Debugging Skill
Provides comprehensive debugging capabilities with integrated extended thinking for complex scenarios.
When to Use This Skill
Activate this skill when working with:
- Error troubleshooting
- Log analysis
- Performance debugging
- Distributed system debugging
- Memory and resource issues
- Complex, multi-layered bugs requiring deep reasoning
Extended Thinking for Complex Debugging
When to Enable Extended Thinking
Use extended thinking (Claude's deeper reasoning mode) for debugging when:
- Root Cause Unknown: Multiple possible causes, unclear failure patterns
- Intermittent Issues: Race conditions, timing issues, non-deterministic failures
- Multi-System Failures: Distributed system bugs spanning multiple services
- Performance Mysteries: Unexpected slowdowns without obvious bottlenecks
- Complex State Issues: Bugs involving intricate state transitions or side effects
- Security Vulnerabilities: Subtle security issues requiring careful analysis
How to Activate Extended Thinking
# In your debugging prompt
Claude, please use extended thinking to help debug this issue:
[Describe the problem with symptoms, context, and what you've tried]Extended thinking will provide:
- Systematic hypothesis generation
- Multi-path investigation strategies
- Deeper pattern recognition
- Cross-domain insights (e.g., network + application + infrastructure)
Hypothesis-Driven Debugging Framework
Use this structured approach for complex bugs:
1. Observation Phase
What happened?
- Error message/stack trace
- Frequency (always/intermittent)
- When it started
- Environmental context
- Recent changes2. Hypothesis Generation
Generate 3-5 plausible hypotheses:
H1: [Most likely cause based on symptoms]
Evidence for: [...]
Evidence against: [...]
Test: [How to validate/invalidate]
H2: [Alternative explanation]
Evidence for: [...]
Evidence against: [...]
Test: [How to validate/invalidate]
H3: [Edge case or rare scenario]
Evidence for: [...]
Evidence against: [...]
Test: [How to validate/invalidate]3. Systematic Testing
Priority order (high to low confidence):
1. Test H1 → Result: [Pass/Fail/Inconclusive]
2. Test H2 → Result: [Pass/Fail/Inconclusive]
3. Test H3 → Result: [Pass/Fail/Inconclusive]
New evidence discovered:
- [Finding 1]
- [Finding 2]
Revised hypotheses if needed:
- [...]4. Root Cause Identification
Confirmed root cause: [...]
Contributing factors: [...]
Why it wasn't caught earlier: [...]5. Fix + Validation
Fix implemented: [...]
Tests added: [...]
Validation: [...]
Prevention: [...]Structured Debugging Templates
Template 1: MECE Bug Analysis (Mutually Exclusive, Collectively Exhaustive)
## Bug: [Title]
### Problem Statement
- **What**: [Precise description]
- **Where**: [System/component]
- **When**: [Conditions/triggers]
- **Impact**: [Severity/scope]
### MECE Hypothesis Tree
**Layer 1: System Boundaries**
- [ ] Frontend issue
- [ ] Backend API issue
- [ ] Database issue
- [ ] Infrastructure/network issue
- [ ] External dependency issue
**Layer 2: Component-Specific** (based on Layer 1 finding)
- [ ] [Sub-component A]
- [ ] [Sub-component B]
- [ ] [Sub-component C]
**Layer 3: Code-Level** (based on Layer 2 finding)
- [ ] Logic error
- [ ] State management
- [ ] Resource handling
- [ ] Configuration
### Investigation Log
| Time | Action | Result | Next Step |
|------|--------|--------|-----------|
| [HH:MM] | [What you tested] | [Finding] | [Decision] |
### Root Cause
[Final determination with evidence]
### Fix
[Solution with rationale]Template 2: 5 Whys Analysis
## Issue: [Brief description]
**Symptom**: [Observable problem]
**Why 1**: Why did this happen?
→ [Answer]
