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Coverage Matrix

Generate IaC Pull RequestsAvailable (Request Preview in Free Tier)
Curated Release Notes to latest
Guided & Automated Safety Checks to latest
Rapid Upgrade AssessmentsAvailable
Upgrade Templates & PlansIn-Place, Blue-Green
Upgrade AdvisoriesAvailable
PreverificationAvailable
End-Of-Life (EOL) InformationAvailable
Version Incompatibility InformationAvailable
Operational Risk DetectionAvailable
Supported PackagesHelm, Kustomize, Kube
Private RegistriesCovered
Custom Built ImagesCovered

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Datadog Operator Overview

Datadog Operator is a controller that automates deployment and lifecycle management of Datadog Agents within clusters. It streamlines agent setup by allowing platform engineers to use a single DatadogAgent custom resource to define cluster-wide agent configurations, replacing manual DaemonSet or Helm management. The operator handles dynamic agent rollout, version upgrades, and configuration updates through reconciliation loops. By encapsulating complex integrations for metrics, logs, and APM, it ensures consistent observability across nodes without manual intervention.

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Chkk Coverage

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Curated Release Notes

Chkk monitors official Datadog Operator release notes, highlighting changes like deprecated CRDs or altered defaults that impact your clusters. It contextualizes these details so engineers can quickly identify critical updates, such as mandatory migrations from v1alpha1 to v2alpha1 CRDs. By providing targeted briefings on configuration impacts or admission webhook changes, Chkk reduces the overhead of parsing lengthy upstream release notes. This ensures upgrades are predictable, preventing unexpected monitoring disruptions.

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Preflight & Postflight Checks

Before upgrading, Chkk validates Kubernetes version compatibility, ensures appropriate CRD migrations (e.g., conversion webhooks for v1alpha1 resources), and detects deprecated configuration fields. After upgrades, it verifies operator health, confirms successful rollout of agent pods, and inspects CR statuses for errors like misconfigured API keys. By automating these checks, Chkk quickly identifies and helps engineers remediate issues such as stuck pods or incomplete rollouts. This proactive approach minimizes monitoring gaps post-upgrade.

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Version Recommendations

Chkk tracks Datadog Operator versions against compatibility and support timelines, alerting teams when their current version approaches end-of-life or poses compatibility risks. It specifically highlights critical issues, such as upcoming CRD removals or incompatibilities with older Kubernetes versions. Chkk’s recommendations include stable, community-validated upgrade paths, balancing the need for new features against operational stability. Engineers can confidently plan upgrades without risking monitoring reliability.

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Upgrade Templates

Chkk offers detailed Upgrade Templates covering necessary steps like CRD conversions and required preparation tasks. These templates provide step-by-step instructions for safely upgrading the operator, including rollback points and validation checks suitable for GitOps or CI/CD pipelines. They ensure essential procedures—such as enabling conversion webhooks or managing operator Deployment upgrades—are not missed. This reduces operational complexity and prevents monitoring outages during upgrades.

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Preverification

Chkk’s preverification simulates Datadog Operator upgrades in isolated environments mirroring your production setup. It tests the entire upgrade sequence, revealing potential issues like increased resource usage or stricter validation rules that may block deployment. Engineers can proactively address these issues by adjusting manifests or resource allocations before production rollout. Preverification substantially reduces the likelihood of surprise failures, making upgrades safe and predictable.

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Supported Packages

Chkk supports Datadog Operator deployments via Helm charts, OperatorHub (OLM), Kustomize, or plain YAML manifests. It seamlessly manages upgrades regardless of your chosen installation method, preserving customizations such as private registries or tailored node selectors and tolerations. Chkk identifies relevant changes between operator versions—such as updated RBAC rules or container images—and provides minimal required edits for safe upgrades. This flexibility allows engineers to integrate Chkk smoothly into existing deployment workflows.

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Additional Resources