kodegen_bundler_sign

Automated code signing and certificate provisioning for Kodegen daemon

Overview

kodegen_bundler_sign is a comprehensive tool for managing code signing workflows across macOS, Linux, and Windows platforms. Its primary focus is macOS, where it provides automated certificate provisioning through Apple's App Store Connect API, builds and signs privileged helper applications, and manages deployment to GitHub releases.

The package serves three main purposes:

1. Certificate Provisioning: Automates the process of obtaining Developer ID Application certificates from Apple using App Store Connect API credentials
2. Helper App Management: Builds, signs, packages, and deploys the macOS privileged helper application (KodegenHelper.app) that enables the Kodegen daemon to execute administrative tasks
3. Notarization & Signing: Provides tools for Apple notarization and direct code signing with entitlements

Quick Start

Interactive Setup (Recommended)

cargo run --package kodegen_bundler_sign -- --interactive

This will guide you through:

1. Checking for existing certificates
2. Providing App Store Connect API credentials
3. Generating and requesting a Developer ID certificate
4. Installing it to your keychain

Build Helper App

cargo run --package kodegen_bundler_sign -- --build-helper

Build and Upload to GitHub

export GITHUB_TOKEN="your_token"
cargo run --package kodegen_bundler_sign -- --build-helper --upload

Notarize an App

export APPLE_API_KEY="your_key_id"
export APPLE_API_ISSUER="your_issuer_id"
export APPLE_API_KEY_PATH="/path/to/AuthKey_XXXXXXXXXX.p8"
cargo run --package kodegen_bundler_sign -- --notarize /path/to/YourApp.app

Sign a Binary

cargo run --package kodegen_bundler_sign -- --sign /path/to/binary \
  --identity "Developer ID Application: Your Name (TEAM_ID)" \
  --entitlements entitlements.plist

CLI Modes

1. Show Configuration

cargo run --package kodegen_bundler_sign -- --show

Displays:

• Developer ID certificates in keychain
• Configuration file location (~/.config/kodegen/signing.toml)

2. Interactive Setup

cargo run --package kodegen_bundler_sign -- --interactive

Guided setup with prompts for:

• App Store Connect Issuer ID
• API Key ID
• Path to .p8 private key file
• Email address

3. Build Helper Mode

cargo run --package kodegen_bundler_sign -- --build-helper [OPTIONS]

Options:

• --upload: Upload to GitHub releases
• --github-token <TOKEN>: GitHub API token (or use GITHUB_TOKEN env var)
• --output-dir <DIR>: Output directory (default: target/helper)

4. Notarization Mode

cargo run --package kodegen_bundler_sign -- --notarize <PATH> [OPTIONS]

Options:

• --wait <BOOL>: Wait for notarization to complete (default: true)

Diagnose notarization setup:

cargo run --package kodegen_bundler_sign -- --diagnose-notarization

Environment Variables:

• APPLE_API_KEY: App Store Connect API Key ID (recommended)
• APPLE_API_ISSUER: App Store Connect Issuer ID
• APPLE_API_KEY_PATH: Path to .p8 file (optional, auto-searches standard locations)
• APPLE_ID: Apple ID email (legacy method)
• APPLE_PASSWORD: App-specific password (legacy method)
• APPLE_TEAM_ID: Team ID (legacy method)

5. Direct Signing Mode

cargo run --package kodegen_bundler_sign -- --sign <BINARY> [OPTIONS]

Options:

• --identity <IDENTITY>: Signing identity (required)
• --entitlements <PATH>: Path to entitlements.plist (optional)
• --hardened-runtime <BOOL>: Enable hardened runtime (default: true)

6. Config File Mode

cargo run --package kodegen_bundler_sign -- --config signing.toml

Example signing.toml:

platform = "macos"
dry_run = false
verbose = true

issuer_id = "xxxxxxxx-xxxx-xxxx-xxxx-xxxxxxxxxxxx"
key_id = "XXXXXXXXXX"
private_key_path = "~/.keys/AuthKey_XXXXXXXXXX.p8"
certificate_type = "developer_id"
common_name = "Kodegen Helper"
keychain = "login.keychain-db"

