tftsr-devops_investigation/docs/architecture/adrs/ADR-005-auto-generate-encryption-keys.md
Shaun Arman fdb4fc03b9 docs(architecture): add C4 diagrams, ADRs, and architecture overview
Comprehensive architecture documentation covering:

- docs/architecture/README.md: Full C4 model diagrams (system context,
  container, component), data flow sequences, security architecture,
  AI provider class diagram, CI/CD pipeline, and deployment diagrams.
  All diagrams use Mermaid for version-controlled diagram-as-code.

- docs/architecture/adrs/ADR-001: Tauri vs Electron decision rationale
- docs/architecture/adrs/ADR-002: SQLCipher encryption choices and
  cipher_page_size=16384 rationale for Apple Silicon
- docs/architecture/adrs/ADR-003: Provider trait + factory pattern
- docs/architecture/adrs/ADR-004: Regex + Aho-Corasick PII detection
- docs/architecture/adrs/ADR-005: Auto-generate encryption keys at
  runtime (documents the fix from PR #24)
- docs/architecture/adrs/ADR-006: Zustand state management rationale

- docs/wiki/Architecture.md: Updated module table (14 migrations, not
  10), corrected integrations description, updated startup sequence to
  reflect key auto-generation, added links to new ADR docs.

- README.md: Fixed stale database paths (tftsr → trcaa) and updated
  env var descriptions to reflect auto-generation behavior.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
2026-04-07 09:35:35 -05:00

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# ADR-005: Auto-generate Encryption Keys at Runtime
**Status**: Accepted
**Date**: 2026-04
**Deciders**: sarman
---
## Context
The application uses two encryption keys:
1. **Database key** (`TFTSR_DB_KEY`): SQLCipher AES-256 key for the full database
2. **Credential key** (`TFTSR_ENCRYPTION_KEY`): AES-256-GCM key for token/API key encryption
The original design required both to be set as environment variables in release builds. This caused:
- **Critical failure on Mac**: Fresh installs would crash at startup with "file is not a database" error
- **Silent failure on save**: Saving AI providers would fail with "TFTSR_ENCRYPTION_KEY must be set in release builds"
- **Developer friction**: Switching from `cargo tauri dev` (debug, plain SQLite) to a release build would crash because the existing plain database couldn't be opened as encrypted
---
## Decision
Auto-generate cryptographically secure 256-bit keys at first launch and persist them to the app data directory with restricted file permissions.
---
## Key Storage
| Key | File | Permissions | Location |
|-----|------|-------------|----------|
| Database | `.dbkey` | `0600` (owner r/w only) | `$TFTSR_DATA_DIR/` |
| Credentials | `.enckey` | `0600` (owner r/w only) | `$TFTSR_DATA_DIR/` |
**Platform data directories:**
- macOS: `~/Library/Application Support/trcaa/`
- Linux: `~/.local/share/trcaa/`
- Windows: `%APPDATA%\trcaa\`
---
## Key Resolution Order
For both keys:
1. Check environment variable (`TFTSR_DB_KEY` / `TFTSR_ENCRYPTION_KEY`) — use if set and non-empty
2. If debug build — use hardcoded dev key (never touches filesystem)
3. If `.dbkey` / `.enckey` exists and is non-empty — load from file
4. Otherwise — generate 32 random bytes via `OsRng`, hex-encode to 64-char string, write to file with `mode 0600`
---
## Plain-to-Encrypted Migration
When a release build encounters an existing plain SQLite database (written by a debug build), rather than crashing:
```
1. Detect plain SQLite via 16-byte header check ("SQLite format 3\0")
2. Copy database to .db.plain-backup
3. Open plain database
4. ATTACH encrypted database at temp path with new key
5. SELECT sqlcipher_export('encrypted') -- copies all tables, indexes, triggers
6. DETACH encrypted
7. rename(temp_encrypted, original_path)
8. Open encrypted database with key
```
---
## Alternatives Considered
| Option | Pros | Cons |
|--------|------|------|
| **Auto-generate keys** (chosen) | Works out-of-the-box, no user config | Key file loss = data loss (acceptable: key + DB on same machine) |
| Require env vars (original) | Explicit — users know their key | Crashes on fresh install, poor UX |
| Derive from machine ID | No file to lose | Machine ID changes break DB on hardware changes |
| OS keychain | Most secure | Complex cross-platform implementation; adds dependency |
| Prompt user for password | User controls key | Poor UX for a tool; password complexity issues |
**Why not OS keychain:**
The `tauri-plugin-stronghold` already provides a keychain-like abstraction for credentials, but integrating SQLCipher key retrieval into Stronghold would create a chicken-and-egg problem: Stronghold itself needs to be initialized before the database that stores Stronghold's key material.
---
## Consequences
**Positive:**
- Zero-configuration installation — app works on first launch
- Developers can freely switch between debug and release builds
- Environment variable override still available for automated/enterprise deployments
- Key files are protected by Unix file permissions (`0600`)
**Negative:**
- If `.dbkey` or `.enckey` are deleted, the database and all stored credentials become permanently inaccessible
- Key files are not themselves encrypted — OS-level protection depends on filesystem permissions
- Not suitable for multi-user scenarios where different users need isolated key material (single-user desktop app — acceptable)
**Mitigation for key loss:**
Document clearly that backing up `$TFTSR_DATA_DIR` (including hidden files) preserves both key files and database. Loss of keys without losing the database = data loss.