**Why 2**: Why did [answer from Why 1] occur?
→ [Answer]
**Why 3**: Why did [answer from Why 2] occur?
→ [Answer]
**Why 4**: Why did [answer from Why 3] occur?
→ [Answer]
**Why 5**: Why did [answer from Why 4] occur?
→ [Root cause]
**Fix**: [Addresses root cause]
**Prevention**: [Process/check to prevent recurrence]Template 3: Timeline Reconstruction
## Incident Timeline: [Event]
**Goal**: Reconstruct exact sequence leading to failure
| Time | Event | System State | Evidence |
|------|-------|--------------|----------|
| T-5min | [Normal operation] | [State] | [Logs] |
| T-2min | [Trigger event] | [State change] | [Logs/metrics] |
| T-30s | [Cascade starts] | [Degraded] | [Alerts] |
| T-0 | [Failure] | [Failed state] | [Error logs] |
| T+5min | [Recovery action] | [Recovering] | [Actions taken] |
**Critical Path**: [Sequence of events that led to failure]
**Alternative Scenarios**: [What could have prevented it at each step]Python Debugging Patterns
Hypothesis-Driven Python Debugging Example
# H1: Cache key collision between users
# Test: Add detailed logging around cache operations
import logging logging.basicConfig(level=logging.DEBUG)
def get_user(user_id): cache_key = f"user:{user_id}" logging.debug(f"Fetching cache key: {cache_key} for user {user_id}")
cached = cache.get(cache_key) if cached: logging.debug(f"Cache hit: {cache_key} -> {cached}") return cached
user = db.query(User).filter_by(id=user_id).first() logging.debug(f"DB fetch for user {user_id}: {user}")
cache.set(cache_key, user, timeout=300) logging.debug(f"Cache set: {cache_key} -> {user}")
return user
# Result: Discovered cache_key had different format in different code paths
# Root cause: String formatting inconsistency (f"user:{id}" vs f"user_{id}")
Advanced Debugging with Context Managers
@contextmanager def debug_timer(operation_name): """Time operations and log if slow""" start = time.perf_counter() try: yield finally: duration = time.perf_counter() - start if duration > 1.0: # Slow operation threshold logging.warning(f"{operation_name} took {duration:.2f}s", extra={'operation': operation_name, 'duration': duration})
# Usage
with debug_timer("database_query"): results = db.query(User).filter(...).all()
@contextmanager def hypothesis_test(hypothesis_name, expected_outcome): """Test and validate debugging hypotheses""" print(f"\n=== Testing: {hypothesis_name} ===") print(f"Expected: {expected_outcome}") start_state = capture_state() try: yield finally: end_state = capture_state() outcome = compare_states(start_state, end_state) print(f"Actual: {outcome}") print(f"Hypothesis {'CONFIRMED' if outcome == expected_outcome else 'REJECTED'}")
# Usage
with hypothesis_test("H1: Database connection pool exhaustion", expected_outcome="pool_size increases during load"): # Run load test for i in range(100): api_call() ```
### pdb Debugger with Advanced Techniques
Basic breakpoint
import pdb; pdb.set_trace()
Python 3.7+
breakpoint()
Conditional breakpoint
if user_id == 12345: breakpoint()
Post-mortem debugging (debug after crash)
import pdb try: risky_function() except Exception: pdb.post_mortem()
Common pdb commands
n(ext) - Execute next line
s(tep) - Step into function
c(ontinue) - Continue execution
p expr - Print expression
pp expr - Pretty print
l(ist) - Show source code
w(here) - Show stack trace
u(p) - Move up stack frame
d(own) - Move down stack frame
b(reak) - Set breakpoint
cl(ear) - Clear breakpoint
q(uit) - Quit debugger
Advanced: Programmatic debugging
import pdb pdb.run('my_function()', globals(), locals()) ```
Logging
logging.basicConfig(level=logging.DEBUG, format='%(asctime)s - %(name)s - %(levelname)s - %(message)s', handlers=[logging.FileHandler('debug.log'), logging.StreamHandler()])
logger = logging.getLogger(**name**)
logger.debug("Debug message") logger.info("Info message") logger.warning("Warning message") logger.error("Error message", exc_info=True) ```
### Exception Handling
try: result = risky_operation() except Exception as e: # Log full traceback logger.error(f"Operation failed: {e}") logger.error(traceback.format_exc())