Architecture

Core Modules

• lib.rs: Library interface with platform-conditional exports and shared utilities
• main.rs: CLI application with six operational modes (show, interactive, build-helper, notarize, sign, config)
• config.rs: Configuration structures for all platforms
• error.rs: Custom error types using thiserror

Platform-Specific Modules

macOS (src/macos/)

• setup.rs: Certificate provisioning workflow
• keychain.rs: Keychain operations with file locking
• notarization.rs: Apple notarization workflow (submit, poll, staple)
• validation.rs: Certificate and setup validation
• prompts.rs: Interactive user prompts
• mod.rs: Module exports and platform entry point

Build & Packaging (macOS)

• build_helper.rs: macOS helper app creation and C code compilation
• sign_helper.rs: Code signing operations with codesign
• package_helper.rs: ZIP packaging and integrity hashing
• apple_api.rs: App Store Connect API client

Cross-Platform

• windows.rs: Cross-platform Authenticode signing using osslsigncode (available on all platforms, not just Windows)
• linux.rs: GPG-based signing guidance

Apple API Integration

App Store Connect API Client

The apple_api.rs module implements JWT-based authentication with Apple's certificate provisioning API.

Authentication Flow

1. Load .p8 Private Key: ECDSA ES256 private key from App Store Connect
2. Generate JWT Token:
   • Algorithm: ES256
   • Header: kid (Key ID), alg: "ES256"
   • Claims: iss (Issuer ID), aud: "appstoreconnect-v1", iat, exp (20 minutes)
3. Sign JWT: Sign with private key using jsonwebtoken crate
4. API Request: Include JWT as Bearer token in Authorization header

Certificate Request API

Endpoint: https://api.appstoreconnect.apple.com/v1/certificates

Request:

{
  "data": {
    "type": "certificates",
    "attributes": {
      "certificateType": "DEVELOPER_ID_APPLICATION",
      "csrContent": "<PEM-encoded CSR>"
    }
  }
}

Response:

{
  "data": {
    "attributes": {
      "certificateContent": "<base64-encoded DER certificate>"
    }
  }
}

Certificate Provisioning Workflow

Prerequisites

1. Apple Developer Account with Admin or Developer role
2. Create App Store Connect API Key:
   • Navigate to App Store Connect
   • Go to: Users and Access → Keys → App Store Connect API
   • Click "+" to create new key
   • Name: "Kodegen Signing"
   • Access: Developer role
   • Download .p8 file (one-time download only)
   • Note the Key ID (10 alphanumeric characters)
   • Note the Issuer ID (UUID format)

Automated Provisioning Process

1. API Authentication: JWT generation with ES256 signature (20-minute lifetime)
2. CSR Generation: RSA key pair with rcgen
3. Request Certificate: POST CSR to Apple's API
4. Create P12 Bundle: Using OpenSSL
5. Import to Keychain: With file locking to prevent race conditions
6. Save Configuration: To ~/.config/kodegen/signing.toml
7. Cleanup: Remove temporary files

Helper App Architecture

Purpose

KodegenHelper.app is a macOS privileged helper that enables the Kodegen daemon to execute administrative tasks without running the entire daemon as root. It follows macOS best practices for privilege separation using the Service Management framework.

Security Model

Authorization Requirements:

• Helper requires admin group membership
• Daemon identity must match SMAuthorizedClients in Info.plist
• Helper identity must match SMPrivilegedExecutables in daemon's Info.plist
• Code signature verification enforced by macOS

Runtime Security:

• Parent Process Validation: Uses proc_pidpath to verify parent is kodegend
• Script Size Limit: Maximum 1MB (1,048,576 bytes)
• Execution Timeout: 5 minutes enforced via SIGALRM
• Temporary File Security: Uses mkstemp for secure random filenames
• Secure Permissions: Files remain 0600 (owner-only) throughout execution
• Automatic Cleanup: Removes temporary files after execution

C Source Code Implementation

The helper is implemented in C and compiled with cc. Key features:

Main Function Flow:

