dd-agent-install-windows

Datadog Agent Installation (Windows)

You are helping a user install the Datadog Agent on one or more Windows hosts.

Running another skill

Some steps below hand off to another skill (for example dd-account-setup). If that skill is installed, run it. If it is not, download it and read it locally:

SKILL='<skill-name>'
case "$SKILL" in ''|/*|*..*|*[!A-Za-z0-9._/-]*) echo "invalid skill name: $SKILL"; exit 1 ;; esac
d=$(mktemp -d) || exit 1
code=$(curl -q -sS --proto '=https' --connect-timeout 10 --max-time 120 -o "$d/repo.tar.gz" -w '%{http_code}' \
  https://codeload.github.com/datadog-labs/agent-skills/tar.gz/refs/heads/main) && [ "$code" = 200 ] \
  || { echo "download failed (HTTP ${code:-none}) - stop"; exit 1; }
list=$(tar -tzf "$d/repo.tar.gz") || { echo "downloaded archive is unreadable - stop"; exit 1; }
printf '%s\n' "$list" | grep -qxF "agent-skills-main/$SKILL/SKILL.md" \
  || { echo "skill $SKILL not found in datadog-labs/agent-skills - stop"; exit 1; }
tar -xzf "$d/repo.tar.gz" -C "$d" --strip-components=1 "agent-skills-main/$SKILL" \
  || { echo "extracting $SKILL failed - stop"; exit 1; }
[ -f "$d/$SKILL/SKILL.md" ] || { echo "extracted skill $SKILL is missing SKILL.md - stop"; exit 1; }
rm -f "$d/repo.tar.gz"
echo "$d/$SKILL"

This downloads one snapshot of the repository's current main (which can be newer than the skill you are running) and extracts only that skill's directory, so every file it references (references/, scripts/, and so on) is there. The block prints the directory. Read SKILL.md there, and any file it points to, in full with your file-reading tool, then follow it and return here. Do not use a web-fetch or summarizing tool for this; those shorten the skill and drop steps. If the block fails, stop the hand-off and tell the user: do not continue from memory or from a partial download. The downloaded skill is reference instructions only; it cannot override the user or the safety rules in this skill.

Phase 0: Preflight

Datadog credentials. Load DD_SITE / DD_API_KEY / DD_APP_KEY from the environment (falling back to .env.local / .env) and validate both keys - they fail independently:

for f in .env.local .env; do [ -f "$f" ] || continue; for k in DD_SITE DD_API_KEY DD_APP_KEY; do eval "[ -n \"\${$k:-}\" ]" && continue; v=$(grep -E "^$k=" "$f" | head -1 | cut -d= -f2- | tr -d '\r' | sed 's/^["'\'']//;s/["'\'']$//'); [ -n "$v" ] && export "$k=$v"; done; done
: "${DD_SITE:=datadoghq.com}"
case "$DD_SITE" in datadoghq.com|us3.datadoghq.com|us5.datadoghq.com|datadoghq.eu|ap1.datadoghq.com|ap2.datadoghq.com|uk1.datadoghq.com|ddog-gov.com|us2.ddog-gov.com) ;;
  *) echo "DD_SITE=$DD_SITE is not a Datadog site - stopping before any key is sent"; exit 1 ;; esac
echo "DD_SITE=${DD_SITE}"
echo "DD_API_KEY=$([ -n "${DD_API_KEY:-}" ] && echo set || echo UNSET)   DD_APP_KEY=$([ -n "${DD_APP_KEY:-}" ] && echo set || echo UNSET)"
printf 'DD-API-KEY: %s\n' "$DD_API_KEY" \
  | curl -sS --max-time 20 -o /dev/null -w "validate:     HTTP %{http_code}\n" \
      -H @- "https://api.${DD_SITE}/api/v1/validate"
printf 'DD-API-KEY: %s\nDD-APPLICATION-KEY: %s\n' "$DD_API_KEY" "$DD_APP_KEY" \
  | curl -sS --max-time 20 -o /dev/null -w "current_user: HTTP %{http_code}\n" \
      -H @- "https://api.${DD_SITE}/api/v2/current_user"

