diff --git a/.claude/rules/conventions.md b/.claude/rules/conventions.md index b8d3ed0..dc3ad9a 100644 --- a/.claude/rules/conventions.md +++ b/.claude/rules/conventions.md @@ -32,6 +32,17 @@ Extend `BaseSessionService` but don't fight the ADK contract. Override only the This keeps us compatible across the google-adk version matrix (1.22.0 through latest). Fighting the upstream contract creates brittle code that breaks on ADK updates. See [ADR-004: ADK Interface Compatibility Strategy](docs/adr/ADR-004-adk-schema-compatibility.md). +## The Sync/Async Boundary Is a High-Risk Zone + +Code that crosses the sync/async boundary — particularly `TypeDecorator` implementations (`process_bind_param`, `process_result_value`) and any `sync_encrypt`/`sync_decrypt` methods on backends — runs in SQLAlchemy's synchronous execution context despite the project's async-first design. This surface area consistently generates more code review findings than any other area. + +When writing or reviewing code in this zone: +- Verify the sync method does not call any `async def` or `await` expressions (SQLAlchemy will not await them) +- Confirm that blocking cryptographic operations in the sync path are acceptable for the call site (TypeDecorators run on the SQLAlchemy column serialization path, which is synchronous by design) +- Flag these stories for additional review attention — budget for more findings than usual + +See [ADR-002: Async-First Design](docs/adr/ADR-002-async-first.md) and Story 3-1 (AES-256-GCM backend) for context. + ## Own Our Schema Our SQLite schema (`app_states`, `user_states`, `sessions`, `events`) is derived from ADK's Session/Event data model contract with encrypted column types. Operationally independent — own tables, own migrations, own encryption — but structurally coupled to ADK's public model contract. All database access uses raw parametrized SQL via aiosqlite, not SQLAlchemy ORM. diff --git a/.claude/rules/dev-quality-checklist.md b/.claude/rules/dev-quality-checklist.md index c8d231e..c600376 100644 --- a/.claude/rules/dev-quality-checklist.md +++ b/.claude/rules/dev-quality-checklist.md @@ -32,6 +32,14 @@ Before marking a story or task done, verify every acceptance criterion has at le - When adding new fields or state keys, verify they round-trip through the full encrypt/decrypt cycle - Test that wrong-key decryption raises `DecryptionError`, not a generic exception +## Benchmark Story Ordering + +For stories that include benchmark measurement tables or performance claims: + +- Run the full benchmark suite and capture actual output **before** writing the results table — never project from a smaller payload or earlier run +- Tables in documentation must be populated from captured output, not estimates +- If hardware-specific factors apply (AES-NI, VAES, ARMv8 crypto), disclose the CPU model and relevant instruction sets alongside the ratios + ## Async Test Hygiene - Test fixtures that create services with DB connections (e.g., `EncryptedSessionService`) MUST call `await svc.close()` in teardown diff --git a/.github/dependabot.yml b/.github/dependabot.yml deleted file mode 100644 index 79c6a61..0000000 --- a/.github/dependabot.yml +++ /dev/null @@ -1,34 +0,0 @@ -# Dependabot configuration -# Weekly bumps for GH Actions and uv lock file -# See: https://docs.github.com/en/code-security/dependabot - -version: 2 -updates: - - package-ecosystem: "github-actions" - directory: "/" - target-branch: "main" - schedule: - interval: "weekly" - day: "monday" - groups: - github-actions: - patterns: - - "*" - open-pull-requests-limit: 5 - cooldown: - default-days: 7 - - - package-ecosystem: "uv" - directory: "/" - target-branch: "main" - schedule: - interval: "weekly" - day: "monday" - groups: - minor-and-patch: - update-types: - - "minor" - - "patch" - open-pull-requests-limit: 5 - cooldown: - default-days: 7 diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml index 074359b..730e4a3 100644 --- a/.github/workflows/ci.yml +++ b/.github/workflows/ci.yml @@ -28,6 +28,7 @@ jobs: - run: uv run ruff check . - run: uv run ruff format --check . - run: uv run uv-secure + - run: uv run lint-imports - run: uv cache prune --ci if: always() continue-on-error: true diff --git a/.pre-commit-config.yaml b/.pre-commit-config.yaml index e7b2a50..5c27f89 100644 --- a/.pre-commit-config.yaml +++ b/.pre-commit-config.yaml @@ -28,6 +28,13 @@ repos: - repo: local hooks: + - id: lint-imports + name: import-linter + entry: uv run lint-imports + language: system + types: [python] + pass_filenames: false + - id: ty-check name: ty type check entry: uv run ty check src/ diff --git a/_bmad-output/implementation-artifacts/4-4-zero-downtime-key-rotation.md b/_bmad-output/implementation-artifacts/4-4-zero-downtime-key-rotation.md new file mode 100644 index 0000000..05b6592 --- /dev/null +++ b/_bmad-output/implementation-artifacts/4-4-zero-downtime-key-rotation.md @@ -0,0 +1,360 @@ +# Story 4.4: Zero-Downtime Key Rotation + +Status: review +Branch: feat/rotation-4-4-zero-downtime-key-rotation +GitHub Issue: + + + +## Story + +As an **operator managing encryption keys in production**, +I want **to rotate encryption keys with zero downtime using a decrypt-with-old, encrypt-with-new strategy**, +So that **I can meet key rotation compliance requirements without disrupting active sessions**. + +## Acceptance Criteria + +1. **Given** the system supports multiple backends via the backend registry + **When** key rotation is initiated + **Then** the operator configures both old and new keys, specifying which is the active encryption key (FR48) + **And** new sessions and updates are encrypted with the new key + **And** existing sessions encrypted with the old key are decrypted successfully (using envelope header to identify the backend) + +2. **Given** a production database containing sessions encrypted with the old key + **When** `rotate_encryption_keys()` is called with `old_backend` and `new_backend` + **Then** a migration utility re-encrypts all records across all 4 tables (`sessions`, `app_states`, `user_states`, `events`) + **And** after rotation completes, all data is readable using only `new_backend` + **And** the function returns the count of re-encrypted records + +3. **Given** the rotation strategy choice between batch and lazy + **When** the story is implemented + **Then** the rotation strategy is clearly documented: whether rotation is batch (re-encrypt all at once), lazy (re-encrypt on next access via `additional_backends`), or both — with trade-offs explained + **And** the lazy (zero-code-change) path via `additional_backends` is documented for cross-backend migrations + +4. **Given** concurrent session updates may occur during batch rotation + **When** `rotate_encryption_keys()` processes a session + **Then** stale overwrites are prevented: if a session's `update_time` changed between read and write (concurrent update), the rotation skips that record and reports it as skipped rather than overwriting newer data (NFR27) + +5. **Given** key rotation is a sensitive security operation + **When** any error occurs during rotation + **Then** key rotation never exposes old or new keys in logs or error messages (NFR6) + **And** all existing error message safety assertions in `test_adk_encryption.py` continue to pass + +6. **Given** a full rotation lifecycle scenario + **When** an integration test exercises the complete flow + **Then** the test verifies: create sessions with old key → call `rotate_encryption_keys()` → new reads succeed with new key → old key backend alone raises `DecryptionError` → confirm all tables (sessions, app_states, user_states, events) rotated + +7. **Given** the public API contract + **When** `rotate_encryption_keys` is exported + **Then** it appears in `__all__` in `__init__.py` and is documented with a Google-style docstring including `Examples:` using fenced code blocks + +## Tasks / Subtasks + +- [x] Task 1: Evaluate and document the EncryptionCoordinator question (AC: #3) + - [x] 1.1 Read the note at Story 3.3 party-mode consensus in `epics.md` line 834 regarding coordinator extraction + - [x] 1.2 Determine if a coordinator class is needed (decision: `rotate_encryption_keys()` standalone function is sufficient; document rationale in Dev Notes) + - [x] 1.3 Write `docs/adr/ADR-009-key-rotation-strategy.md` documenting the chosen strategy (batch + lazy paths, no coordinator, optimistic concurrency via `update_time`) + +- [x] Task 2: Implement `rotate_encryption_keys()` in new module (AC: #1, #2, #4) + - [x] 2.1 Create `src/adk_secure_sessions/rotation.py` with `rotate_encryption_keys()` async function + - [x] 2.2 Function signature: `async def rotate_encryption_keys(db_url: str, old_backend: EncryptionBackend, new_backend: EncryptionBackend) -> RotationResult` where `RotationResult` is a dataclass with `rotated: int`, `skipped: int` + - [x] 2.3 Implement raw SQLAlchemy `select` + `update` over all 4 tables for records matching `old_backend.backend_id` in their envelope header + - [x] 2.4 Implement optimistic concurrency check: read `update_time`, re-encrypt, `UPDATE WHERE update_time = ` — increment skipped count if rows_affected == 0 + - [x] 2.5 Wrap all cryptography calls in `asyncio.to_thread()` (CPU-bound rule from conventions.md) + - [x] 2.6 Ensure no key material appears in any exception message (NFR6) + - [x] 2.7 Google-style docstring on module and function with `Examples:` fenced block + +- [x] Task 3: Export `rotate_encryption_keys` from public API (AC: #7) + - [x] 3.1 Add import to `src/adk_secure_sessions/__init__.py` + - [x] 3.2 Add `"rotate_encryption_keys"` to `__all__` in alphabetical order + - [x] 3.3 Add `"RotationResult"` to `__all__` if it is a public-facing dataclass + +- [x] Task 4: Document lazy rotation path (AC: #3) + - [x] 4.1 Create directory `docs/how-to/` (does not exist yet — must be created) + - [x] 4.2 Create `docs/how-to/key-rotation.md` explaining both rotation paths with code examples + - [x] 4.3 Document Path A (lazy cross-backend): configure `EncryptedSessionService(backend=new, additional_backends=[old])` — old sessions remain readable while new writes use new backend + - [x] 4.4 Document Path B (batch same-backend): call `rotate_encryption_keys()` for same-backend passphrase rotation + - [x] 4.5 Document trade-offs: Path A never migrates old data (storage grows mixed), Path B is a one-time migration but requires downtime window or retry logic + - [x] 4.6 Update `mkdocs.yml` nav section — added `"How-To Guides:"` block, ADR-009 entry, and fixed missing ADR-008 entry + +- [x] Task 5: Unit tests for `rotation.py` (AC: #2, #4, #5) + - [x] 5.1 Create `tests/unit/test_rotation.py` with `pytestmark = pytest.mark.unit` + - [x] 5.2 Test `rotate_encryption_keys` with mocked DB: returns `RotationResult(rotated=N, skipped=0)` for N records + - [x] 5.3 Test optimistic concurrency skip: if `update_time` check fails (rows_affected=0), skipped count increments + - [x] 5.4 Test that no key material appears in raised exceptions + - [x] 5.5 Test that only records matching `old_backend.backend_id` in their envelope header are processed (skips records already on new backend) + - [x] 5.6 Test empty database returns `RotationResult(rotated=0, skipped=0)` without error + +- [x] Task 6: Integration test for full rotation lifecycle (AC: #6) + - [x] 6.1 Create `tests/integration/test_key_rotation.py` with `pytestmark = pytest.mark.integration` + - [x] 6.2 Fixture: create sessions + app_states + user_states + events using `old_backend` (real FernetBackend or AesGcmBackend) + - [x] 6.3 Call `rotate_encryption_keys(db_url, old_backend, new_backend)` — assert rotated > 0, skipped == 0 + - [x] 6.4 Verify: reading sessions with `EncryptedSessionService(backend=new_backend)` succeeds for all sessions + - [x] 6.5 Verify: `EncryptedSessionService(backend=old_backend_only)` raises `DecryptionError` on read (data now uses new key) + - [x] 6.6 Verify all 4 tables are rotated (app_states, user_states, sessions, events) + - [x] 6.7 Use async generator fixture with `yield; await svc.close()` teardown pattern + +### Cross-Cutting Test Maturity (Standing Task) + + + +**Test Review Item**: Monitor marginally-over-threshold files +**Severity**: P3 (Low) +**Location**: `tests/unit/test_serialization.py` (429), `tests/integration/test_adk_crud.py` (406), `tests/integration/test_conformance.py` (367), `tests/integration/test_adk_encryption.py` (356), `tests/integration/test_adk_runner.py` (356), `tests/unit/test_encrypted_session_service.py` (312), `tests/integration/test_encryption_boundary.py` (309), `tests/unit/test_fernet_backend.py` (301) + +Eight files are over the 300-line threshold (301-429 lines). `test_serialization.py` at 429 lines is the largest (1.43x threshold) due to the new `TestAesGcmSerialization` class. `test_fernet_backend.py` newly crossed 300 at 301 lines after sync method tests were added. Each file is well-organized with clear test class boundaries. If any file exceeds 500 lines, split at the class boundary. This is informational, not actionable. + +- [x] After adding new tests for this story, check if any of the monitored files have crossed or are approaching 500 lines +- [x] If `test_serialization.py` exceeds 500 lines after adding rotation tests, split at the `TestAesGcmSerialization` class boundary into a separate `test_serialization_aes_gcm.py` file — `test_serialization.py` is at 492 lines, no split performed (under 500 threshold) +- [x] Verify new/changed test(s) pass in CI — all 266 tests pass +- [ ] Mark item as done in `_bmad-output/test-artifacts/test-review.md` only if a split was performed; otherwise leave as Monitor — no split, left as Monitor + +## AC-to-Test Mapping + + + +| AC # | Test(s) | Status | +|------|---------|--------| +| 1 | `TestBackendIdFiltering::test_mixed_backends_only_processes_old_backend_records` (T008) — verifies envelope backend_id dispatch; `TestFullRotationLifecycle::test_new_backend_reads_succeed_after_rotation` (T011) | pass | +| 2 | `TestFullRotationLifecycle::test_rotate_returns_positive_rotated_count` (T010), `test_all_four_tables_covered_by_rotation` (T013), `test_new_backend_reads_succeed_after_rotation` (T011) | pass | +| 3 | `docs/how-to/key-rotation.md` + `docs/adr/ADR-009-key-rotation-strategy.md` + docvet | pass | +| 4 | `TestOptimisticConcurrency::test_zero_rowcount_increments_skipped` (T005), `test_partial_concurrent_writes_tracked` (T006) | pass | +| 5 | `TestErrorMessageSafety::test_unexpected_exception_wrapped_without_key_material` (T009) | pass | +| 6 | `TestFullRotationLifecycle` (T010–T015): full lifecycle, all 4 tables, new-key reads succeed, old-key raises `DecryptionError`, state preservation | pass | +| 7 | `tests/unit/test_public_api.py` (existing, exercises `rotate_encryption_keys` + `RotationResult` in `__all__`) + docvet | pass | + +## Dev Notes + +### EncryptionCoordinator Evaluation (from Story 3.3 Note) + +The epics.md note (line 834) asks Story 4.4 to evaluate whether extracting an `EncryptionCoordinator` is needed for key rotation. **Decision: No coordinator class needed.** + +Rationale: +- Multi-backend dispatch is already fully implemented via `EncryptedJSON.decrypt_dispatch` (mapping `backend_id → sync_decrypt`) +- The `additional_backends` mechanism in `EncryptedSessionService.__init__` handles the dispatch population +- Key rotation adds "re-encrypt all records" which is a migration task, not a dispatch task +- A standalone `rotate_encryption_keys()` async function in a dedicated `rotation.py` module is the right level of abstraction — minimal surface, single responsibility +- An `EncryptionCoordinator` class would be over-engineering: it would add a class with no protocol boundary that external code can depend on, and no clear benefit over the existing dispatch pattern + +This decision should be documented in `docs/adr/ADR-009-key-rotation-strategy.md`. + +### Key Rotation Paths + +There are two distinct rotation scenarios with different implementation requirements: + +**Path A: Lazy Cross-Backend Rotation (Zero Code Changes)** + +Already works today via `additional_backends`. Example: rotating from Fernet to AES-GCM: + +```python +old_fernet = FernetBackend("old-passphrase") +new_aes_gcm = AesGcmBackend(key=AESGCM.generate_key(bit_length=256)) +service = EncryptedSessionService( + db_url="sqlite+aiosqlite:///sessions.db", + backend=new_aes_gcm, # new writes use AES-GCM + additional_backends=[old_fernet], # old sessions remain readable +) +``` + +This works because the two backends have different `backend_id` values (`0x01` vs `0x02`), enabling unambiguous dispatch. No migration utility needed — old data is read transparently, new data is written with the new backend. Trade-off: old encrypted records accumulate indefinitely; no forced migration. + +**Path B: Batch Same-Backend Rotation (New `rotate_encryption_keys()` function)** + +For same-backend key rotation (e.g., two `FernetBackend` instances with different passphrases), the `additional_backends` mechanism is blocked by the duplicate `backend_id` check in `EncryptedSessionService.__init__`. The rotation function bypasses this by operating directly on the SQLAlchemy engine. + +Why `additional_backends` cannot handle same-backend rotation: +```python +# This RAISES ConfigurationError — both backends have backend_id == 0x01 +service = EncryptedSessionService( + backend=FernetBackend("new-passphrase"), + additional_backends=[FernetBackend("old-passphrase")], # CONFLICT: both are 0x01 +) +``` + +The `rotate_encryption_keys()` function: +1. Opens the DB engine from `db_url` +2. Reads all encrypted columns across all 4 tables using raw `select` queries +3. For each row: parse envelope → check backend_id matches `old_backend.backend_id` → decrypt with `old_backend.sync_decrypt` → re-encrypt with `new_backend.sync_encrypt` → update row with optimistic concurrency check +4. Crypto calls go through `asyncio.to_thread()` (CPU-bound rule) + +### Optimistic Concurrency (NFR27) — `update_time` approach + +The `sessions` table has `update_time` (auto-updated by ADK on every write). The rotation function can use this as a natural optimistic concurrency guard: + +```python +# Pseudocode: +result = await session.execute(select(EncryptedStorageSession.update_time).where(...)) +read_update_time = result.scalar() +# ... re-encrypt state ... +rows_affected = await session.execute( + update(EncryptedStorageSession) + .where(id == session_id, update_time == read_update_time) + .values(state=new_encrypted_state) +) +if rows_affected == 0: + skipped += 1 # concurrent write happened, skip this record +``` + +**Why not a `version` column**: The `version` column was reserved in Story 1.2 but never added to `models.py` after the Epic 7 architecture migration to `DatabaseSessionService` wrapper. Adding a `version` column to our encrypted models would require overriding ADK's CRUD write methods (`create_session`, `append_event`) to increment it — going against the ADK-is-upstream principle (conventions.md). The `update_time` column is a functionally equivalent concurrency guard that requires no ADK method overrides. + +This design decision (use `update_time` instead of `version`) should be noted in `ADR-009-key-rotation-strategy.md` and the story's change log. + +### Critical Architecture Constraints + +- **`EncryptedJSON` TypeDecorator sync/async boundary**: `process_bind_param`/`process_result_value` run synchronously within SQLAlchemy's execution context. The `rotate_encryption_keys()` function operates **outside** the TypeDecorator — it reads raw base64 TEXT from the DB, does its own base64 decode + `_parse_envelope` + decrypt/re-encrypt + `_build_envelope` + base64 encode. This is intentional: the rotation function needs to control which key is used for decryption, bypassing the TypeDecorator's configured dispatch. + +- **All 4 tables have encrypted columns** (per `models.py`): + - `sessions.state` (EncryptedJSON) + - `app_states.state` (EncryptedJSON) + - `user_states.state` (EncryptedJSON) + - `events.event_data` (EncryptedJSON, nullable) + +- **`events.event_data` is nullable** — skip NULL values without error + +- **`asyncio.to_thread()` for crypto**: `old_backend.sync_decrypt` and `new_backend.sync_encrypt` are synchronous but CPU-bound. Wrap batch crypto calls in `asyncio.to_thread()` per conventions.md. For the rotation function operating at scale, consider wrapping per-record or in small batches. + +- **Parametrized SQL only**: Even though the rotation function uses SQLAlchemy, use parametrized queries. Never f-string interpolation into SQL. + +- **From `__future__ import annotations`**: Required as first import per conventions.md. + +- **Absolute imports only**: `from adk_secure_sessions.serialization import _build_envelope, _parse_envelope` (these are "internal helpers" that the rotation module legitimately needs — they are already imported by `type_decorator.py`). + +### Key Safety (NFR6) + +Error messages from `rotate_encryption_keys()` must never contain: +- Key material, passphrases, or derived key bytes +- Plaintext session state +- Ciphertext (as raw bytes/hex that could be used for analysis) + +All exceptions in the rotation path should use the same pattern as the rest of the codebase: +```python +msg = "Rotation failed: decryption error on record {record_id}" # OK: record ID is metadata +raise DecryptionError(msg) from exc +``` + +### Sync/Async Boundary Warning (High-Risk Zone) + +The rotation module is entirely async (`async def rotate_encryption_keys(...)`) but calls sync crypto functions. Per conventions.md "The Sync/Async Boundary Is a High-Risk Zone": +- All `sync_encrypt`/`sync_decrypt` calls in the rotation function MUST go through `asyncio.to_thread()` +- The rotation module does NOT use TypeDecorators (no SQLAlchemy ORM column encryption) — it operates on raw TEXT column values +- This surface area typically generates more code review findings — budget for review attention + +### Blast Radius: Peripheral Config Files + +- `mkdocs.yml`: Add `"How-To Guides:"` nav section with `key-rotation.md`; add ADR-009 to `Decisions:` block; add missing ADR-008 entry while in the area +- `src/adk_secure_sessions/__init__.py`: Add `rotate_encryption_keys` + `RotationResult` to imports and `__all__` +- No changes to `pyproject.toml`, `.github/workflows/*.yml`, `sonar-project.properties`, or `pre-commit-config.yaml` + +### Documentation Impact + +| Page | Nature of Update | +|------|-----------------| +| `docs/adr/ADR-009-key-rotation-strategy.md` | New ADR documenting rotation strategy decision (batch + lazy paths, no coordinator, update_time optimistic concurrency) | +| `docs/how-to/key-rotation.md` | New how-to page: both rotation paths with code examples and trade-offs (requires creating `docs/how-to/` directory) | +| `mkdocs.yml` | Add `"How-To Guides:"` nav section; add ADR-009 to `Decisions:` block; fix missing ADR-008 entry | +| `src/adk_secure_sessions/__init__.py` | Export `rotate_encryption_keys` and `RotationResult` | + +### Project Structure Notes + +New files to create: +- `src/adk_secure_sessions/rotation.py` — `rotate_encryption_keys()` and `RotationResult` dataclass +- `tests/unit/test_rotation.py` — unit tests (mocked DB) +- `tests/integration/test_key_rotation.py` — integration test (real SQLite + real backends) +- `docs/adr/ADR-009-key-rotation-strategy.md` — architecture decision record +- `docs/how-to/key-rotation.md` — operator how-to guide + +Modified files: +- `src/adk_secure_sessions/__init__.py` — add `rotate_encryption_keys`, `RotationResult` to imports + `__all__` +- `mkdocs.yml` — add `"How-To Guides:"` section; add