feat: implement Reader-Guided Reranking — bridge R@5 vs E2E gap (#666)

Resolves #666. RIDER reranks retrieved passages by how well the LLM
can actually answer from them, bridging the gap between high retrieval
recall (98.4% R@5) and low end-to-end accuracy (17%).

agent/rider.py (256 lines):
- RIDER class with rerank(passages, query) method
- Batch LLM prediction from each passage individually
- Confidence-based scoring: specificity, grounding, hedge detection,
  query relevance, refusal penalty
- Async scoring with configurable batch size
- Convenience functions: rerank_passages(), is_rider_available()

tools/session_search_tool.py:
- Wired RIDER into session search pipeline after FTS5 results
- Reranks sessions by LLM answerability before summarization
- Graceful fallback if RIDER unavailable

tests/test_reader_guided_reranking.py (10 tests):
- Empty passages, few passages, disabled mode
- Confidence scoring: short answers, hedging, grounding, refusal
- Convenience function, availability check

Config via env vars: RIDER_ENABLED, RIDER_TOP_K, RIDER_TOP_N,
RIDER_MAX_TOKENS, RIDER_BATCH_SIZE.

agent/rider.py

@@ -0,0 +1,256 @@
+"""RIDER — Reader-Guided Passage Reranking.
+
+Bridges the R@5 vs E2E accuracy gap by using the LLM's own predictions
+to rerank retrieved passages. Passages the LLM can actually answer from
+get ranked higher than passages that merely match keywords.
+
+Research: RIDER achieves +10-20 top-1 accuracy gains over naive retrieval
+by aligning retrieval quality with reader utility.
+
+Usage:
+    from agent.rider import RIDER
+    rider = RIDER()
+    reranked = rider.rerank(passages, query, top_n=3)
+"""
+
+from __future__ import annotations
+
+import asyncio
+import logging
+import os
+from typing import Any, Dict, List, Optional, Tuple
+
+logger = logging.getLogger(__name__)
+
+# Configuration
+RIDER_ENABLED = os.getenv("RIDER_ENABLED", "true").lower() not in ("false", "0", "no")
+RIDER_TOP_K = int(os.getenv("RIDER_TOP_K", "10"))  # passages to score
+RIDER_TOP_N = int(os.getenv("RIDER_TOP_N", "3"))    # passages to return after reranking
+RIDER_MAX_TOKENS = int(os.getenv("RIDER_MAX_TOKENS", "50"))  # max tokens for prediction
+RIDER_BATCH_SIZE = int(os.getenv("RIDER_BATCH_SIZE", "5"))    # parallel predictions
+
+
+class RIDER:
+    """Reader-Guided Passage Reranking.
+
+    Takes passages retrieved by FTS5/vector search and reranks them by
+    how well the LLM can answer the query from each passage individually.
+    """
+
+    def __init__(self, auxiliary_task: str = "rider"):
+        """Initialize RIDER.
+
+        Args:
+            auxiliary_task: Task name for auxiliary client resolution.
+        """
+        self._auxiliary_task = auxiliary_task
+
+    def rerank(
+        self,
+        passages: List[Dict[str, Any]],
+        query: str,
+        top_n: int = RIDER_TOP_N,
+    ) -> List[Dict[str, Any]]:
+        """Rerank passages by reader confidence.
+
+        Args:
+            passages: List of passage dicts. Must have 'content' or 'text' key.
+                May have 'session_id', 'snippet', 'rank', 'score', etc.
+            query: The user's search query.
+            top_n: Number of passages to return after reranking.
+
+        Returns:
+            Reranked passages (top_n), each with added 'rider_score' and
+            'rider_prediction' fields.
+        """
+        if not RIDER_ENABLED or not passages:
+            return passages[:top_n]
+
+        if len(passages) <= top_n:
+            # Score them anyway for the prediction metadata
+            return self._score_and_rerank(passages, query, top_n)
+
+        return self._score_and_rerank(passages[:RIDER_TOP_K], query, top_n)
+
+    def _score_and_rerank(
+        self,
+        passages: List[Dict[str, Any]],
+        query: str,
+        top_n: int,
+    ) -> List[Dict[str, Any]]:
+        """Score each passage with the reader, then rerank by confidence."""
+        try:
+            from model_tools import _run_async
+            scored = _run_async(self._score_all_passages(passages, query))
+        except Exception as e:
+            logger.debug("RIDER scoring failed: %s — returning original order", e)
+            return passages[:top_n]
+
+        # Sort by confidence (descending)
+        scored.sort(key=lambda p: p.get("rider_score", 0), reverse=True)
+
+        return scored[:top_n]
+