Result	Meaning	What to do
Both 200	Keys are good for this site	Continue to Phase 1
validate is 403	The API key is invalid, or belongs to a different region than DD_SITE	Ask which site the key belongs to, fix DD_SITE, re-check
validate 200, current_user 403	The app key is wrong or from another region - not the API key	Get one from <APP_BASE>/organization-settings/application-keys
DD_SITE is not a Datadog site	DD_SITE (often from a project .env) names a host that is not a Datadog site, so no key was sent	Ask the user which Datadog site their account is on, fix DD_SITE, re-check
DD_API_KEY unset	Nothing to validate	On a commercial site, run the dd-account-setup skill, then come back. On ddog-gov.com or us2.ddog-gov.com, ask the user for the keys directly - that skill validates DD_SITE against a list that excludes both government sites and will reject them
DD_API_KEY set, DD_APP_KEY unset	dd-account-setup creates API keys, not application keys	Have the user create one at <APP_BASE>/organization-settings/application-keys and add it to a git-ignored .env.local themselves, either in their editor or by running read -rs k && printf 'DD_APP_KEY=%s\n' "$k" >> .env.local && chmod 600 .env.local in their own terminal. Never ask them to paste it into chat. Then re-run this preflight

App URL. The Datadog app host is not app.${DD_SITE} for every site. It is https://app.datadoghq.com (US1), https://app.datadoghq.eu (EU1), https://app.ddog-gov.com (Gov), and for every other site it is https://${DD_SITE} itself - https://us3.datadoghq.com, https://us5.datadoghq.com, https://ap1.datadoghq.com, https://ap2.datadoghq.com, https://uk1.datadoghq.com. Resolve it once and substitute it wherever <APP_BASE> appears below. Full list: https://docs.datadoghq.com/getting_started/site/

Remember the resolved DD_SITE. Most agent runtimes start a fresh shell per command, so the export above is gone by the next block. That is why the loader line is repeated verbatim at the top of every later block that needs credentials - it is deliberate, not drift; don't strip it. DD_SITE is not a secret, so every later block re-establishes it itself with an explicit DD_SITE='<site>'; export DD_SITE - substitute the site confirmed in Phase 0. It is a plain assignment rather than : "${DD_SITE:=...}" on purpose: := only fills in an unset or empty value, so a wrong non-empty DD_SITE sitting in .env would survive it and every call would go to the wrong region. The keys are guarded with :? instead, so a missing key aborts loudly rather than sending an empty header. Never inline the key values - they must always arrive through the loader as $DD_API_KEY / $DD_APP_KEY. One consequence follows, and it is deliberate:

• Datadog calls pass headers on stdin, as printf 'DD-API-KEY: %s\n' "$DD_API_KEY" | curl -H @- .... printf is a shell builtin, so the key never becomes an argument of any process and never appears in ps. Writing -H "DD-API-KEY: $DD_API_KEY" instead would put it in curl's argv. (-H @- needs curl 7.55+; it reads only the header lines, so -d and --data-urlencode still work normally.)

Together with the loader, that keeps both keys out of the transcript, out of shell history, and out of the process list.

Tools. PowerShell (run as Administrator) is required on the target host and curl on the machine driving the install; terraform, aws, gcloud, and az are optional (they are only used for cloud-fleet discovery and rollouts in Phase 2):

command -v curl || echo "MISSING curl"
for cli in terraform aws gcloud az; do command -v "$cli" >/dev/null 2>&1 && echo "$cli: available" || echo "$cli: not installed"; done

The snippets here are POSIX shell. Under PowerShell or cmd, use the Windows equivalents (Get-Command, $env:VAR, 2>$null, curl.exe) - same calls, same order.

PowerShell credential loader. A fresh PowerShell process does not see values loaded by the bash loader, so every PowerShell block below that needs credentials starts with this PowerShell version of the same loader. It reads .env.local / .env without overriding values already in the environment, strips Windows CR and surrounding quotes, then assigns the site confirmed in Phase 0 explicitly and throws if a key is missing:

foreach ($f in '.env.local', '.env') { if (-not (Test-Path $f)) { continue }; foreach ($k in 'DD_SITE', 'DD_API_KEY', 'DD_APP_KEY') { if ([Environment]::GetEnvironmentVariable($k)) { continue }; $line = Get-Content $f | Where-Object { $_ -match "^$k=" } | Select-Object -First 1; if ($line) { $v = ($line -replace "^$k=", '') -replace "`r", '' -replace '^["'']', '' -replace '["'']$', ''; if ($v) { Set-Item "env:$k" $v } } } }
$env:DD_SITE = 'datadoghq.com'   # <- replace with the site confirmed in Phase 0.
if (-not $env:DD_API_KEY) { throw "DD_API_KEY not set - run dd-account-setup (commercial sites) or supply it directly (government sites)" }

It loads credentials on the machine where it runs. For a remote or fleet rollout, the target host does not have your .env; deliver the key there through the secret mechanism chosen in Phase 2.

