Agent Install

> 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 .

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