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Evaluation and Prompt Optimization (turnstone-eval)

turnstone-eval is the evaluation and prompt optimization system for turnstone. It runs test cases against the LLM, scores tool call sequences against expected actions, and optionally uses the model to self-optimize the developer prompt.

Source: turnstone/eval.py


Overview

The system works in an iterative loop:

  1. Run each test case N times against the current developer prompt.
  2. Score each run by comparing the actual tool call sequence to expected actions.
  3. If not all tests pass, use the model to rewrite the prompt based on failures.
  4. Repeat until all tests pass or max iterations are reached.

When optimization is disabled (--no-optimize), only step 1 and 2 execute (a single iteration).


Test Case Format

Test suites are JSON files with this structure:

{
  "defaults": {
    "n_runs": 3
  },
  "cases": [
    {
      "id": "test_name",
      "user_prompt": "the prompt to send to the model",
      "setup": {
        "files": {
          "filename.py": "file content here",
          "src/utils.py": "another file"
        }
      },
      "expected_actions": [
        {"tool": "read_file", "args": {"path": "filename.py"}},
        {"tool": "bash", "args_pattern": {"command": "python.*test"}},
        {"tool": "edit_file"}
      ],
      "match_mode": "ordered_subset",
      "max_turns": 10,
      "n_runs": 5
    }
  ]
}

Fields

Field Required Default Description
id yes -- Unique test case identifier.
user_prompt yes -- The message sent to the model.
setup.files no {} Files to create in the temp directory before running. Keys are relative paths, values are file content.
expected_actions no [] List of expected tool calls to match against.
match_mode no "ordered_subset" How to match actual vs expected actions (see Scoring).
max_turns no 10 Maximum conversation turns before stopping.
n_runs no suite default or 3 Per-case override for number of runs.

Expected Action Specs

Each entry in expected_actions can contain:

  • tool (required): The tool name to match (e.g. "read_file", "bash").
  • args: Exact key-value matching. Each key in args must exist in the actual call with the same string value.
  • args_pattern: Regex key-value matching. Each key's value is a regex pattern tested against the actual argument value.
  • If neither args nor args_pattern is specified, only the tool name is matched.

Scoring

Scoring is handled by score_run(), which compares a run's tool call log against the expected actions.

Match Modes

Mode Description
exact Tool calls must match expected actions in exact order and exact count. Extra or missing calls cause failure.
ordered_subset Expected actions must appear in order within the actual tool log, but extra calls between them are allowed. This is the default.
subset Expected actions must all appear somewhere in the tool log, in any order. Each actual call can only match one expected action.
contains_any Passes if at least one expected action appears anywhere in the tool log.

Action Matching (_match_action)

A single actual tool call matches an expected action when:

  1. The tool names are equal.
  2. If args is specified: every key in args must exist in the actual call's arguments with the same string value (partial key matching -- extra actual args are ignored).
  3. If args_pattern is specified: every key's regex pattern must match the corresponding actual argument value via re.search().
  4. If the actual args contain only _raw (unparseable JSON fallback), the action matches only when no args or args_pattern is expected.

Score Calculation

  • Score = number of matched expected actions / total expected actions.
  • Pass = score equals 1.0 (all expected actions matched).
  • The return dict includes: pass, score, matched (indices), unmatched (indices), extra_tools, and detail (human-readable summary).

JSON Dump Detection

When a run fails and the model's final text content contains JSON that looks like a tool call (keys like "tool", "command", "path"), the run is flagged with json_dump: true. This indicates the model tried to call a tool but emitted JSON as text instead of using the function-calling interface.


HeadlessSession

HeadlessSession extends ChatSession for headless evaluation. It provides deterministic, non-interactive execution suitable for automated testing.

Differences from ChatSession

Aspect ChatSession HeadlessSession
Streaming Streaming API Non-streaming (stream=False)
Tool approval User confirmation auto_approve = True
UI Terminal/Web UI NullUI (discards output)
Stdout Normal Suppressed during execution
Tool logging Display only Structured tool_call_log
System prompt Built-in developer prompt Overridable via constructor

NullUI

A minimal UI adapter that satisfies the SessionUI protocol by discarding all output. approve_tools() always returns (True, None).

send_headless()

def send_headless(
    self,
    user_input: str,
    max_turns: int = 10,
    verbose: bool = False,
    log_prefix: str = "",
) -> list[dict]:

Runs a complete multi-turn conversation:

  1. Appends the user message.
  2. Calls the model API (non-streaming).
  3. If tool calls are returned, executes them (with stdout suppressed) and logs each call to self.tool_call_log.
  4. Repeats up to max_turns or until the model responds without tool calls.
  5. Returns the tool call log: list of dicts with keys tool, args, result (truncated to 500 chars), and turn.

Parallel tool calls are capped at 10 per turn to prevent degenerate repetition.

Retry Logic

send_headless() is called inside _run_single_test() with retry logic: 3 attempts with exponential backoff (sleep 2^attempt seconds) on any exception. This prevents transient API errors from poisoning eval scores.


