When to Use

Workflow

Step 1: Secure API Key Generation

import secrets
import hashlib
import hmac
import time
import json
from datetime import datetime, timedelta

class APIKeyManager:
    """Manages secure API key lifecycle: generation, storage, validation, rotation."""

    # Key format: prefix_base64random (e.g., sk_live_a1b2c3d4e5f6...)
    # Prefix identifies the key type and environment for leak detection
    KEY_PREFIXES = {
        "live_secret": "sk_live_",
        "test_secret": "sk_test_",
        "live_public": "pk_live_",
        "test_public": "pk_test_",
    }

    def __init__(self, db_connection, redis_connection):
        self.db = db_connection
        self.redis = redis_connection

    def generate_key(self, key_type="live_secret", owner_id=None, scopes=None,
                     rate_limit=None, ip_allowlist=None, expires_days=365):
        """Generate a new API key with metadata."""
        prefix = self.KEY_PREFIXES.get(key_type, "sk_live_")

        # Generate 32 bytes (256 bits) of randomness
        random_bytes = secrets.token_bytes(32)
        key_body = secrets.token_urlsafe(32)  # Base64url-encoded

        # Full API key that the client receives (shown only once)
        full_key = f"{prefix}{key_body}"

        # Hash the key for storage (never store the raw key)
        key_hash = hashlib.sha256(full_key.encode()).hexdigest()

        # Create a short key ID for reference (first 8 chars)
        key_id = f"{prefix}{key_body[:8]}..."

        # Store the hashed key with metadata
        key_metadata = {
            "key_hash": key_hash,
            "key_id": key_id,
            "key_type": key_type,
            "owner_id": owner_id,
            "scopes": scopes or ["read"],
            "rate_limit": rate_limit or {"requests": 1000, "window": 3600},
            "ip_allowlist": ip_allowlist or [],
            "created_at": datetime.utcnow().isoformat(),
            "expires_at": (datetime.utcnow() + timedelta(days=expires_days)).isoformat(),
            "last_used": None,
            "is_active": True,
            "usage_count": 0,
        }

        # Store in database
        self.db.execute(
            "INSERT INTO api_keys (key_hash, key_id, metadata) VALUES (?, ?, ?)",
            (key_hash, key_id, json.dumps(key_metadata))
        )

        # Cache in Redis for fast validation
        self.redis.setex(
            f"apikey:{key_hash}",
            86400,  # 24-hour cache TTL
            json.dumps(key_metadata)
        )

        return {
            "api_key": full_key,       # Show to user ONCE
            "key_id": key_id,          # For reference/management
            "scopes": key_metadata["scopes"],
            "expires_at": key_metadata["expires_at"],
        }

    def validate_key(self, api_key):
        """Validate an API key and return its metadata."""
        key_hash = hashlib.sha256(api_key.encode()).hexdigest()

        # Check Redis cache first
        cached = self.redis.get(f"apikey:{key_hash}")
        if cached:
            metadata = json.loads(cached)
        else:
            # Fall back to database
            row = self.db.execute(
                "SELECT metadata FROM api_keys WHERE key_hash = ?",
                (key_hash,)
            ).fetchone()
            if not row:
                return None, "invalid_key"
            metadata = json.loads(row[0])
            # Refresh cache
            self.redis.setex(f"apikey:{key_hash}", 86400, row[0])

        # Validation checks
        if not metadata.get("is_active"):
            return None, "key_revoked"

        if metadata.get("expires_at"):
            if datetime.fromisoformat(metadata["expires_at"]) < datetime.utcnow():
                return None, "key_expired"

