agent-observability-session-classify

Backend

Detection — At the start of every invocation, before taking any action, determine which backend to use:

1. If the user passed --backend pup anywhere in their invocation → use pup mode immediately, regardless of whether MCP tools are present. Skip steps 2–4.
2. Check whether MCP tools are present in your active tool list. The canonical signal is whether mcp__datadog-llmo-mcp__search_llmobs_spans appears in your available tools.
3. If MCP tools are present → use MCP mode throughout. Call MCP tools exactly as named in this skill's workflow sections.
4. If MCP tools are absent → check whether pup is executable: run pup --version via Bash. A JSON response containing "version" confirms pup is available.
5. If pup responds → use pup mode throughout. Translate every MCP tool call to its pup equivalent using the Tool Reference appendix at the bottom of this file.
6. If neither is available → stop and tell the user:

   "Neither the Datadog MCP server nor the pup CLI is available. Connect the MCP server (claude mcp add --scope user --transport http datadog-llmo-mcp 'https://mcp.datadoghq.com/api/unstable/mcp-server/mcp?toolsets=llmobs,rum') or install pup."

--backend pup is accepted anywhere in the invocation arguments and is stripped before passing remaining args to the skill logic.

pup invocation rules:

• Invoke via Bash: pup llm-obs <subcommand> [flags]
• pup always outputs JSON. Parse directly — no content-block unwrapping (unlike MCP results, which may wrap JSON in [{"type": "text", "text": "<json>"}]).
• If pup returns an auth error, tell the user to run pup auth login and stop.
• Parallelization: issue multiple Bash tool calls in a single message (one pup command per call).
• Time flags: pup accepts bare duration strings (1h, 7d, 30m) and RFC3339 timestamps. Do not use now--prefixed strings — strip the prefix when converting from a skill --timeframe argument: now-7d → 7d, now-24h → 24h, now-30d → 30d.
• --summary on pup llm-obs spans search strips payload fields to essential metadata only. Use it in bulk/search phases where content is not needed.

pup mode notes by entry mode:

• session_id mode: Steps 1–3 and Step 5 work fully. Step 4 (RUM) uses pup rum aggregate --user-email EMAIL instead of analyze_rum_events — see Tool Reference. Step 4b (audit trail) is pup-native and queries the active user's own org via OAuth.
• trace_id mode: Full parity with MCP mode.
• ml_app mode: Option A (aggregate_spans) is unavailable in pup — skip it and proceed directly to Option B.

Invocation ID: At the very start of each invocation, before any MCP tool call, generate an 8-character hex invocation ID (e.g., 3a9f1c2b). Keep it constant for the entire invocation.

Intent tagging: On every MCP tool call, prefix telemetry.intent with skill:agent-observability-session-classify[<inv_id>] — followed by a description of why the tool is being called. On the first MCP tool call only, use skill:agent-observability-session-classify:start[<inv_id>] — instead (note the :start suffix). Example first call: skill:agent-observability-session-classify:start[3a9f1c2b] — Step 1: enumerate turn root spans for session abc-123