authentication-jwt-testing

name	authentication-jwt-testing
description	JWT and OIDC security testing covering token forgery, algorithm confusion, and claim manipulation

Authentication Jwt Testing

penkit51 AI — professional penetration testing skill pack. Authorized testing only.

Deep Exploitation Guide

Authentication / JWT / OIDC

JWT/OIDC failures often enable token forgery, token confusion, cross-service acceptance, and durable account takeover. Do not trust headers, claims, or token opacity without strict validation bound to issuer, audience, key, and context.

Attack Surface

• Web/mobile/API authentication using JWT (JWS/JWE) and OIDC/OAuth2
• Access vs ID tokens, refresh tokens, device/PKCE/Backchannel flows
• First-party and microservices verification, gateways, and JWKS distribution

Reconnaissance

Endpoints

• Well-known: /.well-known/openid-configuration, /oauth2/.well-known/openid-configuration
• Keys: /jwks.json, rotating key endpoints, tenant-specific JWKS
• Auth: /authorize, /token, /introspect, /revoke, /logout, device code endpoints
• App: /login, /callback, /refresh, /me, /session, /impersonate

Token Features

• Headers: {"alg":"RS256","kid":"...","typ":"JWT","jku":"...","x5u":"...","jwk":{...}}
• Claims: {"iss":"...","aud":"...","azp":"...","sub":"user","scope":"...","exp":...,"nbf":...,"iat":...}
• Formats: JWS (signed), JWE (encrypted). Note unencoded payload option ("b64":false) and critical headers ("crit")

Key Vulnerabilities

Signature Verification

• RS256→HS256 confusion: change alg to HS256 and use the RSA public key as HMAC secret if algorithm is not pinned
• "none" algorithm acceptance: set "alg":"none" and drop the signature if libraries accept it
• ECDSA malleability/misuse: weak verification settings accepting non-canonical signatures

Header Manipulation

• kid injection: path traversal ../../../../keys/prod.key, SQL/command/template injection in key lookup, or pointing to world-readable files
• jku/x5u abuse: host attacker-controlled JWKS/X509 chain; if not pinned/whitelisted, server fetches and trusts attacker keys
• jwk header injection: embed attacker JWK in header; some libraries prefer inline JWK over server-configured keys
• SSRF via remote key fetch: exploit JWKS URL fetching to reach internal hosts

Key and Cache Issues

• JWKS caching TTL and key rollover: accept obsolete keys; race rotation windows; missing kid pinning → accept any matching kty/alg
• Mixed environments: same secrets across dev/stage/prod; key reuse across tenants or services
• Fallbacks: verification succeeds when kid not found by trying all keys or no keys (implementation bugs)

Claims Validation Gaps

• iss/aud/azp not enforced: cross-service token reuse; accept tokens from any issuer or wrong audience
• scope/roles fully trusted from token: server does not re-derive authorization; privilege inflation via claim edits when signature checks are weak
• exp/nbf/iat not enforced or large clock skew tolerance; accept long-expired or not-yet-valid tokens
• typ/cty not enforced: accept ID token where access token required (token confusion)

Token Confusion and OIDC

• Access vs ID token swap: use ID token against APIs when they only verify signature but not audience/typ
• OIDC mix-up: redirect_uri and client mix-ups causing tokens for Client A to be redeemed at Client B
• PKCE downgrades: missing S256 requirement; accept plain or absent code_verifier
• State/nonce weaknesses: predictable or missing → CSRF/logical interception of login
• Device/Backchannel flows: codes and tokens accepted by unintended clients or services

Refresh and Session

• Refresh token rotation not enforced: reuse old refresh token indefinitely; no reuse detection
• Long-lived JWTs with no revocation: persistent access post-logout
• Session fixation: bind new tokens to attacker-controlled session identifiers or cookies

Transport and Storage

• Token in localStorage/sessionStorage: susceptible to XSS exfiltration; cookie vs header trade-offs with SameSite/CSRF
• Insecure CORS: wildcard origins with credentialed requests expose tokens and protected responses
• TLS and cookie flags: missing Secure/HttpOnly; lack of mTLS or DPoP/"cnf" binding permits replay from another device

