Install the Datadog Agent on Kubernetes

Before doing anything else: Fully resolve all variables in ## Context to resolve before acting. Do not begin Step 1 until every variable has a concrete value.

Phase 0: Load Credentials

[ -f environment ] && source environment
echo "DD_API_KEY set: $([ -n "${DD_API_KEY:-}" ] && echo yes || echo no)"
echo "DD_SITE: ${DD_SITE:-not set}"
echo "helm: $(helm version --short 2>/dev/null || echo NOT FOUND)"

If helm is not found — tell the user:

helm is required for this skill. Install it with: ``bash brew install helm # macOS # or see https://helm.sh/docs/intro/install/ for other platforms `` Once installed, let me know and I'll continue.

Do not proceed until helm is available.

If DD_API_KEY is already set — proceed to Prerequisites.

If DD_API_KEY is not set — tell the user:

I need two things to continue: 1. Datadog API Key — used to authenticate the Agent with your Datadog account. You can find or create one at: https://app.datadoghq.com/organization-settings/api-keys 2. Datadog Site — the region your Datadog account is on. Most accounts use datadoghq.com. Check your Datadog URL to confirm (e.g. app.datadoghq.eu → site is datadoghq.eu). Other options: us3.datadoghq.com, us5.datadoghq.com, ap1.datadoghq.com. Please run the following in this chat to set your credentials (the ! prefix executes it in this session): `` ! export DD_API_KEY=your-api-key-here ! export DD_SITE=datadoghq.com ``

Wait for the user to run the commands, then re-run the check above before continuing.

---

Prerequisites

• [ ] Kubernetes v1.20+ — kubectl version
• [ ] helm v3+ — helm version
• [ ] kubectl configured to target cluster — kubectl config current-context
• [ ] pup-cli installed — check with pup --version; if missing, install it now:

  if [[ "$(uname)" == "Darwin" ]]; then
    brew tap datadog-labs/pack && brew install pup
  else
    PUP_VERSION=$(curl -s https://api.github.com/repos/datadog-labs/pup/releases/latest | grep '"tag_name"' | cut -d'"' -f4)
    curl -L "https://github.com/datadog-labs/pup/releases/download/${PUP_VERSION}/pup_linux_amd64.tar.gz" | tar xz -C /usr/local/bin pup
    chmod +x /usr/local/bin/pup
  fi
  pup --version

Do not skip — proceed only once pup --version succeeds.

---

Context to resolve before acting

---

Step 1: Check for an Existing Agent Installation

Claude runs

helm list -A | grep -i datadog

If a release shows deployed — Agent already installed. Skip to Step 5 to confirm health, then exit.

If there is no output — no existing install. Continue to Step 2.

---

Step 2: Install the Datadog Operator

Claude runs

helm repo add datadog https://helm.datadoghq.com
helm repo update

helm upgrade --install datadog-operator datadog/datadog-operator \
  --namespace <AGENT_NAMESPACE> \
  --create-namespace \
  --version <CHART_VERSION>

kubectl wait --for=condition=Ready pod \
  -l app.kubernetes.io/name=datadog-operator \
  -n <AGENT_NAMESPACE> \
  --timeout=120s

If the Operator pod is Running — continue to Step 3.

ERROR: Pod not ready after 120s — check image pull: kubectl describe pod -l app.kubernetes.io/name=datadog-operator -n <AGENT_NAMESPACE>.

---

Step 3: Create the API Key Secret

What you need to do in a terminal

export DD_API_KEY=<your-api-key>

kubectl create secret generic datadog-secret \
  --from-literal api-key=$DD_API_KEY \
  --namespace <AGENT_NAMESPACE>

If secret/datadog-secret created — continue to Step 4.

ERROR: AlreadyExists — confirm which key it holds via Step 5 before deciding whether to recreate.

---

Step 4: Deploy the DatadogAgent Resource

[DECISION: cluster type]

• Self-hosted (minikube, kind): include kubelet.tlsVerify: false inside spec.global
• Managed (GKE, EKS, AKS): omit kubelet.tlsVerify entirely

[DECISION: APM/SSI also being enabled in this session]

• If yes: do not create a separate DatadogAgent for APM — extend this same manifest with features.apm per enable-ssi. One manifest, not two.
• If no: use the manifest below as-is.

Save the following as datadog-agent.yaml:

apiVersion: datadoghq.com/v2alpha1
kind: DatadogAgent
metadata:
  name: datadog
  namespace: <AGENT_NAMESPACE>
spec:
  global:
    clusterName: <CLUSTER_NAME>
    site: <DD_SITE>
    credentials:
      apiSecret:
        secretName: datadog-secret
        keyName: api-key
    # Self-hosted clusters only (minikube, kind):
    # kubelet:
    #   tlsVerify: false
  features:
    orchestratorExplorer:
      enabled: true
    clusterChecks:
      enabled: true
    logCollection:
      enabled: true
      containerCollectAll: false

Claude runs

kubectl apply -f datadog-agent.yaml

kubectl wait --for=condition=Ready pod \
  -l app.kubernetes.io/component=agent \
  -n <AGENT_NAMESPACE> \
  --timeout=120s 2>/dev/null || true

---

Step 5: Verify the API Key

Claude runs

kubectl logs -l app.kubernetes.io/component=agent \
  -n <AGENT_NAMESPACE> \
  --tail=50 2>/dev/null \
  | grep -iE "invalid.*api\.?key|api\.?key.*invalid" \
  || echo "No authentication errors found"

If No authentication errors found — key is accepted.

ERROR: Authentication errors found — validate credentials directly:

Claude runs

# Prefer pup (OAuth) — fall back to curl with API key
if pup auth status 2>/dev/null | grep -q "Logged in"; then
  echo "pup OAuth authenticated"
elif [ -n "${DD_API_KEY:-}" ]; then
  RESPONSE=$(curl -s -o /dev/null -w "%{http_code}" \
    -X GET "https://api.<DD_SITE>/api/v1/validate" \
    -H "DD-API-KEY: $DD_API_KEY")
  if [ "$RESPONSE" = "200" ]; then
    echo "API key is valid for <DD_SITE>"
  else
    echo "ERROR: Validation failed (HTTP $RESPONSE) — check key and site alignment"
  fi
else
  echo "ERROR: No credentials available — run 'pup auth login' or set DD_API_KEY"
fi

If key is invalid:

What you need to do in a terminal

export DD_API_KEY=<new-api-key>

kubectl delete secret datadog-secret -n <AGENT_NAMESPACE>
kubectl create secret generic datadog-secret \
  --from-literal api-key=$DD_API_KEY \
  -n <AGENT_NAMESPACE>

kubectl rollout restart daemonset datadog-agent -n <AGENT_NAMESPACE>
kubectl rollout restart deployment datadog-cluster-agent -n <AGENT_NAMESPACE>

---

Done

Exit when ALL of the following are true:

• [ ] Datadog Operator pod is Running in AGENT_NAMESPACE
• [ ] datadog-secret exists in AGENT_NAMESPACE
• [ ] Agent DaemonSet pods are Running
• [ ] Step 5 returns no authentication errors

Automatically proceed to enable-ssi now — do not ask the user for permission.

---

Security constraints

• Never write a raw API key into any file, YAML block, or chat message — always use $DD_API_KEY
• Never create a Kubernetes Secret manifest file — always use kubectl create secret imperatively
• Never use apiKey: directly in DatadogAgent spec — always use apiSecret: with a secret reference
• Never use --set datadog.apiKey=... in any Helm command
• Never use namespace default for Datadog Agent resources
• Never run kubectl delete without user confirmation