LangSmith Dataset

Auto-generate evaluation datasets from LangSmith traces for testing and validation.

Setup

Environment Variables

LANGSMITH_API_KEY=lsv2_pt_your_api_key_here          # Required
LANGSMITH_PROJECT=your-project-name                   # Optional: default project
LANGSMITH_WORKSPACE_ID=your-workspace-id              # Optional: for org-scoped keys

Dependencies

pip install langsmith click rich python-dotenv

Usage

Navigate to

skills/langsmith-dataset/scripts/

Scripts

generate_datasets.py

query_datasets.py

Common Flags

All dataset generation commands support:

• --root-run-name <name>

  - Filter traces by root run name (e.g., "LangGraph" for DeepAgents)

• --limit <n>

  - Number of traces to process (default: 30)

• --last-n-minutes <n>

  - Only recent traces

• --output <path>

  - Output file (.json or .csv)

• --upload <name>

  - Upload to LangSmith with this dataset name

• --replace

  - Overwrite existing file/dataset (will prompt for confirmation)

• --yes

  - Skip confirmation prompts (use with caution)

IMPORTANT - Safety Prompts:

• The script prompts for confirmation before deleting existing datasets with

  --replace

• ALWAYS respect these prompts - wait for user input before proceeding
• NEVER use

  --yes

  flag unless the user explicitly requests it
• The

  --yes

  flag skips all safety prompts and should only be used in automated workflows when explicitly authorized by the user

Understanding Trace Hierarchy

Traces have depth levels based on parent-child relationships:

Depth 0: Root agent (e.g., "LangGraph")
  ├── Depth 1: Middleware/chains (model, tools, SummarizationMiddleware)
  │     ├── Depth 2: Tool calls (sql_db_query, retriever, etc.)
  │     └── Depth 2: LLM calls (ChatOpenAI, ChatAnthropic)
  └── Depth 3+: Nested subagent calls

Use

--root-run-name

• DeepAgents:

  --root-run-name LangGraph

• Custom agents: Use your root node name

Dataset Types

1. Final Response

Full conversation with expected output - tests complete agent behavior.

# Basic usage
python generate_datasets.py --type final_response \
  --project my-project \
  --root-run-name LangGraph \
  --limit 30 \
  --output /tmp/final_response.json

# With custom output fields
python generate_datasets.py --type final_response \
  --project my-project \
  --output-fields "answer,result" \
  --output /tmp/final.json

# Messages only (ignore output dict keys)
python generate_datasets.py --type final_response \
  --project my-project \
  --messages-only \
  --output /tmp/final.json

Structure:

{
  "trace_id": "...",
  "inputs": {"query": "What are the top 3 genres?"},
  "outputs": {
    "expected_response": "The top 3 genres based on the number of tracks are:\n\n1. Rock with 1,297 tracks\n2. Latin with 579 tracks\n3. Metal with 374 tracks"
  }
}

Extraction Priority:

1. Messages from root run (AI responses with content)
2. User-specified output fields (

   --output-fields

   )
3. Common keys (answer, output)
4. Full output dict

Important: Always checks root run first for final response to avoid intermediate tool outputs.

2. Single Step

Single node inputs/outputs - tests any specific node's behavior. Supports multiple occurrences per trace to capture conversation evolution.

# Extract all occurrences (default)
python generate_datasets.py --type single_step \
  --project my-project \
  --root-run-name LangGraph \
  --run-name model \
  --output /tmp/single_step.json

# Sample 2 occurrences per trace
python generate_datasets.py --type single_step \
  --project my-project \
  --root-run-name LangGraph \
  --run-name model \
  --sample-per-trace 2 \
  --output /tmp/single_step_sampled.json

# Target specific tool at depth 2
python generate_datasets.py --type single_step \
  --project my-project \
  --root-run-name LangGraph \
  --run-name sql_db_query \
  --output /tmp/sql_query.json

Structure:

{
  "trace_id": "...",
  "run_id": "...",
  "occurrence": 2,
  "inputs": {
    "messages": [
      {"type": "human", "content": "What are the top 3 genres?"},
      {"type": "ai", "content": "", "tool_calls": [...]},
      {"type": "tool", "content": "...results..."},
      ...
    ]
  },
  "outputs": {
    "expected_output": {
      "messages": [
        {"type": "ai", "content": "", "tool_calls": [...]}
      ]
    },
    "node_name": "model"
  }
}

Key Features:

• occurrence

  field tracks which invocation (1st, 2nd, 3rd, etc.)
• Later occurrences have more conversation history → tests context handling

• --sample-per-trace

  randomly samples N occurrences per trace
• Use

  --run-name

  to target any node at any depth

Common targets:

• model

  (depth 1) - LLM invocations with growing context

• tools

  (depth 1) - Tool execution chain
• Any custom node name

3. Trajectory

Tool call sequence - tests execution path with configurable depth.

