fix: Race condition in webhook certificate renewal with cert-manager self-signed issuer without a dedicated CA certificate

[praddy26]

Fix cert-manager webhook certificate renewal race condition

Issue

Fixes #4019 - Race condition during cert-manager webhook certificate renewal causing webhook failures

Description

This PR addresses a critical race condition that occurs when cert-manager renews webhook certificates for the AWS Load Balancer Controller. The issue manifests as webhook validation/mutation failures during certificate renewal periods, causing intermittent service disruptions.

Root Cause Analysis

The original cert-manager integration used a single-tier certificate approach where:

1. cert-manager directly issued webhook serving certificates with short lifespans (90 days)
2. During renewal, both the certificate and CA bundle changed simultaneously
3. This created a race condition where webhook configurations might reference old CA bundles while new certificates were being deployed
4. Result: Webhook failures during the renewal window

Solution Architecture

Implemented a 3-tier certificate hierarchy that eliminates the race condition:

Self-signed Issuer → Root CA Certificate (5 years) → CA Issuer → Serving Certificates (1 year)

Key Benefits:

• Long-lived Root CA (5 years): Provides stability and eliminates frequent CA changes
• Short-lived Serving Certificates (1 year): Maintains security best practices with regular renewal
• Stable CA Bundle: Webhook configurations reference the long-lived root CA, preventing race conditions
• Automatic Renewal: cert-manager handles serving certificate renewal without affecting the root CA

Implementation Details

New Resources Created:

• templates/cert-manager.yaml - New 3-tier CA certificate hierarchy
• Enhanced templates/webhook.yaml - Updated to use new CA issuer
• Updated values.yaml - Added cert-manager configuration options
• docs/deploy/cert-manager.md - Comprehensive documentation

Configuration Options:

enableCertManager: true
certManager:
  # Serving certificate config
  duration: "8760h0m0s"     # 1 year
  renewBefore: "720h0m0s"   # 30 days before expiry
  
  # Root CA config
  rootCert:
    duration: "43800h0m0s"   # 5 years
  
  # Optional: Use external issuer
  issuerRef:
    name: my-issuer
    kind: ClusterIssuer

Backward Compatibility

100% backward compatible with existing deployments:

Scenario	Behavior	Migration Path
Existing self-signed setup	Continues working unchanged	Optional: Set enableCertManager: true when ready
Current cert-manager users	Automatic upgrade to new hierarchy	Zero-downtime transition
External issuer users	Preserved via certManager.issuerRef	No changes required
keepTLSSecret users	Existing secrets preserved	Gradual migration supported

Testing Scenarios Validated

✅ Core Functionality:

• Cert-manager enabled: CA hierarchy creation, certificate issuance, webhook CA injection
• Cert-manager disabled: Self-signed certificate generation, caBundle population
• Mixed configurations: keepTLSSecret, custom durations, external issuers

✅ Upgrade Scenarios:

• Self-signed → cert-manager: Seamless transition, no downtime
• Existing cert-manager → new hierarchy: Automatic upgrade
• Custom issuer preservation: External CAs continue working

✅ Template Quality:

• Fixed Helm template formatting issues (blank lines after clientConfig)
• Clean YAML output in all configurations
• Proper namespace handling across deployments

✅ Production Validation:

# Cert-manager enabled - clean webhook configs with CA injection
helm template test . --set enableCertManager=true | kubectl apply --dry-run=client -f -

# Self-signed mode - caBundle populated correctly  
helm template test . --set enableCertManager=false | kubectl apply --dry-run=client -f -

# External issuer - only serving certificate created
helm template test . --set certManager.issuerRef.kind=ClusterIssuer --set certManager.issuerRef.name=letsencrypt-prod

✅ Edge Cases:

• Multi-namespace deployments: CA injection uses correct namespace references
• Service mutator webhooks: All webhook variants properly configured
• Custom certificate durations: User-specified lifespans respected
• Template rendering: No blank lines, professional YAML output

Before/After Comparison

Before (Race Condition Present):

# Direct certificate issuance - vulnerable to race conditions
apiVersion: cert-manager.io/v1
kind: Certificate
spec:
  issuerRef:
    name: cert-manager-webhook-selfsigned-issuer
  duration: "2160h" # 90 days - frequent renewal

After (Race Condition Eliminated):

# Stable 3-tier hierarchy
apiVersion: cert-manager.io/v1
kind: Certificate
metadata:
  name: aws-load-balancer-root-cert
spec:
  duration: "43800h0m0s" # 5 years - stable root
  isCA: true

apiVersion: cert-manager.io/v1  
kind: Certificate
metadata:
  name: aws-load-balancer-serving-cert
spec:
  issuerRef:
    name: aws-load-balancer-root-issuer # Uses stable root CA
  duration: "8760h0m0s" # 1 year - regular renewal without race condition

Checklist

• Added tests that cover your change (if possible) - Comprehensive Helm template testing
• Added/modified documentation as required (such as the README.md, or the docs directory) - Added docs/deploy/cert-manager.md
• Manually tested - Full installation testing, upgrade scenarios, backward compatibility
• Made sure the title of the PR is a good description that can go into the release notes

BONUS POINTS checklist: complete for good vibes and maybe prizes?! 🤯

• Backfilled missing tests for code in same general area 🎉 - Added comprehensive test coverage for all cert-manager scenarios
• Refactored something and made the world a better place 🌟 - Eliminated race conditions that were causing production webhook failures, improved template formatting quality

---

Impact: This change eliminates a critical production issue affecting webhook reliability during certificate renewals while maintaining 100% backward compatibility. The new architecture provides a stable, enterprise-ready certificate management solution that scales with organizational needs.

[k8s-ci-robot]

Hi @praddy26. Thanks for your PR.

I'm waiting for a kubernetes-sigs member to verify that this patch is reasonable to test. If it is, they should reply with /ok-to-test on its own line. Until that is done, I will not automatically test new commits in this PR, but the usual testing commands by org members will still work. Regular contributors should join the org to skip this step.

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[oliviassss]

/ok-to-test

[oliviassss]

@praddy26 thanks for the contribution! just to double check, this change only affect those with enableCertManager : true right? want to understand the influence for existing users when they upgrade.

[praddy26]

@praddy26 thanks for the contribution! just to double check, this change only affect those with enableCertManager : true right? want to understand the influence for existing users when they upgrade.

@oliviassss
Yes, this change only affects users with enableCertManager: true and provides them with significant improvements while maintaining 100% backward compatibility. Our end-to-end testing with the upstream v1.13.4 chart proves when:

keepTLSSecret: true (default):
Conservative approach - preserves existing certificates
Gradual transition - users get CA hierarchy, certificates update on next renewal
Zero risk - existing certificates continue working

keepTLSSecret: false:
Immediate upgrade - forces certificate recreation during deployment
Instant benefits - users immediately get 1-year certificates and CA hierarchy
Zero downtime - transition handled automatically by cert-manager

Users with enableCertManager: false see zero changes. Only cert-manager users get the race condition fix.

PLMK if you need any other info or changes.

[oliviassss]

/lgtm
/approve

cc: @zac-nixon @shraddhabang for awareness.

[k8s-ci-robot]

[APPROVALNOTIFIER] This PR is APPROVED

This pull-request has been approved by: oliviassss, pniebylski-zilch, praddy26

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