        # Update last used
        metadata["last_used"] = datetime.utcnow().isoformat()
        metadata["usage_count"] = metadata.get("usage_count", 0) + 1
        self.redis.setex(f"apikey:{key_hash}", 86400, json.dumps(metadata))

        return metadata, "valid"

    def revoke_key(self, key_id):
        """Immediately revoke an API key."""
        row = self.db.execute(
            "SELECT key_hash, metadata FROM api_keys WHERE key_id = ?",
            (key_id,)
        ).fetchone()
        if row:
            key_hash = row[0]
            metadata = json.loads(row[1])
            metadata["is_active"] = False
            metadata["revoked_at"] = datetime.utcnow().isoformat()

            self.db.execute(
                "UPDATE api_keys SET metadata = ? WHERE key_id = ?",
                (json.dumps(metadata), key_id)
            )
            # Invalidate cache immediately
            self.redis.delete(f"apikey:{key_hash}")
            return True
        return False

    def rotate_key(self, old_key_id, grace_period_hours=24):
        """Rotate an API key with a grace period where both old and new keys work."""
        old_row = self.db.execute(
            "SELECT key_hash, metadata FROM api_keys WHERE key_id = ?",
            (old_key_id,)
        ).fetchone()
        if not old_row:
            return None, "key_not_found"

        old_metadata = json.loads(old_row[1])

        # Generate new key with same settings
        new_key_data = self.generate_key(
            key_type=old_metadata["key_type"],
            owner_id=old_metadata["owner_id"],
            scopes=old_metadata["scopes"],
            rate_limit=old_metadata["rate_limit"],
            ip_allowlist=old_metadata["ip_allowlist"],
        )

        # Schedule old key revocation after grace period
        revoke_at = datetime.utcnow() + timedelta(hours=grace_period_hours)
        old_metadata["scheduled_revocation"] = revoke_at.isoformat()
        self.db.execute(
            "UPDATE api_keys SET metadata = ? WHERE key_id = ?",
            (json.dumps(old_metadata), old_key_id)
        )

        return {
            "new_key": new_key_data,
            "old_key_id": old_key_id,
            "old_key_revokes_at": revoke_at.isoformat(),
            "message": f"Old key will be revoked in {grace_period_hours} hours"
        }, "success"

Step 2: API Key Validation Middleware

from flask import Flask, request, jsonify, g
from functools import wraps

app = Flask(__name__)

def require_api_key(required_scopes=None):
    """Middleware to validate API key and check scopes."""
    def decorator(f):
        @wraps(f)
        def wrapped(*args, **kwargs):
            # Extract API key from header
            api_key = request.headers.get("X-API-Key")
            if not api_key:
                # Also check Authorization: Bearer <key>
                auth_header = request.headers.get("Authorization", "")
                if auth_header.startswith("Bearer "):
                    api_key = auth_header[7:]

            if not api_key:
                return jsonify({"error": "missing_api_key"}), 401

            # Validate the key
            metadata, status = key_manager.validate_key(api_key)
            if status != "valid":
                return jsonify({"error": status}), 401

            # Check IP allowlist
            if metadata.get("ip_allowlist"):
                client_ip = request.remote_addr
                if client_ip not in metadata["ip_allowlist"]:
                    return jsonify({"error": "ip_not_allowed"}), 403

            # Check scopes
            if required_scopes:
                key_scopes = set(metadata.get("scopes", []))
                if not key_scopes.intersection(required_scopes):
                    return jsonify({"error": "insufficient_scope"}), 403

            # Attach metadata to request context
            g.api_key_metadata = metadata
            return f(*args, **kwargs)
        return wrapped
    return decorator

@app.route('/api/v1/data', methods=['GET'])
@require_api_key(required_scopes=["read", "admin"])
def get_data():
    return jsonify({"data": "sensitive information"})

@app.route('/api/v1/data', methods=['POST'])
@require_api_key(required_scopes=["write", "admin"])
def create_data():
    return jsonify({"created": True})

Step 3: Automated Key Leakage Detection

# Scan GitHub repositories for leaked API keys using gitleaks
gitleaks detect --source=/path/to/repo --config=gitleaks.toml --report-path=leaks.json

# Custom gitleaks configuration for API key prefix detection
# gitleaks.toml
cat <<'EOF'
[[rules]]
id = "company-api-key-live"
description = "Company Live API Key"
regex = '''sk_live_[A-Za-z0-9_-]{32,}'''
tags = ["api-key", "live", "critical"]