# Or get traceback as string
tb = traceback.format_exception(type(e), e, e.__traceback__)
error_details = ''.join(tb)
## JavaScript/Node.js Debugging
### Hypothesis-Driven JavaScript Debugging Example
- Bug: Memory leak in websocket connections
- Symptoms: Memory grows over time, eventually crashes
- Hypothesis: Event listeners not cleaned up on disconnect */
// H1: Event listeners accumulating // Test: Track listener counts class WebSocketManager {constructor() {this.connections = new Map(); this.debugListenerCounts = true;}
addConnection(userId, socket) {console.debug([H1 Test] Adding connection for user ${userId});
if (this.debugListenerCounts) {
console.debug(\`[H1] Listener count before: \${socket.listenerCount('message')}\`);
}
socket.on('message', (data) => this.handleMessage(userId, data));
socket.on('close', () => this.removeConnection(userId));
if (this.debugListenerCounts) {
console.debug(\`[H1] Listener count after: \${socket.listenerCount('message')}\`);
}
this.connections.set(userId, socket);}
removeConnection(userId) {console.debug([H1 Test] Removing connection for user ${userId});
const socket = this.connections.get(userId);
if (socket) {
const messageListenerCount = socket.listenerCount('message');
console.debug(\`[H1] Listeners still attached: \${messageListenerCount}\`);
// Result: Found 3+ listeners on same event!
// Root cause: Not removing listeners on reconnect
socket.removeAllListeners();
this.connections.delete(userId);
}}} ```
Advanced Console Debugging
// Object inspection with depth console.dir(object, {depth: null, colors: true}); console.table(array);
// Performance timing console.time('operation'); //... code... console.timeEnd('operation');
// Memory usage console.memory; // Chrome only
// Stack trace console.trace('Trace point');
// Grouping for organized logs console.group('User Authentication Flow'); console.log('Step 1: Validate credentials'); console.log('Step 2: Generate token'); console.groupEnd();
// Conditional logging const debug = (label, data) => {if (process.env.DEBUG) {console.log(`[DEBUG] ${label}:`, JSON.stringify(data, null, 2));}};
// Hypothesis testing helper function testHypothesis(name, test, expected) {console.group(`Testing: ${name}`); console.log(`Expected: ${expected}`); const actual = test(); console.log(`Actual: ${actual}`); console.log(`Result: ${actual === expected? 'PASS': 'FAIL'}`); console.groupEnd(); return actual === expected;}
// Usage testHypothesis('H1: Cache returns stale data', () => cache.get('key').timestamp, Date.now()); ```
### Debugging Async/Promise Issues
// Usage await debugPromise('DB Query', db.users.findOne({id: 123}));
// Debugging race conditions async function debugRaceCondition() {const operations = [{name: 'Op1', fn: async () => {await delay(100); return 'A';}}, {name: 'Op2', fn: async () => {await delay(50); return 'B';}}, {name: 'Op3', fn: async () => {await delay(150); return 'C';}}];
const results = await Promise.allSettled(operations.map(async op => {const start = Date.now(); const result = await op.fn(); const duration = Date.now() - start; console.log(${op.name} completed in ${duration}ms: ${result}); return {op: op.name, result, duration};}));
console.table(results.map(r => r.value));}
// Debugging memory leaks with weak references class DebugMemoryLeaks {constructor() {this.weakMap = new WeakMap(); this.strongRefs = new Map();}
trackObject(id, obj) {// Weak reference - will be GC'd if no other references this.weakMap.set(obj, {id, created: Date.now()});
// Strong reference - prevents GC (potential leak source)
this.strongRefs.set(id, obj);
console.log(\`Tracking \${id}: Strong refs=\${this.strongRefs.size}\`);}
release(id) {this.strongRefs.delete(id); console.log(Released ${id}: Strong refs=${this.strongRefs.size});}
checkLeaks() {console.log(Potential leaks: ${this.strongRefs.size} strong references); return Array.from(this.strongRefs.keys());}} ```