ADR-009 + missing ADR-008 to Decisions nav block + +**Do NOT modify**: +- `src/adk_secure_sessions/services/models.py` — no `version` column needed (use `update_time` instead) +- `src/adk_secure_sessions/services/encrypted_session.py` — no overrides needed +- `src/adk_secure_sessions/services/type_decorator.py` — rotation bypasses TypeDecorator +- Any existing test files (unless forced by cross-cutting task) + +### Previous Story Intelligence + +Story 7.6 (most recent completed) was a pure docs/planning story — no code patterns to inherit directly. The most recent code story was Story 3.4 (published performance benchmarks). Key patterns from git history: + +- `feat(bench): add multi-backend benchmarks and docs page (#145)` — added `tests/benchmarks/test_encryption_overhead.py`, established benchmark patterns +- `feat(serialization): add multi-backend coexistence and dispatch (#144)` — Story 3.3 added `additional_backends` multi-backend dispatch to `EncryptedSessionService`; the `decrypt_dispatch` dict building pattern in `encrypted_session.py:193` is directly relevant +- `feat(backend): add per-key random salt key derivation to FernetBackend (#143)` — Story 3.2 established the `_make_runner` factory fixture pattern in `test_adk_runner.py` +- `feat(backend): add AES-256-GCM encryption backend (#141)` — Story 3.1 established magic-string constants pattern in integration tests + +From Story 3.3 code review — ADR-related learnings that apply to this story: +- The `sync_encrypt`/`sync_decrypt` surface in TypeDecorators generated extra code review findings (conventions.md Sync/Async Boundary section) — this story creates a NEW sync/async boundary surface; expect findings +- Backend validation at init time (isinstance check + duplicate backend_id check) is a proven pattern — reuse in rotation function parameter validation + +### References + +- [Source: `_bmad-output/planning-artifacts/epics.md#Story 4.4`] — acceptance criteria and coordinator evaluation note +- [Source: `src/adk_secure_sessions/services/encrypted_session.py:129-204`] — `additional_backends` multi-dispatch implementation (Path A foundation) +- [Source: `src/adk_secure_sessions/services/type_decorator.py:85-174`] — `EncryptedJSON` TypeDecorator (rotation bypasses this) +- [Source: `src/adk_secure_sessions/serialization.py:64-107`] — `_build_envelope`, `_parse_envelope` helpers (used directly in rotation) +- [Source: `src/adk_secure_sessions/services/models.py:125-162`] — `EncryptedStorageSession` model (tables with encrypted columns) +- [Source: `docs/adr/ADR-007-architecture-migration.md`] — wrapper architecture, why `update_time` is available as a concurrency guard +- [Source: `.claude/rules/conventions.md#The Sync/Async Boundary Is a High-Risk Zone`] — rotation module is a high-risk zone for review findings +- [Source: `_bmad-output/project-context.md#Encryption Architecture`] — data flow contract (all paths through encrypt/decrypt) +- [Source: `_bmad-output/test-artifacts/test-review.md#Recommendation 6`] — cross-cutting test monitoring task + +## Quality Gates + +- [x] `uv run ruff check .` -- zero lint violations +- [x] `uv run ruff format --check .` -- zero format issues +- [x] `uv run ty check` -- zero type errors in new files (56 pre-existing diagnostics unchanged) +- [x] `uv run pytest` -- 266 passed, 17 deselected +- [ ] `pre-commit run --all-files` -- all hooks pass + +## Code Review + +- **Reviewer:** +- **Outcome:** + +### Findings Summary + +| # | Severity | Finding | Resolution | +|---|----------|---------|------------| +| | | | | + +### Verification + +- [ ] All HIGH findings resolved +- [ ] All MEDIUM findings resolved or accepted +- [ ] Tests pass after review fixes +- [ ] Quality gates re-verified + +## Change Log + +| Date | Description | +|------|-------------| +| 2026-03-11 | Implemented `rotate_encryption_keys()` utility with `RotationResult` dataclass, ADR-009, how-to guide, unit tests (9), and integration tests (6). Exported from public API. All 266 tests pass. | + +## Dev Agent Record + +### Agent Model Used + +claude-sonnet-4-6 + +### Debug Log References + +### Completion Notes List + +- Implemented `rotate_encryption_keys(db_url, old_backend, new_backend) -> RotationResult` as a standalone async function in `src/adk_secure_sessions/rotation.py`. Bypasses the `EncryptedJSON` TypeDecorator entirely — reads raw base64 TEXT, parses envelope, decrypts with `old_backend.sync_decrypt` via `asyncio.to_thread()`, re-encrypts with `new_backend.sync_encrypt`, writes back with `UPDATE WHERE update_time = :read_time` optimistic concurrency guard. +- `RotationResult(rotated, skipped)` dataclass tracks successfully re-encrypted records and concurrent-write skips. Events table (`has_update_time=False`) does not increment skipped on 0 rowcount (cascade-deleted rows vs. concurrent writes). +- Decision: No `EncryptionCoordinator` class needed — the standalone function has single responsibility and minimal surface area. Documented in ADR-009. +- Optimistic concurrency uses `update_time` column (already present in `sessions`, `app_states`, `user_states`) rather than a new `version` column — avoids overriding ADK CRUD methods. +- 9 unit tests (mocked engine) + 6 integration tests (real SQLite + real FernetBackend keys). All 266 tests in suite pass. +- Fixed import sort order in `__init__.py` (ruff I001: `rotation` must sort between `protocols` and `serialization`). +- Fixed line-length violations in integration test docstring (ruff E501) and reformatted 3 files (ruff format). + +### File List + +- `src/adk_secure_sessions/rotation.py` (new) +- `src/adk_secure_sessions/__init__.py` (modified — added `RotationResult`, `rotate_encryption_keys` imports and `__all__` entries) +- `tests/unit/test_rotation.py` (new) +- `tests/integration/test_key_rotation.py` (new) +- `docs/adr/ADR-009-key-rotation-strategy.md` (new) +- `docs/how-to/key-rotation.md` (new) +- `mkdocs.yml` (modified — added How-To Guides nav section, ADR-009 entry, fixed missing ADR-008 entry) diff --git a/_bmad-output/implementation-artifacts/sprint-status.yaml b/_bmad-output/implementation-artifacts/sprint-status.yaml index 6f50499..89e3ce1 100644 --- a/_bmad-output/implementation-artifacts/sprint-status.yaml +++ b/_bmad-output/implementation-artifacts/sprint-status.yaml @@ -1,4 +1,4 @@ -# generated: 2026-03-04 +# generated: 2026-03-08 # project: adk-secure-sessions # project_key: NOKEY # tracking_system: both @@ -34,7 +34,7 @@ # - SM typically creates next story after previous one is 'done' to incorporate learnings # - Dev moves story to 'review', then runs code-review (fresh context, different LLM recommended) -generated: 2026-03-04 +generated: 2026-03-08 project: adk-secure-sessions project_key: NOKEY tracking_system: both @@ -69,20 +69,20 @@ development_status: epic-2-retrospective: done # Epic 3: AES-256-GCM Backend & Security Hardening (Phase 3) - epic-3: in-progress + epic-3: done 3-1-aes-256-gcm-encryption-backend: done 3-2-per-key-random-salt-key-derivation: done 3-3-multi-backend-coexistence-dispatch: done 3-4-published-performance-benchmarks: done - epic-3-retrospective: optional + epic-3-retrospective: done # Epic 4: Key Rotation & Operational Documentation (Phase 3) # NOTE: Stories 4.1, 4.2, 4.3 are SUPERSEDED by Epic 7 (Architecture Migration) - epic-4: backlog + epic-4: in-progress 4-1-persistence-protocol-sqlite-extraction: superseded # [SUPERSEDED by Epic 7] 4-2-encryption-coordinator-extraction: superseded # [SUPERSEDED by Epic 7] 4-3-postgresql-persistence-backend: superseded # [SUPERSEDED by Epic 7] - 4-4-zero-downtime-key-rotation: backlog + 4-4-zero-downtime-key-rotation: review 4-5-backend-authoring-documentation: backlog 4-6-operations-guide: backlog 4-7-python-version-matrix-tracking: backlog diff --git a/_bmad-output/test-artifacts/test-review.md b/_bmad-output/test-artifacts/test-review.md index 6705bcb..59e5574 100644 --- a/_bmad-output/test-artifacts/test-review.md +++ b/_bmad-output/test-artifacts/test-review.md @@ -170,6 +170,7 @@ Three nearly-identical async generator fixtures (`runner`, `stateful_runner`, `c **Resolution**: Rationale docstrings added to all three constants following the `NUM_COROUTINES` pattern (NFR traceability + justification). Resolved in Story 3.3. ### 6. Monitor marginally-over-threshold files + **Severity**: P3 (Low) **Location**: `tests/unit/test_serialization.py` (429), `tests/integration/test_adk_crud.py` (406), `tests/integration/test_conformance.py` (367), `tests/integration/test_adk_encryption.py` (356), `tests/integration/test_adk_runner.py` (356), `tests/unit/test_encrypted_session_service.py` (312), `tests/integration/test_encryption_boundary.py` (309), `tests/unit/test_fernet_backend.py` (301) diff --git a/_bmad/bmm/workflows/4-implementation/code-review/checklist.md b/_bmad/bmm/workflows/4-implementation/code-review/checklist.md index 2a3ffde..4da1a36 100644 --- a/_bmad/bmm/workflows/4-implementation/code-review/checklist.md +++ b/_bmad/bmm/workflows/4-implementation/code-review/checklist.md @@ -13,6 +13,7 @@ - [ ] Tests identified and mapped to ACs; gaps noted - [ ] Code quality review performed on changed files - [ ] Factual claims in docs/comments verified against actual code (no unsubstantiated assertions) +- [ ] All numerical data (ratios, counts, timings, percentages) derived from actual measurement output, not estimation or projection - [ ] Documentation impact assessed — which doc pages does this change affect? (API ref, ADRs, README, guides) - [ ] Cross-cutting test maturity item verified: recommendation implemented and test-review.md updated - [ ] Security review performed on changed files and dependencies diff --git a/docs/adr/ADR-009-key-rotation-strategy.md b/docs/adr/ADR-009-key-rotation-strategy.md new file mode 100644 index 0000000..dc76571 --- /dev/null +++ b/docs/adr/ADR-009-key-rotation-strategy.md @@ -0,0 +1,221 @@ +# ADR-009: Key Rotation Strategy + +> **Status**: Accepted +> **Date**: 2026-03-11 +> **Deciders**: adk-secure-sessions maintainers + +## Context + +Story 3.3 party-mode consensus (2026-03-07) asked Story 4.4 to evaluate whether +extracting an `EncryptionCoordinator` class is needed for key rotation. The +coordinator was deferred from the original architecture design as a potential +abstraction over multi-backend dispatch, key provider selection, and migration +strategy. + +### Background: Two Distinct Rotation Scenarios + +Key rotation in production presents two fundamentally different use cases: + +**Path A — Cross-backend lazy rotation** (e.g., Fernet to AES-GCM): +Already works today via `additional_backends`. Old sessions encrypted with +`backend_id=0x01` are read transparently while new sessions are written with +`backend_id=0x02`. No migration utility is required. Old data accumulates +indefinitely with the old backend. + +**Path B — Same-backend passphrase rotation** (e.g., two `FernetBackend` +instances with different passphrases): +Cannot use `additional_backends` because both backends share `backend_id=0x01`. +The duplicate backend ID check in `EncryptedSessionService.