Advanced Techniques

Microservices and Gateways

• Audience mismatch: internal services verify signature but ignore aud → accept tokens for other services
• Header trust: edge or gateway injects X-User-Id; backend trusts it over token claims
• Asynchronous consumers: workers process messages with bearer tokens but skip verification on replay

JWS Edge Cases

• Unencoded payload (b64=false) with crit header: libraries mishandle verification paths
• Nested JWT (JWT-in-JWT) verification order errors; outer token accepted while inner claims ignored

Special Contexts

Mobile

• Deep-link/redirect handling bugs leak codes/tokens; insecure WebView bridges exposing tokens
• Token storage in plaintext files/SQLite/Keychain/SharedPrefs; backup/adb accessible

SSO Federation

• Misconfigured trust between multiple IdPs/SPs, mixed metadata, or stale keys lead to acceptance of foreign tokens

Chaining Attacks

• XSS → token theft → replay across services with weak audience checks
• SSRF → fetch private JWKS → sign tokens accepted by internal services
• Host header poisoning → OIDC redirect_uri poisoning → code capture
• IDOR in sessions/impersonation endpoints → mint tokens for other users

Testing Methodology

1. Inventory issuers/consumers - Identity providers, API gateways, services, mobile/web clients
2. Capture tokens - Access and ID tokens for multiple roles; note header, claims, signature
3. Map verification endpoints - /.well-known, /jwks.json
4. Build matrix - Token Type × Audience × Service; attempt cross-use
5. Mutate components - Headers (alg, kid, jku/x5u/jwk), claims (iss/aud/azp/sub/exp), signatures
6. Verify enforcement - What is actually checked vs assumed

Validation

1. Show forged or cross-context token acceptance (wrong alg, wrong audience/issuer, or attacker-signed JWKS)
2. Demonstrate access token vs ID token confusion at an API
3. Prove refresh token reuse without rotation detection or revocation
4. Confirm header abuse (kid/jku/x5u/jwk) leading to key selection under attacker control
5. Provide owner vs non-owner evidence with identical requests differing only in token context

False Positives

• Token rejected due to strict audience/issuer enforcement
• Key pinning with JWKS whitelist and TLS validation
• Short-lived tokens with rotation and revocation on logout
• ID token not accepted by APIs that require access tokens

Impact

• Account takeover and durable session persistence
• Privilege escalation via claim manipulation or cross-service acceptance
• Cross-tenant or cross-application data access
• Token minting by attacker-controlled keys or endpoints

Pro Tips

1. Pin verification to issuer and audience; log and diff claim sets across services
2. Attempt RS256→HS256 and "none" first only if algorithm pinning is unclear; otherwise focus on header key control (kid/jku/x5u/jwk)
3. Test token reuse across all services; many backends only check signature, not audience/typ
4. Exploit JWKS caching and rotation races; try retired keys and missing kid fallbacks
5. Exercise OIDC flows with PKCE/state/nonce variants and mixed clients; look for mix-up
6. Try DPoP/mTLS absence to replay tokens from different devices
7. Treat refresh as its own surface: rotation, reuse detection, and audience scoping
8. Validate every acceptance path: gateway, service, worker, WebSocket, and gRPC
9. Favor minimal PoCs that clearly show cross-context acceptance and durable access
10. When in doubt, assume verification differs per stack (mobile vs web vs gateway) and test each

Tooling

• jwt_tool -t <url> -rh "Authorization: Bearer <token>" -M at runs the full attack matrix (alg=none, RS→HS confusion, kid injection, claim edits) and reports which mutations the server still accepts.
• jwt_tool <token> -C -d <wordlist> brute-forces HMAC secrets when an HS-family signature is in use.
• Use jwt_tool to mint a token under a key you control once you find an acceptance path (kid/jku/x5u/jwk), then replay via repeat_request.

Summary

Verification must bind the token to the correct issuer, audience, key, and client context on every acceptance path. Any missing binding enables forgery or confusion.

Platform Methodology

Authentication Jwt Testing

penkit51 AI — professional penetration testing skill pack. Authorized testing only.

Deep Exploitation Guide

Authentication / JWT / OIDC

JWT/OIDC failures often enable token forgery, token confusion, cross-service acceptance, and durable account takeover. Do not trust headers, claims, or token opacity without strict validation bound to issuer, audience, key, and context.

