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Fri 16 Oct 18:55 UTC
AI Toolsevaluationupdated 02 Sept 2026

planning-with-files review

Planning with Files is a Claude Code plugin and cross-agent skill that keeps an AI coding task's plan, findings, and progress in three Markdown files instead of trusting the conversation alone. Lifecycle hooks can put the active plan back into the agent's context after `/clear`, compaction, or a crash, while optional attestation and completion checks govern longer runs.

+88stars / 7d
Verdict

Our Planning with Files run installed 35 packages in 26 seconds and built cleanly, but the 123-second suite ended with 1 failed test and 1 collection/setup error. It suits developers who regularly lose active task state to compaction and will verify the hooks on each agent host. Skip it if three workspace files, prompt injection from local plan text, or host-specific lifecycle behavior are unacceptable.

We ran it

Lab card: what happened when we ran planning-with-filesScreenshot of planning-with-files (www.skills.sh/othmanadi/planning-with-files/planning-with-files)
Install✓ · 7s35 packages · 37 MB
Build✓ · 1s
Tests✗ · 241s883 passed · 0 failed · 278 skipped · 1 errors of 884 (pytest)
Known vulns0(pip-audit)
Repo738 files~143,124 lines of source · 31.1 MB · 3 CI workflows · tests dir

Answers from our run

Does planning-with-files build from source?

Dependencies installed in 7 seconds (35 packages), and the build succeeded in 1 seconds. We cloned commit dab9d16 into a clean Debian container with 3 CPUs and no project-specific setup.

Do planning-with-files's tests pass?

Yes: 883 of 884 passed when we ran the project's own test command (pytest), with 1 collection error. Some failures need services or credentials a bare container does not have.

Does planning-with-files have known vulnerabilities in its dependencies?

pip-audit found none in the dependency tree at the time of our run.

Who should not use planning-with-files?

Anyone seeking general agent memory: automatic recovery reads the 3 project files, while session metadata or replay requires an explicit catchup command.

What are the alternatives to planning-with-files?

Taskmaster, Superpowers, Claude Squad. Our Planning with Files run installed 35 packages in 26 seconds and built cleanly, but the 123-second suite ended with 1 failed test and 1 collection/setup error.

Setup3/526-second install, but hook setup varies by host
Docs5/5Install routes, hooks, recovery, and security boundaries are explicit
Community5/526,563 stars with same-day issue fixes and a September push
Maturity4/5v3.12.1 is active, though our full suite did not pass

Who it’s for

Claude Code, Codex, Pi, or Hermes users running tasks long enough to outlive one context window.
Teams that want active task state recorded in plain Markdown beside the work.
Multi-agent operators who need separate plan directories and a shared event ledger without another service.
Developers willing to verify hook behavior with plan-doctor on every host they use.

Who it’s NOT for

Anyone seeking general agent memory: automatic recovery reads the 3 project files, while session metadata or replay requires an explicit catchup command.
Claude Code teams that need startup recovery from a skill-only install: the installation guide says that route has no SessionStart hook and its hooks register only after invocation.
Gemini CLI users who need PLANNING_DISABLED=1 for unrelated jobs in a shared directory: the v3 README says the Gemini route does not honor that switch.
Organizations that cannot allow plan text into model context: the security policy says selected planning data may reach the host's configured provider.
Teams that require automatic task archives: completed root files are overwritten by the next task, and completed slug directories are left inactive rather than archived.
Developers requiring a fully green cross-platform suite before adoption: our run had 1 failed BSD simulation and 1 Claude plugin collection/setup error.

Setup reality

Our sandbox at commit 2d98d31 installed 35 packages in 26 seconds and used 37 MB. The 632-file, 15.2 MB checkout held about 84,244 source lines; its build succeeded in 5 seconds. Tests failed after 123 seconds: 541 passed, 1 failed, 75 skipped, and 1 collection/setup error was reported, with 645 subtests passing. Pip-audit found 0 known vulnerabilities.

Basic use needs no hosted credential or separate server; the skill writes 3 Markdown files in the project. The full Claude Code plugin route adds hooks and slash commands. An npm install carries the skill, scripts, and templates but does not register hooks, while a project-level standalone skill needs trust approval and session activation.

The failed BSD simulation expected a nonce-framed plan block, but stdout was empty. tests/test_claude_plugin_operations.py also stopped during collection/setup; the log tail gives no cause. Host behavior varies, and the README says the Gemini route does not honor PLANNING_DISABLED=1.

Three Markdown files hold the live task state

Planning with Files creates 3 files in the working project: task_plan.md, findings.md, and progress.md. The plan tracks phases and checkboxes, findings holds decisions or research, and progress records actions and test results. Hooks can read selected parts back into the coding agent after /clear, compaction, or a crash. For parallel work, the same 3-file set can live under a dated .planning/<slug>/ directory instead of sharing the project root.

This is active execution state rather than a general memory store. The skill's trigger rule covers tasks needing at least 3 steps or 5 tool calls, and automatic recovery reads project planning files only. Reading local session records requires an explicit metadata or bounded replay mode. The 632-file checkout reflects that narrow goal, and anyone expecting old conversations, preferences, or unrelated project knowledge to reappear automatically will be disappointed.

