Menu

Individual skill

os-what-could-go-wrong

ALWAYS invoke this skill before anything hard to undo gets agreed to - a contract, a purchase, a migration, a launch, a price change, a reorganisation - and whenever the user asks "what could go wrong", "what are we missing", "poke holes in this", or for a premortem or a red team, in any language. Assumes the decision already failed and works backwards to find out why, in a fresh agent that had no hand in making it. Sweeps nine areas and shows what each produced, including the empty ones. Ends on one verdict: go ahead, go but fix these first, try it small first, think again, do not do this.

skills/os-what-could-go-wrong/SKILL.md

Read pinned source

Source commit 4fa744ba8ea06ccf128a39853824c46ac391dd00

What was checked

Matches the observed repository HEAD
Yes
Scanner rules are current
No
Repository scan complete
No
Skill scan complete
No
Observed behavior
Not checked yet
Last checked
Nov 3, 2026

These are observations at the recorded commit, not a guarantee of safety. Review the source before running it.

Install this skill

Choose an agent in your Stack or copy a command below. Commands fetch the pinned commit and copy only this skill directory. Existing destinations are refused. Copying a command does not install anything.

An install command is unavailable: current rules, complete repository and skill scans, an eligible behavior level and a permitted license are required.

Repository context

Repository stars (not skill ratings)
1,279
Repository last updated
Oct 5, 2026
License
MIT

Observed agent integration: No specific integration evidence. Standard SKILL.md installation does not imply verified compatibility.

Files and excerpt

File metadata and permitted, redacted excerpts come from the recorded scan. Source links are pinned to that commit.

Browse files
Read excerpt

# os-what-could-go-wrong

Assume it already failed, then work backwards to find out why - while there is
still time to change it. The attack runs in a fresh agent that had no part in
the decision, because an agent that helped shape one reviews it far too
gently: it defends its own reasoning, and it misses the thing that kills the
plan out of politeness.

`os-ask-simple` screens a choice before the user picks one. This one runs
after the choice is made and before it can no longer be taken back.

## Language

Write in the language the user speaks in this session, detected from the