1. Validate parent process name contains "kodegen" (macOS: proc_pidpath)
2. Accept script content as argv[1]
3. Validate script size <= 1MB
4. Set up SIGALRM timeout handler (300 seconds)
5. Create temporary file with mkstemp: /tmp/kodegend_helper_XXXXXX
6. Write script content (0600 permissions preserved for security)
7. Fork child process
8. Child: execl("/bin/sh", "sh", temp_path, NULL)
9. Parent: waitpid for completion
10. Clean up temporary file
11. Return child exit status

Error Handling:

• Exit code 1: Validation or setup failures
• Exit code 124: Timeout reached
• Exit code 128 + N: Killed by signal N
• Otherwise: Child process exit code

App Bundle Structure

KodegenHelper.app/
├── Contents/
│   ├── Info.plist          # Bundle metadata
│   └── MacOS/
│       └── KodegenHelper   # Compiled C executable

Info.plist Configuration

Key Settings:

• Bundle ID: ai.kodegen.kodegend.helper
• LSUIElement: true (background agent, no dock icon)
• Minimum macOS: 10.15

Authorization Settings:

<key>SMPrivilegedExecutables</key>
<dict>
    <key>ai.kodegen.kodegend.helper</key>
    <string>identifier "ai.kodegen.kodegend.helper" and anchor apple generic</string>
</dict>
<key>SMAuthorizedClients</key>
<array>
    <string>identifier "ai.kodegen.kodegend" and anchor apple generic</string>
</array>

Code Signing Process

Signing Workflow

The sign_helper.rs module implements a multi-step signing process:

1. Certificate Check: security find-identity -v -p codesigning
   • Falls back to ad-hoc signing (-) for development if no Developer ID found
2. Entitlements Creation: Generates helper.entitlements with admin authorization requirements
3. Sign Executable: codesign --force --sign <identity> --options runtime --entitlements helper.entitlements Contents/MacOS/KodegenHelper
4. Sign App Bundle: codesign --force --deep --sign <identity> --options runtime KodegenHelper.app
5. Verify Signature: codesign --verify --deep --strict KodegenHelper.app

Signing Identities

Production:

• Identity: "Developer ID Application: Your Name (TEAM_ID)"
• Obtained via automated provisioning or manual certificate installation

Development:

• Identity: "-" (ad-hoc signing)
• Set via: export KODEGEN_SIGNING_IDENTITY="-"
• Warnings instead of errors for signing failures

Hardened Runtime

All production builds use --options runtime flag, enabling:

• Library validation
• Hardened runtime protections
• Required for notarization

Notarization

Notarization Workflow

Apple notarization is a security process where Apple scans your app for malware and signs it with a notarization ticket.

Submit for notarization:

cargo run --package kodegen_bundler_sign -- --notarize /path/to/App.app

Non-blocking submission:

cargo run --package kodegen_bundler_sign -- --notarize /path/to/App.app --wait false

Diagnose setup issues:

cargo run --package kodegen_bundler_sign -- --diagnose-notarization

Authentication Methods

Modern (Recommended): App Store Connect API Key

export APPLE_API_KEY="XXXXXXXXXX"
export APPLE_API_ISSUER="xxxxxxxx-xxxx-xxxx-xxxx-xxxxxxxxxxxx"
export APPLE_API_KEY_PATH="/path/to/AuthKey_XXXXXXXXXX.p8"

Legacy: Apple ID with app-specific password

export APPLE_ID="your@email.com"
export APPLE_PASSWORD="xxxx-xxxx-xxxx-xxxx"
export APPLE_TEAM_ID="XXXXXXXXXX"

Process Flow

1. Upload: App is uploaded to Apple's notarization service using xcrun notarytool submit
2. Poll: Tool polls for completion status
3. Staple: On success, notarization ticket is stapled to the app using xcrun stapler staple

Packaging and Distribution

ZIP Creation

The package_helper.rs module creates compressed packages:

Features:

• Compression: Deflated (standard ZLIB)
• Unix Permissions: 0755 preserved
• Recursive directory traversal
• Maintains app bundle structure

Output Files:

• KodegenHelper.app.zip: Compressed app bundle
• KodegenHelper.app.zip.sha256: SHA-256 integrity hash (hex-encoded)
• app_zip_data.rs: Generated Rust code with include_bytes! macro