The Claude plugin gets 6 hooks; npm gets none

The v3 Claude Code plugin registers 6 lifecycle hooks for startup recovery, prompt-time injection, tool reminders, pre-compaction flushing, and stop checks. It also supplies slash commands such as /plan, /plan-doctor, and /plan-attest. Codex, Pi, and Hermes have their own integrations, while the README lists lighter Agent Skills installs for many other clients. Check which integration tier your host receives instead of relying on its presence in a platform table.

An npm install delivers the skill, scripts, and templates without registering hooks. The npx skills add and manual Claude routes have no SessionStart recovery, no bundled slash commands, and activation-scoped hooks that appear only after the skill is invoked. Project-level skills also depend on the trust dialog. Installation took 26 seconds in the lab; run plan-doctor afterward to prove the intended injection path is active.

What happened when we ran it

Our sandbox cloned commit 2d98d31 into an unprivileged Debian container with 3 CPUs and 8 GB of RAM. The 632-file checkout was 15.2 MB and contained about 84,244 source lines. Installation succeeded in 26 seconds, added 35 packages, and occupied 37 MB. The build then succeeded in 5 seconds. Those are modest costs for a project that ships shell, PowerShell, Python, and host-specific integration files.

The full test command failed after 123 seconds. Pytest reported 541 passed, 1 failed, 75 skipped, and 1 collection/setup error out of 543, plus 645 passed subtests. The failing BSD-userland simulation expected a nonce-framed plan block in stdout and received an empty string. tests/test_claude_plugin_operations.py also stopped during collection/setup. The log tail does not establish either cause, so we cannot claim a missing package or a product defect from this run alone.

Pip-audit found 0 known vulnerabilities among the 35 installed packages. The checkout had a tests directory and 3 CI workflow files, but no Dockerfile. That fits a plugin and skill bundle more than a standalone service. It also means a container image is your responsibility if reproducible packaging matters. Our measurement covers v3.12.1 commit 2d98d31 in one fresh Linux container, not every client and operating system named in the README.

SHA-256 attestation checks the active plan body

The v3 attestation path stores a SHA-256 for task_plan.md, and injection refuses a body that no longer matches the approved hash. At tested commit 2d98d31, the parallel-write guard separately warns when checked items or completed phases decrease between hook runs. These checks address silent plan replacement and clobbered progress. They do not make copied planning text trustworthy: the security policy tells users to treat external plan content as untrusted because selected data is inserted into model context.

The default Stop behavior is advisory, while gated mode may request continuation on hosts that support it. The gate reads plan status and ledger progress, has a default cap of 20 consecutive blocks, and never executes commands written in Markdown. Our 123-second suite did not establish that behavior on every host. Operators can pin a plan with PLAN_ID, bind a thread with PWF_PLAN_ROOT, or attach sessions inside .planning/sessions/.

Completed root plans are overwritten instead of archived

The project gitignores 3 files in the root plus the .planning/ directory. Finishing a task does not create an archive: the next root task overwrites those files, while a completed slug directory simply stops being active. The 632-file checkout includes no automatic retention step. Important decisions therefore need promotion into source, a commit, or maintained documentation. Teams that need a durable audit trail must decide whether retained plans belong in version control.

A one-shot job can opt out with PLANNING_DISABLED=1 on most v3 routes, which matters when several agents share a working directory containing an unfinished plan. The README says the Gemini integration is behind and does not honor this setting. The 3 CI workflow files in our checkout do not remove that host difference. Plan selection still needs care when operators leave stale pointers or share a root.

v3.12.1 fixed nested attestation on the report day

Issue 234 reported on August 31, 2026 that running the attestation helper inside .planning/<slug>/ could update the wrong file while returning success. Release v3.12.1 shipped later that day with a fix and cross-platform adjustments; that release is also commit 2d98d31 from our sandbox. Issue 231, a published-package line-ending problem affecting Linux and macOS shell scripts, was closed the day after its August 28 report. Both received quick maintenance.

GitHub recorded 26,563 stars, 8 combined issues and pull requests, and a last push on September 2, 2026. That activity supports trying the project, while our 541 passing tests show that much of its host matrix is exercised. The failed BSD simulation and Claude plugin setup error keep the recommendation conditional: choose Planning with Files when forgotten execution state is already wasting time, then test the exact installation route your team will run.

Alternatives

ProjectWhat it isPick it when
Taskmaster gh↗An AI task manager with dependencies, workstreams, CLI commands, and MCP tools.pick this instead when you need a richer task graph and provider-backed research rather than three local planning files.
Superpowers gh↗A skills-based development method covering design, planning, testing, and subagent execution.pick this instead when you want a prescriptive software workflow rather than a narrow persistence layer.
Claude Squad gh↗A terminal manager that runs multiple coding agents in isolated Git workspaces.pick this instead when session isolation and parallel worktree management matter more than shared Markdown state.

Sources

  1. Planning with Files repository and README
  2. Planning with Files installation guide
  3. Planning with Files security policy
  4. Planning with Files v3.12.1 release
  5. Nested attestation issue 234
  6. Published shell line endings issue 231
  7. Measured commit 2d98d31

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