feat(cli): CLI-to-Web upgrade flow with entitlement storage (#405) by Prateeks16 · Pull Request #444 · sreerevanth/AgentWatch

Prateeks16 · 2026-06-19T17:01:45Z

Closes part of #405 (CLI client slice).

Stacked on #443 (#406). This branch builds on the RS256 entitlement verification from #406, so the diff currently includes those files until #443 merges. Review #443 first.

What

Adds the client side of the premium monetization flow: a CLI command that hands off to web checkout and stores the resulting entitlement.

Changes

agentwatch upgrade — generates a short-lived, single-use checkout session token and opens the browser to the hosted checkout portal, passing the token so the web flow can bind the entitlement back to this CLI run. After paying, the user runs agentwatch upgrade --activate <token> to verify (RS256) and store the entitlement. --status shows the current tier; --no-browser / --dry-run for headless use.
checkout.py — new_session() (random secrets token + 10-min expiry) and checkout_url().
entitlement_store.py — persists/loads the entitlement token in ~/.agentwatch/config.toml. Every load re-verifies cryptographically, so a hand-edited or tampered store simply falls back to free tier — storage is not the security boundary.
_ensure_premium(feature) — feature gate that prompts agentwatch upgrade on free tier.

Acceptance criteria mapping (#405)

✅ Running a premium feature on free tier prompts the user to upgrade (_ensure_premium).
✅ agentwatch upgrade opens the browser to the payment portal.
✅ The CLI receives and stores the premium entitlement token post-payment (--activate → verified → config.toml).
⏳ Payment-gateway processing and webhook provisioning are backend concerns — out of scope for this client PR.

Test

pytest tests/test_monetization.py   # 12 passed
ruff check                          # clean

Note for maintainers (pre-existing, not introduced here)

Cold import agentwatch.cli.main fails with a circular import (governance ↔ tracing.collector), and agentwatch/cli/main.py registers two Typer groups named session. Both reproduce on main independent of this PR; flagging for a separate fix. Existing test_cli_api_key / test_cli_export failures on Windows are also pre-existing.

🤖 Generated with Claude Code

…forcement (sreerevanth#406) Add the client-side verification primitive for premium entitlements: a JWT signed by the backend with an RS256 private key, verified by the CLI against the matching public key. Asymmetric signing means the client holds only the public key and cannot mint its own tokens, so premium gating becomes a signature check rather than a patchable boolean. - verify_entitlement(): RS256-only decode, required claims, expiry, and optional machine binding; fails closed if PyJWT is unavailable. - current_machine_id(): stable, hashed device fingerprint for binding. - require_feature(): entitlement-gated feature check (no bare boolean). - pyjwt added to the optional `crypto` extra. Scope: client verification + device binding only. Server-side enforcement and token issuance are tracked in sreerevanth#405. Co-Authored-By: Claude Opus 4.8 <noreply@anthropic.com>

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📥 Commits

Reviewing files that changed from the base of the PR and between e3012c5 and 1721805.

📒 Files selected for processing (8)

agentwatch/cli/main.py
agentwatch/security/checkout.py
agentwatch/security/entitlement_store.py
agentwatch/security/license.py
pyproject.toml
tests/test_cli_export.py
tests/test_license.py
tests/test_monetization.py

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github-actions · 2026-06-19T17:02:53Z

🧪 PR Test Results

Check	Result
Tests (`pytest tests/`)	✅ success
Lint (`ruff check .`)	✅ success
Coverage (`agentwatch`)	73.76%

_{Python 3.12 · commit 1721805}

Co-Authored-By: Claude Opus 4.8 <noreply@anthropic.com>

…lement (sreerevanth#406) Guard the 'sub'/'tier'/'features' claims so a malformed token raises LicenseInvalidError at the boundary instead of an uncaught TypeError, preserving the typed error contract. (exp is already validated as numeric by PyJWT during decode.) Adds regression tests for non-numeric exp, non-string tier, and non-iterable features. Addresses CodeRabbit review feedback on sreerevanth#443. Co-Authored-By: Claude Opus 4.8 <noreply@anthropic.com>

…nth#405) Add the client side of the premium monetization flow, paired with the RS256 entitlement verification from sreerevanth#406. - agentwatch upgrade: generates a short-lived, single-use checkout session token, opens the browser to the hosted checkout, then stores the entitlement token returned via --activate (verified before save). --status shows the current tier; --no-browser/--dry-run for headless. - checkout.py: session-token handoff + checkout URL builder. - entitlement_store.py: persists/loads the entitlement in ~/.agentwatch/config.toml; every load is cryptographically verified, so a tampered store falls back to free tier. - _ensure_premium(): feature gate that prompts upgrade on free tier. Scope: CLI client only. Payment-gateway processing and webhook provisioning are backend concerns (out of scope here). Co-Authored-By: Claude Opus 4.8 <noreply@anthropic.com>

Co-Authored-By: Claude Opus 4.8 <noreply@anthropic.com>

…erevanth#405) Pre-existing bug surfaced by CI: `agentwatch/cli/main.py` reassigned `session_app` to a fresh `typer.Typer(name="session")` near the rollback/ prune definitions and re-registered it, so the "session" group resolved to that partial group and `session export` / `session list` failed with "No such command 'export'" (10 failing tests). Remove the stray reassignment and an earlier empty duplicate so all session subcommands share one group. Also fix test_export_invalid_format, which read result.stderr (not separately captured by this Click version) — use result.output. Co-Authored-By: Claude Opus 4.8 <noreply@anthropic.com>

Copilot AI review requested due to automatic review settings June 19, 2026 17:01

Copilot AI reviewed Jun 19, 2026

style: apply ruff format to license module (sreerevanth#406)

ddcd72c

Co-Authored-By: Claude Opus 4.8 <noreply@anthropic.com>

Prateeks16 force-pushed the feat/monetization-upgrade-405 branch from f411898 to ccead56 Compare June 19, 2026 17:04

Prateeks16 and others added 4 commits June 19, 2026 22:39

style: apply ruff format to upgrade command (sreerevanth#405)

5607d20

Co-Authored-By: Claude Opus 4.8 <noreply@anthropic.com>

Prateeks16 force-pushed the feat/monetization-upgrade-405 branch from ccead56 to 1721805 Compare June 19, 2026 17:15

Prateeks16 mentioned this pull request Jun 19, 2026

fix: break governance↔tracing circular import on cold CLI start #445

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sreerevanth added the not-ready-to-merge label Jun 20, 2026

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feat(cli): CLI-to-Web upgrade flow with entitlement storage (#405)#444

feat(cli): CLI-to-Web upgrade flow with entitlement storage (#405)#444
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Prateeks16 commented Jun 19, 2026

What

Changes

Acceptance criteria mapping (#405)

Test

Note for maintainers (pre-existing, not introduced here)

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