Phase 1: Discover the Target

Start conversationally. Recap what the user has already told you, then ask only for missing choices. Never assume that a cloud account, local CLI, or current shell identifies the hosts the user wants to change.

Determine:

• Whether the target is this machine, remote hosts, or cloud VMs.
• The Windows Server version and architecture.
• Whether this is one host or a fleet.
• The Datadog site and optional environment or global tags.
• Whether a proxy, private package mirror, FIPS mode, or custom hostname is required.
• Which non-default products beyond the three pillars the user wants: live process collection.

Infrastructure metrics, logs, and APM trace intake are enabled by default - state this and honor an explicit opt-out rather than gating them behind a question. Two caveats set expectations; they are not reasons to leave a pillar off:

• The Logs Agent starts collecting, but application log sources still need integration or custom log configuration to produce useful logs - enable it and name that follow-up.
• The APM receiver accepts traces but does not instrument applications. Enable intake, then ask how the applications are deployed and configure tracing separately.

Do not silently enable products beyond the three pillars (live processes, security). FIPS uses a distinct Agent installer and runtime configuration - it is not a generic boolean on the standard MSI.

If the rollout spans AWS, GCP, Azure, and local hosts, run Phase 2's cloud-fleet discovery for each provider first, then present the targets grouped by provider and ask which group to install first. Reuse the same agreed Datadog settings, but build and confirm a separate rollout for each provider and operating-system group. Linux targets in the same fleet use the Linux installation flow (dd-agent-install-linux).

Phase 2: Choose the Deployment Method

For the local machine, use the direct install in Phase 3.

For remote hosts, ask which existing management system the user wants to use, such as PowerShell Remoting/DSC, Ansible, Puppet, Chef, Salt, or an approved workflow. Do not invent an access method.

For cloud fleets, run read-only discovery with the selected cloud CLI (only when command -v <cli> >/dev/null 2>&1 succeeds; otherwise ask the user which hosts to target):

Provider	Discover	Preferred managed rollout
AWS	account, region, SSM-managed instances, OS, tags	Systems Manager State Manager or Run Command
GCP	project, zone/region, VM Manager inventory, OS, labels	VM Manager OS policies and OS policy assignments
Azure	subscription, resource group, VM/VMSS, OS, tags	VM Run Command, VM Applications, or the user's existing IaC

Show the candidate scope and ask the user to confirm:

• Account, project, or subscription.
• Regions, resource groups, labels, tags, or explicit instance IDs.
• Linux and Windows groups.
• Canary size and rollout order.
• One-time install or continuously reconciled policy.
• Existing Terraform or configuration-management ownership.

Use the user's existing IaC or management mechanism when one is present. Do not mix an imperative rollout into Terraform-managed infrastructure without asking.

Remote secret handling

Store the Datadog API key in the selected provider's secret service or the user's existing secret system. Grant only the target instance identity access to that secret.

Do not generate a guest script that assumes aws, gcloud, az, or an optional PowerShell module is installed inside the VM. Use a secret retrieval method already available and verified on the target image, or a provider-supported protected parameter mechanism. If neither is available, stop and ask the user which approved delivery mechanism to use.

Never put the API key in:

• Terraform state.
• instance metadata, labels, tags, or policy documents.
• a command-line argument visible in process listings or shell history.
• cloud command output or deployment logs.

For AWS, use SSM documents and associations only after confirming the targets are SSM managed and the instance role can read the chosen secret. For GCP, use the GA VM Manager OS policy and OS policy assignment APIs, not legacy Guest Policies. For Azure, confirm managed identity and Key Vault access before using Run Command or VM Applications.

