Cases6 cases

1 to 5 of 6

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-0180 A GKE control plane auto-upgrade from 1.22 to 1.23 removed the v1beta1 Ingress and ValidatingWebhookConfiguration APIs that Istio 1.7.4 still used, and Istio stopped working in production

   Sunwoo Park2023

   Symptoms

   On 2023-05-18 a Slack alert arrived at 20:01 and Istio stopped working properly in the production GKE cluster. The istiod error logs said that the v1beta1.Ingress and v1beta1.ValidatingWebhookConfiguration resources could not be found.

   Service outage

   Trigger

   GKE automatically upgraded the production cluster's control plane from 1.22.17-gke.7500 to 1.23.17-gke.1700 at 19:52 on 2023-05-18.

   Root cause

   Breaking change in an upgrade

   Component

   IstioGKE control planeAdmission webhook

   Contributing factor

   Deferred upgrades

   Detection

   A Slack alert at 20:01 on 2023-05-18, nine minutes after the control plane upgrade. The istiod error logs showed that the v1beta1 Ingress and ValidatingWebhookConfiguration resources could not be found.

   Remediation

   • upgraded Istio from 1.7.4 to 1.13.3

   Lessons

   The first diagnosis, end of support for Istio, was wrong; the real cause was found by matching the alert time against the cluster's UPGRADE_MASTER operations in Logs Explorer. The author recommends checking the version compatibility matrices of Kubernetes, Istio and other packages, keeping a production version for at least six months and upgrading three months before end of support, keeping the test environment on the latest version, backing up before upgrades, managing deployments and versions with a tool such as Argo CD, and testing upgrades in a test environment before production.

   View case
3. IL-0060 Kubernetes 1.24 upgrade removed the master node label that Calico route reflectors selected on, dropping all pod routes and taking Reddit down for 314 minutes

   Reddit2023

   Symptoms

   About two minutes after an engineer started the Kubernetes 1.23 to 1.24 upgrade of the cluster running Reddit's legacy stack, just after 19:00 UTC, the site stopped. The CDN edge request graph, which is kept separate from the cluster, showed traffic by status collapsing. Users saw the error page, a homepage with no posts, or plain errors.

   Service outageHigh error rateDNS resolution failuresMonitoring outagePods stuck in ContainerCreatingControl plane lag

   Trigger

   An in-place upgrade of the legacy cluster from Kubernetes 1.23 to 1.24; in 1.24 the node-role.kubernetes.io/master label is removed even from running clusters.

   Root cause

   Breaking change in an upgrade

   Component

   CalicoKubernetes API serverAdmission webhooketcd

   Contributing factor

   Configuration not in codeUnrepresentative stagingUntested backupMonitoring blind spotSingle point of failure

   Detection

   The site broke about two minutes into the upgrade; an incident was opened immediately and responders were on the call within three minutes, working from CDN edge graphs because the cluster's own metrics were gone.

   Remediation

   • deleted the Open Policy Agent webhook configurations to stop API server timeouts
   • terminated all worker nodes of the cluster
   • restored the control plane from the pre-upgrade backup onto the first control plane node
   • switched off the cluster autoscaler until the control plane was stable
   • generated new TLS certificates so replacement control plane nodes could join etcd
   • brought traffic back in steps from 1% to 100%
   • restarted legacy services that had been stopped by hand

   Action items

   • Codify cluster configuration so every choice has a record, and document in detail what cannot be codified
   • Standardise components across clusters and replace bespoke configurations
   • Build tooling to manage the lifecycle of whole clusters so they can be recreated or replicated
   • Add pre-production clusters that can be tested with confidence
   • Improve the backup restore process and make cluster upgrades safe

   Lessons

   Configuration that exists only in a live cluster, edited by hand through a special tool, can be forgotten, as the route reflector setup was, and then break on an upgrade nobody connects it to. A Kubernetes upgrade cannot be reverted without a restore, so the restore procedure has to be kept current and practised. Consistent, codified clusters are what make upgrades testable; bespoke clusters keep producing outages.

   View case
4. 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
5. IL-0008 An unresponsive OPA validating webhook crash-looped the API server during a GKE master upgrade, and node auto-repair then recreated every node

   Jetstack2019

   Symptoms

   Jetstack was upgrading the master of a development cluster that many teams use to test their apps during the working day, a regional Google Kubernetes Engine (GKE) cluster in europe-west1. The upgrade ran through Jetstack's GKE Terraform pipeline and did not finish before the 20-minute Terraform timeout, while the GKE console still showed the cluster as upgrading.

   Upgrade stallControl plane unresponsiveNode recreation loopService outage

   Trigger

   A planned master upgrade of the shared development cluster. The same upgrade had been done on another pre-production environment earlier that day, and no API downtime was expected.

   Root cause

   Configuration change

   Component

   Admission webhookGKE control planeKubernetes API serverkubelet

   Contributing factor

   Excessive blast radiusNo health probesMonitoring blind spotAutomation amplification

   Detection

   The first sign was the master upgrade missing the 20-minute Terraform timeout; re-running the pipeline returned the kube-apiserver unhealthy error. The cause was identified with the help of Google Support.

   Remediation

   • Deleted the OPA ValidatingAdmissionWebhook resource during a window of API server access

   Action items

   • Limit the OPA webhook to the namespaces where the policy applies and development teams have access
   • Enable the webhook only for Ingress and Service resources, the only resources the policy validates
   • Add a liveness probe so OPA is restarted when it stops responding, and update the OPA documentation
   • Follow the open upstream Kubernetes issue about this behaviour

   Lessons

   With alerting on API server response times, the team might have seen CREATE and UPDATE requests slow down across the board as soon as the OPA-backed webhook was first deployed. Every workload needs probes: OPA looked so simple to deploy that the team skipped the Helm chart, which adds a livenessProbe for the admission controller containers among other adjustments to the tutorial configuration. Others had hit the same problem, and an upstream issue to improve it was still open.

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