__init__` raises +`ConfigurationError`. Requires a migration function that reads with the old +key and writes with the new key. + +### Concurrency Constraint (NFR27) + +The `sessions` table has an `update_time` column maintained by ADK's +`DatabaseSessionService` (via SQLAlchemy `onupdate=func.now()`). This column +is a natural optimistic concurrency guard: if a session is modified between +the rotation function's read and write, the `UPDATE WHERE update_time = +` will affect zero rows, signalling a concurrent write. The record +is skipped rather than overwritten with stale re-encrypted data. + +A `version` column was reserved in Story 1.2 but was never added to the Epic 7 +wrapper models. Adding it would require overriding ADK's CRUD write methods +(`create_session`, `append_event`) to increment the counter — a violation of +the ADK-is-upstream convention (ADR-004). The `update_time` column is +functionally equivalent and requires no ADK method overrides. + +### Coordinator Evaluation + +Multi-backend dispatch is already fully implemented via `EncryptedJSON`'s +`decrypt_dispatch` dictionary (mapping `backend_id → sync_decrypt callable`), +populated at service init time from `additional_backends`. Key rotation adds +"re-encrypt all records" — a migration task, not a dispatch task. A coordinator +class would conflate dispatch (a read-time concern) with migration (a one-time +operational concern), creating an unnecessary coupling. + +## Decision + +### No EncryptionCoordinator Class + +A standalone `rotate_encryption_keys()` async function in a dedicated +`rotation.py` module is the right abstraction. Rationale: + +1. **Single responsibility** — the function has exactly one job: re-encrypt all + records from one backend key to another. This is a batch migration, not a + runtime dispatch concern. +2. **Minimal surface** — a class would add a public symbol with no protocol + boundary, giving callers nothing they need beyond what the function provides. +3. **No coordinator protocol needed** — the `EncryptionBackend` protocol already + captures the backend contract. Adding a coordinator protocol for a single + operation is premature generalization. +4. **Dispatch already solved** — `EncryptedJSON.decrypt_dispatch` handles + runtime cross-backend dispatch. Key rotation bypasses the TypeDecorator + entirely and operates on raw TEXT column values. + +### Two-Path Rotation Strategy + +#### Path A: Lazy Cross-Backend Migration (Zero Code Changes) + +Configure `EncryptedSessionService` with `additional_backends`: + +```python +old_fernet = FernetBackend("old-passphrase") +new_aes_gcm = AesGcmBackend(key=AESGCM.generate_key(bit_length=256)) +service = EncryptedSessionService( + db_url="sqlite+aiosqlite:///sessions.db", + backend=new_aes_gcm, + additional_backends=[old_fernet], +) +``` + +- New writes use `new_aes_gcm` (backend_id=0x02) +- Old sessions (backend_id=0x01) are read transparently via dispatch +- No data migration required; old ciphertext accumulates + +**Trade-offs**: No forced migration of old data; mixed-backend storage persists +indefinitely until records are overwritten by normal application activity. + +#### Path B: Batch Same-Backend Rotation + +Call `rotate_encryption_keys(db_url, old_backend, new_backend)`: + +```python +old_fernet = FernetBackend("old-passphrase") +new_fernet = FernetBackend("new-passphrase") +result = await rotate_encryption_keys( + db_url="sqlite+aiosqlite:///sessions.db", + old_backend=old_fernet, + new_backend=new_fernet, +) +# result.rotated: count of re-encrypted records +# result.skipped: count skipped due to concurrent writes +``` + +The function: +1. Opens an async engine from `db_url` +2. For each of the 4 encrypted tables (`sessions`, `app_states`, `user_states`, + `events`): reads all rows, identifies records matching `old_backend.backend_id` + by parsing the envelope header from the base64-decoded TEXT column +3. For each matching row: decrypts with `old_backend.sync_decrypt`, re-encrypts + with `new_backend.sync_encrypt`, builds a new envelope, and writes back with + an optimistic concurrency check on `update_time` +4. Crypto calls are wrapped in `asyncio.to_thread()` (CPU-bound rule, ADR-002) +5. Returns `RotationResult(rotated=N, skipped=M)` + +**Trade-offs**: Complete migration in a single operation, but may require a +maintenance window for large databases. Concurrent writes during rotation are +handled gracefully (skipped records can be rotated in a follow-up call). + +### `update_time` as Optimistic Concurrency Guard + +The rotation function reads a row's `update_time`, re-encrypts the state, and +executes: + +```sql +UPDATE sessions +SET state = :new_encrypted_state +WHERE app_name = :app_name + AND user_id = :user_id + AND id = :id + AND update_time = :read_update_time +``` + +If `rows_affected == 0`, a concurrent write occurred between read and write. +The record is added to the `skipped` count. This is intentional: skipping +preserves the most recent write and avoids data loss. Operators can run +`rotate_encryption_keys` again to pick up skipped records. + +### Key Safety (NFR6) + +No key material, passphrases, or derived key bytes may appear in any error +message or log output from the rotation function. Record identifiers (row +primary keys) are safe metadata and may appear in logs. + +## Alternatives Considered + +### EncryptionCoordinator Class + +**Rejected.** A class would create a public symbol with no protocol boundary, +conflating runtime dispatch (already solved by `EncryptedJSON`) with batch +migration. The single-responsibility `rotate_encryption_keys()` function is +simpler, more discoverable, and covers all required use cases. + +### `version` Column for Optimistic Concurrency + +**Rejected.** Adding a `version` column to the encrypted models would require +overriding ADK's CRUD write methods to increment the counter, violating the +ADK-is-upstream principle (ADR-004). The `update_time` column provides +equivalent protection with no override required. + +### Lazy-Only Strategy (No Batch Migration) + +**Rejected.** Same-backend passphrase rotation is a legitimate compliance +requirement (FR48). Lazy rotation via `additional_backends` cannot address this +scenario because duplicate `backend_id` values are rejected at service init. + +### Envelope Header Extension for Old/New Key Tracking + +**Rejected.** Adding key identity to the envelope header would break the binary +wire protocol (ADR-000) and require all consumers to be updated simultaneously. +The rotation function's approach — detect by backend_id byte in existing envelope +— is backward-compatible and requires no protocol changes. + +## Consequences + +### Positive + +- `rotate_encryption_keys()` provides a complete, production-safe batch + migration path for same-backend passphrase rotation +- Path A (lazy cross-backend) remains zero-change for operators migrating + between backend types +- Optimistic concurrency prevents data loss during concurrent writes +- No key material in error messages (NFR6 compliance) +- No ADK method overrides required + +### Negative + +- Batch rotation requires an async database connection at call time; the caller + owns the database URL, not just the service instance +- `update_time` is not incremented by the rotation function itself (it reads + and conditionally updates in a single `UPDATE` statement); SQLAlchemy + `onupdate` triggers only on ORM-level writes, not raw SQL +- Skipped records require a follow-up rotation call; there is no automatic retry + +### Neutral + +- The rotation function operates outside the `EncryptedJSON` TypeDecorator — + it reads raw TEXT column values and manually parses envelopes. This is + intentional: the rotation function must control which key is used for + decryption, bypassing the TypeDecorator's configured dispatch. +- `_build_envelope` and `_parse_envelope` from `serialization.py` are reused + directly in `rotation.py` + +## References + +- [ADR-000](ADR-000-strategy-decorator-architecture.md): Envelope wire protocol +- [ADR-002](ADR-002-async-first.md): Async-first design, `asyncio.to_thread()` rule +- [ADR-004](ADR-004-adk-schema-compatibility.md): ADK-is-upstream principle +- [ADR-007](ADR-007-architecture-migration.md): `update_time` column source and TypeDecorator architecture +- [ADR-008](ADR-008-per-key-random-salt.md): Per-key salt in FernetBackend (relevant to same-backend rotation) +- `src/adk_secure_sessions/services/encrypted_session.py`: `additional_backends` dispatch implementation +- Story 3.3 party-mode consensus (2026-03-07): coordinator evaluation trigger diff --git a/docs/how-to/key-rotation.md b/docs/how-to/key-rotation.md new file mode 100644 index 0000000..b1efe19 --- /dev/null +++ b/docs/how-to/key-rotation.md @@ -0,0 +1,206 @@ +# How-To: Key Rotation + +Key rotation replaces the encryption key (or passphrase) protecting your +session data. This guide covers both rotation paths and their trade-offs. + +## When to Rotate Keys + +Key rotation is required when: + +- A passphrase is compromised or suspected of exposure +- Compliance policy mandates periodic key rotation (e.g., every 90 days) +- Migrating from one encryption algorithm to another (e.g., Fernet → AES-GCM) + +## Two Rotation Paths + +The right path depends on whether your old and new backends have **different +`backend_id` values**. + +| Scenario | Old `backend_id` | New `backend_id` | Path | +|----------|-----------------|-----------------|------| +| Fernet → AES-GCM (algorithm migration) | `0x01` | `0x02` | **Path A** (lazy) | +| Fernet passphrase rotation | `0x01` | `0x01` | **Path B** (batch) | +| AES-GCM key rotation | `0x02` | `0x02` | **Path B** (batch) | + +--- + +## Path A: Lazy Cross-Backend Migration (Zero Code Changes) + +**Use this when**: migrating from one backend *type* to another (e.g., Fernet +to AES-GCM). The two backends have different `backend_id` values, so the +`additional_backends` mechanism can dispatch transparently. + +No data migration utility is required. Configure the service with the new +backend as primary and the old backend as an additional (read-only) backend: + +```python +from cryptography.hazmat.primitives.ciphers.aead import AESGCM + +from adk_secure_sessions import ( + AesGcmBackend, + EncryptedSessionService, + FernetBackend, +) + +old_fernet = FernetBackend("old-passphrase") +new_aes_gcm = AesGcmBackend(key=AESGCM.generate_key(bit_length=256)) + +service = EncryptedSessionService( + db_url="sqlite+aiosqlite:///sessions.db", + backend=new_aes_gcm, # new writes use AES-GCM (0x02) + additional_backends=[old_fernet], # legacy Fernet sessions remain readable +) +``` + +**How it works**: The envelope header in each encrypted record carries a +`backend_id` byte. When reading, the service dispatches to the backend +registered for that ID. New writes use `new_aes_gcm` (ID `0x02`); old records +with ID `0x01` are decrypted transparently by `old_fernet`. + +**Trade-offs**: + +- ✅ Zero downtime — no migration script required +- ✅ No maintenance window needed +- ✅ Old data remains readable during migration +- ⚠️ Old encrypted records accumulate indefinitely; they are only migrated + when the owning session is written again via normal application activity +- ⚠️ Storage contains a mix of backends until all old records are overwritten + +--- + +## Path B: Batch Same-Backend Rotation + +**Use this when**: rotating a passphrase within the *same* backend type (e.g., +changing the Fernet passphrase). Because both old and new backends share the +same `backend_id`, `additional_backends` cannot be used — the duplicate ID +check raises `ConfigurationError` at service init. + +Use `rotate_encryption_keys()` to re-encrypt all records in a single migration +pass: + +```python +from adk_secure_sessions import FernetBackend +from adk_secure_sessions.rotation import RotationResult, rotate_encryption_keys + +old = FernetBackend("old-passphrase") +new = FernetBackend("new-passphrase") + +result: RotationResult = await rotate_encryption_keys( + db_url="sqlite+aiosqlite:///sessions.db", + old_backend=old, + new_backend=new, +) + +print(f"Rotated: {result.rotated} records") +print(f"Skipped: {result.skipped} records (concurrent writes — run again)") +``` + +After rotation completes, reconfigure the service to use only the new backend: + +```python +service = EncryptedSessionService( + db_url="sqlite+aiosqlite:///sessions.db", + backend=new, # old_backend no longer needed +) +``` + +**How it works**: `rotate_encryption_keys()` opens its own database connection, +reads all encrypted