the only one in it is a bot that posts “🚀 LGTM” on every PR.
EVP: Fine. Then we read the code and fix it.
DAVE: We tried. It’s 340,000 lines of Python that calls a Rust binary that calls a PowerShell script that curls a Gist. The Gist’s README just says “dont touch this lol.”
EVP: Documentation?
DAVE: One Confluence page called “Architecture (TODO).” Last edited in 2024. The only content is a Mermaid diagram that fails to render.
EVP: Jesus Christ. Can we roll back?
DAVE: To what? The rollback pipeline was also vibe coded. The last time someone ran it, it rolled back to a version that only existed in the AI’s hallucination of what the service should look like.
EVP: So what the fuck have we actually been doing for nine hours?
DAVE: Rebooting servers one at a time and praying. Comms is calling that “restarting affected infrastructure.”
EVP: …Is there anyone left who understands how any of this works?
DAVE: Gary.
EVP: Who’s Gary?
DAVE: Contractor. 61 years old. He wrote the original Exchange routing logic in 2003 and he’s the only one who knows why there’s a sleep(7) in the auth handshake. We let him go in January, but HR forgot to disable his VPN.
EVP: Call Gary.
DAVE: Gary says his rate is now $900 an hour, with a 40-hour minimum, and he wants it in writing that he was right about everything.
EVP: …Pay Gary.
DAVE: Also, the board wants to know if this will affect the AI efficiency numbers for the earnings call.
EVP: Tell them the outage was caused by “an unexpected interaction during a routine change,” and that AI agents are “actively assisting with remediation.”
DAVE: Are they?
EVP: Copilot opened a ticket.
DAVE: What did the ticket say?
EVP: “Have you tried turning it off and on again?”
If there is an object-lesson here, it is about having a single point of failure.
(And you can read larger into that whatever you want about turning any operation over to Fancy Autocomplete.)