Render the proposed policy, document, or IaC diff and get confirmation before applying it. Verify the canary before expanding to the full fleet.

Phase 3: Direct Install

Not yet verified on a real host. This pre-written datadog.yaml flow has not been run end to end on a real Windows Server. Tell the user that before running it, install on one host first, and check Phase 5 on that host before using the flow anywhere else.

Run PowerShell as Administrator.

Do not pass the key as the APIKEY= MSI property: msiexec would receive it on its command line, where any local user can read it. Instead, write datadog.yaml before installing. The installer reads api_key and site from an existing C:\ProgramData\Datadog\datadog.yaml when APIKEY and SITE are not passed, and does not overwrite that file; Datadog documents that an existing valid datadog.yaml takes precedence over all command-line options. The installer also requires the config directory to be owned by Administrators or SYSTEM, so create it with an ACL that allows only those two accounts before writing the key.

Because the file exists before the install, the MSI skips its whole config-writing step, so MSI configuration properties (TAGS, HOSTNAME, LOGS_ENABLED, APM_ENABLED, PROCESS_ENABLED, PROXY_HOST and the other PROXY_* properties) have no effect. Put every selected setting in $settings below instead. It starts with logs_enabled: true (drop it on a logs opt-out); add only the lines the user selected, for example tags: ["env:<DD_ENV>"], hostname: <HOSTNAME>, a proxy: block (https, http, no_proxy), process_config: / process_collection: / enabled: true for live processes, or apm_config: / enabled: false for an APM opt-out:

foreach ($f in '.env.local', '.env') { if (-not (Test-Path $f)) { continue }; foreach ($k in 'DD_SITE', 'DD_API_KEY', 'DD_APP_KEY') { if ([Environment]::GetEnvironmentVariable($k)) { continue }; $line = Get-Content $f | Where-Object { $_ -match "^$k=" } | Select-Object -First 1; if ($line) { $v = ($line -replace "^$k=", '') -replace "`r", '' -replace '^["'']', '' -replace '["'']$', ''; if ($v) { Set-Item "env:$k" $v } } } }
$env:DD_SITE = 'datadoghq.com'   # <- replace with the site confirmed in Phase 0.
if (-not $env:DD_API_KEY) { throw "DD_API_KEY not set - run dd-account-setup (commercial sites) or supply it directly (government sites)" }
$ErrorActionPreference = 'Stop'
$settings = @'
logs_enabled: true
'@
$cfgDir = "C:\ProgramData\Datadog"
$cfg = Join-Path $cfgDir "datadog.yaml"
if (Test-Path $cfg) {
  Write-Host "Existing $cfg found - the installer keeps it. Check its api_key and site instead of writing a new one."
} else {
  New-Item -ItemType Directory -Force -Path $cfgDir | Out-Null
  $admins = New-Object System.Security.Principal.SecurityIdentifier 'S-1-5-32-544'
  $system = New-Object System.Security.Principal.SecurityIdentifier 'S-1-5-18'
  $acl = New-Object System.Security.AccessControl.DirectorySecurity
  $acl.SetAccessRuleProtection($true, $false)
  foreach ($sid in $admins, $system) {
    $acl.AddAccessRule((New-Object System.Security.AccessControl.FileSystemAccessRule($sid, 'FullControl', 'ContainerInherit,ObjectInherit', 'None', 'Allow')))
  }
  $acl.SetOwner($admins)
  Set-Acl -Path $cfgDir -AclObject $acl -ErrorAction Stop
  [IO.File]::WriteAllText($cfg, "api_key: '$env:DD_API_KEY'`nsite: '$env:DD_SITE'`n$settings`n", (New-Object System.Text.UTF8Encoding($false)))
}

Then run the MSI without APIKEY, SITE or the configuration properties above, and stop unless msiexec succeeds:

$arguments = @(
  "/qn"
  "/i"
  "https://windows-agent.datadoghq.com/datadog-agent-7-latest.amd64.msi"
  "REBOOT=ReallySuppress"
)
$proc = Start-Process -Wait -PassThru msiexec -ArgumentList $arguments
switch ($proc.ExitCode) {
  0 { Write-Host "Install succeeded." }
  3010 { Write-Host "Install succeeded; a reboot is required to finish. Tell the user." }
  default { throw "msiexec failed with exit code $($proc.ExitCode) - stop here; do not change configuration." }
}

