Design proposal: Token exchange to acquire tokens for external auth

[jhrozek]

Adds a design for #2041

[JAORMX]

@claude please review this with extra focus on security. Do the review in English. Please provide some jokes in Czech at the end of the review.

[claude]

Claude finished @JAORMX's task —— View job

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Security Review of Token Exchange Design Proposal

I've completed a thorough security analysis of the token exchange middleware design. Here's my comprehensive review:

Todo List:

• Read the token exchange design proposal document
• Analyze security implications and potential vulnerabilities
• Review authentication and authorization flows
• Check for proper token handling and storage practices
• Evaluate attack vectors and mitigation strategies
• Provide comprehensive security feedback
• Add Czech jokes as requested

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Security Analysis

🛡️ Strengths

1. RFC 8693 Compliance: Following the standard RFC 8693 token exchange specification provides a solid security foundation with well-defined behaviors.

2. Proper Middleware Ordering: Placing token exchange middleware after auth middleware ensures incoming tokens are validated before exchange attempts.

3. Audience Validation: The design properly validates token audiences (aud=proxy → aud=upstream), which is critical for preventing token misuse.

4. Secret Management: Using SecretKeyRef in Kubernetes and proper client secret handling shows awareness of credential security.

⚠️ Security Concerns & Recommendations

1. Token Caching Security Gap (docs/proposals/token-exchange-middleware.md:67)

   • Issue: "run the token exchange for each request" creates performance issues and potential rate limiting
   • Risk: No mention of secure token caching mechanisms
   • Recommendation: Implement secure in-memory token cache with:
     • Encrypted token storage
     • Proper cache invalidation based on token expiry
     • Memory clearing on process termination

2. Client Secret Exposure Risk (docs/proposals/token-exchange-middleware.md:74-79)

   • Issue: Client secrets in CLI arguments could be exposed in process lists
   • Risk: Secrets visible via ps commands, shell history, logs
   • Recommendation: Support environment variables and secret files only, never CLI args for secrets

3. Token Storage in Transit (docs/proposals/token-exchange-middleware.md:35-39)

   • Issue: No explicit mention of token handling security during exchange
   • Risk: Tokens in memory, logs, or temporary storage
   • Recommendation:
     • Ensure all HTTP requests use TLS
     • Clear sensitive data from memory after use
     • Implement structured logging that redacts tokens

4. Missing Token Validation (docs/proposals/token-exchange-middleware.md:33)

   • Issue: Token extraction lacks validation before exchange
   • Risk: Malformed or expired tokens sent to OAuth server
   • Recommendation: Pre-validate token format and expiry before exchange attempt

5. OAuth Server Trust Boundary (docs/proposals/token-exchange-middleware.md:35)

   • Issue: No certificate pinning or validation requirements mentioned
   • Risk: MITM attacks on token exchange endpoint
   • Recommendation: Implement certificate validation and consider certificate pinning

6. Error Information Disclosure (General concern)

   • Issue: OAuth errors might leak sensitive information
   • Risk: Token details, internal service info exposed in error messages
   • Recommendation: Sanitize error responses and log detailed errors server-side only

7. Replay Attack Prevention (Missing consideration)

   • Issue: No mention of replay attack prevention
   • Risk: Intercepted requests could be replayed
   • Recommendation: Consider implementing nonce or timestamp validation

🔒 Additional Security Recommendations

1. Rate Limiting: Implement rate limiting on token exchange to prevent abuse
2. Audit Logging: Log all token exchange attempts with correlation IDs
3. Token Revocation: Handle token revocation scenarios gracefully
4. Circuit Breaker: Implement circuit breaker pattern for OAuth server failures
5. Metrics & Monitoring: Add security metrics for token exchange failures/anomalies

✅ Implementation Security Checklist

• Use secure HTTP client with proper TLS verification
• Implement token cache with encryption and expiry
• Add comprehensive audit logging
• Sanitize all error messages before client response
• Use secure random generators for any nonces/IDs
• Implement proper cleanup of sensitive data from memory
• Add rate limiting and circuit breaker patterns

📋 Testing Requirements

• Security testing with invalid/malformed tokens
• MITM attack simulation tests
• Token cache security validation
• Error message sanitization verification
• Performance testing under high load

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Czech Jokes 🇨🇿

Vtip 1:
Proč programátoři nemají rádi token exchange?
Protože pořád vyměňují tokeny, ale nikdy nevymění svou kávu za spánek! ☕

Vtip 2:
Jak se řekne "bezpečnostní chyba" česky?
"Hele, ta autentikace se rozbila, ale aspoň máme hezký error message!" 😅

Vtip 3:
Proč OAuth servery nespí?
Protože pořád někdo klepe na jejich /token endpoint! 🔑

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[codecov]

Codecov Report

✅ All modified and coverable lines are covered by tests.
✅ Project coverage is 48.28%. Comparing base (5285ed4) to head (18b0fb8).
⚠️ Report is 30 commits behind head on main.

Additional details and impacted files

@@            Coverage Diff             @@
##             main    #2063      +/-   ##
==========================================
+ Coverage   48.20%   48.28%   +0.08%     
==========================================
  Files         233      236       +3     
  Lines       29229    29690     +461     
==========================================
+ Hits        14089    14337     +248     
- Misses      14106    14277     +171     
- Partials     1034     1076      +42     

☔ View full report in Codecov by Sentry.
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[jhrozek]

Thank you for the thorough security review! We've updated the proposal to address all concerns raised. Responses inline below:

Security Concerns & Recommendations

1. Token Caching Security Gap (docs/proposals/token-exchange-middleware.md:67)
   • Issue: "run the token exchange for each request" creates performance issues and potential rate limiting
   • Risk: No mention of secure token caching mechanisms
   • Recommendation: Implement secure in-memory token cache with encrypted token storage, proper cache invalidation based on token expiry, memory clearing on process termination

Addressed: The proposal already mentioned using oauth2.ReuseTokenSource for caching. We've now created #2067 with detailed implementation notes and added a link in the proposal (line 67). This follows ToolHive's existing pattern in pkg/auth/oauth/flow.go:453-454. The Go oauth2.ReuseTokenSource provides thread-safe caching and automatic token refresh - no custom encryption needed for short-lived tokens in container-isolated environments.