# Include all tool calls (all depths)
python generate_datasets.py --type trajectory \
  --project my-project \
  --root-run-name LangGraph \
  --limit 30 \
  --output /tmp/trajectory_all.json

# Only tool calls up to depth 2
python generate_datasets.py --type trajectory \
  --project my-project \
  --root-run-name LangGraph \
  --depth 2 \
  --output /tmp/trajectory_depth2.json

# Only root-level tool calls (depth 0) - usually empty if tools are at depth 2+
python generate_datasets.py --type trajectory \
  --project my-project \
  --depth 0 \
  --output /tmp/trajectory_root.json

Structure:

{
  "trace_id": "...",
  "inputs": {"query": "What are the top 3 genres?"},
  "outputs": {
    "expected_trajectory": [
      "sql_db_list_tables",
      "sql_db_schema",
      "sql_db_query_checker",
      "sql_db_query"
    ]
  }
}

Depth Control:

• Omit

  --depth

  = all levels (includes subagent tool calls)

• --depth 2

  = root + 2 levels (typical for capturing all main tools)

• --depth 1

  = often only middleware/chains, no actual tool calls

• --depth 0

  = root only (no tool calls)

Note: Tool calls are typically at depth 2 in LangGraph/DeepAgents architecture.

4. RAG

Question/chunks/answer/citations - tests retrieval quality.

python generate_datasets.py --type rag \
  --project my-project \
  --limit 30 \
  --output /tmp/rag_ds.csv  # Supports .json or .csv

Structure (CSV format):

question,retrieved_chunks,answer,cited_chunks
"How do I...","Chunk 1\n\nChunk 2","The answer is...","[\"Chunk 1\"]"

Output Formats

All dataset types support both JSON and CSV:

# JSON output (default)
python generate_datasets.py --type trajectory --project my-project --output ds.json

# CSV output (use .csv extension)
python generate_datasets.py --type trajectory --project my-project --output ds.csv

Upload to LangSmith

# Generate and upload in one command
python generate_datasets.py --type trajectory \
  --project my-project \
  --root-run-name LangGraph \
  --limit 50 \
  --output /tmp/trajectory_ds.json \
  --upload "Skills: Trajectory"

# Use --replace to overwrite existing dataset
python generate_datasets.py --type final_response \
  --project my-project \
  --output /tmp/final.json \
  --upload "Skills: Final Response" \
  --replace

Naming Convention: Use "Skills: <Type>" format for consistency:

• "Skills: Final Response"
• "Skills: Single Step (model)"
• "Skills: Single Step (sql_db_query)"
• "Skills: Trajectory (all depths)"
• "Skills: Trajectory (depth=2)"

Query Datasets

# List all datasets
python query_datasets.py list-datasets

# Filter by name pattern
python query_datasets.py list-datasets | grep "Skills:"

# View dataset examples
python query_datasets.py show "Skills: Trajectory" --limit 5

# View local file
python query_datasets.py view-file /tmp/trajectory_ds.json --limit 3

# Analyze structure
python query_datasets.py structure /tmp/trajectory_ds.json

# Export from LangSmith to local
python query_datasets.py export "Skills: Final Response" /tmp/exported.json --limit 100

Tips for Dataset Generation

1. Always use

   --root-run-name

   - Filter for specific agent framework (e.g., "LangGraph")
2. Start with successful traces - Use recent successful runs for baseline datasets
3. Use time windows -

   --last-n-minutes 1440

   for last 24 hours of data
4. Sample for single_step - Use

   --sample-per-trace 2

   to capture conversation evolution
5. Match depth to needs -

   --depth 2

   typically captures all main tool calls
6. Review before upload - Use

   query_datasets.py view-file

   to inspect first
7. Iterative refinement - Generate small batches (10-20) first, validate, then scale up
8. Use

   --replace

   carefully - Overwrites existing datasets, useful for iteration

Example Workflow

# 1. Generate fresh traces (if needed)
python tests/test_agent.py --batch  # Your test agent

# 2. Generate all dataset types from LangGraph traces
python generate_datasets.py --type final_response \
  --project skills --root-run-name LangGraph --limit 10 \
  --output /tmp/final.json --upload "Skills: Final Response" --replace

python generate_datasets.py --type single_step \
  --project skills --root-run-name LangGraph --run-name model \
  --sample-per-trace 2 --limit 10 \
  --output /tmp/model.json --upload "Skills: Single Step (model)" --replace

python generate_datasets.py --type trajectory \
  --project skills --root-run-name LangGraph --limit 10 \
  --output /tmp/traj.json --upload "Skills: Trajectory (all depths)" --replace

python generate_datasets.py --type trajectory \
  --project skills --root-run-name LangGraph --depth 2 --limit 10 \
  --output /tmp/traj_d2.json --upload "Skills: Trajectory (depth=2)" --replace

# 3. Review in LangSmith UI
# Visit https://smith.langchain.com → Datasets → Filter for "Skills:"

# 4. Query locally if needed
python query_datasets.py show "Skills: Final Response" --limit 3

Troubleshooting

Empty final_response outputs:

• Ensure

  --root-run-name

  matches your agent's root node
• Check that root run has messages with AI responses
• Use

  --messages-only

  if output dict is empty

No trajectory examples:

• Tools might be at different depth - try removing

  --depth

  or use

  --depth 2

• Verify tool calls exist:

  python query_traces.py trace <id> --show-hierarchy

Too many single_step examples:

• Use

  --sample-per-trace 2

  to limit examples per trace
• Reduces dataset size while maintaining diversity

Dataset upload fails:

• Check dataset doesn't exist or use

  --replace

• Verify LANGSMITH_API_KEY is set

Related Skills

• Use langsmith-trace skill to query and export traces
• Use langsmith-evaluator skill to create evaluators and measure performance