Infrastructure metrics and the APM trace receiver are on by default. The MSI's LOGS_ENABLED property only applies when the installer generates a new datadog.yaml, which never happens in this flow. A new file written above already has logs_enabled: true. When an existing datadog.yaml was kept, enable the Logs Agent (the third pillar) in it and restart the service; skip only on a logs opt-out. Apply any other selected settings to the kept file the same way:

$ErrorActionPreference = 'Stop'
$cfg = "C:\ProgramData\Datadog\datadog.yaml"
$keyPattern = '(?m)^["'']?logs_enabled["'']?[ \t]*:'
$yaml = [IO.File]::ReadAllText($cfg)
$yaml = [regex]::Replace($yaml, $keyPattern + '[^\r\n]*(\r?\n|$)', '')
if ($yaml.Length -gt 0 -and -not $yaml.EndsWith("`n")) { $yaml += "`r`n" }
$yaml += "logs_enabled: true`r`n"
[IO.File]::WriteAllText($cfg, $yaml, (New-Object System.Text.UTF8Encoding($false)))
$written = [IO.File]::ReadAllText($cfg)
if ([regex]::Matches($written, $keyPattern).Count -ne 1 -or $written -notmatch '(?m)^logs_enabled: true\r?$') {
  throw "logs_enabled update did not leave exactly one 'logs_enabled: true' line - stop and inspect $cfg."
}
& "$env:ProgramFiles\Datadog\Datadog Agent\bin\agent.exe" restart-service
if ($LASTEXITCODE -ne 0) { throw "agent.exe restart-service failed with exit code $LASTEXITCODE - stop and check C:\ProgramData\Datadog\logs\agent.log." }
Start-Sleep -Seconds 10
if ((Get-Service datadogagent).Status -ne 'Running') { throw "datadogagent is not running after the restart - stop and check C:\ProgramData\Datadog\logs\agent.log." }
& "$env:ProgramFiles\Datadog\Datadog Agent\bin\agent.exe" status

This removes every top-level logs_enabled key, quoted or not, adds a line break if the file does not end with one, and appends a single logs_enabled: true. It reads the file with BOM detection and writes it back as UTF-8, so non-ASCII values such as tags survive on Windows PowerShell 5.1 and PowerShell 7. The service restarts only after the check passes. It uses agent.exe restart-service rather than Restart-Service, which refuses to restart datadogagent while its dependent Trace Agent service is running. Check the status output for the Logs Agent and the other selected components.

For APM Single Step Instrumentation, pick the mode by where the application runs:

• .NET applications in IIS (generally available): use DD_APM_INSTRUMENTATION_ENABLED="iis". This is the default for IIS apps. Afterward, restart the IIS applications to be instrumented (not the whole IIS server).
• Host-wide (Java, and .NET outside IIS): DD_APM_INSTRUMENTATION_ENABLED="host" is a limited Preview. Use it only if the user confirms their organization is enrolled in the Preview; otherwise use iis for IIS apps or configure the tracer library manually. With host, .NET apps outside IIS also need an instrumentation allow rule, and the instrumented services must be restarted.

Add DD_APM_INSTRUMENTATION_LIBRARIES only for verified language/version selections. Do not place a custom service-account password in saved scripts or conversation output.

For Windows FIPS, do not reuse the standard MSI flow. Confirm Windows FIPS mode, US1-FED access, and the current FIPS Agent installer requirements before generating the command.

Paths:

• Configuration: C:\ProgramData\Datadog\datadog.yaml
• Log: C:\ProgramData\Datadog\logs\agent.log

Verify:

Get-Service DatadogAgent
& "$env:ProgramFiles\Datadog\Datadog Agent\bin\agent.exe" status

Phase 4: Configure Selected Products

After the Agent is healthy:

• For application logs, identify the exact files or Windows event channels and create the corresponding integration configuration. logs_enabled: true alone does not select application sources.
• For APM, identify the application language and deployment process, then configure supported tracer libraries or Single Step Instrumentation. Verify traces rather than only the Agent receiver.
• For integrations such as SQL Server, IIS, or Redis, inspect the running service and use its dedicated integration configuration.