2. Client Secret Exposure Risk (docs/proposals/token-exchange-middleware.md:74-79)
   • Issue: Client secrets in CLI arguments could be exposed in process lists
   • Risk: Secrets visible via ps commands, shell history, logs
   • Recommendation: Support environment variables and secret files only, never CLI args for secrets

Addressed: Updated the proposal to document secure secret handling (lines 71-114):

• Added --token-exchange-client-secret-file flag (follows existing --remote-auth-client-secret-file pattern in cmd/thv/app/auth_flags.go)
• Added environment variable support: TOOLHIVE_TOKEN_EXCHANGE_CLIENT_SECRET
• Updated examples to show file-based (recommended) and environment variable approaches
• Added explicit security warning about inline secrets

The Kubernetes operator already uses ClientSecretRef for secure secret management.

3. Token Storage in Transit (docs/proposals/token-exchange-middleware.md:35-39)
   • Issue: No explicit mention of token handling security during exchange
   • Risk: Tokens in memory, logs, or temporary storage
   • Recommendation: Ensure all HTTP requests use TLS, clear sensitive data from memory after use, implement structured logging that redacts tokens

Addressed: Added comprehensive "Security Considerations" section (lines 116-153) documenting ToolHive's existing security infrastructure:

• HTTPS enforcement: All OAuth endpoints validated for HTTPS (pkg/auth/oauth/oidc.go:69-72)
• TLS 1.2+ minimum: Enforced by default (pkg/networking/http_client.go:150-151)
• Token memory handling: Using Go's standard oauth2 library patterns - secure for short-lived tokens in containers
• Logging: Documented token redaction requirements (SHA256 hash prefix only, never full tokens)

4. Missing Token Validation (docs/proposals/token-exchange-middleware.md:33)
   • Issue: Token extraction lacks validation before exchange
   • Risk: Malformed or expired tokens sent to OAuth server
   • Recommendation: Pre-validate token format and expiry before exchange attempt

Addressed: Added explicit statement at line 63:

"This ensures that only tokens with valid signatures, non-expired timestamps, and correct audiences are sent to the OAuth server for exchange. Malformed or invalid tokens are rejected before any exchange attempt occurs."

The architecture already ensures this through middleware ordering - auth middleware validates tokens before token exchange middleware runs.

5. OAuth Server Trust Boundary (docs/proposals/token-exchange-middleware.md:35)
   • Issue: No certificate pinning or validation requirements mentioned
   • Risk: MITM attacks on token exchange endpoint
   • Recommendation: Implement certificate validation and consider certificate pinning

Addressed: Security Considerations section documents:

• TLS certificate validation enabled by default
• Custom CA bundle support (existing ToolHive infrastructure in pkg/networking/http_client.go:137-154)
• Certificate pinning considered but deemed unnecessary for enterprise deployments

Standard TLS validation is sufficient for this use case.

6. Error Information Disclosure (General concern)
   • Issue: OAuth errors might leak sensitive information
   • Risk: Token details, internal service info exposed in error messages
   • Recommendation: Sanitize error responses and log detailed errors server-side only

Addressed: Added error handling documentation with example (lines 134-148):

• Generic errors to clients: {"error": "token_exchange_failed"}
• Detailed server-side logging with token redaction
• Example showing proper error sanitization pattern

7. Replay Attack Prevention (Missing consideration)
   • Issue: No mention of replay attack prevention
   • Risk: Intercepted requests could be replayed
   • Recommendation: Consider implementing nonce or timestamp validation

Addressed: Added section at lines 150-152 explaining RFC 8693/OAuth2 standard protections:

• Short-lived tokens (1 hour expiry) minimize attack window
• OAuth server validates tokens on every exchange
• Expired/revoked tokens automatically rejected

No additional replay protection needed beyond RFC 8693 standard mechanisms.

Additional Security Recommendations

1. Rate Limiting: Implement rate limiting on token exchange to prevent abuse
2. Audit Logging: Log all token exchange attempts with correlation IDs
3. Token Revocation: Handle token revocation scenarios gracefully
4. Circuit Breaker: Implement circuit breaker pattern for OAuth server failures
5. Metrics & Monitoring: Add security metrics for token exchange failures/anomalies

These are valuable production-hardening features. The initial implementation focuses on core RFC 8693 compliance. These enhancements can be added in future iterations based on operational experience. ToolHive has an existing audit event system in pkg/events that token exchange should integrate with.

Summary

The proposal now includes:

1. Link to Create a caching layer using ReuseTokenSource for exchanged tokens #2067 for token caching implementation
2. Complete CLI flags documentation including file-based secrets and environment variables
3. New "Security Considerations" section with code references to existing infrastructure
4. Explicit token pre-validation statement
5. Error handling examples with sanitization patterns
6. Replay attack prevention explanation

Most security concerns were already addressed through ToolHive's existing infrastructure (HTTPS enforcement, TLS 1.2+, certificate validation, oauth2.ReuseTokenSource patterns). The proposal now explicitly documents these existing protections with code references.

[jhrozek]

I'm going to merge this BUT at the same time I'm hacking on a branch to add the split external auth CRD. I'll update the design if that turns out to not be too much code (meaning not take too much time)