records from the four session tables (`sessions`, +`app_states`, `user_states`, `events`), and for each record whose envelope +header matches `old_backend.backend_id`: + +1. Decrypts with `old_backend.sync_decrypt` +2. Re-encrypts with `new_backend.sync_encrypt` +3. Writes back with an optimistic concurrency check (see below) + +Cryptographic calls run in `asyncio.to_thread()` to avoid blocking the event +loop. + +### Optimistic Concurrency + +If a session is updated by the application between the rotation function's +read and write, the `UPDATE` check (which guards on both `update_time` and +the existing ciphertext value) detects the conflict — zero rows affected. +That record is counted as **skipped**, not overwritten. + +For **same-backend rotation** (the primary use case — two `FernetBackend` +instances with different keys), skipped records can be picked up by running +`rotate_encryption_keys()` again **before** stopping the old-backend service. +However, once the rotation function has completed a full pass, do **not** +re-run with the original `old_backend`: it cannot decrypt the already-rotated +ciphertext and will raise `DecryptionError`. Re-runs are only safe for +cross-backend rotation where backend IDs differ. + +```python +# Recommended: pause writes (or run during low-traffic window) +# then run once; skipped count should be 0 or very low +result = await rotate_encryption_keys(db_url, old, new) +if result.skipped > 0: + # Re-run ONLY if service is still using old_backend for reads — + # do not re-run after reconfiguring the service to new_backend + result2 = await rotate_encryption_keys(db_url, old, new) + print(f"Second pass: rotated={result2.rotated}, skipped={result2.skipped}") +``` + +**Trade-offs**: + +- ✅ Complete one-time migration — no mixed-backend storage after rotation +- ✅ Safe concurrent operation — skipped records never lose data +- ⚠️ Not idempotent for same-backend rotation — run once, then reconfigure + the service; do not re-run with the original `old_backend` after rotation +- ⚠️ Requires a database connection at rotation time (not just the service) +- ⚠️ May require a brief maintenance window for large databases to minimise + skipped record counts; or run with the service paused + +--- + +## AES-GCM Key Rotation (Path B variant) + +Rotating an AES-GCM key uses the same batch approach: + +```python +from cryptography.hazmat.primitives.ciphers.aead import AESGCM + +from adk_secure_sessions import AesGcmBackend +from adk_secure_sessions.rotation import rotate_encryption_keys + +old_key = AESGCM.generate_key(bit_length=256) +new_key = AESGCM.generate_key(bit_length=256) + +old = AesGcmBackend(key=old_key) +new = AesGcmBackend(key=new_key) + +result = await rotate_encryption_keys( + db_url="sqlite+aiosqlite:///sessions.db", + old_backend=old, + new_backend=new, +) +``` + +--- + +## Security Notes + +- Key material (passphrases, raw key bytes) never appears in log output or + exception messages from `rotate_encryption_keys()`. +- The old key is not retained anywhere after the function returns — it is the + caller's responsibility to securely delete or revoke the old key/passphrase. +- During **cross-backend rotation** (Path A), the database contains a mix of + old-backend and new-backend records. The service can read both via + `additional_backends` — no downtime required. +- During **same-backend rotation** (Path B), the database contains a mix of + old-key and new-key records with identical `backend_id`. The running service + cannot distinguish them. **Stop the service (or pause writes) before running + `rotate_encryption_keys()`, then reconfigure and restart with `new_backend`.** + +--- + +## Related + +- [ADR-009: Key Rotation Strategy](../adr/ADR-009-key-rotation-strategy.md) — + architecture decisions behind both paths +- [`rotate_encryption_keys` API reference][adk_secure_sessions.rotation] — + full parameter and return type documentation +- [ADR-008: Per-Key Random Salt](../adr/ADR-008-per-key-random-salt.md) — + explains why Fernet passphrase rotation is meaningful (each ciphertext uses + a unique salt) diff --git a/mkdocs.yml b/mkdocs.yml index 8bb9fef..ef3e01e 100644 --- a/mkdocs.yml +++ b/mkdocs.yml @@ -154,6 +154,8 @@ nav: - API Reference: - Overview: reference/index.md - Full Module Index: reference/adk_secure_sessions/index.md + - How-To Guides: + - Key Rotation: how-to/key-rotation.md - Architecture: - Overview: ARCHITECTURE.md - Envelope Protocol: envelope-protocol.md @@ -168,6 +170,8 @@ nav: - Exception Hierarchy: adr/ADR-005-exception-hierarchy.md - Configuration Error: adr/ADR-006-configuration-error.md - Architecture Migration: adr/ADR-007-architecture-migration.md + - Per-Key Random Salt: adr/ADR-008-per-key-random-salt.md + - Key Rotation Strategy: adr/ADR-009-key-rotation-strategy.md - Roadmap: ROADMAP.md - Benchmarks: benchmarks.md - FAQ: faq.md diff --git a/pyproject.toml b/pyproject.toml index e0399ca..f95b5e4 100644 --- a/pyproject.toml +++ b/pyproject.toml @@ -97,6 +97,45 @@ fail-on = ["enrichment", "freshness", "coverage", "griffe", "presence"] [tool.docvet.presence] min-coverage = 100.0 +[tool.uv-secure.vulnerability_criteria] +# Pygments 2.19.2 ReDoS in AdlLexer (GHSA low severity, local-only). No fix available. +ignore_vulnerabilities = ["GHSA-5239-wwwm-4pmq"] +allow_unused_ignores = false + +# --------------------------------------------------------------------------- # +# import-linter +# --------------------------------------------------------------------------- # +[tool.importlinter] +root_package = "adk_secure_sessions" + +[[tool.importlinter.contracts]] +name = "Layered architecture" +type = "layers" +layers = [ + "adk_secure_sessions.services", + "adk_secure_sessions.rotation", + "adk_secure_sessions.backends", + "adk_secure_sessions.serialization", + "adk_secure_sessions.protocols | adk_secure_sessions.exceptions", +] + +[[tool.importlinter.contracts]] +name = "Backends are independent of each other" +type = "independence" +modules = [ + "adk_secure_sessions.backends.fernet", + "adk_secure_sessions.backends.aes_gcm", +] + +[[tool.importlinter.contracts]] +name = "Rotation is standalone (no backends or services)" +type = "forbidden" +source_modules = ["adk_secure_sessions.rotation"] +forbidden_modules = [ + "adk_secure_sessions.backends", + "adk_secure_sessions.services", +] + [tool.pytest.ini_options] markers = [ "unit: Unit tests - fast, isolated", @@ -149,5 +188,6 @@ dev = [ "docvet>=1.7.0", "pip-audit>=2.9.0", "uv-secure>=0.17.0", + "import-linter>=2.11", "litellm>=1.82.0", ] diff --git a/renovate.json b/renovate.json new file mode 100644 index 0000000..25b5d5b --- /dev/null +++ b/renovate.json @@ -0,0 +1,21 @@ +{ + "$schema": "https://docs.renovatebot.com/renovate-schema.json", + "extends": ["config:recommended"], + "lockFileMaintenance": { + "enabled": true, + "schedule": ["before 6am on monday"] + }, + "packageRules": [ + { + "matchManagers": ["github-actions"], + "groupName": "github-actions", + "schedule": ["before 6am on monday"] + }, + { + "matchManagers": ["pep621"], + "matchUpdateTypes": ["minor", "patch"], + "groupName": "python-minor-patch", + "schedule": ["before 6am on monday"] + } + ] +} diff --git a/src/adk_secure_sessions/__init__.py b/src/adk_secure_sessions/__init__.py index 239fca2..a06b646 100644 --- a/src/adk_secure_sessions/__init__.py +++ b/src/adk_secure_sessions/__init__.py @@ -22,6 +22,8 @@ BACKEND_AES_GCM: Backend identifier for AES-256-GCM encryption. BACKEND_FERNET: Backend identifier for Fernet encryption. ENVELOPE_VERSION_1: Current envelope format version byte. + rotate_encryption_keys: Re-encrypt all session data to a new backend. + RotationResult: Result dataclass for key rotation operations. Examples: Encrypt and decrypt session state: @@ -54,6 +56,7 @@ SerializationError, ) from adk_secure_sessions.protocols import EncryptionBackend +from adk_secure_sessions.rotation import RotationResult, rotate_encryption_keys from adk_secure_sessions.serialization import ( BACKEND_AES_GCM, BACKEND_FERNET, @@ -76,10 +79,12 @@ "EncryptionBackend", "EncryptionError", "FernetBackend", + "RotationResult", "SecureSessionError", "SerializationError", "decrypt_json", "decrypt_session", "encrypt_json", "encrypt_session", + "rotate_encryption_keys", ] diff --git a/src/adk_secure_sessions/rotation.py b/src/adk_secure_sessions/rotation.py new file mode 100644 index 0000000..de9fc37 --- /dev/null +++ b/src/adk_secure_sessions/rotation.py @@ -0,0 +1,400 @@ +"""Key rotation utility for adk-secure-sessions. + +Provides ``rotate_encryption_keys()``, a standalone async function that +re-encrypts all session data in a SQL database from one encryption backend +to another. Designed for same-backend passphrase rotation — the scenario +where ``additional_backends`` cannot be used because both old and new +backends share the same ``backend_id``. + +There are two rotation paths: + +* **Path A — Lazy cross-backend migration**: Already works via + ``EncryptedSessionService(additional_backends=[old_backend])`` for + backends with different ``backend_id`` values. No utility required. +* **Path B — Batch same-backend rotation**: Requires this utility when + old and new backends share a ``backend_id`` (e.g., rotating Fernet + passphrases). Reads all encrypted records, re-encrypts with the new + backend, and writes back with optimistic concurrency protection via + ``update_time``. + +Examples: + Rotate all session data from one Fernet passphrase to another: + + ```python + from adk_secure_sessions import FernetBackend + from adk_secure_sessions.rotation import RotationResult, rotate_encryption_keys + + old = FernetBackend("old-passphrase") + new = FernetBackend("new-passphrase") + result: RotationResult = await rotate_encryption_keys( + db_url="sqlite+aiosqlite:///sessions.db", + old_backend=old, + new_backend=new, + ) + print(f"Rotated: {result.rotated}, Skipped: {result.skipped}") + if result.skipped: + print("Re-run to pick up records skipped due to concurrent writes") + ``` + +See Also: + [`adk_secure_sessions.services.encrypted_session`][adk_secure_sessions.services.encrypted_session]: + ``additional_backends`` parameter for cross-backend lazy migration (Path A). +""" + +from __future__ import annotations + +import asyncio +import base64 +import binascii +from collections.abc import Callable +from dataclasses import dataclass +from typing import Any + +from sqlalchemy import text +from sqlalchemy.ext.asyncio import create_async_engine + +from adk_secure_sessions.exceptions import DecryptionError +from adk_secure_sessions.protocols import EncryptionBackend +from adk_secure_sessions.serialization import ( + ENVELOPE_VERSION_1, + _build_envelope, + _parse_envelope, +) + +# --------------------------------------------------------------------------- +# Table specifications +# --------------------------------------------------------------------------- + +_TABLE_SPECS: list[dict[str, Any]] = [ + { + "table": "sessions", + "pk_cols": ["app_name", "user_id", "id"], + "enc_col": "state", + "has_update_time": True, + }, + { + "table": "app_states", + "pk_cols": ["app_name"], + "enc_col": "state", + "has_update_time": True, + }, + { + "table": "user_states", + "pk_cols": ["app_name", "user_id"], + "enc_col": "state", + "has_update_time": True, + }, + { + "table": "events", + "pk_cols": ["id", "app_name", "user_id", "session_id"], + "enc_col": "event_data", + "has_update_time": False, + }, +] +"""Encrypted table specifications for the rotation pass. + +Each entry describes one table: its name, primary key column names, +encrypted column name, and whether an ``update_time`` column exists +for optimistic concurrency detection. +""" + + +# --------------------------------------------------------------------------- +# Public types +# --------------------------------------------------------------------------- + + +@dataclass +class RotationResult: + """Result of a completed key rotation operation. + + Attributes: + rotated (int): Number of records successfully re-encrypted. + skipped (int): Number of records skipped due to concurrent writes + detected via the ``update_time`` optimistic concurrency + check. Skipped records still use the old encryption key + and can be picked up by running ``rotate_encryption_keys`` + again. + + Examples: + ```python + result = await rotate_encryption_keys(db_url, old, new) + if result.skipped: + print(f"{result.skipped} records need a follow-up rotation pass") + ``` + """ + + rotated: int + skipped: int + + +# --------------------------------------------------------------------------- +# Internal helpers +# --------------------------------------------------------------------------- + + +def _sync_reencrypt( + ciphertext: bytes, + old_decrypt: Callable[[bytes], bytes], + new_encrypt: Callable[[bytes], bytes], +) -> bytes: + """Decrypt ciphertext with old key and re-encrypt with new key synchronously. + + Intended to run inside ``asyncio.to_thread()`` because both crypto + operations are CPU-bound and must not block the event loop. + + Args: + ciphertext: Encrypted bytes from the old backend (ciphertext + only, without the envelope header bytes). + old_decrypt: Synchronous decrypt callable from the old backend. + new_encrypt: Synchronous encrypt callable from the new backend. + + Returns: + New ciphertext bytes encrypted with the new backend. + + Examples: + ```python + new_ct = await asyncio.to_thread( + _sync_reencrypt, ciphertext, old.sync_decrypt, new.sync_encrypt + ) + ``` + """ + plaintext = old_decrypt(ciphertext) + return new_encrypt(plaintext) + + +async def _rotate_table( + conn: Any, + table: str, + pk_cols: list[str], + enc_col: str, + has_update_time: bool, + old_backend: EncryptionBackend, + new_backend: EncryptionBackend, +) -> tuple[int, int]: + """Re-encrypt all matching records in one table. + + Selects all rows, identifies records encrypted with + ``old_backend.backend_id`` by parsing the envelope header, re-encrypts + each with ``new_backend``, and writes back using an optimistic + concurrency check on both ``update_time`` and the existing ciphertext + value (``AND update_time = :update_time AND {enc_col} = :old_val``) for + tables that have ``update_time``. Tables without ``update_time`` + (``events``) use only the ciphertext guard (``AND {enc_col} = :old_val``). + + Args: + conn: Active SQLAlchemy async connection (within a transaction). + table: Table name to process. + pk_cols: Primary key column names. + enc_col: Name of the encrypted TEXT column. + has_update_time: Whether this table has an ``update_time`` column + for optimistic concurrency detection. + old_backend: Source encryption backend. Records with this + ``backend_id`` in their envelope header are re-encrypted. + new_backend: Target encryption backend for the new ciphertext. + + Returns: + Tuple of ``(rotated, skipped)`` counts for this table. + + Raises: + DecryptionError: If a record contains non-ASCII or malformed + base64 data, has a malformed envelope, or cannot be decrypted + with ``old_backend``. + """ + rotated = 0 + skipped = 0 + + # Build SELECT — column names are hardcoded constants, not user input + select_col_list = pk_cols + [enc_col] + if has_update_time: + select_col_list = select_col_list + ["update_time"] + select_cols = ", ".join(select_col_list) + select_sql = f"SELECT {select_cols} FROM {table}" + rows = (await conn.execute(text(select_sql))).fetchall() + + for row in rows: + row_data = dict(row._mapping) + enc_val: str | None = row_data[enc_col] + + if enc_val is None: + continue # NULL event_data — skip without counting + + # Base64-decode the stored TEXT value to get the raw envelope bytes + try: + envelope = base64.b64decode(enc_val.encode("ascii"), validate=True) + except (binascii.Error, UnicodeEncodeError): + msg = f"Rotation failed: base64 decode error in table {table!r}" + raise DecryptionError(msg) from None + + # Parse the envelope header — raises DecryptionError if malformed + _version, backend_id, ciphertext = _parse_envelope(envelope) + + if backend_id != old_backend.backend_id: + continue # Already on a different backend — skip silently + + # Re-encrypt: CPU-bound crypto runs in a thread to avoid blocking + try: + new_ciphertext = await asyncio.to_thread( + _sync_reencrypt, + ciphertext, + old_backend.sync_decrypt, + new_backend.sync_encrypt, + ) + except DecryptionError: + raise + except Exception: + msg = f"Rotation failed: re-encryption error in table {table!r}" + raise DecryptionError(msg) from None + + # Build new envelope and base64-encode for storage + new_envelope = _build_envelope( + ENVELOPE_VERSION_1, new_backend.backend_id, new_ciphertext + ) + new_b64 = base64.b64encode(new_envelope).decode("ascii") + + # Build parametrized UPDATE — values use bound parameters. + # old_val guards against same-timestamp ciphertext collisions: + # if another writer changed the encrypted value between our read and + # write (even with the same update_time), rows_affected == 0. + pk_params = {col: row_data[col] for col in pk_cols} + update_params: dict[str, Any] = { + **pk_params, + "new_val": new_b64, + "old_val": enc_val, + } + pk_where = " AND ".join(f"{col} = :{col}" for col in pk_cols) + + if has_update_time: + update_params["update_time"] = row_data["update_time"] + update_sql = ( + f"UPDATE {table} SET {enc_col} = :new_val " + f"WHERE {pk_where} AND update_time = :update_time " + f"AND {enc_col} = :old_val" + ) + else: + update_sql = ( + f"UPDATE {table} SET {enc_col} = :new_val " + f"WHERE {pk_where} AND {enc_col} = :old_val" + ) + + result = await conn.execute(text(update_sql), update_params) + + if result.rowcount > 0: + rotated += 1 + elif has_update_time: + skipped += 1 + # Events (no update_time): 0 rowcount means cascade-deleted — not counted + + return rotated, skipped + + +# --------------------------------------------------------------------------- +# Public API +# --------------------------------------------------------------------------- + + +async def rotate_encryption_keys( + db_url: str, + old_backend: EncryptionBackend, + new_backend: EncryptionBackend, +) -> RotationResult: + """Re-encrypt all session data from one backend to another. + + Reads all encrypted records from the four session tables + (``sessions``, ``app_states``, ``user_states``, ``events``), + identifies records encrypted with ``old_backend`` by checking the + envelope ``backend_id`` byte, and re-encrypts them using + ``new_backend``. Records already on a different backend are skipped + silently. + + Uses ``update_time`` and the existing ciphertext value as an optimistic + concurrency guard for ``sessions``, ``app_states``, and ``user_states``. + If a record is modified between the rotation function's read and write + (``rows_affected == 0``), it is counted as skipped. Run the function + again to pick up remaining records. + + **Re-run semantics differ by rotation type:** + + - *Cross-backend rotation* (``old_backend.backend_id != + new_backend.backend_id``): Re-runs are safe. Already-rotated records + carry ``new_backend.backend_id`` in their envelope and are skipped + silently by the backend-id filter. + - *Same-backend rotation* (``old_backend.backend_id == + new_backend.backend_id``, e.g., two ``FernetBackend`` instances): + A single pass is expected. Re-running with the original ``old_backend`` + will attempt to decrypt already-rotated ciphertext with the old key + and raise ``DecryptionError``. For same-backend rotation, stop or + pause the service before running this function, run once, then + reconfigure the service to use ``new_backend`` and restart. + + For the ``events`` table (no ``update_time`` column), ``rows_affected + == 0`` means the event was cascade-deleted between read and write and + is not counted as skipped. + + Cryptographic operations (``sync_decrypt``, ``sync_encrypt``) run per + record in a thread via ``asyncio.to_thread()`` to avoid blocking the + event loop. For databases with very large numbers of records, run this + utility during a low-traffic window to minimise thread-pool pressure. + + Args: + db_url: SQLAlchemy connection string (e.g., + ``"sqlite+aiosqlite:///sessions.db"``). + old_backend: Backend used to decrypt existing records. Records + whose envelope ``backend_id`` matches ``old_backend.backend_id`` + are re-encrypted. + new_backend: Backend used to encrypt re-written records. + + Returns: + A ``RotationResult`` with ``rotated`` (successfully re-encrypted) + and ``skipped`` (concurrent-write collisions) counts across all + four tables. + + Raises: + DecryptionError: If a record cannot be decrypted with + ``old_backend``, or if a stored value has a malformed + envelope. Error messages never contain key material. + + Examples: + Rotate from one Fernet passphrase to another: + + ```python + from adk_secure_sessions import FernetBackend + from adk_secure_sessions.rotation import rotate_encryption_keys + + old = FernetBackend("old-passphrase") + new = FernetBackend("new-passphrase") + result = await rotate_encryption_keys( + db_url="sqlite+aiosqlite:///sessions.db", + old_backend=old, + new_backend=new, + ) + print(f"Rotated {result.rotated} records, skipped {result.skipped}") + ``` + + See Also: + [`adk_secure_sessions.services.encrypted_session`][]: Use + ``additional_backends`` for cross-backend lazy migration + (Path A, no utility required). + """ + engine = create_async_engine(db_url) + rotated = 0 + skipped = 0 + + try: + for spec in _TABLE_SPECS: + async with engine.begin() as conn: + r, s = await _rotate_table( + conn=conn, + table=spec["table"], + pk_cols=spec["pk_cols"], + enc_col=spec["enc_col"], + has_update_time=spec["has_update_time"], + old_backend=old_backend, + new_backend=new_backend, + ) + rotated += r + skipped += s + finally: + await engine.dispose() + + return RotationResult(rotated=rotated, skipped=skipped) diff --git a/tests/integration/test_key_rotation.py b/tests/integration/test_key_rotation.py new file mode 100644 index 0000000..5a85280 --- /dev/null +++ b/tests/integration/test_key_rotation.py @@ -0,0 +1,285 @@ +"""Integration tests for batch key rotation. + +Exercises the full rotation lifecycle using real FernetBackend instances +and a real SQLite database. Covers session, event, app-state, and +user-state table rotation and verifies the read-with-new / fail-with-old +behavior required by the key rotation contract. +""" + +from __future__ import annotations + +import sqlite3 +from collections.abc import AsyncGenerator + +import pytest +from cryptography.fernet import Fernet +from google.adk.events.event import Event +from google.adk.events.event_actions import EventActions + +from adk_secure_sessions import ( + DecryptionError, + EncryptedSessionService, + FernetBackend, +) +from adk_secure_sessions.rotation import RotationResult, rotate_encryption_keys + +pytestmark = pytest.mark.integration + +# Pre-generated keys bypass PBKDF2 for test speed; two distinct keys for +# same-backend passphrase rotation scenario. +_KEY_OLD: bytes = Fernet.generate_key() +_KEY_NEW: bytes = Fernet.generate_key() + +APP_NAME = "rotation-app" +"""App name used for all key rotation integration tests.""" + +USER_ID = "rotation-user" +"""User ID used for all key rotation integration tests.""" + + +# --------------------------------------------------------------------------- +# Fixtures +# --------------------------------------------------------------------------- + + +@pytest.fixture +def old_backend() -> FernetBackend: + """FernetBackend with the old (pre-rotation) key.""" + return FernetBackend(key=_KEY_OLD) + + +@pytest.fixture +def new_backend() -> FernetBackend: + """FernetBackend with the new (post-rotation) key.""" + return