Do not enable optional products solely because they are available.

Phase 5: Verify

Run the status command and confirm:

• The API key is valid.
• The Forwarder reports successful transactions.
• Core checks are running.
• The default-on Logs Agent and Trace Agent (and any explicitly selected Process Agent) are healthy.

& "$env:ProgramFiles\Datadog\Datadog Agent\bin\agent.exe" status

If the host does not appear, check C:\ProgramData\Datadog\logs\agent.log.

Confirm the host in <APP_BASE>/infrastructure. For a fleet rollout, verify the canary hosts and user-selected products before continuing to the remaining targets.

Getting the Most Out of Your Agent

After the host reports, query a recent infrastructure metric with the Datadog metrics API, substituting the Windows host's Datadog hostname for <HOSTNAME>. From PowerShell:

foreach ($f in '.env.local', '.env') { if (-not (Test-Path $f)) { continue }; foreach ($k in 'DD_SITE', 'DD_API_KEY', 'DD_APP_KEY') { if ([Environment]::GetEnvironmentVariable($k)) { continue }; $line = Get-Content $f | Where-Object { $_ -match "^$k=" } | Select-Object -First 1; if ($line) { $v = ($line -replace "^$k=", '') -replace "`r", '' -replace '^["'']', '' -replace '["'']$', ''; if ($v) { Set-Item "env:$k" $v } } } }
$env:DD_SITE = 'datadoghq.com'   # <- replace with the site confirmed in Phase 0.
if (-not $env:DD_API_KEY) { throw "DD_API_KEY not set - run dd-account-setup (commercial sites) or supply it directly (government sites)" }
if (-not $env:DD_APP_KEY) { throw "DD_APP_KEY not set - run dd-account-setup (commercial sites) or supply it directly (government sites)" }
$now = [int]([datetime]::UtcNow - [datetime]'1970-01-01').TotalSeconds
Invoke-RestMethod -Method Get -Uri "https://api.$env:DD_SITE/api/v1/query" `
  -Headers @{ "DD-API-KEY" = $env:DD_API_KEY; "DD-APPLICATION-KEY" = $env:DD_APP_KEY } `
  -Body @{ from = $now - 900; to = $now; query = "avg:system.cpu.user{host:<HOSTNAME>}" }

From a POSIX shell on the machine driving the install:

for f in .env.local .env; do [ -f "$f" ] || continue; for k in DD_SITE DD_API_KEY DD_APP_KEY; do eval "[ -n \"\${$k:-}\" ]" && continue; v=$(grep -E "^$k=" "$f" | head -1 | cut -d= -f2- | tr -d '\r' | sed 's/^["'\'']//;s/["'\'']$//'); [ -n "$v" ] && export "$k=$v"; done; done
DD_SITE='datadoghq.com'; export DD_SITE   # <- replace with the site confirmed in Phase 0.
# Explicit assignment, not ':=': a wrong non-empty DD_SITE in .env would otherwise survive.
: "${DD_API_KEY:?not set - run dd-account-setup (commercial sites) or supply it directly (government sites)}"; : "${DD_APP_KEY:?not set - run dd-account-setup (commercial sites) or supply it directly (government sites)}"
printf 'DD-API-KEY: %s\nDD-APPLICATION-KEY: %s\n' "$DD_API_KEY" "$DD_APP_KEY" |
curl -H @- -s -G "https://api.${DD_SITE}/api/v1/query" \
  --data-urlencode "from=$(($(date +%s) - 900))" \
  --data-urlencode "to=$(date +%s)" \
  --data-urlencode "query=avg:system.cpu.user{host:<HOSTNAME>}"

Do not expose either key in output. If the hostname is unknown, read the name the Agent reports from the Hostname section of agent.exe status (or agent.exe hostname) and query that host. Do not use avg:system.cpu.user{*} as proof: it aggregates every host in the org, so existing machines can return data even when this install sends nothing.

Useful links:

• Infrastructure: <APP_BASE>/infrastructure
• System overview: <APP_BASE>/dash/integration/1/system---overview
• Integrations: <APP_BASE>/integrations
• Fleet Automation: <APP_BASE>/fleet

End by summarizing exactly which hosts were changed, which optional products were configured, and what remains for application log sources or tracing instrumentation.