[[rules]]
id = "company-api-key-test"
description = "Company Test API Key"
regex = '''sk_test_[A-Za-z0-9_-]{32,}'''
tags = ["api-key", "test"]

[[rules]]
id = "company-public-key"
description = "Company Public API Key"
regex = '''pk_live_[A-Za-z0-9_-]{32,}'''
tags = ["api-key", "public"]
EOF

# Automated leaked key revocation
import json

def process_leaked_keys(leaks_file):
    """Automatically revoke API keys detected in public repositories."""
    with open(leaks_file) as f:
        leaks = json.load(f)

    for leak in leaks:
        key_match = leak.get("match", "")
        # Extract the key from the match
        for prefix in ["sk_live_", "sk_test_", "pk_live_"]:
            if prefix in key_match:
                start = key_match.index(prefix)
                potential_key = key_match[start:start+50]  # Max key length
                # Validate and revoke
                metadata, status = key_manager.validate_key(potential_key)
                if status == "valid":
                    key_manager.revoke_key(metadata["key_id"])
                    print(f"[REVOKED] Key {metadata['key_id']} leaked in {leak.get('file')}")
                    # Notify the key owner
                    notify_owner(metadata["owner_id"], metadata["key_id"], leak)

Key Concepts

Tools & Systems

• GitHub Secret Scanning: Built-in GitHub feature that detects exposed secrets in repositories and alerts key providers
• gitleaks: Open-source tool for detecting secrets in git repositories using customizable regex patterns
• truffleHog: Secret scanning tool that searches entire git history for high-entropy strings and known secret patterns
• HashiCorp Vault: Enterprise secret management system for API key storage, rotation, and dynamic credential generation
• AWS Secrets Manager: Managed secret storage with automatic rotation support for API keys and credentials

Common Scenarios

Scenario: API Key Security Program for Developer Platform

Context: A developer platform provides public APIs authenticated with API keys. The platform has 10,000+ API consumers generating 50M+ requests per day. Keys are frequently leaked in public GitHub repositories.

Approach:

1. Implement prefixed API keys (sk_live_, sk_test_) with 256-bit entropy for leak detection
2. Store only SHA-256 hashes of keys in the database, cache validated keys in Redis
3. Implement per-key scoping: each key restricted to specific endpoints, rate limits, and optional IP allowlists
4. Build key rotation API with 24-hour grace period for seamless transitions
5. Integrate with GitHub Secret Scanning to automatically detect and revoke leaked keys within minutes
6. Run gitleaks in CI/CD pipelines to prevent key commits in first place
7. Implement anomaly detection: alert on keys used from unusual IPs or with abnormal traffic patterns
8. Add key expiration policy: all keys expire after 365 days with 30-day advance notification

Pitfalls:

• Storing API keys in plaintext in the database (use SHA-256 hashing)
• Using predictable or low-entropy key generation (use cryptographically secure random generators)
• Not implementing key prefixes, making it impossible to identify leaked keys in automated scans
• Allowing API keys in URL query parameters where they leak in logs, browser history, and Referer headers
• Not implementing rate limiting per key, allowing a single compromised key to abuse the entire API

Output Format

## API Key Security Implementation Report

**Platform**: Developer API v3
**Total Active Keys**: 12,450
**Daily Key Validations**: 52M

### Security Controls

| Control | Implementation | Status |
|---------|---------------|--------|
| Key Entropy | 256-bit (secrets.token_urlsafe(32)) | Implemented |
| Key Format | sk_live_/sk_test_ prefixed | Implemented |
| Storage | SHA-256 hashed, Redis cached | Implemented |
| Scoping | Per-key endpoint/IP/rate limits | Implemented |
| Rotation | 24-hour grace period API | Implemented |
| Expiration | 365-day max TTL | Implemented |
| Leak Detection | GitHub Secret Scanning + gitleaks | Active |
| Auto-Revocation | Leaked keys revoked within 5 min | Active |

### Key Leakage Stats (Last 30 Days)
- Keys detected in public repos: 23
- Average time to revocation: 3.2 minutes
- Keys detected in CI/CD pre-commit: 7 (prevented)