Datadog Auto-Detector Skill

Datadog Auto-Detector Skill

Purpose: Detect when user mentions Datadog resources and intelligently fetch relevant observability data.

Architecture: Three-tier pattern (Skill → Command → Subagent) for context isolation.

Detection Patterns

Pattern 1: Datadog URLs

Detect full Datadog URLs across all resource types:

Logs:

• https://app.datadoghq.com/​.../​logs?query=...
• https://app.datadoghq.com/​.../​logs?...

APM / Traces:

• https://app.datadoghq.com/​.../​apm/​traces?query=...
• https://app.datadoghq.com/​.../​apm/​trace/[trace-id]
• https://app.datadoghq.com/​.../​apm/​services/[service-name]

Metrics:

• https://app.datadoghq.com/​.../​metric/​explorer?query=...
• https://app.datadoghq.com/​.../​metric/​summary?metric=...

Dashboards:

• https://app.datadoghq.com/​.../​dashboard/[dashboard-id]

Monitors:

• https://app.datadoghq.com/​.../​monitors/[monitor-id]
• https://app.datadoghq.com/​.../​monitors?query=...

Incidents:

• https://app.datadoghq.com/​.../​incidents/[incident-id]
• https://app.datadoghq.com/​.../​incidents?...

Services:

• https://app.datadoghq.com/​.../​services/[service-name]

Events:

• https://app.datadoghq.com/​.../​event/​stream?query=...

RUM:

• https://app.datadoghq.com/​.../​rum/​...

Infrastructure/​Hosts:

• https://app.datadoghq.com/​.../​infrastructure/​...

Pattern 2: Natural Language Queries

Detect observability-related requests:

Metrics Queries:

• "error rate of [service]"
• "check metrics for [service]"
• "CPU usage of [service]"
• "latency of [service]"
• "throughput for [service]"
• "request rate"
• "response time"

Log Queries:

• "logs for [service]"
• "log errors in [service]"
• "show logs from [service]"
• "check [service] logs"
• "error logs"

Trace Queries:

• "traces for [service]"
• "trace [trace-id]"
• "slow requests in [service]"
• "APM data for [service]"

Incident Queries:

• "active incidents"
• "show incidents"
• "SEV-1 incidents"
• "current incidents for [team]"

Monitor Queries:

• "alerting monitors"
• "check monitors for [service]"
• "show triggered monitors"

Service Queries:

• "status of [service]"
• "health of [service]"
• "[service] dependencies"

Pattern 3: Service Name References

Detect service names in context of observability:

• Common patterns: pb-*, service-*, microservice names
• Context keywords: "service", "application", "component", "backend", "frontend"
• Combined with observability verbs: "check", "show", "analyze", "investigate"

Intelligence: When to Fetch

✅ DO Fetch When:

1. Direct Request: User explicitly asks for Datadog data

   • "Can you check the error rate?"
   • "Show me logs for pb-backend-web"
   • "What's happening in Datadog?"

2. Datadog URL Provided: User shares Datadog link

   • "Look at this: https://app.datadoghq.com/.../logs?..."
   • "Here's the dashboard: [URL]"

3. Investigation Context: User is troubleshooting

   • "I'm seeing errors in pb-backend-web, can you investigate?"
   • "Something's wrong with the service, check Datadog"

4. Proactive Analysis: User asks for analysis that requires observability data

   • "Analyze the performance of [service]"
   • "Is there an outage?"

5. Comparative Analysis: User wants to compare or correlate

   • "Compare error rates between services"
   • "Check if logs match the incident"

❌ DON'T Fetch When:

1. Past Tense Without URL: User mentions resolved issues

   • "I fixed the error rate yesterday"
   • "The logs showed X" (without asking for current data)

2. Already Fetched: Datadog data already in conversation

   • Check conversation history for recent Datadog summary
   • Reuse existing data unless user requests refresh

3. Informational Discussion: User discussing concepts

   • "Datadog is a monitoring tool"
   • "We use Datadog for observability"

4. Vague Reference: Unclear what to fetch

   • "Something in Datadog" (too vague)
   • Ask for clarification instead

5. Historical Context: User providing background

   • "Last week Datadog showed..."
   • "According to Datadog docs..."

Intent Classification

Before spawning subagent, classify the user's intent:

Intent Type 1: Full Context (default)

• User wants comprehensive analysis
• Fetch all relevant data for the resource
• Example: "Analyze error rate of pb-backend-web"

Intent Type 2: Specific Query

• User wants specific metric/​log/​trace
• Focus fetch on exact request
• Example: "Show me error logs for pb-backend-web in last hour"

Intent Type 3: Quick Status Check

• User wants high-level status
• Fetch summary data only
• Example: "Is pb-backend-web healthy?"

Intent Type 4: Investigation

• User is debugging an issue
• Fetch errors, incidents, traces
• Example: "Users report 500 errors, investigate pb-backend-web"

Intent Type 5: Comparison

• User wants to compare metrics/​services
• Fetch data for multiple resources
• Example: "Compare error rates of pb-backend-web and pb-frontend"

Workflow

Step 1: Detect Mention

Scan user message for:

1. Datadog URLs (Pattern 1)
2. Natural language queries (Pattern 2)
3. Service names with observability context (Pattern 3)

If none detected, do nothing.

Step 2: Check Conversation History

Before fetching, check if:

• Same resource already fetched in last 5 messages
• Recent Datadog summary covers this request
• User explicitly requests refresh ("latest data", "check again")

If already fetched and no refresh requested, reuse existing data.

