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November 6, 2025
Introducing the Chkk Free Tier for cert-manager: Agentic Upgrades You Can Trust
Written by
Fawad Khaliq
Infrastructure evolves fast. Keeping it current shouldn’t come at the cost of reliability or peace of mind.
At Chkk, we’ve built Lifecycle Management (LCM) Agents—AI-powered systems that understand your running state, reason about dependencies, and co-execute safe, deterministic upgrade workflows alongside you.They don’t guess. They don’t generalize. They build confidence by grounding every action in your real environment and help teams move faster without losing control.
Today, we’re making that experience available to everyone.
The new Chkk Free Tier includes full-fidelity LCM Agents and workflows for cert-manager—one of the most widely used Cloud Native projects—so you can experience the complete lifecycle management loop: discover → analyze → reason → act, end-to-end, in your own environment and at no cost.
Behind every modern platform lies a constant, invisible struggle: an endless loop of upgrades, patches, and fixes. Teams spend countless hours interpreting changelogs, aligning dependencies, and responding to yet another “critical update.”
Across thousands of open-source components and hundreds of releases each year, complexity compounds fast. Security and compliance pressures require immediate patching. Application teams demand continuous delivery. Cloud providers enforce upgrade cadences. Open-source maintainers ship new versions every few weeks.
It’s a cycle that rarely stops—and one that few teams manage well.
Despite all our automation, most lifecycle management remains manual, slow, and error-prone. Engineers still trace dependencies across YAML and Helm values, run unverified scripts in production, and troubleshoot cascading failures caused by minor oversights.
The result is fatigue: a perpetual sense of running to stay in place.
But it doesn’t have to be this way.
Lifecycle management can be systematic, predictable, and safe—powered by intelligent agents that understand your environment and guide upgrades from start to finish.
The Free Tier brings Chkk’s full lifecycle management model to life, starting with cert-manager. You can explore every stage of the workflow—from discovery to review-ready PRs—and see how agentic automation transforms day-to-day upgrade work.
Upgrade Copilot & LCM Agents for cert-manager: AI Agents determine safe next versions, detect breaking changes, highlight application-client impact, and generate Helm values / RBAC diffs + CRD modifications—so reviewers understand exactly what is changing and why.
Included Free: cert-manager
Upgrade Assessments: One-click, cluster-specific assessments, surface dependencies, API deprecations, misconfigured PDBs, recommendations and target-version selections.
Included in Free Tier: 300+ Cloud-Native OSS projects
Artifact Register: Live inventory of images, charts, registries, node groups, control planes—real-time alerts for EOL or incompatible versions.
Included in Free Tier: 300+ Cloud-Native OSS projects
Application Guardrails: Operational best practices surfaced where teams work—keeping reviews focused and aligned.
Included in Free Tier: 300+ Cloud-Native OSS projects
Operational Risk Ledger: Continuous scans for known misconfigurations, defects, incompatibilities—so you fix issues before they cause outages.
Included in Free Tier: 300+ Cloud-Native OSS projects
Cursor & Claude Code integration: Use your coding assistant to open a review-ready upgrade PR from your IDE. Chkk AI agents discover your IaC pattern (Helm/Kustomize/YAML), attach pre- & post-flight checks, and align to your workflow.
Included in Free Tier: cert-manager
You can explore the full flow—onboarding, assessment, templates, plans, PR generation—on our How It Works page.
We’re launching the Free Tier to show how lifecycle management works end to end. By choosing cert-manager, a widely adopted Cloud-Native project, you experience the full loop in a familiar context before expanding across your stack.
Every upgrade starts with uncertainty—what to change, when, and in what order. Chkk’s AI-curated upgrade workflows remove that guesswork by automatically constructing an environment-specific, production-safe plan.
Each workflow is built from a deep understanding of your running state and the upstream change intelligence curated by Chkk’s agents. It maps dependencies, sequences upgrade stages, and surfaces the context behind every change—so you know why a version is recommended and how it will behave in your environment.
Plans are version-aware, reproducible, and fully auditable. Each step—whether configuration update, CRD apply, or Helm value adjustment—is grounded in verified release data and tested pre-flight checks.
Knowing that a new version exists is easy; knowing whether you should upgrade to it is hard. Chkk’s LCM Agents bridge that gap by distilling upstream release notes, breaking-change advisories, and issue trackers into actionable, environment-aware insights.
Each recommendation is grounded in your running context—current versions, dependent components, cluster configuration, and operational posture. Instead of simply suggesting “the latest,” the agent identifies the safest and most relevant path forward, considering multi-hop compatibility, end-of-life timelines, and dependency constraints across your stack.
For every upgrade, you get clear, source-linked reasoning. This transforms version selection from guesswork into a transparent, evidence-driven decision.
Not every breaking change happens inside the cluster. Many come from application clients—code, CRDs, or APIs that depend on cert-manager’s behavior.
Chkk automatically analyzes release notes, schema updates, and API diffs to identify client-facing changes and unknown incompatibilities. Whether it’s a default rotation policy, logging format, or a subtle CRD field change, the agent surfaces them early—so you know which applications will be affected and why.
See every change that matters—grouped by release, explained in plain language, and ready for action through your upgrade workflow.
Even small version bumps can hide impactful configuration changes. Chkk makes them visible. The LCM Agent automatically compares your current configuration against the target version’s manifests, surfacing inline, annotated diffs that explain exactly what changed and why it matters.
Each diff is scoped to your packaging pattern—Helm, Kustomize, or raw YAML—so you only see what’s relevant to your deployment. CRD field additions and removals, default-value shifts, and RBAC permission updates are highlighted with clear reasoning and source-linked references.
Every annotation is context-aware: not just what changed, but why it changed and how it affects your workloads. Reviewers can trace each difference back to an upstream release note, making approval decisions faster and safer.
Upgrades don’t end when a pull request is merged. Chkk’s LCM Agents enforce reliability across the entire upgrade lifecycle with built-in pre-flight, in-flight, and post-flight checks that verify readiness, monitor execution, and confirm stability after rollout.
Before any change is applied, pre-flight checks validate prerequisites such as CRD schemas, controller health, and dependency versions. During rollout, in-flight monitoring tracks key metrics and events to catch unexpected behavior in real time. Once the upgrade completes, post-flight verification confirms that workloads, webhooks, and controllers are healthy and behaving as expected.
Each check is tailored to your environment and version path—automatically generated and version-aware.
Open the pull request from your IDE. The agent brings context, evidence, and checks—making merges simple.
Sign up for Free Tier, connect your first environment, and run a cert-manager Upgrade Assessment.
Generate an Upgrade Plan, let the agent raise the PR directly from your IDE, review, and merge with confidence.
See agents observe running state, map dependencies, propose changes, and generate review-ready PRs. Once you’ve experienced that loop in action, you’ll be ready to expand it across the rest of your stack—Istio, Cilium, Keycloak, Prometheus, and hundreds more cloud native OSS projects.
We’re excited for you to experience it.
Explore How It Works
