Wave 3: Error branch tests + production error handling fixes

[oblangatas]

Summary

• 43 new tests covering error branches across lock, unlock, wrap, up, and bootstrap commands + Hypothesis-powered security property tests (split/reconstruct roundtrip, shard independence, zero-after-use, repr redaction, tamper detection)
• Production fix: All CLI commands now wrap bare exceptions with WorthlessError(WRTLS-NNN) — users see clean error messages instead of Python tracebacks
• Security fix: shard_a memory leak on unlock ambiguity path — bytearray is now zeroed on all exit paths
• Quality pass: Addressed all gaps from Brutus/Karen review (proxy crash test, gate-before-decrypt SR-03, sanitize-never-leaks SR-05, nonce tamper, binary key strategies)

Commits (7)

1. 7b9c4a9 — lock/unlock error branch tests (compensation paths, symlink rejection, multi-enrollment)
2. dac7d7b — wrap/up error branch tests (spawn failure, health timeout, child spawn, cleanup edge cases)
3. 545924c — Hypothesis security property tests (19 tests across 7 classes)
4. 9acfa67 — quality pass addressing Brutus/Karen review gaps
5. 426a2a9 — production fix: proper error handling in bootstrap, lock, unlock, up, wrap
6. c5193f4 — complete error branch coverage + bootstrap tests
7. f2be29c — security fix: shard_a memory leak + narrowed _init_db catch

Test plan

• Full suite: 594 passed (up from 551 before Wave 3)
• Security property tests with Hypothesis (binary + text key strategies)
• All error branches exercise production error wrapping
• Bootstrap tests assert specific WorthlessError codes
• Regression review cleared (regression-dog + 4 expert agents)

Follow-up

• worthless-t7h: @error_boundary decorator + --debug flag + error message sanitization (P3 backlog)

🤖 Generated with Claude Code

Summary by CodeRabbit

• Bug Fixes

  • CLI commands now report errors consistently and exit with reliable codes for bootstrap, lock, unlock, up, and wrap flows.
  • Improved handling of filesystem, database, and subprocess failures to avoid crashes and leave state consistent.

• Tests

  • Added extensive tests covering CLI error paths, startup/daemon behavior, and edge cases for lock/unlock/wrap.
  • New security property tests for cryptography, zeroization, tamper detection, and sanitized upstream error handling.

[coderabbitai]

ℹ️ Recent review info

⚙️ Run configuration

Configuration used: Path: .coderabbit.yaml

Review profile: CHILL

Plan: Free

Run ID: 62837265-668c-414f-8d79-c4757f7dceaf

📥 Commits

Reviewing files that changed from the base of the PR and between f2be29c and 5873470.

📒 Files selected for processing (11)

• src/worthless/cli/bootstrap.py
• src/worthless/cli/commands/lock.py
• src/worthless/cli/commands/unlock.py
• src/worthless/cli/commands/up.py
• src/worthless/cli/commands/wrap.py
• tests/test_cli_bootstrap.py
• tests/test_cli_lock.py
• tests/test_cli_unlock.py
• tests/test_cli_up.py
• tests/test_cli_wrap.py
• tests/test_security_properties.py

✅ Files skipped from review due to trivial changes (1)

• src/worthless/cli/commands/wrap.py

🚧 Files skipped from review as they are similar to previous changes (6)

• src/worthless/cli/commands/lock.py
• tests/test_cli_bootstrap.py
• tests/test_cli_up.py
• tests/test_cli_unlock.py
• src/worthless/cli/commands/up.py
• tests/test_cli_wrap.py

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📝 Walkthrough

Walkthrough

Added granular error handling across CLI bootstrap and command flows: filesystem and Fernet key creation, database initialization, key protection/enrollment, proxy/process startup, and wrapping CLI commands now catch specific exceptions and convert them to WorthlessError codes; extensive tests and property tests exercise these failure paths and security invariants.