Attack Surface

• Web/mobile/API authentication using JWT (JWS/JWE) and OIDC/OAuth2
• Access vs ID tokens, refresh tokens, device/PKCE/Backchannel flows
• First-party and microservices verification, gateways, and JWKS distribution

Reconnaissance

Endpoints

• Well-known: /.well-known/openid-configuration, /oauth2/.well-known/openid-configuration
• Keys: /jwks.json, rotating key endpoints, tenant-specific JWKS
• Auth: /authorize, /token, /introspect, /revoke, /logout, device code endpoints
• App: /login, /callback, /refresh, /me, /session, /impersonate

Token Features

• Headers: {"alg":"RS256","kid":"...","typ":"JWT","jku":"...","x5u":"...","jwk":{...}}
• Claims: {"iss":"...","aud":"...","azp":"...","sub":"user","scope":"...","exp":...,"nbf":...,"iat":...}
• Formats: JWS (signed), JWE (encrypted). Note unencoded payload option ("b64":false) and critical headers ("crit")

Key Vulnerabilities

Signature Verification

• RS256→HS256 confusion: change alg to HS256 and use the RSA public key as HMAC secret if algorithm is not pinned
• "none" algorithm acceptance: set "alg":"none" and drop the signature if libraries accept it
• ECDSA malleability/misuse: weak verification settings accepting non-canonical signatures

Header Manipulation

• kid injection: path traversal ../../../../keys/prod.key, SQL/command/template injection in key lookup, or pointing to world-readable files
• jku/x5u abuse: host attacker-controlled JWKS/X509 chain; if not pinned/whitelisted, server fetches and trusts attacker keys
• jwk header injection: embed attacker JWK in header; some libraries prefer inline JWK over server-configured keys
• SSRF via remote key fetch: exploit JWKS URL fetching to reach internal hosts

Key and Cache Issues

• JWKS caching TTL and key rollover: accept obsolete keys; race rotation windows; missing kid pinning → accept any matching kty/alg
• Mixed environments: same secrets across dev/stage/prod; key reuse across tenants or services
• Fallbacks: verification succeeds when kid not found by trying all keys or no keys (implementation bugs)

Claims Validation Gaps

• iss/aud/azp not enforced: cross-service token reuse; accept tokens from any issuer or wrong audience
• scope/roles fully trusted from token: server does not re-derive authorization; privilege inflation via claim edits when signature checks are weak
• exp/nbf/iat not enforced or large clock skew tolerance; accept long-expired or not-yet-valid tokens
• typ/cty not enforced: accept ID token where access token required (token confusion)

Token Confusion and OIDC

• Access vs ID token swap: use ID token against APIs when they only verify signature but not audience/typ
• OIDC mix-up: redirect_uri and client mix-ups causing tokens for Client A to be redeemed at Client B
• PKCE downgrades: missing S256 requirement; accept plain or absent code_verifier
• State/nonce weaknesses: predictable or missing → CSRF/logical interception of login
• Device/Backchannel flows: codes and tokens accepted by unintended clients or services

Refresh and Session

• Refresh token rotation not enforced: reuse old refresh token indefinitely; no reuse detection
• Long-lived JWTs with no revocation: persistent access post-logout
• Session fixation: bind new tokens to attacker-controlled session identifiers or cookies

Transport and Storage

• Token in localStorage/sessionStorage: susceptible to XSS exfiltration; cookie vs header trade-offs with SameSite/CSRF
• Insecure CORS: wildcard origins with credentialed requests expose tokens and protected responses
• TLS and cookie flags: missing Secure/HttpOnly; lack of mTLS or DPoP/"cnf" binding permits replay from another device

Advanced Techniques

Microservices and Gateways

• Audience mismatch: internal services verify signature but ignore aud → accept tokens for other services
• Header trust: edge or gateway injects X-User-Id; backend trusts it over token claims
• Asynchronous consumers: workers process messages with bearer tokens but skip verification on replay

JWS Edge Cases

• Unencoded payload (b64=false) with crit header: libraries mishandle verification paths
• Nested JWT (JWT-in-JWT) verification order errors; outer token accepted while inner claims ignored

