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

bash

[ -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:

bash

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

Variable	How to resolve
`CLUSTER_NAME`	Check repo IaC, scripts, or `kubectl config current-context`
`DD_SITE`	Ask the user. Default: `datadoghq.com` . Common options: `datadoghq.eu` , `us3.datadoghq.com` , `us5.datadoghq.com` , `ap1.datadoghq.com` . Full list: https://docs.datadoghq.com/getting_started/site/
`AGENT_NAMESPACE`	Use `datadog` unless the repo already uses `datadog-agent` consistently
`CHART_VERSION`	Run `helm search repo datadog/datadog-operator --versions \| head -5` and use the latest stable

Step 1: Check for an Existing Agent Installation

Claude runs

bash

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

bash

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

bash

export DD_API_KEY=<your-api-key>

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

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

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

bash

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

bash

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"

No authentication errors found

— key is accepted.

ERROR: Authentication errors found — validate credentials directly:

Claude runs

bash

# 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

bash

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

agent-install

NPX Install

Tags

SKILL.md Content

Install the Datadog Agent on Kubernetes

Phase 0: Load Credentials

Prerequisites

Context to resolve before acting

Step 1: Check for an Existing Agent Installation

Claude runs

Step 2: Install the Datadog Operator

Claude runs

Step 3: Create the API Key Secret

What you need to do in a terminal

Step 4: Deploy the DatadogAgent Resource

Claude runs

Step 5: Verify the API Key

Claude runs

Claude runs

What you need to do in a terminal

Done

Security constraints