Workspace Bootstrap

Use this skill when the task is to make a DocMason workspace ready for use, or when ask has discovered that the workspace is not yet ready for a safe answer path.

This is also the correct first explicit setup workflow when the current agent is not running on the native Codex path and needs to determine whether adapter-specific guidance should be refreshed.

Required Capabilities

• local file access
• shell or command execution
• ability to inspect command output

If the agent cannot perform these capabilities, stop and explain that the environment is not capable enough for the workflow.

Procedure

1. Inspect runtime/bootstrap_state.json when it exists.
   • if it already says the current workspace root is ready and .venv still exists, do not rerun deep bootstrap work by default
   • if it belongs to another workspace root, treat that as a moved-repo repair case
   • treat self-contained as the only ordinary ask-time ready environment grade
     • in practice this means the repo-local steady-state runtime is trusted for ordinary work
   • treat mixed and degraded as repair-needed states
2. If .venv is absent or docmason is not yet runnable from the repo-local environment, start with:
   • ./scripts/bootstrap-workspace.sh --yes
   • add --json when machine-readable output helps
   • on native Codex ordinary cold starts, treat ./scripts/bootstrap-workspace.sh --yes --json as the single governed mutation surface before ask-time workspace work can continue
   • the launcher should run a capability-aware preflight first, then either continue silently or stop once with a structured host-access-upgrade boundary
   • in Codex Default permissions, the ordinary path should use repo-local bootstrap cache only; it should not probe shared user cache paths first
   • the launcher should prefer the controlled UV bootstrap asset path for ordinary native cold starts instead of broad local-machine Python scavenging
   • the launcher may honor an explicit DOCMASON_BOOTSTRAP_PYTHON override for operator repair, but that is not the ordinary first-run path
3. Once the launcher succeeds, prefer the repo-local environment for subsequent commands:
   • ./.venv/bin/python -m docmason doctor --json
   • ./.venv/bin/python -m docmason prepare --json --yes
   • or the docmason executable installed inside .venv
4. Run docmason doctor --json when you need a readiness snapshot after launcher completion or on an already prepared workspace.
5. Run docmason prepare --json --yes when the launcher was not used, or when bootstrap needs an explicit rerun to repair or complete the repo-local environment.
6. If prepare reports a degraded result, follow the reported next steps and rerun only the necessary deterministic command.
7. Use docs/setup/manual-workspace-recovery.md only when the launcher or prepare still cannot finish honestly after the governed automatic path has already had enough access.
8. If the corpus already contains PPTX, DOCX, or XLSX files and LibreOffice is missing or detected but unusable:
   • LibreOffice is required only for an Office-rendering corpus; it is not a universal machine baseline dependency
   • on macOS with Homebrew already present, DocMason may use brew install --cask libreoffice-still
   • on macOS without Homebrew, DocMason should use the official LibreOffice installer path instead of trying to install Homebrew first
   • on macOS, if LibreOffice is already detected but fails the governed smoke probe, prepare --yes should treat that as a repair or reinstall case rather than as a fake ready state
   • on Linux, install LibreOffice with the distro package manager or the official packages, then ensure soffice is on PATH
9. Run docmason status --json when you need to confirm the resulting workspace stage.
10. Recommend docmason sync --json when source files are present and the user needs a usable knowledge base next.
11. If the current agent ecosystem is a compatibility target such as Claude Code rather than the native Codex path, decide here whether generated adapter guidance is needed.
12. Recommend docmason sync-adapters --json only when the current agent ecosystem depends on generated adapter files or those files are missing or stale.
13. Once .venv exists, prefer the repo-local interpreter for subsequent repository commands instead of switching back to an arbitrary system Python.
14. Return the final readiness judgment to the main agent. Do not delegate environment sign-off.

Escalation Rules

• If the platform or Python version is unsupported, stop and surface that blocker directly.
• If prepare can only proceed through a higher-intrusion install step, explain it explicitly rather than hiding it inside automation.
• If system-level installation requires additional permissions, request them when the current platform supports that flow; otherwise give the user the exact command or GUI step to run.
• On native Codex/macOS, if the thread is still in Default permissions and higher access is required for downloads or machine-level setup, stop once with an explicit Full access upgrade instruction. After Full access is available, continue through the governed automatic repair or reinstall path instead of stopping at diagnosis alone.
• For Claude Code or another compatibility host, keep the fallback wording short and host-generic; do not expand it into a second native bootstrap story.
• Deterministic shell setup steps may run as background or main-agent commands, but the final environment judgment returns to the main agent.

Completion Signal

• The workflow is complete when prepare and follow-up readiness checks leave the workspace ready, or when an actionable environment blocker has been surfaced to the main agent.

Notes

• prepare bootstraps repo-local state only.
• ./scripts/bootstrap-workspace.sh --yes is the preferred zero-to-working launcher from a raw checkout because it can prepare .venv before the package is importable from the src/ layout.
• The launcher now performs governed preflight first, then probes bootstrap-Python liveness in bounded time and prefers repo-local candidates before shared ones.
• The launcher and prepare now trust real LibreOffice smoke conversion, not only soffice --version, before declaring an Office-rendering machine baseline ready.
• runtime/bootstrap_state.json is the cached ready marker that ordinary ask-time work should reuse.
• The steady-state runtime is repo-local managed Python 3.13 under .docmason/toolchain/python/.
• On the native Codex path, bootstrap should refresh repo-local skill shims under .agents/skills/ rather than writing into ~/.codex/skills.
• prepare may use shared/system Python only as a bootstrap or repair helper; ordinary steady-state commands should not depend on it.
• When uv is missing, prepare should provision the repo-local bootstrap helper venv under .docmason/toolchain/bootstrap/venv and install uv there.
• On the native macOS path, ordinary cold starts should prefer the controlled UV bootstrap asset path first, use repo-local cache in Codex Default permissions, and auto-attempt only the real missing dependency installs when host access allows it.
• Homebrew is optional. If it is already on PATH, DocMason may use it as a convenience backend, but DocMason should not spend time installing or preparing Homebrew itself.
• After preparation, prefer ./.venv/bin/python -m docmason ... or the CLI installed inside .venv for ordinary workspace operations.
• For Office rendering, DocMason detects the standard macOS soffice path inside /Applications/LibreOffice.app/Contents/MacOS/soffice, so shell-profile changes are usually unnecessary.
• Not every Codex-first first-answer path requires sync-adapters before work can proceed.
• Avoid shell-profile mutation unless it is clearly required and explicitly explained to the user.
• Do not silently upgrade the host from Codex Default permissions to Full access; explain that boundary explicitly.