perplexity-advanced-troubleshooting by jeremylongshore

---
name: perplexity-advanced-troubleshooting
description: |
  Apply Perplexity advanced debugging techniques for hard-to-diagnose issues.
  Use when standard troubleshooting fails, investigating complex race conditions,
  or preparing evidence bundles for Perplexity support escalation.
  Trigger with phrases like "perplexity hard bug", "perplexity mystery error",
  "perplexity impossible to debug", "difficult perplexity issue", "perplexity deep debug".
allowed-tools: Read, Grep, Bash(kubectl:*), Bash(curl:*), Bash(tcpdump:*)
version: 1.0.0
license: MIT
author: Jeremy Longshore <jeremy@intentsolutions.io>
---

# Perplexity Advanced Troubleshooting

## Overview
Deep debugging techniques for complex Perplexity issues that resist standard troubleshooting.

## Prerequisites
- Access to production logs and metrics
- kubectl access to clusters
- Network capture tools available
- Understanding of distributed tracing

## Evidence Collection Framework

### Comprehensive Debug Bundle
```bash
#!/bin/bash
# advanced-perplexity-debug.sh

BUNDLE="perplexity-advanced-debug-$(date +%Y%m%d-%H%M%S)"
mkdir -p "$BUNDLE"/{logs,metrics,network,config,traces}

# 1. Extended logs (1 hour window)
kubectl logs -l app=perplexity-integration --since=1h > "$BUNDLE/logs/pods.log"
journalctl -u perplexity-service --since "1 hour ago" > "$BUNDLE/logs/system.log"

# 2. Metrics dump
curl -s localhost:9090/api/v1/query?query=perplexity_requests_total > "$BUNDLE/metrics/requests.json"
curl -s localhost:9090/api/v1/query?query=perplexity_errors_total > "$BUNDLE/metrics/errors.json"

# 3. Network capture (30 seconds)
timeout 30 tcpdump -i any port 443 -w "$BUNDLE/network/capture.pcap" &

# 4. Distributed traces
curl -s localhost:16686/api/traces?service=perplexity > "$BUNDLE/traces/jaeger.json"

# 5. Configuration state
kubectl get cm perplexity-config -o yaml > "$BUNDLE/config/configmap.yaml"
kubectl get secret perplexity-secrets -o yaml > "$BUNDLE/config/secrets-redacted.yaml"

tar -czf "$BUNDLE.tar.gz" "$BUNDLE"
echo "Advanced debug bundle: $BUNDLE.tar.gz"
```

## Systematic Isolation

### Layer-by-Layer Testing

```typescript
// Test each layer independently
async function diagnosePerplexityIssue(): Promise<DiagnosisReport> {
  const results: DiagnosisResult[] = [];

  // Layer 1: Network connectivity
  results.push(await testNetworkConnectivity());

  // Layer 2: DNS resolution
  results.push(await testDNSResolution('api.perplexity.com'));

  // Layer 3: TLS handshake
  results.push(await testTLSHandshake('api.perplexity.com'));

  // Layer 4: Authentication
  results.push(await testAuthentication());

  // Layer 5: API response
  results.push(await testAPIResponse());

  // Layer 6: Response parsing
  results.push(await testResponseParsing());

  return { results, firstFailure: results.find(r => !r.success) };
}
```

### Minimal Reproduction

```typescript
// Strip down to absolute minimum
async function minimalRepro(): Promise<void> {
  // 1. Fresh client, no customization
  const client = new PerplexityClient({
    apiKey: process.env.PERPLEXITY_API_KEY!,
  });

  // 2. Simplest possible call
  try {
    const result = await client.ping();
    console.log('Ping successful:', result);
  } catch (error) {
    console.error('Ping failed:', {
      message: error.message,
      code: error.code,
      stack: error.stack,
    });
  }
}
```

## Timing Analysis

```typescript
class TimingAnalyzer {
  private timings: Map<string, number[]> = new Map();

  async measure<T>(label: string, fn: () => Promise<T>): Promise<T> {
    const start = performance.now();
    try {
      return await fn();
    } finally {
      const duration = performance.now() - start;
      const existing = this.timings.get(label) || [];
      existing.push(duration);
      this.timings.set(label, existing);
    }
  }

  report(): TimingReport {
    const report: TimingReport = {};
    for (const [label, times] of this.timings) {
      report[label] = {
        count: times.length,
        min: Math.min(...times),
        max: Math.max(...times),
        avg: times.reduce((a, b) => a + b, 0) / times.length,
        p95: this.percentile(times, 95),
      };
    }
    return report;
  }
}
```

## Memory and Resource Analysis

```typescript
// Detect memory leaks in Perplexity client usage
const heapUsed: number[] = [];

setInterval(() => {
  const usage = process.memoryUsage();
  heapUsed.push(usage.heapUsed);

  // Alert on sustained growth
  if (heapUsed.length > 60) { // 1 hour at 1/min
    const trend = heapUsed[59] - heapUsed[0];
    if (trend > 100 * 1024 * 1024) { // 100MB growth
      console.warn('Potential memory leak in perplexity integration');
    }
  }
}, 60000);
```

## Race Condition Detection

```typescript
// Detect concurrent access issues
class PerplexityConcurrencyChecker {
  private inProgress: Set<string> = new Set();

  async execute<T>(key: string, fn: () => Promise<T>): Promise<T> {
    if (this.inProgress.has(key)) {
      console.warn(`Concurrent access detected for ${key}`);
    }

    this.inProgress.add(key);
    try {
      return await fn();
    } finally {
      this.inProgress.delete(key);
    }
  }
}
```

## Support Escalation Template

```markdown
## Perplexity Support Escalation

**Severity:** P[1-4]
**Request ID:** [from error response]
**Timestamp:** [ISO 8601]

### Issue Summary
[One paragraph description]

### Steps to Reproduce
1. [Step 1]
2. [Step 2]

### Expected vs Actual
- Expected: [behavior]
- Actual: [behavior]

### Evidence Attached
- [ ] Debug bundle (perplexity-advanced-debug-*.tar.gz)
- [ ] Minimal reproduction code
- [ ] Timing analysis
- [ ] Network capture (if relevant)

### Workarounds Attempted
1. [Workaround 1] - Result: [outcome]
2. [Workaround 2] - Result: [outcome]
```

## Instructions

### Step 1: Collect Evidence Bundle
Run the comprehensive debug script to gather all relevant data.

### Step 2: Systematic Isolation
Test each layer independently to identify the failure point.

### Step 3: Create Minimal Reproduction
Strip down to the simplest failing case.

### Step 4: Escalate with Evidence
Use the support template with all collected evidence.

## Output
- Comprehensive debug bundle collected
- Failure layer identified
- Minimal reproduction created
- Support escalation submitted

## Error Handling
| Issue | Cause | Solution |
|-------|-------|----------|
| Can't reproduce | Race condition | Add timing analysis |
| Intermittent failure | Timing-dependent | Increase sample size |
| No useful logs | Missing instrumentation | Add debug logging |
| Memory growth | Resource leak | Use heap profiling |

## Examples

### Quick Layer Test
```bash
# Test each layer in sequence
curl -v https://api.perplexity.com/health 2>&1 | grep -E "(Connected|TLS|HTTP)"
```

## Resources
- [Perplexity Support Portal](https://support.perplexity.com)
- [Perplexity Status Page](https://status.perplexity.com)

## Next Steps
For load testing, see `perplexity-load-scale`.