Integrity Verification

Hash Generation:

SHA256(KodegenHelper.app.zip) = <64-character hex string>

Verification Process:

• Checks for required files: Info.plist, executable
• Validates executable is not empty
• Verifies all files readable without corruption
• Ensures Info.plist is at least 100 bytes

Build System Integration

Generated Rust Code:

const APP_ZIP_DATA: &[u8] = include_bytes!("/path/to/KodegenHelper.app.zip");

Cargo Environment Variables:

• HELPER_ZIP_PATH: Path to ZIP file
• HELPER_ZIP_INCLUDE_FILE: Path to generated Rust file
• MACOS_HELPER_ZIP_HASH: SHA-256 hash

Atomic Operations

All build operations are atomic:

1. Create temporary working directory
2. Validate output directory is writable
3. Build and sign helper app
4. Validate helper structure
5. Create ZIP in temporary location
6. Verify ZIP integrity
7. Atomic rename to final location
8. Cleanup temporary files (success or failure)

Rollback on Failure: All temporary files removed if any step fails.

GitHub Integration

Upload Process

Target Repository: cyrup-ai/kodegen

Workflow:

1. Build and sign helper app
2. Create ZIP package
3. Calculate SHA-256 hash
4. Detect system architecture (e.g., aarch64, x86_64)
5. Get latest release via GitHub API
6. Upload as asset: KodegenHelper.app-macos-{arch}.zip

Authentication:

• GitHub token via --github-token flag
• Or GITHUB_TOKEN environment variable
• Requires repo scope for releases

Upload Command:

cargo run --package kodegen_bundler_sign -- \
  --build-helper \
  --upload \
  --github-token "ghp_xxxxxxxxxxxxxxxxxxxx"

Asset Naming Convention

Format: KodegenHelper.app-macos-{arch}.zip

Examples:

• KodegenHelper.app-macos-aarch64.zip (Apple Silicon)
• KodegenHelper.app-macos-x86_64.zip (Intel)

Windows Cross-Platform Signing

The windows module provides cross-platform Authenticode signing using osslsigncode, available on all platforms (not just Windows). This enables macOS and Linux developers to sign Windows binaries.

Usage

use kodegen_bundler_sign::windows::{SignConfig, sign_binary_with_fallback};

let config = SignConfig {
    cert_path: "path/to/cert.pfx".into(),
    key_path: None,  // Not needed for PKCS#12
    password: Some("password".to_string()),
    timestamp_url: Some("http://timestamp.digicert.com".to_string()),
    app_name: Some("MyApp".to_string()),
    app_url: Some("https://example.com".to_string()),
};

sign_binary_with_fallback(Path::new("myapp.exe"), &config).await?;

Features

• Automatic Fallback: Tries multiple timestamp servers if primary fails
• Last Resort: Signs without timestamp if all servers fail
• Cross-Platform: Uses osslsigncode for non-Windows platforms
• Certificate Formats: Supports PEM, PFX/PKCS#12

Timestamp Servers

Built-in fallback list includes:

• DigiCert
• Sectigo (Comodo)
• GlobalSign
• Others

Dependencies

Core Dependencies

Package	Version	Purpose
clap	4	Command-line argument parsing with derive macros
anyhow	1	Error handling with context
serde	1	Serialization framework
serde_json	1	JSON parsing
toml	0.9	TOML configuration parsing
thiserror	2	Custom error types
tokio	1	Async runtime (full feature set)
tempfile	3	Secure temporary file creation

macOS-Specific Dependencies

Package	Version	Purpose
rcgen	0.14	CSR and key pair generation
jsonwebtoken	9	JWT creation with ES256
base64	0.22	Base64 encoding/decoding
reqwest	0.12	HTTP client for Apple API
dirs	6	Platform-specific paths
shellexpand	3	Tilde expansion

Build & Packaging Dependencies

Package	Version	Purpose
cc	1	C code compilation
zip	6	ZIP archive creation
sha2	0.10	SHA-256 hashing
hex	0.4	Hexadecimal encoding
bytes	1	Byte buffers for uploads

