I'm going to offer a counterpoint suggestion. You need to watch Claude try to implement small features many times without planning to see where it is likely to fail. It will often do the same mistakes over and over (e.g. trying to SSH without opening a bastion, mangling special characters in bash shell, trying to communicate with a server that self-shuts down after 10 minutes). Once you have a sense for all the repeated failure points of your workflow, then you can add them to future plan files.
An approach that's worked fairly well is asking Codex to summarize mistakes made in a session use the lessons learned to modify the AGENTS.md file for future agents to avoid similar errors. It also helps to audit the AGENTS.md file every once in a while to clean up/compact instructions