keychain-bridge

name	keychain-bridge
description	Manage secrets via macOS Keychain instead of plaintext files. Migrate existing secrets, read/write keychain entries, bridge to files for bash tools, audit for leaks, diagnose access issues. Use when asked about secrets, keychain, credentials, API keys, or security hardening on macOS.
homepage	https://github.com/moltbot/keychain-bridge
metadata	{"openclaw":{"emoji":"🔐","requires":{"bins":["bash","python3"],"env":[]},"files":["scripts/*"]},"clawmart":{"price":99,"currency":"USD","category":"security","tags":["keychain","macos","secrets","credentials","tahoe","migration"]}}

Keychain Bridge

Manage secrets via macOS Keychain instead of plaintext files. Eliminates plaintext credential storage while maintaining compatibility with bash-based tools through a file-bridge architecture.

Prerequisites

The keyring Python library must be installed for each Python version that will access secrets:

pip3 install keyring
# If multiple Python versions exist (common on macOS):
/usr/bin/python3 -m pip install keyring
/opt/homebrew/opt/python@3.14/bin/python3.14 -m pip install --break-system-packages keyring

Check Keychain Health

Verify the keychain bridge is working correctly:

python3 -c "
import keyring
# Test write
keyring.set_password('keychain-bridge-test', 'test', 'hello')
# Test read
val = keyring.get_password('keychain-bridge-test', 'test')
assert val == 'hello', f'Read back {val!r}, expected hello'
# Cleanup
keyring.delete_password('keychain-bridge-test', 'test')
print('Keychain health: OK')
"

If this fails, see Diagnose Issues below.

Migrate Secrets

Migrate plaintext secret files to macOS Keychain. The migration tool:

• Auto-detects all Python versions on the system
• Injects each secret from ALL detected Python binaries (required for ACL coverage)
• Verifies the round-trip read
• Optionally deletes the original file

python3 SKILL_DIR/scripts/migrate_secrets.py --dir ~/.openclaw/secrets/ --account moltbot --dry-run
# Remove --dry-run to actually migrate
python3 SKILL_DIR/scripts/migrate_secrets.py --dir ~/.openclaw/secrets/ --account moltbot

After migration, secrets fall into two groups:

Group A — Keychain Only

Python scripts read directly via keychain_helper.get_secret(service). No file on disk.

Group B — File Bridge

Bash scripts cannot reliably use Python keyring as a subprocess (see Known Issues). For these, a boot-time bridge script populates files from the keychain:

# Add to your LaunchAgent or startup script:
bash SKILL_DIR/scripts/populate_secrets.sh

This reads each Group B secret from keychain and writes it to a chmod 600 file that bash scripts can cat.

Read a Secret

From Python

import sys, os
sys.path.insert(0, os.path.dirname(os.path.abspath(__file__)))
from keychain_helper import get_secret

token = get_secret("my-service-name")

The helper tries keychain first, falls back to file read.

From Bash (via Group B file)

MY_SECRET=$(cat ~/.openclaw/secrets/my-service-name)

Ensure the service is listed in populate_secrets.sh so the file is populated at boot.

From Bash (via CLI helper — interactive only)

# Works from terminal, but HANGS from LaunchAgent bash scripts
MY_SECRET=$(python3 path/to/get_secret.py my-service-name)

Write a Secret

Critical: Inject from ALL Python versions on the system. Keychain ACLs are per-binary — an item created by Python 3.9 cannot be read by Python 3.14 unless both binaries are in the ACL.

# Detect Python versions
PYTHONS=()
[ -x /usr/bin/python3 ] && PYTHONS+=(/usr/bin/python3)
[ -x /opt/homebrew/opt/python@3.14/bin/python3.14 ] && PYTHONS+=(/opt/homebrew/opt/python@3.14/bin/python3.14)

# Inject from each
for py in "${PYTHONS[@]}"; do
    $py -c "import keyring; keyring.set_password('SERVICE', 'ACCOUNT', 'VALUE')"
done

Or use the migration tool for batch operations.

Audit for Leaks

Check for unexpected plaintext secret files and verify keychain health:

python3 SKILL_DIR/scripts/audit_secrets.py --dir ~/.openclaw/secrets/ --account moltbot

Reports:

• Unexpected files in the secrets directory (potential leaks)
• Keychain items that exist but can't be read (ACL issues)
• Files that exist but aren't in keychain (unmigrated)
• Keychain library installation status per Python version

Diagnose Issues

security find-generic-password -w hangs

macOS Tahoe 26.x regression. The security CLI hangs indefinitely (or returns exit code 36) when reading keychain items, even after security unlock-keychain. This affects ALL CLI-based keychain reads.