Security & Reliability Dependencies

Package	Version	Purpose
fs4	0.13	File locking with async support
rand	0.9	Random password generation
zeroize	1	Secure memory clearing
chrono	0.4	Certificate expiry handling

Integration Dependencies

Package	Version	Purpose
kodegen_tools_github	local	GitHub API client
octocrab	0.47	GitHub API library
cyrup_termcolor	2	Terminal colors (required)
which	8	Binary path finding for osslsigncode

System Dependencies (macOS)

• OpenSSL: PKCS#12 bundle creation (openssl command)
• Security Framework: Keychain management (security command)
• Codesign: Code signature operations (codesign command)
• Xcode Command Line Tools: C compiler (cc command)
• Notarytool: Apple notarization (xcrun notarytool)
• Stapler: Notarization ticket stapling (xcrun stapler)

Platform Support

macOS (Full Support ✅)

Features:

• Automated certificate provisioning
• App Store Connect API integration
• Helper app building and compilation
• Code signing with Developer ID
• Apple notarization (submit, poll, staple)
• Direct binary signing with entitlements
• Hardened runtime support
• ZIP packaging with integrity hashing
• GitHub release uploads

Requirements:

• macOS 10.15 or later
• Xcode Command Line Tools
• Apple Developer Account (for certificate provisioning)
• App Store Connect API key

Windows (Cross-Platform Support ⚠️)

Current Implementation:

• Cross-platform Authenticode signing via osslsigncode
• Works on macOS, Linux, and Windows
• Automatic timestamp server fallback
• Supports PEM and PKCS#12 certificates
• Configuration parsing supported
• Guidance for native Windows tools

Recommendations for Native Windows:

# Import certificate
certutil -user -importpfx code_signing_cert.pfx

# View certificates
certmgr.msc

Linux (Minimal Support ⚠️)

Current Implementation:

• GPG setup guidance only
• No automated provisioning
• Configuration parsing supported

Recommendations:

# Generate GPG key
gpg --full-generate-key

# List keys
gpg --list-secret-keys --keyid-format LONG

Security Considerations

Certificate Security

1. Private Key Protection

   • Store .p8 files securely with restricted permissions: chmod 600
   • Never commit to version control
   • Use environment variables in CI/CD
   • Rotate API keys periodically

2. Keychain Security

   • Certificates stored in macOS Keychain
   • Access Control List restricts to /usr/bin/codesign
   • Requires user authentication on first use

3. JWT Token Security

   • Tokens expire after 20 minutes
   • Generated on-demand, not stored
   • Signed with ES256 algorithm

Helper App Security

1. Code Signing Verification

   • Hardened Runtime enabled
   • Signature checked by macOS before execution
   • Tampering detected and prevented

2. Authorization Model

   • Requires admin group membership
   • Parent process validation
   • Identity matching via Service Management

3. Execution Limits

   • 1MB script size limit prevents abuse
   • 5-minute timeout prevents hangs
   • Automatic cleanup prevents file leaks

4. Input Validation

   • Parent process name verification
   • Script size validation
   • Proper error handling for all system calls

GitHub Upload Security

1. Token Permissions

   • Minimum: repo scope
   • Recommended: Fine-grained token scoped to repository
   • Never expose tokens in logs or error messages

2. Asset Verification

   • SHA-256 hash published with release
   • Users should verify hash before use
   • Download only from official releases

Troubleshooting

Certificate Provisioning

Issue: Certificate request failed: Unauthorized

Solutions:

• Verify Issuer ID and Key ID are correct
• Ensure .p8 file is not corrupted
• Check API key has "Developer" role in App Store Connect
• Confirm API key is not revoked

---

Issue: Failed to import to keychain

Solutions:

# Unlock keychain
security unlock-keychain login.keychain-db

# List keychains
security list-keychains

# Verify OpenSSL installation
which openssl
openssl version

---

Issue: No Developer ID certificate found

Solutions:

• Run interactive setup: cargo run --package kodegen_bundler_sign -- --interactive
• Or use ad-hoc signing: export KODEGEN_SIGNING_IDENTITY="-"

Helper Building

Issue: Failed to compile helper: cc not found

Solutions:

# Install Xcode Command Line Tools
xcode-select --install

# Verify installation
cc --version
xcode-select -p

---

Issue: Failed to sign executable: code object is not signed at all

Solution: This is a warning in development mode, not an error. The build continues with ad-hoc signing.