Test Execution

Each test case runs in isolation:

  1. A fresh temp directory is created.
  2. Setup files are written to the temp directory.
  3. The working directory is changed to the temp directory.
  4. A new HeadlessSession is created with the current developer prompt.
  5. send_headless() runs the user prompt through the conversation loop.
  6. The tool log is scored against expected actions.
  7. The temp directory is cleaned up.

The memory database is also isolated per test (an ephemeral SQLite database in the temp directory) so tests do not pollute each other or the user's real memory store.


Optimization Loop

run_optimization() is the main entry point for iterative prompt optimization.

Flow

for iteration in 0..max_iterations:
    1. Run all test cases n_runs times with current prompt
    2. Score and aggregate results
    3. Save intermediate results to JSON
    4. If all tests pass -> stop
    5. Every 3 iterations (at iteration 2, 5, 8, ...):
       -> Observer reviews optimizer strategy
       -> Reset prompt to best-performing iteration
    6. Propose new prompt via optimizer model call
    7. If prompt unchanged -> stop
    8. Continue with new prompt

Prompt Proposal (_propose_prompt_modification)

Uses the model to rewrite the developer prompt based on test results:

  • Input: Current prompt, test case definitions, per-case results with actual vs expected tool sequences, and a history of the last 3 iterations.
  • Optimizer system prompt (OPTIMIZER_SYSTEM): Instructs the model to act as a text rewriter. Key guidance includes:
    • Address critical failure modes (text-only responses, write_file vs edit_file, unnecessary search before create, missing plan calls).
    • Preserve phrasing that drives 100% pass rate on passing tests.
    • Use direct imperative style with concrete tool call examples.
    • Stay within 130% of original prompt length.
  • Output: The rewritten prompt text (stripped of reasoning tags and code fences).

Observer System (_observe_and_update_optimizer)

Every 3 iterations, a meta-level "observer" reviews the optimizer's strategy:

  • Analyzes the iteration history: score trends, regressions, prompt length changes, and diffs between iterations.
  • Summarizes the optimizer's behavioral patterns (list style, header usage, length).
  • Uses OBSERVER_SYSTEM to rewrite the optimizer's own system prompt.
  • Rejects degenerate outputs (over 200% of input length).
  • After updating the optimizer prompt, resets the developer prompt to the best-performing iteration so far.

This two-level optimization (optimizer + observer) helps the system escape local minima and adjust its rewriting strategy.

Result Persistence

After each iteration, results are written to the output JSON file. The structure is:

{
  "meta": {
    "model": "model-name",
    "base_url": "http://localhost:8000/v1",
    "started": "2025-01-01T00:00:00",
    "test_suite": "tests.json",
    "n_runs_default": 3
  },
  "iterations": [
    {
      "iteration": 0,
      "prompt": "the developer prompt used",
      "prompt_diff": null,
      "optimizer_system": "the optimizer system prompt",
      "timestamp": "2025-01-01T00:01:00",
      "cases": {
        "test_name": {
          "runs": [
            {
              "pass": true,
              "score": 1.0,
              "matched": [0, 1],
              "unmatched": [],
              "extra_tools": [],
              "detail": "Ordered subset: 2/2",
              "tool_sequence": ["read_file", "edit_file"],
              "tool_args": [{"read_file": {"path": "f.py"}}, ...],
              "elapsed": 3.2
            }
          ],
          "pass_rate": 1.0,
          "avg_score": 1.0
        }
      },
      "aggregate": {
        "total_cases": 5,
        "total_runs": 15,
        "overall_pass_rate": 0.8,
        "overall_avg_score": 0.87,
        "json_dumps": 0,
        "per_case_pass_rates": {"test_name": 1.0, ...}
      }
    }
  ]
}

CLI Usage

The entry point is turnstone-eval (installed as a console script) or python -m turnstone.eval.

turnstone-eval tests.json                          # evaluate + optimize
turnstone-eval tests.json --no-optimize            # evaluate only (single iteration)
turnstone-eval tests.json --n-runs 5 --max-iter 10 # more thorough evaluation
turnstone-eval tests.json --prompt custom.txt      # start from a custom prompt
turnstone-eval tests.json -v                       # verbose per-turn logging

All Options

Flag Default Description
test_file (positional, required) Path to test cases JSON file.
--base-url http://localhost:8000/v1 API base URL.
--model auto-detect Model name. Auto-detected from the API if not specified.
--prompt turnstone built-in prompt Path to initial prompt text file.
--n-runs from tests.json or 3 Number of runs per test case.
--max-iter 5 Maximum optimization iterations.
--no-optimize false Run evaluation only (sets max-iter to 1).
--temperature 0.7 Sampling temperature.
--max-tokens 32768 Max completion tokens.
--reasoning-effort medium Reasoning effort: low, medium, or high.
--context-window 131072 Context window size.
--output eval_results.json Output results file path.
-v, --verbose false Show detailed per-turn logging (API calls, tool args, results).

Precedence for n_runs

The number of runs per test case is resolved in this order:

  1. Per-case n_runs field in the test case definition.
  2. CLI --n-runs argument (if provided).
  3. Suite-level defaults.n_runs in the test JSON file.
  4. Code default: 3.