The hard part of Platform upgrades isn’t the IaC syntax (TF, Jsonnet, CDK, Pulumi, etc.); it’s other “stuff”. This “stuff” has two main dimensions: 1. Gathering environment context: what’s actually running, which version is compatible for your stack, which breaking changes matter, and what IaC patterns you use, etc. 2. Making upgrade choices and getting team’s +1: Once you’ve got the environment context nailed down, you choose a version that will hold in production, applying diffs in a meaningful way (e.g. only surgical Helm values / RBAC changes, while CRDs can be overwritten), and surfacing “the why” and “the what” of these upgrade choices to PR reviewers so they can provide meaningful feedback.
Chkk Upgrade Context Server + Upgrade Agent focuses on those two problems. - Version recommendations are computed against your constraints and policies so targets are compatible and stable, not simply recent. - Diffs are scoped to what you actually run, with ordering and selectors that make changes deterministic and auditable. - Breaking changes, critical fixes, and upgrade considerations appear next to the change, so reviews move quickly and the blast radius for each change is well-understood upfront.
Initial support includes the Cursor IDE and Helm IaC across 260+ open-source projects, including Networking (Istio, Cilium, …), Databases (PostgreSQL, Redis, …), Data Jobs (Argo Workflows, Jenkins, …), Data Streams (Kafka, RabbitMQ, …), Observability (Datadog, Grafana, …), Security (cert-manager, Kyverno, …), Autoscaling (Karpenter, KEDA, …), and Developer Tooling (ArgoCD, Bitbucket, …).
Workflow walkthrough is in the launch blog linked with this post. Or you can just dive directly into setup and docs here: https://docs.chkk.io/ai/chkk-plus-cursor
It’s early and we would really appreciate feedback from the HN community, especially from teams juggling multi-cluster upgrades or inherited IaC. Looking forward to your feedback and happy to answer questions .