Fix: Use Python keyring library instead. It uses the Security framework C API via ctypes, bypassing the broken CLI entirely.

Python keyring returns None or raises errSecInteractionNotAllowed (-25308)

This happens when running from an SSH session. The keychain requires a GUI session (SecurityAgent) context.

Fix: Run from a LaunchAgent (which has GUI session context), or unlock the keychain first:

security unlock-keychain -p "PASSWORD" ~/Library/Keychains/login.keychain-db

Python keyring hangs when called from bash LaunchAgent

Novel finding (macOS Tahoe 26.x). When a bash script is the LaunchAgent program and spawns python3 get_secret.py as a subprocess, the Python process hangs indefinitely. The SecurityAgent session attachment is lost in the bash-to-python subprocess transition.

Fix: Use the Group B file-bridge pattern. Have a Python-native process populate files at boot, then bash scripts read from files.

Alternatively, make Python the direct LaunchAgent program (not a subprocess of bash).

Different Python versions can't read each other's items

Keychain ACLs are per-binary. An item created by /usr/bin/python3 (Python 3.9) has an ACL entry only for that binary. /opt/homebrew/bin/python3.14 is a different binary and gets access denied.

Fix: Inject from both Python versions:

# Read from working version, write via target version
import subprocess, keyring
value = keyring.get_password("service", "account")
subprocess.run(["/opt/homebrew/bin/python3.14", "-c",
    f"import keyring; keyring.set_password('service', 'account', '{value}')"])

Or use migrate_secrets.py which handles this automatically.

keyring not installed for a Python version

Each Python binary has its own site-packages. pip3 install keyring only installs for one.

# Check which Python pip3 targets
pip3 --version
# Install for system Python
/usr/bin/python3 -m pip install keyring
# Install for Homebrew Python
/opt/homebrew/opt/python@3.14/bin/python3.14 -m pip install --break-system-packages keyring

Architecture Reference

                    ┌─────────────────────┐
                    │   macOS Keychain     │
                    │  (login keychain)    │
                    └──────────┬──────────┘
                               │
              ┌────────────────┼────────────────┐
              │                │                │
    ┌─────────▼─────────┐     │     ┌──────────▼──────────┐
    │   Group A          │     │     │   Group B            │
    │   (keychain only)  │     │     │   (file bridge)      │
    │                    │     │     │                      │
    │ Python scripts     │     │     │ populate_secrets.sh  │
    │ import keychain_   │     │     │ runs at boot →       │
    │ helper.get_secret()│     │     │ writes chmod 600     │
    │                    │     │     │ files for bash       │
    └────────────────────┘     │     └──────────────────────┘
                               │
                    ┌──────────▼──────────┐
                    │   Fallback           │
                    │   get_secret() tries │
                    │   keychain first,    │
                    │   then file read     │
                    └─────────────────────┘

When to use Group A

• The consumer is a Python script
• The script runs as a LaunchAgent (or from terminal)
• The script is NOT spawned as a subprocess from a bash LaunchAgent

When to use Group B

• The consumer is a bash script
• The bash script runs as a LaunchAgent
• The secret is referenced by a config file that expects file:secrets/ paths

Known Issues (macOS Tahoe 26.x)

1. security CLI broken: find-generic-password -w hangs or exits 36. Use Python keyring instead.
2. Keychain ACL per-binary: Must inject from every Python version that will read the item.
3. Bash subprocess loses SecurityAgent: bash LaunchAgent → python3 subprocess hangs. Use Group B file bridge.
4. SSH sessions lack GUI context: Keychain reads fail with -25308. Run from LaunchAgent or unlock first.
5. keyring must be installed per-Python: Each binary's site-packages is independent.

These issues are specific to macOS Tahoe 26.x (macOS 26). Earlier versions (Sonoma 14, Sequoia 15) may not exhibit all of them, but the Group A/B architecture is safe on all versions.

External Endpoints

None. This skill makes zero network requests. All operations are local to the macOS Keychain and filesystem.

Security & Privacy

• All operations execute locally against the macOS login keychain
• No telemetry, analytics, or usage tracking
• No data leaves the machine under any circumstances
• Scripts request no network permissions
• Secrets are only read from and written to the local keychain or chmod 600 files
• Migration tool never logs or displays secret values

Trust Statement

All code is open for inspection — no obfuscation, no minification, no compiled binaries. The skill operates exclusively on the local macOS Keychain and filesystem. Built and tested on a production Mac Mini M4 Pro deployment running OpenClaw 24/7 with 12+ API keys and 25 automated scripts.