Special Contexts

Mobile

• Deep-link/redirect handling bugs leak codes/tokens; insecure WebView bridges exposing tokens
• Token storage in plaintext files/SQLite/Keychain/SharedPrefs; backup/adb accessible

SSO Federation

• Misconfigured trust between multiple IdPs/SPs, mixed metadata, or stale keys lead to acceptance of foreign tokens

Chaining Attacks

• XSS → token theft → replay across services with weak audience checks
• SSRF → fetch private JWKS → sign tokens accepted by internal services
• Host header poisoning → OIDC redirect_uri poisoning → code capture
• IDOR in sessions/impersonation endpoints → mint tokens for other users

Testing Methodology

1. Inventory issuers/consumers - Identity providers, API gateways, services, mobile/web clients
2. Capture tokens - Access and ID tokens for multiple roles; note header, claims, signature
3. Map verification endpoints - /.well-known, /jwks.json
4. Build matrix - Token Type × Audience × Service; attempt cross-use
5. Mutate components - Headers (alg, kid, jku/x5u/jwk), claims (iss/aud/azp/sub/exp), signatures
6. Verify enforcement - What is actually checked vs assumed

Validation

1. Show forged or cross-context token acceptance (wrong alg, wrong audience/issuer, or attacker-signed JWKS)
2. Demonstrate access token vs ID token confusion at an API
3. Prove refresh token reuse without rotation detection or revocation
4. Confirm header abuse (kid/jku/x5u/jwk) leading to key selection under attacker control
5. Provide owner vs non-owner evidence with identical requests differing only in token context

False Positives

• Token rejected due to strict audience/issuer enforcement
• Key pinning with JWKS whitelist and TLS validation
• Short-lived tokens with rotation and revocation on logout
• ID token not accepted by APIs that require access tokens

Impact

• Account takeover and durable session persistence
• Privilege escalation via claim manipulation or cross-service acceptance
• Cross-tenant or cross-application data access
• Token minting by attacker-controlled keys or endpoints

Pro Tips

1. Pin verification to issuer and audience; log and diff claim sets across services
2. Attempt RS256→HS256 and "none" first only if algorithm pinning is unclear; otherwise focus on header key control (kid/jku/x5u/jwk)
3. Test token reuse across all services; many backends only check signature, not audience/typ
4. Exploit JWKS caching and rotation races; try retired keys and missing kid fallbacks
5. Exercise OIDC flows with PKCE/state/nonce variants and mixed clients; look for mix-up
6. Try DPoP/mTLS absence to replay tokens from different devices
7. Treat refresh as its own surface: rotation, reuse detection, and audience scoping
8. Validate every acceptance path: gateway, service, worker, WebSocket, and gRPC
9. Favor minimal PoCs that clearly show cross-context acceptance and durable access
10. When in doubt, assume verification differs per stack (mobile vs web vs gateway) and test each

Tooling

• jwt_tool -t <url> -rh "Authorization: Bearer <token>" -M at runs the full attack matrix (alg=none, RS→HS confusion, kid injection, claim edits) and reports which mutations the server still accepts.
• jwt_tool <token> -C -d <wordlist> brute-forces HMAC secrets when an HS-family signature is in use.
• Use jwt_tool to mint a token under a key you control once you find an acceptance path (kid/jku/x5u/jwk), then replay via repeat_request.

Summary

Verification must bind the token to the correct issuer, audience, key, and client context on every acceptance path. Any missing binding enables forgery or confusion.

Validation & Reporting

• Confirm every finding with reproducible PoC before reporting
• Document: severity (CVSS), affected asset, steps, evidence, remediation
• Use record_vulnerability when running inside the penkit51 platform
• Chain low-severity findings into higher-impact attack paths
• Never report without evidence — distinguish hypothesis from confirmed vuln

Validation & Reporting

• Confirm every finding with reproducible PoC before reporting
• Document: severity (CVSS), affected asset, steps, evidence, remediation
• Use record_vulnerability when running inside the penkit51 platform
• Chain low-severity findings into higher-impact attack paths
• Never report without evidence — distinguish hypothesis from confirmed vuln