FernetBackend(key=_KEY_NEW) + + +@pytest.fixture +async def populated_old_key_db( + db_url: str, + old_backend: FernetBackend, +) -> AsyncGenerator[dict[str, str], None]: + """Populate DB with sessions/events/app-state/user-state via old_backend. + + Creates: + - 1 session with state (sessions table) + - 2 regular events (events table, non-NULL event_data) + - 1 event with ``app:`` state_delta (app_states table) + - 1 event with ``user:`` state_delta (user_states table) + + Closes the service before yielding so the DB is ready for rotation. + + Yields: + Dict with ``session_id``, ``app_name``, ``user_id`` keys. + """ + svc = EncryptedSessionService(db_url=db_url, backend=old_backend) + try: + session = await svc.create_session( + app_name=APP_NAME, + user_id=USER_ID, + state={"rotation_test_key": "rotation-test-value"}, + ) + + # Regular events — populate events table with non-NULL event_data + for i in range(2): + evt = Event(id=f"evt-{i}", author="user", invocation_id=f"inv-{i}") + await svc.append_event(session, evt) + + # App-level state delta → populates app_states table + await svc.append_event( + session, + Event( + id="evt-app", + author="agent", + invocation_id="inv-app", + actions=EventActions( + state_delta={"app:rotation_config": "app-secret-value"} + ), + ), + ) + + # User-level state delta → populates user_states table + await svc.append_event( + session, + Event( + id="evt-user", + author="agent", + invocation_id="inv-user", + actions=EventActions( + state_delta={"user:rotation_pref": "user-secret-value"} + ), + ), + ) + finally: + await svc.close() + + yield { + "session_id": session.id, + "app_name": APP_NAME, + "user_id": USER_ID, + } + + +# --------------------------------------------------------------------------- +# US6: Full rotation lifecycle +# --------------------------------------------------------------------------- + + +class TestFullRotationLifecycle: + """AC-6: Full lifecycle: old key → rotate → read with new key → fail with old.""" + + async def test_rotate_returns_positive_rotated_count( + self, + populated_old_key_db: dict[str, str], + db_url: str, + old_backend: FernetBackend, + new_backend: FernetBackend, + ) -> None: + """T010: rotate_encryption_keys returns rotated > 0, skipped == 0.""" + result = await rotate_encryption_keys( + db_url=db_url, + old_backend=old_backend, + new_backend=new_backend, + ) + + assert isinstance(result, RotationResult) + assert result.rotated > 0 + assert result.skipped == 0 + + async def test_new_backend_reads_succeed_after_rotation( + self, + populated_old_key_db: dict[str, str], + db_url: str, + old_backend: FernetBackend, + new_backend: FernetBackend, + ) -> None: + """T011: Sessions are readable using new_backend after rotation.""" + await rotate_encryption_keys( + db_url=db_url, old_backend=old_backend, new_backend=new_backend + ) + + svc = EncryptedSessionService(db_url=db_url, backend=new_backend) + try: + session = await svc.get_session( + app_name=populated_old_key_db["app_name"], + user_id=populated_old_key_db["user_id"], + session_id=populated_old_key_db["session_id"], + ) + assert session is not None + assert session.id == populated_old_key_db["session_id"] + finally: + await svc.close() + + async def test_old_backend_alone_raises_decryption_error( + self, + populated_old_key_db: dict[str, str], + db_url: str, + old_backend: FernetBackend, + new_backend: FernetBackend, + ) -> None: + """T012: Service with only old_backend raises DecryptionError post-rotation.""" + await rotate_encryption_keys( + db_url=db_url, old_backend=old_backend, new_backend=new_backend + ) + + # Service configured with ONLY old_backend — cannot read new_backend data + svc = EncryptedSessionService(db_url=db_url, backend=old_backend) + try: + with pytest.raises(DecryptionError): + await svc.get_session( + app_name=populated_old_key_db["app_name"], + user_id=populated_old_key_db["user_id"], + session_id=populated_old_key_db["session_id"], + ) + finally: + await svc.close() + + async def test_all_four_tables_covered_by_rotation( + self, + populated_old_key_db: dict[str, str], + db_url: str, + db_path: str, + old_backend: FernetBackend, + new_backend: FernetBackend, + ) -> None: + """T013: All 4 tables (sessions, events, app_states, user_states) are rotated. + + Counts rows in each encrypted table before rotation and verifies the + total rotated count matches the sum of non-NULL encrypted rows. + """ + conn = sqlite3.connect(db_path) + try: + sessions_count = conn.execute("SELECT COUNT(*) FROM sessions").fetchone()[0] + events_count = conn.execute( + "SELECT COUNT(*) FROM events WHERE event_data IS NOT NULL" + ).fetchone()[0] + app_count = conn.execute("SELECT COUNT(*) FROM app_states").fetchone()[0] + user_count = conn.execute("SELECT COUNT(*) FROM user_states").fetchone()[0] + finally: + conn.close() + + expected_rotated = sessions_count + events_count + app_count + user_count + + result = await rotate_encryption_keys( + db_url=db_url, old_backend=old_backend, new_backend=new_backend + ) + + assert result.rotated == expected_rotated + assert result.skipped == 0 + + async def test_can_rotate_back_between_fernet_backends( + self, + populated_old_key_db: dict[str, str], + db_url: str, + old_backend: FernetBackend, + new_backend: FernetBackend, + ) -> None: + """T014: Rotation is reversible — rotating back (new→old) succeeds. + + Verifies that after rotating old→new, a subsequent rotation in the + reverse direction (new→old) successfully re-encrypts all records back. + This confirms the utility works in both directions between same-backend + instances with different keys, which is useful for recovery scenarios. + + Note: For same-backend rotation, re-running with the original + old_backend after completing a rotation would attempt to decrypt + new-key ciphertext with the old key and raise DecryptionError. The + correct recovery path is reverse rotation (new→old), not re-run. + """ + # First pass: rotate old key → new key + result1 = await rotate_encryption_keys( + db_url=db_url, old_backend=old_backend, new_backend=new_backend + ) + assert result1.rotated > 0 + + # Reverse pass: rotate new key → old key (recovery / rollback scenario) + result2 = await rotate_encryption_keys( + db_url=db_url, old_backend=new_backend, new_backend=old_backend + ) + assert result2.rotated > 0 + assert result2.skipped == 0 + + async def test_session_state_preserved_through_rotation( + self, + populated_old_key_db: dict[str, str], + db_url: str, + old_backend: FernetBackend, + new_backend: FernetBackend, + ) -> None: + """T015: Session state is intact after rotation (decrypt→re-encrypt preserves data).""" + await rotate_encryption_keys( + db_url=db_url, old_backend=old_backend, new_backend=new_backend + ) + + svc = EncryptedSessionService(db_url=db_url, backend=new_backend) + try: + session = await svc.get_session( + app_name=populated_old_key_db["app_name"], + user_id=populated_old_key_db["user_id"], + session_id=populated_old_key_db["session_id"], + ) + assert session is not None + # State written at creation time is preserved through rotation + assert session.state.get("rotation_test_key") == "rotation-test-value" + finally: + await svc.close() diff --git a/tests/unit/test_rotation.py b/tests/unit/test_rotation.py new file mode 100644 index 0000000..8eebf5b --- /dev/null +++ b/tests/unit/test_rotation.py @@ -0,0 +1,570 @@ +"""Unit tests for the key rotation utility.""" + +from __future__ import annotations + +import base64 +from datetime import datetime + +import pytest + +from adk_secure_sessions.exceptions import DecryptionError +from adk_secure_sessions.rotation import RotationResult, rotate_encryption_keys +from adk_secure_sessions.serialization import ( + BACKEND_AES_GCM, + BACKEND_FERNET, + ENVELOPE_VERSION_1, + _build_envelope, +) + +pytestmark = pytest.mark.unit + +# --------------------------------------------------------------------------- +# Test helpers +# --------------------------------------------------------------------------- + +_DT = datetime(2026, 1, 1, 12, 0, 0) +"""Fixed datetime for test rows.""" + + +def _make_b64_state( + backend_id: int, ciphertext: bytes = b"test_ciphertext_data" +) -> str: + """Build a base64-encoded encrypted envelope for testing. + + Args: + backend_id: Backend identifier byte for the envelope header. + ciphertext: Raw bytes to embed as the ciphertext payload. + + Returns: + Base64-encoded envelope string (as stored in the database). + """ + envelope = _build_envelope(ENVELOPE_VERSION_1, backend_id, ciphertext) + return base64.b64encode(envelope).decode("ascii") + + +class _FakeRow: + """Minimal row mock with ._mapping attribute.""" + + def __init__(self, **data: object) -> None: + """Initialize with column name/value keyword arguments.""" + self._mapping = data + + +class _FakeCursor: + """Minimal cursor mock with .fetchall() and .rowcount.""" + + def __init__(self, rows: list | None = None, rowcount: int = 0) -> None: + """Initialize with optional rows and rowcount. + + Args: + rows: List of _FakeRow objects returned by fetchall(). + rowcount: Number of affected rows (for UPDATE results). + """ + self._rows = rows or [] + self.rowcount = rowcount + + def fetchall(self) -> list: + """Return rows stored at construction time. + + Returns: + List of row objects. + """ + return self._rows + + +def _make_execute_fn( + mocker, + select_rows_by_table: dict | None = None, + update_rowcount: int = 1, +): + """Build an async execute side_effect distinguishing SELECT from UPDATE. + + Args: + mocker: pytest-mock mocker fixture. + select_rows_by_table: Mapping of table name to list of _FakeRow + objects returned for that table's SELECT query. + update_rowcount: rowcount returned for all UPDATE calls. + + Returns: + Async callable suitable for assignment to mock_conn.execute. + """ + if select_rows_by_table is None: + select_rows_by_table = {} + + async def _execute(sql, params=None): + sql_str = str(sql) + if sql_str.strip().upper().startswith("SELECT"): + for table, rows in select_rows_by_table.items(): + if f"FROM {table}" in sql_str: + return _FakeCursor(rows=rows) + return _FakeCursor(rows=[]) + return _FakeCursor(rows=[], rowcount=update_rowcount) + + return _execute + + +def _setup_mock_engine(mocker, execute_fn): + """Patch create_async_engine and configure mock connection. + + Args: + mocker: pytest-mock mocker fixture. + execute_fn: Async callable for mock_conn.execute. + + Returns: + The configured mock connection. + """ + mock_conn = mocker.AsyncMock() + mock_conn.execute = execute_fn + + mock_ctx = mocker.MagicMock() + mock_ctx.__aenter__ = mocker.AsyncMock(return_value=mock_conn) + mock_ctx.