Connaisseur is a Kubernetes mutating admission controller that protects your software supply chain by allowing only container images signed by trusted sources into your clusters. It verifies signatures (Docker Content Trust/Notary v1 and Sigstore Cosign), pins images to immutable digests, and lets platform teams centrally enforce image provenance—without changing application code. Powerful as it is, upgrading Connaisseur can be risky: webhook availability, key rotations, and validator configuration can turn into outages or blocked deployments if anything is missed.

In this post, we’ll show how Chkk’s Operational Safety Platform provides an end‑to‑end approach to managing Connaisseur upgrades. From curated release notes and preflight checks to structured Upgrade Templates and preverification, Chkk helps you upgrade Connaisseur confidently, without the usual risk of disruptions or downtime.

Chkk’s Coverage for Connaisseur

Curated Release Notes

Chkk continuously monitors Connaisseur releases and distills the changes that matter to your environment. Instead of combing through upstream changelogs, you get concise, actionable highlights—like changes in supported signing backends, webhook configuration updates, mandatory Helm chart parameters, and critical security patches—with guidance on what to change and why. These summaries help platform teams assess impact quickly and avoid surprises during rollouts.

Preflight & Postflight Checks

Before an upgrade, Chkk validates cluster and Connaisseur compatibility end‑to‑end: admission webhook readiness, policy definitions, validator settings, ConfigMaps/Secrets, and the presence/validity of trusted signing keys. It catches issues like deprecated APIs, schema mismatches, or skipped intermediate upgrades in advance.

After the upgrade, postflight checks confirm healthy webhooks, digest enforcement, and expected logging for verification failures—so you detect misconfigurations immediately, not after deployments start failing.

Version Recommendations

Chkk tracks Connaisseur’s release cadence, security advisories, and Kubernetes-version compatibility, alerting you when your deployed version is vulnerable or drifting behind your cluster’s supported versions. It recommends a stable, community-tested chart release that balances reliability with features—aligned with your Helm or rendered-YAML/GitOps workflow—so you can plan upgrades proactively instead of scrambling after issues surface.

Upgrade Templates

Chkk provides structured Upgrade Templates for in‑place and blue‑green strategies using Helm or raw YAML. Templates detail safe webhook transitions, rollback points, and contingency steps for HA clusters (including temporary policy‑mode adjustments). They’re GitOps‑ and CI/CD‑friendly, so upgrades are repeatable and auditable. You can export these steps as pipeline tasks to standardize execution across teams and environments.

Preverification

Before you touch production, Chkk rehearses the upgrade on a digital twin of your environment. It validates signature verification paths, admission policies, keys, and resource SLOs—surfacing problems like missing trust roots or misconfigured validators early. Preverification drastically reduces the odds of live‑upgrade surprises. Results are captured as evidence for change management and compliance audits, complete with reproducible logs and diffs.

Supported Packages

Whether you use Helm, Kustomize, or plain manifests, Chkk adapts. It respects customized forks, private registries, and GitOps‑managed repos—mapping current configuration to new releases accurately and preserving your deployment patterns. The platform parses your current state and tailors its checks and upgrade steps to fit your approach—so you keep your preferred GitOps model while benefiting from Chkk’s automated guidance.

Chkk’s Core Benefits

Chkk Operational Safety Platform simplifies upgrades, reduces risk, and keeps your Kubernetes infrastructure operational. Here’s how that applies to Connaisseur upgrades:

• Speed Up and De-Risk Upgrades: Manually upgrading Connaisseur is time-consuming. Chkk accelerates the process and makes it safer by generating a detailed Upgrade Plan for each cluster. This plan spans all components—control plane, node versions, add-ons, and dependencies—and flags required changes, including recommended add-on versions or deprecated APIs. Instead of piecing together requirements from various release notes, teams receive a clear and actionable upgrade path. Chkk’s automation can cut upgrade preparation time by 3-5x, reducing weeks of planning to just days.
• Eliminate Redundant Effort: Many organizations squander countless hours on repetitive upgrade planning and research. By unifying upgrade workflows across teams, Chkk prevents duplication of effort and ensures that insights and processes don’t need to be reinvented with every release. This consolidation of efforts can save thousands of hours.
• Delegate, Parallelize, and Standardize Workflows: Chkk makes it easy to break out upgrade tasks among team members, all while maintaining standardized workflows that reduce confusion and boost efficiency. Engineers spend less time context-switching, and institutional knowledge is retained and shared effectively. During staff turnover or organizational changes, having a historical record of upgrade best practices prevents delays.
• Enhance Operational Safety: Kubernetes upgrades introduce inherent risk, but Chkk helps you detect and fix potential problems before they cause disruptions. With automated risk detection, your team can prevent hundreds of potential breakages annually—for every hundred clusters—saving significant break-fix effort. By focusing on proactive measures, you can innovate rather than constantly firefighting.

Simplify Upgrades for Connaisseur and 100s of Other Kubernetes Add-ons

Try Chkk Upgrade Copilot to experience how these extended capabilities can simplify your upgrade processes for Connaisseur and 100s of other Kubernetes Add-ons, Application Services, and Open Source Projects. We look forward to helping you achieve seamless, secure, and efficient operations. 

Click below to start for free or book a demo to learn more.