Step 3: Determine Intent

Analyze user message to classify intent (Full Context, Specific Query, Quick Status, Investigation, Comparison).

Extract:

• Resource Type: logs, metrics, traces, incidents, monitors, services, dashboards
• Service Name: If mentioned (e.g., "pb-backend-web")
• Time Range: If specified (e.g., "last hour", "today", "last 24h")
• Filters: Any additional filters (e.g., "status:error", "SEV-1")

Step 4: Construct Subagent Prompt

Build prompt for datadog-analyzer subagent:

Fetch and summarize [resource type] for [context].

[If URL provided]:
Datadog URL: [url]

[If natural language query]:
Service: [service-name]
Query Type: [logs/​metrics/​traces/​etc.]
Time Range: [from] to [to]
Additional Context: [user's request]

Intent: [classified intent]

Focus on: [specific aspects user cares about]

Step 5: Spawn Subagent

Use Task tool with:

• subagent_type: "schovi:datadog-auto-detector:datadog-analyzer"
• prompt: Constructed prompt from Step 4
• description: Short description (e.g., "Fetching Datadog logs summary")

Step 6: Present Summary

When subagent returns:

1. Present the summary to user
2. Offer to investigate further if issues found
3. Suggest related queries if relevant

Examples

Example 1: Datadog URL

User: "Look at this: https://app.datadoghq.com/.../logs?query=service:pb-backend-web%20status:error"

Action:

1. Detect: Datadog logs URL
2. Check: Not in recent conversation
3. Intent: Full Context (investigation)
4. Prompt: "Fetch and summarize logs from Datadog URL: [url]"
5. Spawn: datadog-analyzer subagent
6. Present: Summary of error logs

Example 2: Natural Language Query

User: "Can you check the error rate of pb-backend-web service in the last hour?"

Action:

1. Detect: "error rate" + "pb-backend-web" + "last hour"
2. Check: Not in recent conversation
3. Intent: Specific Query (metrics)
4. Prompt: "Fetch and summarize metrics for error rate. Service: pb-backend-web, Time Range: last 1h"
5. Spawn: datadog-analyzer subagent
6. Present: Metrics summary with error rate trend

Example 3: Investigation Context

User: "Users are reporting 500 errors on the checkout flow. Can you investigate?"

Action:

1. Detect: "500 errors" (observability issue)
2. Check: Not in recent conversation
3. Intent: Investigation
4. Prompt: "Investigate 500 errors in checkout flow. Query Type: logs and traces, Filters: status:500 OR status:error, Time Range: last 1h. Focus on: error patterns, affected endpoints, trace analysis"
5. Spawn: datadog-analyzer subagent
6. Present: Investigation summary with findings

Example 4: Already Fetched

User: "Show me error rate for pb-backend-web"

[Datadog summary for pb-backend-web fetched 2 messages ago]

Action:

1. Detect: "error rate" + "pb-backend-web"
2. Check: Already fetched in message N-2
3. Skip fetch: "Based on the Datadog data fetched earlier, the error rate for pb-backend-web is [value]..."

Example 5: Past Tense (No Fetch)

User: "Yesterday Datadog showed high error rates"

Action:

1. Detect: "Datadog" + "error rates"
2. Check: Past tense ("Yesterday", "showed")
3. Skip fetch: User is providing historical context, not requesting current data

Example 6: Comparison

User: "Compare error rates of pb-backend-web and pb-frontend over the last 24 hours"

Action:

1. Detect: "error rates" + multiple services + "last 24 hours"
2. Check: Not in recent conversation
3. Intent: Comparison
4. Prompt: "Fetch and compare metrics for error rate. Services: pb-backend-web, pb-frontend. Time Range: last 24h. Focus on: comparative analysis, trends, spikes"
5. Spawn: datadog-analyzer subagent
6. Present: Comparative metrics summary

Edge Cases

Ambiguous Service Name

User: "Check the backend service error rate"

Action:

• Detect: "backend service" (ambiguous)
• Ask: "I can fetch error rate data from Datadog. Which specific service? (e.g., pb-backend-web, pb-backend-api)"
• Wait for clarification before spawning subagent

URL Parsing Failure

User: Provides malformed or partial Datadog URL

Action:

• Detect: Datadog domain but unparseable
• Spawn: Subagent with URL and note parsing might fail
• Subagent will attempt to extract what it can or report error

Multiple Resources in One Request

User: "Show me logs, metrics, and traces for pb-backend-web"

Action:

• Detect: Multiple resource types requested
• Intent: Full Context (investigation)
• Prompt: "Fetch comprehensive observability data for pb-backend-web: logs (errors), metrics (error rate, latency), traces (slow requests). Time Range: last 1h"
• Spawn: Single subagent call (let subagent handle multiple queries)

Integration Notes

Proactive Activation: This skill should activate automatically when Datadog resources are mentioned.

No User Prompt: The skill should work silently - user doesn't need to explicitly invoke it.

Commands Integration: This skill can be used within commands like /​schovi:analyze to fetch Datadog context automatically.

Token Efficiency: By using the subagent pattern, we reduce context pollution from 10k-50k tokens to ~800-1200 tokens.

Quality Checklist

Before spawning subagent, verify:

• Clear detection of Datadog resource or query
• Not already fetched in recent conversation (unless refresh requested)
• Not past tense reference without current data request
• Intent classified correctly
• Prompt for subagent is clear and specific
• Fully qualified subagent name used: schovi:datadog-auto-detector:datadog-analyzer