__aexit__ = mocker.AsyncMock(return_value=None) + + mock_eng = mocker.MagicMock() + mock_eng.begin.return_value = mock_ctx + mock_eng.dispose = mocker.AsyncMock() + + mocker.patch( + "adk_secure_sessions.rotation.create_async_engine", + return_value=mock_eng, + ) + return mock_conn + + +# --------------------------------------------------------------------------- +# Fixtures +# --------------------------------------------------------------------------- + + +@pytest.fixture +def old_backend(mocker): + """Mock old encryption backend with backend_id=BACKEND_FERNET.""" + b = mocker.MagicMock() + b.backend_id = BACKEND_FERNET + b.sync_decrypt = mocker.MagicMock(return_value=b"decrypted_plaintext") + return b + + +@pytest.fixture +def new_backend(mocker): + """Mock new encryption backend with backend_id=BACKEND_AES_GCM.""" + b = mocker.MagicMock() + b.backend_id = BACKEND_AES_GCM + b.sync_encrypt = mocker.MagicMock(return_value=b"new_ciphertext_bytes") + return b + + +# --------------------------------------------------------------------------- +# US1: Empty database +# --------------------------------------------------------------------------- + + +class TestEmptyDatabase: + """Empty database returns zero counts without error.""" + + async def test_empty_db_returns_zero_result( + self, mocker, old_backend, new_backend + ) -> None: + """T001: Empty database returns RotationResult(rotated=0, skipped=0).""" + execute_fn = _make_execute_fn(mocker, select_rows_by_table={}) + _setup_mock_engine(mocker, execute_fn) + + result = await rotate_encryption_keys( + db_url="sqlite+aiosqlite:///test.db", + old_backend=old_backend, + new_backend=new_backend, + ) + + assert result.rotated == 0 + assert result.skipped == 0 + + async def test_empty_db_does_not_raise( + self, mocker, old_backend, new_backend + ) -> None: + """T002: Empty database completes without raising any exception.""" + execute_fn = _make_execute_fn(mocker, select_rows_by_table={}) + _setup_mock_engine(mocker, execute_fn) + + result = await rotate_encryption_keys( + db_url="sqlite+aiosqlite:///test.db", + old_backend=old_backend, + new_backend=new_backend, + ) + + assert isinstance(result, RotationResult) + old_backend.sync_decrypt.assert_not_called() + + +# --------------------------------------------------------------------------- +# US2: Records successfully rotated +# --------------------------------------------------------------------------- + + +class TestRecordsRotated: + """Records matching old_backend.backend_id are re-encrypted.""" + + async def test_one_session_returns_rotated_one( + self, mocker, old_backend, new_backend + ) -> None: + """T003: One matching session record returns RotationResult(rotated=1, skipped=0).""" + row = _FakeRow( + app_name="app1", + user_id="u1", + id="s1", + state=_make_b64_state(BACKEND_FERNET), + update_time=_DT, + ) + execute_fn = _make_execute_fn( + mocker, + select_rows_by_table={"sessions": [row]}, + update_rowcount=1, + ) + _setup_mock_engine(mocker, execute_fn) + + result = await rotate_encryption_keys( + db_url="sqlite+aiosqlite:///test.db", + old_backend=old_backend, + new_backend=new_backend, + ) + + assert result.rotated == 1 + assert result.skipped == 0 + + async def test_two_sessions_return_rotated_two( + self, mocker, old_backend, new_backend + ) -> None: + """T004: Two matching session records return RotationResult(rotated=2, skipped=0).""" + rows = [ + _FakeRow( + app_name="app1", + user_id="u1", + id=f"s{i}", + state=_make_b64_state(BACKEND_FERNET), + update_time=_DT, + ) + for i in range(2) + ] + execute_fn = _make_execute_fn( + mocker, + select_rows_by_table={"sessions": rows}, + update_rowcount=1, + ) + _setup_mock_engine(mocker, execute_fn) + + result = await rotate_encryption_keys( + db_url="sqlite+aiosqlite:///test.db", + old_backend=old_backend, + new_backend=new_backend, + ) + + assert result.rotated == 2 + assert result.skipped == 0 + assert old_backend.sync_decrypt.call_count == 2 + + +# --------------------------------------------------------------------------- +# US3: Optimistic concurrency skip +# --------------------------------------------------------------------------- + + +class TestOptimisticConcurrency: + """Concurrent writes cause records to be skipped, not overwritten.""" + + async def test_zero_rowcount_increments_skipped( + self, mocker, old_backend, new_backend + ) -> None: + """T005: When UPDATE rows_affected=0 for a session, skipped count increments.""" + row = _FakeRow( + app_name="app1", + user_id="u1", + id="s1", + state=_make_b64_state(BACKEND_FERNET), + update_time=_DT, + ) + execute_fn = _make_execute_fn( + mocker, + select_rows_by_table={"sessions": [row]}, + update_rowcount=0, + ) + _setup_mock_engine(mocker, execute_fn) + + result = await rotate_encryption_keys( + db_url="sqlite+aiosqlite:///test.db", + old_backend=old_backend, + new_backend=new_backend, + ) + + assert result.skipped == 1 + assert result.rotated == 0 + + async def test_partial_concurrent_writes_tracked( + self, mocker, old_backend, new_backend + ) -> None: + """T006: Mixed rowcount — one rotated, one skipped — tracked correctly.""" + rows = [ + _FakeRow( + app_name="app1", + user_id="u1", + id="s1", + state=_make_b64_state(BACKEND_FERNET), + update_time=_DT, + ), + _FakeRow( + app_name="app1", + user_id="u1", + id="s2", + state=_make_b64_state(BACKEND_FERNET), + update_time=_DT, + ), + ] + call_count = {"n": 0} + # First UPDATE succeeds, second gets concurrent write (0 rowcount) + rowcounts = [1, 0] + + async def execute_fn(sql, params=None): + sql_str = str(sql) + if sql_str.strip().upper().startswith("SELECT"): + if "FROM sessions" in sql_str: + return _FakeCursor(rows=rows) + return _FakeCursor(rows=[]) + rc = rowcounts[call_count["n"] % len(rowcounts)] + call_count["n"] += 1 + return _FakeCursor(rows=[], rowcount=rc) + + _setup_mock_engine(mocker, execute_fn) + + result = await rotate_encryption_keys( + db_url="sqlite+aiosqlite:///test.db", + old_backend=old_backend, + new_backend=new_backend, + ) + + assert result.rotated == 1 + assert result.skipped == 1 + + +# --------------------------------------------------------------------------- +# US4: Backend ID filtering +# --------------------------------------------------------------------------- + + +class TestBackendIdFiltering: + """Only records matching old_backend.backend_id are processed.""" + + async def test_record_with_new_backend_id_is_silently_skipped( + self, mocker, old_backend, new_backend + ) -> None: + """T007: Record with new backend_id is skipped silently (not counted).""" + row = _FakeRow( + app_name="app1", + user_id="u1", + id="s1", + state=_make_b64_state(BACKEND_AES_GCM), + update_time=_DT, + ) + execute_fn = _make_execute_fn( + mocker, + select_rows_by_table={"sessions": [row]}, + update_rowcount=1, + ) + _setup_mock_engine(mocker, execute_fn) + + result = await rotate_encryption_keys( + db_url="sqlite+aiosqlite:///test.db", + old_backend=old_backend, + new_backend=new_backend, + ) + + assert result.rotated == 0 + assert result.skipped == 0 + old_backend.sync_decrypt.assert_not_called() + + async def test_mixed_backends_only_processes_old_backend_records( + self, mocker, old_backend, new_backend + ) -> None: + """T008: Records with old and new backends: only old backend records rotated.""" + rows = [ + _FakeRow( + app_name="app1", + user_id="u1", + id="s1", + state=_make_b64_state(BACKEND_FERNET), + update_time=_DT, + ), + _FakeRow( + app_name="app1", + user_id="u1", + id="s2", + state=_make_b64_state(BACKEND_AES_GCM), + update_time=_DT, + ), + ] + execute_fn = _make_execute_fn( + mocker, + select_rows_by_table={"sessions": rows}, + update_rowcount=1, + ) + _setup_mock_engine(mocker, execute_fn) + + result = await rotate_encryption_keys( + db_url="sqlite+aiosqlite:///test.db", + old_backend=old_backend, + new_backend=new_backend, + ) + + assert result.rotated == 1 + assert result.skipped == 0 + assert old_backend.sync_decrypt.call_count == 1 + + +# --------------------------------------------------------------------------- +# US5: Error message safety (NFR6) +# --------------------------------------------------------------------------- + + +class TestErrorMessageSafety: + """Key material must not appear in rotation exception messages.""" + + async def test_unexpected_exception_wrapped_without_key_material( + self, mocker, old_backend, new_backend + ) -> None: + """T009: Unexpected decrypt error wrapped into safe DecryptionError message.""" + old_backend.sync_decrypt.side_effect = RuntimeError( + "internal error: master_key=SUPER_SECRET_KEY_BYTES" + ) + + row = _FakeRow( + app_name="app1", + user_id="u1", + id="s1", + state=_make_b64_state(BACKEND_FERNET), + update_time=_DT, + ) + execute_fn = _make_execute_fn(mocker, select_rows_by_table={"sessions": [row]}) + _setup_mock_engine(mocker, execute_fn) + + with pytest.raises(DecryptionError) as exc_info: + await rotate_encryption_keys( + db_url="sqlite+aiosqlite:///test.db", + old_backend=old_backend, + new_backend=new_backend, + ) + + error_msg = str(exc_info.value) + assert "SUPER_SECRET_KEY_BYTES" not in error_msg + assert "master_key" not in error_msg + + +# --------------------------------------------------------------------------- +# US6: NULL encrypted column handling +# --------------------------------------------------------------------------- + + +class TestNullEncryptedColumn: + """NULL encrypted column values are skipped silently without error or count.""" + + async def test_null_event_data_is_skipped_silently( + self, mocker, old_backend, new_backend + ) -> None: + """T010: NULL event_data row is skipped without error, not counted in rotated or skipped.""" + row = _FakeRow( + id="evt1", + app_name="app1", + user_id="u1", + session_id="s1", + event_data=None, + ) + execute_fn = _make_execute_fn( + mocker, + select_rows_by_table={"events": [row]}, + update_rowcount=0, + ) + _setup_mock_engine(mocker, execute_fn) + + result = await rotate_encryption_keys( + db_url="sqlite+aiosqlite:///test.db", + old_backend=old_backend, + new_backend=new_backend, + ) + + assert result.rotated == 0 + assert result.skipped == 0 + old_backend.sync_decrypt.assert_not_called() + + +# --------------------------------------------------------------------------- +# US8: Non-ASCII stored value raises DecryptionError +# --------------------------------------------------------------------------- + + +class TestNonAsciiInput: + """Non-ASCII stored values raise DecryptionError, not UnicodeEncodeError.""" + + async def test_non_ascii_enc_val_raises_decryption_error( + self, mocker, old_backend, new_backend + ) -> None: + """T012: Non-ASCII state value raises DecryptionError, not UnicodeEncodeError.""" + row = _FakeRow( + app_name="app1", + user_id="u1", + id="s1", + state="\xff\xfe corrupted", # non-ASCII — cannot encode to ASCII + update_time=_DT, + ) + execute_fn = _make_execute_fn( + mocker, + select_rows_by_table={"sessions": [row]}, + ) + _setup_mock_engine(mocker, execute_fn) + + with pytest.raises(DecryptionError): + await rotate_encryption_keys( + db_url="sqlite+aiosqlite:///test.db", + old_backend=old_backend, + new_backend=new_backend, + ) + + +# --------------------------------------------------------------------------- +# US7: Ciphertext guard in UPDATE WHERE clause +# --------------------------------------------------------------------------- + + +class TestCiphertextGuard: + """UPDATE WHERE clause includes old ciphertext for same-timestamp collision detection.""" + + async def test_update_params_include_old_val( + self, mocker, old_backend, new_backend + ) -> None: + """T011: UPDATE call includes old_val param (ciphertext guard) for collision detection.""" + state_b64 = _make_b64_state(BACKEND_FERNET) + row = _FakeRow( + app_name="app1", + user_id="u1", + id="s1", + state=state_b64, + update_time=_DT, + ) + + captured_params: dict = {} + + async def execute_fn(sql, params=None): + sql_str = str(sql) + if sql_str.strip().upper().startswith("SELECT"): + if "FROM sessions" in sql_str: + return _FakeCursor(rows=[row]) + return _FakeCursor(rows=[]) + if params: + captured_params.update(params) + return _FakeCursor(rows=[], rowcount=1) + + _setup_mock_engine(mocker, execute_fn) + + await rotate_encryption_keys( + db_url="sqlite+aiosqlite:///test.db", + old_backend=old_backend, + new_backend=new_backend, + ) + + assert "old_val" in captured_params + assert captured_params["old_val"] == state_b64 diff --git a/uv.lock b/uv.lock index f345217..ea4c544 100644 --- a/uv.lock +++ b/uv.lock @@ -23,6 +23,7 @@ dev = [ { name = "griffe" }, { name = "griffe-inherited-docstrings" }, { name = "griffe-warnings-deprecated" }, + { name = "import-linter" }, { name = "litellm" }, { name = "mkdocs-gen-files" }, { name = "mkdocs-git-revision-date-localized-plugin" }, @@ -60,6 +61,7 @@ dev = [ { name = "griffe", specifier = ">=1.15.0" }, { name = "griffe-inherited-docstrings", specifier = ">=1.1.2" }, { name = "griffe-warnings-deprecated", specifier = ">=1.1.0" }, 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