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Engineering Challenges

Diagnose, debug and fix realistic production AI problems. Each challenge gives you symptoms, evidence and a scoring rubric.

DebuggingArchitecturePromptingRAGAgentsEvaluationPerformanceSecurityFDE
RAG
Intermediate
Good Retrieval, Bad Answers
Your RAG system over internal docs has excellent retrieval scores (recall@5 = 0.91) but users complain the answers are wrong, vague or cite the wrong source. Diagnose the problem.
Retrieval recall@5 is 0.91 — top chunks are relevantUsers report answers 'miss the point'Citations sometimes point to the wrong chunk
Agents
Advanced
The Agent That Wouldn't Stop
Your research agent occasionally runs for 40+ minutes and costs $15 per run before timing out. The agent keeps calling the same tool with slightly different arguments. Diagnose and fix.
Mean run: 90 seconds. P99 run: 40+ minutes.Cost spikes — some runs cost $15+Agent calls search() 20+ times with paraphrased queries
Security
Advanced
Injection via Retrieved Documents
Your RAG system over user-uploaded docs started producing outputs that reveal the system prompt and refuse to answer normally. One user uploaded a document that 'broke' the assistant.
Assistant reveals system prompt to certain usersNormal answers replaced with 'I cannot help with that'Issue started after a specific document upload
Performance
Intermediate
Cost Blowup After Launch
Your AI feature launched 2 weeks ago. Costs were $200/day in week 1. Today is $4,800/day. Traffic is up 3x but cost is up 24x. Find the leak.
Requests up 3x, cost up 24xP95 latency up from 1.2s to 4.8sMost cost on the frontier model, not the small model
Evaluation
Advanced
Eval Regression After Model Upgrade
You upgraded gpt-4o to gpt-4o-2025-01. Production metrics look fine but eval scores dropped 15%. Users haven't complained yet but you're worried.
Eval faithfulness dropped 0.81 → 0.69Production latency improved 200msUsers haven't complained
Agents
Advanced
Tool Error Cascade
Your agent depends on a weather API. When the API returns 500s, the agent retries 8 times, then crashes with an unhandled exception instead of answering with available information.
Agent fails on weather API 500sTool retries 8x then throwsAgent crashes instead of graceful degradation
Performance
Intermediate
Vision Model Misreads Charts
Your multimodal assistant answers questions about uploaded charts. It's confident but wrong on ~30% of numeric values. Users lose trust.
30% of numeric values are wrongModel is confident even when wrongBar charts and line charts affected
FDE
Expert
FDE: 50,000 Document Assistant
A customer wants to deploy an internal AI assistant across 50,000 internal policy, procedure and support documents for 12,000 employees. Design the solution.
12,000 employees, 50,000 documentsMixed content: policies (PDF), procedures (Confluence), support tickets (CSV)Strict access control — not all docs visible to all employees
Debugging
Advanced
Tool Call Split Across Chunks
Your streaming agent occasionally crashes with 'Invalid tool call: missing arguments'. It only happens for long tool calls and is intermittent.
Intermittent 'Invalid tool call' errorsHappens for longer tool call argumentsParser crashes mid-stream
RAG
Advanced
Embedding Model Version Drift
You upgraded your embedding model from text-embedding-3-small to text-embedding-3-large. Search quality dropped 40% overnight despite the new model being 'better'.
Recall@5 dropped 0.88 → 0.53New model is objectively better on benchmarksDrop happened immediately after upgrade