🧪 Help Test: Isolated Planning Sessions (experimental branch)

[OthmanAdi]

We just merged a big feature into the experimental branch and I need your help testing it before it goes to master.

What's New

Right now, planning files live in your project root:

task_plan.md
findings.md
progress.md

The new isolated planning feature puts each planning session in its own folder with a UUID:

.planning/
├── .active_plan
├── a1b2c3d4/
│   ├── task_plan.md
│   ├── findings.md
│   └── progress.md
└── e5f6g7h8/
    ├── task_plan.md
    ├── findings.md
    └── progress.md

Why This Matters

1. Multiple plans can run in parallel without overwriting each other
2. You can pin a terminal to a specific plan using PLAN_ID env var
3. Old plans stick around for reference
4. Less context pollution across different tasks

How to Test

git clone https://github.com/OthmanAdi/planning-with-files.git
cd planning-with-files
git checkout experimental/isolated-planning

Then copy the skill to your project and try it out. Run a few planning sessions, try opening multiple terminals, see if things break.

What I Need From You

1. Does it work on your system? (Mac, Linux, Windows)
2. Any bugs or weird behavior?
3. Does the .active_plan pointer work correctly?
4. Is the workflow intuitive or confusing?
5. Would you actually use this over the current root file approach?

Timeline

If we get solid feedback and no critical bugs in the next 2 weeks, this becomes v3.0.0.

This is a significant change to how the skill works so I want to get it right. Your testing helps make that happen.

Credit

This feature was contributed by @ciberponk in PR #77. Big thanks for the work.

Ahmad

[ciberponk]

Tested in production workflow today (2026-02-24) using the planning-with-files skill with isolated ./.planning/{uuid} sessions and PLAN_ID pinning. The workflow behaves as expected and avoids cross-task plan collisions in concurrent work. Also validated that plan artifacts (task_plan.md, findings.md, progress.md) are created and updated correctly.