Add crash reporting to the CLI (frozen-gated, filtered) + fix latent config dep

[abrichr]

Context

Error reporting was removed in c1efbece — "refactor: Convert to meta-package architecture (#960)", which deleted openadapt/error_reporting.py and dropped the sentry dependency. It looks like collateral damage of the meta-package split, not a deliberate decision — so this re-adds it, built for the new thin-meta-package architecture.

(The GlitchTip dashboard noise that prompted this is from old external deployments running pre-refactor versions; separately triaged/muted. This PR is about restoring crash visibility for the current app, done right.)

What

• openadapt/error_reporting.py — initializes Sentry/GlitchTip from the CLI entry point.
  • Gated on sys.frozen (packaged build) by default — not the old fragile active_branch == "main" check. So dev / source / CI / headless runs never report (that source-run flooding is exactly what buried real issues, e.g. the admin123-nexus headless containers).
  • Master switch OPENADAPT_ERROR_REPORTING_ENABLED=0; force from source OPENADAPT_ERROR_REPORTING_FORCE=1.
  • before_send filter drops unactionable unsupported-environment errors (no display, wrong platform, broken native deps).
  • Never raises; no-op if sentry-sdk isn't installed.
• config.py — OPENADAPT_ERROR_REPORTING_{ENABLED,FORCE,DSN,ENVIRONMENT} settings; DSN defaults to GlitchTip openadaptai/openadapt (3798). (DSN public key is an ingestion key, not a secret.)
• cli.py — configure_error_reporting() in the main() group, covering all subcommands.
• pyproject.toml — add sentry-sdk; also add pydantic-settings, a latent missing base dep — config.py imported it but it wasn't declared, so a clean pip install openadapt couldn't import openadapt.config (masked in CI by a transitive install).
• tests/test_error_reporting.py — filtering + gating (8 tests, no network).

Validated

Clean-base venv install → import openadapt.config / openadapt.error_reporting OK, CLI import OK, 8 new tests pass, existing test_cli_smoke / test_import_integrity unaffected.

How to test reporting end-to-end

OPENADAPT_ERROR_REPORTING_FORCE=1 openadapt <cmd-that-errors> → event appears in GlitchTip 3798 (filtered for env noise).

Note

Supersedes #1004 (which targeted the abandoned feat/deploy branch — main had a different/removed structure). Closing that one.

🤖 Generated with Claude Code

[abrichr]

Triage 2026-07-17 — assessed against the post-#1012/#1013/#1014 launcher. Recommend CLOSE (superseded by the architecture, not by other code).

Rationale:

1. The gate can never fire in the current distribution. Reporting is (correctly) gated on sys.frozen, but OpenAdapt now ships as wheel + sdist only (1.6.x releases have no frozen binaries), so the shipped artifact would never report — the PR is a no-op for users except via the FORCE env var.
2. It cuts against the thin canonical-launcher role. Post-fix: version reads from metadata + doctor core/optional sets + pyproject description #1013/feat: make OpenAdapt the canonical openadapt-flow launcher #1014, runtime deps are deliberately just click + openadapt-flow; adding sentry-sdk (+ pydantic-settings) as hard deps of the meta-launcher expands the supply-chain surface for a wire that can't fire.
3. The branch is 3 weeks stale against a rewritten cli.py/config.py/pyproject (CONFLICTING); a rebase would be a substantial rewrite.
4. Where crash reporting will actually pay off is the frozen desktop bundle — the openadapt-desktop Tauri shell + PyInstaller engine sidecar. The frozen-gated + filtered design from this PR is the right template to port there when those builds go out to users.

Salvageable nugget worth a tiny separate PR if desired: openadapt/config.py on main still imports pydantic_settings, which is not a declared dependency — either declare it or make the import lazy/optional (nothing in the CLI imports openadapt.config today, so it only breaks direct imports on a clean install).