Datadog

Datadog Operations

Use this skill for read-only Datadog observability investigations.

Reference loading

Load references conditionally based on the request:

Workflow

1. Resolve the operation and target:

• Determine whether the request is a log search, metric query, trace/span inspection, monitor lookup, incident lookup, dashboard/notebook lookup, service/host listing, or service-dependency map.

• Prefer explicit env, service, host, monitor/incident IDs, trace IDs, or Datadog URLs when the user provides them.

• When the user did not specify a scope, treat datadog.env and datadog.service conversation config as optional defaults. Explicit user input always wins over config.

• Only set or change datadog.env and datadog.service when the user explicitly asks to store a default for this conversation or channel.

• If the request refers to an earlier telemetry item indirectly, inspect the current thread for the existing ID or URL before asking the user to restate it.

• Ask one concise follow-up only when a search is genuinely under-specified, for example when the user asks about "errors" with no env, service, or time window hint and the thread has no prior context.

• If an active repository context exists (cloned repo or configured github.repo), check the repo root for TELEMETRY.md before forming queries. When present, use its query recipes, service/env mappings, and investigation pivots as repo-specific guidance. Explicit user targets, IDs, URLs, and conversation config still win. If absent, continue normally.

2. Use Pup:

• Run Datadog commands with pup --read-only --agent .... The plugin also sets read-only/agent env vars, but include the flags so command transcripts show the intended mode.
• If you are unsure about a command or flag, inspect Pup's schema with pup --read-only --agent agent schema --compact or the relevant pup --read-only --agent <group> --help output before guessing.
• Start narrow: pick the single most direct command for the request before broader search.
  • Known incident ID: pup --read-only --agent incidents get <incident_id>
  • Known monitor ID: pup --read-only --agent monitors get <monitor_id>
  • Known notebook ID: pup --read-only --agent notebooks get <notebook_id>
  • Known metric name: pup --read-only --agent metrics query --query="avg:<metric>{...}" --from="15m" --to="now"; use metrics metadata get or metrics tags list when the user wants available tags or dimensions.
• For exploratory questions, prefer one focused Pup search/list/aggregate command, then one follow-up fetch if needed.
• For "current error rate / log volume / top offenders" questions, prefer pup logs aggregate over pulling raw log pages back through pup logs search.
• For service-topology questions ("what calls checkout?", "what does the payment API depend on?"), prefer pup apm dependencies list or pup apm flow-map over stitching spans together manually.
• Use pup monitors search or pup monitors list for "is this alerting?" and pup incidents list / pup incidents get for incident context.
• Use RUM commands only when the user asks about real-user / browser telemetry, not for backend issues.

3. Bound every query:

• Always constrain time windows. Default to the last 15 minutes for "right now" questions and the last 24 hours for retrospective questions; otherwise use the window the user named.
• Always include env: when datadog.env is set or the user named an env.
• Always include service: when the user named a service or datadog.service is set and the command is service-scoped.
• Cap result size. Prefer the default or small page sizes; do not page through thousands of logs when an aggregate command answers the question.

4. Report the result:

• Return the concrete answer first (counts, status, incident severity, trace timing, top offenders), then a short evidence block.
• Include Datadog deep links when Pup returns them or when you can construct a stable app link from an ID. Do not fabricate links from incomplete identifiers.
• Preserve interesting spans, log lines, or metric values inline only when they are evidence for the answer. Do not dump raw command output.
• Keep routine tool chatter silent. Do not narrate every Pup search or fetch step.

Guardrails

• Read-only only in this skill. Do not create, edit, mute, delete, import, submit, or resolve monitors, incidents, notebooks, dashboards, SLOs, metrics, API keys, RUM resources, or other Datadog objects.
• Log, RUM, APM, and incident payloads can contain PII or sensitive customer data. Quote only the minimum needed to answer the question. Do not paste full raw log bodies or span payloads when a summary plus a deep link is enough.
• If Pup returns 403, permission denied, or similar, stop and tell the user the Datadog credentials could not access the requested resource. Do not guess at missing RBAC scopes.
• If Datadog responds with 429 Too Many Requests, wait briefly and retry the same query once. If it still fails, report the throttle and stop.
• For large traces or span responses that are incomplete, report that fact; do not pretend the shown spans are complete.
• Do not use this skill for Sentry issues, Linear/GitHub ticketing, or source-code investigation. Hand those off to the matching skill.