---

Issue: Helper validation failed: Helper executable not executable

Solutions:

# Check permissions
ls -l target/helper/KodegenHelper.app/Contents/MacOS/KodegenHelper

# Fix permissions
chmod +x target/helper/KodegenHelper.app/Contents/MacOS/KodegenHelper

Notarization

Issue: No notarization credentials found in environment

Solutions:

# Set API key credentials (recommended)
export APPLE_API_KEY="XXXXXXXXXX"
export APPLE_API_ISSUER="xxxxxxxx-xxxx-xxxx-xxxx-xxxxxxxxxxxx"
export APPLE_API_KEY_PATH="/path/to/AuthKey_XXXXXXXXXX.p8"

# Or use Apple ID (legacy)
export APPLE_ID="your@email.com"
export APPLE_PASSWORD="xxxx-xxxx-xxxx-xxxx"
export APPLE_TEAM_ID="XXXXXXXXXX"

---

Issue: Notarization failed

Solutions:

• Run diagnostics: cargo run --package kodegen_bundler_sign -- --diagnose-notarization
• Check app is signed with Developer ID
• Verify hardened runtime is enabled
• Ensure all frameworks and executables are signed
• Check notarization log for specific errors

GitHub Upload

Issue: GitHub token required for upload

Solutions:

# Set environment variable
export GITHUB_TOKEN="ghp_xxxxxxxxxxxxxxxxxxxx"

# Or use CLI flag
cargo run --package kodegen_bundler_sign -- --build-helper --upload --github-token "ghp_xxx"

---

Issue: Failed to get latest release

Solutions:

• Verify repository exists: cyrup-ai/kodegen
• Check token has repo scope
• Ensure at least one release exists
• Verify network connectivity

Development

Local Development Setup

# 1. Clone repository (adjust path for your setup)
cd kodegen-bundler-sign

# 2. Provision certificate (one-time)
cargo run --package kodegen_bundler_sign -- --interactive

# 3. Build helper app
cargo run --package kodegen_bundler_sign -- --build-helper

# 4. Verify output
ls -lh target/helper/

Testing

# Run with verbose output (via config file with verbose = true)
cargo run --package kodegen_bundler_sign -- --config signing.toml

# Dry-run mode (via config file with dry_run = true)
cargo run --package kodegen_bundler_sign -- --config signing.toml

# Show current configuration
cargo run --package kodegen_bundler_sign -- --show

# Diagnose notarization setup
cargo run --package kodegen_bundler_sign -- --diagnose-notarization

CI/CD Integration

GitHub Actions Example:

name: Build Helper

on:
  push:
    branches: [main]
  release:
    types: [created]

jobs:
  build-macos:
    runs-on: macos-latest
    steps:
      - uses: actions/checkout@v4

      - name: Setup Rust
        uses: dtolnay/rust-toolchain@nightly
        with:
          components: rustfmt, clippy

      - name: Provision Certificate
        env:
          ISSUER_ID: ${{ secrets.APP_STORE_CONNECT_ISSUER_ID }}
          KEY_ID: ${{ secrets.APP_STORE_CONNECT_KEY_ID }}
          PRIVATE_KEY: ${{ secrets.APP_STORE_CONNECT_PRIVATE_KEY }}
        run: |
          echo "$PRIVATE_KEY" > AuthKey.p8
          chmod 600 AuthKey.p8
          cargo run --package kodegen_bundler_sign -- \
            --issuer-id "$ISSUER_ID" \
            --key-id "$KEY_ID" \
            --private-key AuthKey.p8

      - name: Build Helper
        run: |
          cargo run --package kodegen_bundler_sign -- --build-helper

      - name: Upload to Release
        if: github.event_name == 'release'
        env:
          GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
        run: |
          cargo run --package kodegen_bundler_sign -- \
            --build-helper \
            --upload

License

See LICENSE.md in the repository root.