Node.js Inspector
# Start with inspector
node --inspect app.js node --inspect-brk app.js # Break on first line
# Debug with Chrome DevTools
# Open chrome://inspect
VS Code Debug Configuration
## Container Debugging
### Docker
View logs
docker logs --tail=100 -f
Execute shell
docker exec -it /bin/sh
Inspect container
docker inspect
Resource usage
docker stats
Debug running container
docker run -it --rm --network=container: nicolaka/netshoot ```
Kubernetes
# Pod logs
kubectl logs -n agents -f kubectl logs -n agents --previous # Previous crash
# Execute in pod
kubectl exec -it -n agents -- /bin/sh
# Debug with ephemeral container
kubectl debug -n agents -it --image=busybox
# Port forward for local debugging
kubectl port-forward 8080:8080 -n agents
# Events
kubectl get events -n agents --sort-by='.lastTimestamp'
# Resource usage
kubectl top pods -n agents ```
## Log Analysis
### Pattern Matching
Search logs for errors
grep -i "error|exception|failed" app.log
Count occurrences
grep -c "ERROR" app.log
Context around matches
grep -B 5 -A 5 "OutOfMemory" app.log
Filter by time range
awk '/2024-01-15 10:00/,/2024-01-15 11:00/' app.log ```
JSON Logs
# Parse JSON logs with jq
cat app.log | jq 'select(.level == "error")' cat app.log | jq 'select(.timestamp > "2024-01-15T10:00:00")'
# Extract specific fields
cat app.log | jq -r '[.timestamp,.level,.message] | @tsv' ```
## Performance Debugging
### Python Profiling
cProfile
import cProfile cProfile.run('main()', 'output.prof')
Line profiler
@profile def slow_function(): pass
Memory profiler
from memory_profiler import profile
@profile def memory_heavy(): pass ```
Network Debugging
# Check connectivity
ping telnet nc -zv
# DNS resolution
nslookup dig
# HTTP debugging
curl -v [http://localhost:8080/health](http://localhost:8080/health) curl -X POST -d '{"test": true}' -H "Content-Type: application/json" [http://localhost:8080/api](http://localhost:8080/api) ```
## Common Debug Checklist
1. **Check Logs**: Application, system, container logs
2. **Verify Configuration**: Environment variables, config files
3. **Test Connectivity**: Network, database, external services
4. **Check Resources**: CPU, memory, disk space
5. **Review Recent Changes**: Git log, deployment history
6. **Reproduce Locally**: Same environment, same data
7. **Binary Search**: Isolate the problem scope
## Debugging Decision Tree
Use this decision tree to determine the right debugging approach:
START: What kind of bug? │ ├─ Known error message/stack trace │ └─ Use: Direct log analysis + Stack trace walkthrough │ ├─ Intermittent/Race condition │ └─ Use: Extended thinking + Timeline reconstruction + Hypothesis-driven │ ├─ Performance degradation │ └─ Use: Profiling + Hypothesis-driven + MECE analysis │ ├─ Distributed system failure │ └─ Use: Extended thinking + Timeline reconstruction + Multi-system tracing │ ├─ Complex state bug │ └─ Use: Extended thinking + Hypothesis-driven + pdb/debugger │ ├─ Memory leak │ └─ Use: Memory profiling + Hypothesis-driven + Weak reference analysis │ └─ Unknown root cause └─ Use: Extended thinking + MECE analysis + 5 Whys
## Best Practices for Complex Debugging
### 1. Document Your Investigation
Always maintain a debugging log:
Bug Investigation: [Title]
Start Time: 2024-01-15 10:00 Investigator: [Name]
Timeline
- 10:00 - Started investigation, checked logs
- 10:15 - Found error pattern in auth service
- 10:30 - Hypothesis: Cache expiration race condition
- 10:45 - Added debug logging, confirmed hypothesis
- 11:00 - Implemented fix, testing
Hypotheses Tested
- [x] H1: Cache race condition (CONFIRMED)
- [ ] H2: Database connection pool (REJECTED)
- [ ] H3: Network timeout (NOT TESTED)
Root Cause
[Final determination]
Fix Applied
[Solution details]
Prevention
[How to prevent recurrence]
### 2. Use the Scientific Method
1. **Observe**: Gather symptoms, error messages, logs
2. **Hypothesize**: Generate 3-5 plausible explanations
3. **Predict**: What would you see if hypothesis is true?