Changes

Cohort / File(s)	Summary
Bootstrap src/worthless/cli/bootstrap.py	Wrapped filesystem/permission and Fernet key generation steps in OSError handling mapped to WorthlessError(ErrorCode.BOOTSTRAP_FAILED); wrapped DB init in OSError/sqlite3.DatabaseError mapped to WorthlessError(ErrorCode.SHARD_STORAGE_FAILED).
Lock / Unlock CLI src/worthless/cli/commands/lock.py, src/worthless/cli/commands/unlock.py	Replaced bare excepts with explicit exception capture and rewrap non-WorthlessError exceptions as WorthlessError(ErrorCode.SHARD_STORAGE_FAILED or ErrorCode.UNKNOWN); guarded zeroization when DB retrieval fails; added generic command-level exception handlers that print sanitized WorthlessError and exit with code 1.
Up (daemon/proxy) CLI src/worthless/cli/commands/up.py	Broadened exception handling around PID/port resolution and proxy startup; re-raise typer.Exit/SystemExit, print WorthlessError for known errors, and wrap unexpected exceptions as WorthlessError(ErrorCode.UNKNOWN). Daemon subprocess spawn failure now prints WorthlessError(ErrorCode.PROXY_UNREACHABLE) and exits.
Wrap CLI src/worthless/cli/commands/wrap.py	Enclosed end-to-end wrap flow in a try/except: re-raise typer.Exit/SystemExit, print WorthlessError for known errors, and wrap unexpected exceptions as WorthlessError(ErrorCode.UNKNOWN) then exit with code 1; no functional change to staged failure checks.
CLI Tests (bootstrap/lock/unlock/up/wrap) tests/test_cli_bootstrap.py, tests/test_cli_lock.py, tests/test_cli_unlock.py, tests/test_cli_up.py, tests/test_cli_wrap.py	Added and expanded tests to exercise error branches: permission failures, file-write errors, sqlite3.DatabaseError, multiple enrollments ambiguity, PID file/process helpers, proxy health/timeouts, subprocess spawn failures, and cleanup semantics; assertions verify exit codes, WorthlessError codes/messages, and resource/state cleanup.
Security Property Tests tests/test_security_properties.py	New Hypothesis-driven suite validating split/reconstruct correctness, shard non-degeneracy, zeroization behavior, redaction of secret material in repr/str, tamper detection raising ShardTamperedError, edge-case rejection, and static checks for gate-before-decrypt and upstream error sanitization (SR-03, SR-05).

Sequence Diagram(s)

sequenceDiagram
    participant CLI
    participant FS as Filesystem
    participant DB as Database (sqlite3)
    participant Proc as Subprocess/Proxy

    CLI->>FS: ensure .worthless dir + permissions
    alt OSError / PermissionError
        FS-->>CLI: raise OSError
        CLI-->>CLI: wrap -> WorthlessError(ErrorCode.BOOTSTRAP_FAILED)
    else success
        CLI->>FS: ensure fernet.key exists (create if missing)
        alt write error
            FS-->>CLI: raise OSError
            CLI-->>CLI: wrap -> WorthlessError(ErrorCode.BOOTSTRAP_FAILED)
        else success
            CLI->>DB: _init_db(worthless.db)
            alt sqlite3.DatabaseError / OSError
                DB-->>CLI: raise DatabaseError/OSError
                CLI-->>CLI: wrap -> WorthlessError(ErrorCode.SHARD_STORAGE_FAILED)
            else success
                CLI-->>CLI: return home ready
            end
        end
    end

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sequenceDiagram
    participant UserCLI as CLI Command
    participant Repo as ShardRepository/DB
    participant FS as Filesystem
    participant Proc as Proxy/Subprocess

    UserCLI->>Repo: retrieve/store operations
    alt Repo raises sqlite3.DatabaseError
        Repo-->>UserCLI: raise DatabaseError
        UserCLI-->>UserCLI: wrap -> WorthlessError(ErrorCode.SHARD_STORAGE_FAILED)
    else success
        UserCLI->>FS: read/write shard files / .env
        alt FS raises OSError/PermissionError
            FS-->>UserCLI: raise OSError
            UserCLI-->>UserCLI: wrap -> WorthlessError(ErrorCode.BOOTSTRAP_FAILED or UNKNOWN)
        else success
            UserCLI->>Proc: spawn proxy / child process
            alt subprocess.Popen fails
                Proc-->>UserCLI: raise OSError
                UserCLI-->>UserCLI: print WorthlessError(ErrorCode.PROXY_UNREACHABLE) / exit(1)
            else success
                Proc-->>UserCLI: running
            end
        end
    end

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Estimated code review effort

🎯 4 (Complex) | ⏱️ ~55 minutes

Poem

🐰 Hops and handlers, tidy and bright,

I caught the errors late at night.
Keys and shards now snug and sound,
Tests hop round to guard the ground.
A rabbit's wrap — safe, stitched tight.

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