Cases2 cases

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1. IL-0405 An expired AWS Load Balancer Controller webhook certificate left no healthy targets and took BSEE SaaS down

   PortSwigger2026

   Symptoms

   From 10:00 UTC on 11 January 2026 every BSEE SaaS instance in PortSwigger's US and Canada regions was unavailable: customers could not open the Web UI or start scans. The platform team learned of it only when customers reported it through support at 09:52 UTC the next day.

   Service outageTLS certificate errors

   Trigger

   The upgrade of the AWS Load Balancer Controller from v1.14.1 to v1.16.0 on 28 November 2025 left an orphaned webhook TLS secret that cert-manager could not renew, and the certificate in it expired on 8 January 2026.

   Root cause

   Breaking change in an upgrade

   Component

   Ingress controllerAdmission webhookcert-managerHelmConfigMaps and SecretsCloud load balancer

   Contributing factor

   Change with a delayed effectMonitoring blind spot

   Detection

   Customers reported the outage through support at 09:52 UTC on 12 January 2026, almost 24 hours after impact began, and the platform team began investigating at 10:00 UTC.

   Remediation

   • Deleted the orphaned aws-load-balancer-tls secrets in the US and Canada clusters
   • Redeployed the AWS Load Balancer Controller configuration with Helm
   • Verified that new certificates were generated and the webhooks worked again

   Action items

   • Audit all clusters for orphaned secrets that have no owning Certificate resource and resolve them
   • Add high-level application access alerting for each SaaS cluster from an external probe

   View case
2. IL-0522 An ingress-nginx chart upgrade deleted the jenkins.io Ingress and Fastly served HTTP/503 errors for hours

   Jenkins project2021

   Symptoms

   At 11:32 UTC on 18 November 2021, a user reported in the jenkinsci/jenkins Gitter channel that https://www.jenkins.io/doc/pipeline/steps/ was answering HTTP/503 errors with the message "Guru meditation" from Fastly's varnish.

   Service outageResources deleted

   Trigger

   The ingress-nginx Helm chart was upgraded from 4.0.6 to 4.0.8 at 10:42 UTC, and the new chart added an admission webhook rule that forbids Nginx configuration blocks in Ingress annotations.

   Root cause

   Breaking change in an upgrade

   Component

   Ingress controllerAdmission webhookHelmCDN and edge network

   Contributing factor

   Unverified assumptionCache-masked failureMonitoring blind spotHarmful manual action

   Detection

   A user reported in the jenkinsci/jenkins Gitter channel at 11:32 UTC that a jenkins.io page answered HTTP/503 errors, and status.jenkins.io reported the incident at 11:49 UTC.

   Remediation

   • Disabled the automated systems, rolled the ingress-nginx chart back to 4.0.6 and deleted the admission webhook by hand
   • Removed the forbidden annotations from the jenkins.io configuration
   • Upgraded the jenkins.io Helm chart to the last version known to work with ingress-nginx 4.0.8
   • Redeployed the jenkins.io Helm chart through the automated system and told Fastly to drop all cached pages

   Action items

   • Always read the changelog in depth when updating the ingress controllers, with two people pairing in real time
   • Add custom Datadog monitoring for www.origin.jenkins.io so that such an outage is detected
   • Make the monitor send the Host header www.jenkins.io so it is not redirected to Fastly
   • Check a set of pages, such as the pipeline steps page, not only the front page
   • Consider an ephemeral k3s end-to-end test before deploying to production

   Lessons

   Trusting a patch version of a Helm chart for the Ingress controller without reading its changelog in depth let a new admission rule remove the jenkins.io Ingress in production. Without monitoring on origin.jenkins.io, a user found the outage. A complete staging cluster with the same DNS setup would have caught the problem before production.

   View case

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