4. **Test**: Design experiments to validate/invalidate
5. **Analyze**: Compare predictions vs actual results
6. **Conclude**: Confirm root cause with evidence
### 3. Leverage Extended Thinking
When to activate extended thinking:
- **Complexity threshold**: More than 3 interacting systems
- **Uncertainty high**: Multiple equally plausible causes
- **Stakes high**: Production outage, security issue, data loss
- **Pattern unclear**: No obvious error messages or logs
- **Time-sensitive**: Need systematic approach under pressure
### 4. Avoid Common Pitfalls
AVOID:
- ❌ Changing multiple things at once (can't isolate cause)
- ❌ Assuming first hypothesis is correct (confirmation bias)
- ❌ Debugging without logs/evidence (guessing)
- ❌ Not documenting what you tried (repeating failed attempts)
- ❌ Skipping reproduction step (fix might not work)
DO:
- ✅ Change one variable at a time
- ✅ Test multiple hypotheses systematically
- ✅ Add instrumentation before debugging
- ✅ Keep investigation log
- ✅ Write regression test after fix
### 5. Debugging Instrumentation Patterns
Python: Comprehensive debugging decorator
import functools import time import logging
def debug_trace(func): """Decorator to trace function execution with timing and state""" @functools.wraps(func) def wrapper(*args, **kwargs): func_name = func.__qualname__ logger.debug(f"→ Entering {func_name}") logger.debug(f" Args: {args}") logger.debug(f" Kwargs: {kwargs}")
start = time.perf_counter() try: result = func(*args, **kwargs) duration = time.perf_counter() - start logger.debug(f"← Exiting {func_name} ({duration:.3f}s)") logger.debug(f" Result: {result}") return result except Exception as e: duration = time.perf_counter() - start logger.error(f"✗ Exception in {func_name} ({duration:.3f}s): {e}") raise
return wrapper
Usage
@debug_trace def complex_operation(user_id, data): # Your code here pass
// JavaScript: Comprehensive debugging wrapper function debugTrace(label) { return function(target, propertyKey, descriptor) { const originalMethod = descriptor.value;
descriptor.value = async function(...args) { console.log(\→ Entering \${label || propertyKey}\); console.log(\ Args:\, args);
const start = performance.now(); try { const result = await originalMethod.apply(this, args); const duration = performance.now() - start; console.log(\← Exiting \${label || propertyKey} (\${duration.toFixed(2)}ms)\); console.log(\ Result:\, result); return result; } catch (error) { const duration = performance.now() - start; console.error(\✗ Exception in \${label || propertyKey} (\${duration.toFixed(2)}ms):\, error); throw error; } };
return descriptor; }; }
// Usage class UserService { @debugTrace('UserService.getUser') async getUser(userId) { // Your code here } }
## Cross-References and Related Skills
### Related Skills
This debugging skill integrates with:
1. **extended-thinking** (`.claude/skills/extended-thinking/SKILL.md`)
- Use for: Complex bugs with unknown root causes
- Activation: Add "use extended thinking" to your debugging prompt
- Benefit: Deeper pattern recognition, systematic hypothesis generation
2. **complex-reasoning** (`.claude/skills/complex-reasoning/SKILL.md`)
- Use for: Multi-step debugging requiring logical chains
- Patterns: Chain-of-thought, tree-of-thought for bug investigation
- Benefit: Structured reasoning through complex bug scenarios
3. **deep-analysis** (`.claude/skills/deep-analysis/SKILL.md`)
- Use for: Post-mortem analysis, root cause investigation
- Patterns: Comprehensive code review, architectural analysis
- Benefit: Identifies systemic issues beyond surface bugs
4. **testing** (`.claude/skills/testing/SKILL.md`)
- Use for: Writing regression tests after bug fix
- Integration: Bug → Debug → Fix → Test → Validate
- Benefit: Ensures bug doesn't recur
5. **kubernetes** (`.claude/skills/kubernetes/SKILL.md`)
- Use for: Distributed system debugging in K8s
- Tools: kubectl logs, exec, debug, events
- Integration: Container debugging patterns
### When to Combine Skills
| Scenario | Skills to Combine | Reasoning |
| --- | --- | --- |
| Production outage | debugging + extended-thinking + kubernetes | Complex distributed system requires deep reasoning |
| Intermittent test failure | debugging + testing + complex-reasoning | Need systematic hypothesis testing |
| Performance regression | debugging + deep-analysis | Root cause may be architectural |
| Security vulnerability | debugging + extended-thinking + deep-analysis | Requires careful, thorough analysis |
| Memory leak | debugging + complex-reasoning | Multi-step investigation needed |
### Integration Examples
#### Example 1: Complex Production Bug
Prompt combining skills
Claude, I have a complex production bug affecting multiple services. Please use extended thinking and the debugging skill to help investigate.
Symptoms:
- API requests timeout intermittently (1 in 50 requests)
- Only affects authenticated users
- Started after recent deployment
- No obvious errors in logs
Please use:
- MECE analysis to categorize possible causes
- Hypothesis-driven debugging framework
- Timeline reconstruction of recent changes
#### Example 2: Memory Leak Investigation
Prompt combining skills
Claude, use complex reasoning and debugging skills to investigate a memory leak.
Context:
- Node.js service memory grows from 200MB to 2GB over 6 hours
- No errors logged
- Happens only in production, not staging
Apply:
- Hypothesis-driven framework (generate 5 hypotheses)
- Memory leak detection patterns (weak references)
- Extended thinking for pattern recognition across codebase
## Quick Reference Card
### Debugging Workflow Summary
- OBSERVE
- Collect error messages, logs, metrics - Identify patterns (frequency, conditions, scope) - Document symptoms
- HYPOTHESIZE (use extended thinking if complex)
- Generate 3-5 plausible hypotheses - Rank by likelihood - Design tests for each
- TEST
- Change one variable at a time - Add instrumentation (logging, tracing) - Collect evidence
- ANALYZE
- Compare predictions vs results - Eliminate invalidated hypotheses - Refine remaining hypotheses
- FIX
- Implement solution - Add regression test - Document root cause
- VALIDATE
- Verify fix in affected environment - Monitor metrics - Update documentation
### Tool Selection Guide
| Problem Type | Primary Tool | Secondary Tools |
| --- | --- | --- |
| Logic error | pdb/debugger | Logging, unit tests |
| Performance | Profiler | Hypothesis testing, metrics |
| Memory leak | Memory profiler | Weak references, heap dumps |
| Async/timing | Timeline reconstruction | Extended thinking, logging |
| Distributed | Tracing (logs) | Kubernetes tools, MECE analysis |
| Unknown cause | Extended thinking | MECE, 5 Whys, hypothesis-driven |
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**Skill version**: 2.0 (Enhanced with extended thinking integration) **Last updated**: 2024-01-15 **Maintained by**: Golden Armada AI Agent Fleet