+    async def _score_all_passages(
+        self,
+        passages: List[Dict[str, Any]],
+        query: str,
+    ) -> List[Dict[str, Any]]:
+        """Score all passages in batches."""
+        scored = []
+
+        for i in range(0, len(passages), RIDER_BATCH_SIZE):
+            batch = passages[i:i + RIDER_BATCH_SIZE]
+            tasks = [
+                self._score_single_passage(p, query, idx + i)
+                for idx, p in enumerate(batch)
+            ]
+            results = await asyncio.gather(*tasks, return_exceptions=True)
+
+            for passage, result in zip(batch, results):
+                if isinstance(result, Exception):
+                    logger.debug("RIDER passage %d scoring failed: %s", i, result)
+                    passage["rider_score"] = 0.0
+                    passage["rider_prediction"] = ""
+                    passage["rider_confidence"] = "error"
+                else:
+                    score, prediction, confidence = result
+                    passage["rider_score"] = score
+                    passage["rider_prediction"] = prediction
+                    passage["rider_confidence"] = confidence
+                scored.append(passage)
+
+        return scored
+
+    async def _score_single_passage(
+        self,
+        passage: Dict[str, Any],
+        query: str,
+        idx: int,
+    ) -> Tuple[float, str, str]:
+        """Score a single passage by asking the LLM to predict an answer.
+
+        Returns:
+            (confidence_score, prediction, confidence_label)
+        """
+        content = passage.get("content") or passage.get("text") or passage.get("snippet", "")
+        if not content or len(content) < 10:
+            return 0.0, "", "empty"
+
+        # Truncate passage to reasonable size for the prediction task
+        content = content[:2000]
+
+        prompt = (
+            f"Question: {query}\n\n"
+            f"Context: {content}\n\n"
+            f"Based ONLY on the context above, provide a brief answer to the question. "
+            f"If the context does not contain enough information to answer, respond with "
+            f"'INSUFFICIENT_CONTEXT'. Be specific and concise."
+        )
+
+        try:
+            from agent.auxiliary_client import get_text_auxiliary_client, auxiliary_max_tokens_param
+
+            client, model = get_text_auxiliary_client(task=self._auxiliary_task)
+            if not client:
+                return 0.5, "", "no_client"
+
+            response = client.chat.completions.create(
+                model=model,
+                messages=[{"role": "user", "content": prompt}],
+                **auxiliary_max_tokens_param(RIDER_MAX_TOKENS),
+                temperature=0,
+            )
+
+            prediction = (response.choices[0].message.content or "").strip()
+
+            # Confidence scoring based on the prediction
+            if not prediction:
+                return 0.1, "", "empty_response"
+
+            if "INSUFFICIENT_CONTEXT" in prediction.upper():
+                return 0.15, prediction, "insufficient"
+
+            # Calculate confidence from response characteristics
+            confidence = self._calculate_confidence(prediction, query, content)
+
+            return confidence, prediction, "predicted"
+
+        except Exception as e:
+            logger.debug("RIDER prediction failed for passage %d: %s", idx, e)
+            return 0.0, "", "error"
+
+    def _calculate_confidence(
+        self,
+        prediction: str,
+        query: str,
+        passage: str,
+    ) -> float:
+        """Calculate confidence score from prediction quality signals.
+
+        Heuristics:
+        - Short, specific answers = higher confidence
+        - Answer terms overlap with passage = higher confidence
+        - Hedging language = lower confidence
+        - Answer directly addresses query terms = higher confidence
+        """
+        score = 0.5  # base
+
+        # Specificity bonus: shorter answers tend to be more confident
+        words = len(prediction.split())
+        if words <= 5:
+            score += 0.2
+        elif words <= 15:
+            score += 0.1
+        elif words > 50:
+            score -= 0.1
+
+        # Passage grounding: does the answer use terms from the passage?
+        passage_lower = passage.lower()
+        answer_terms = set(prediction.lower().split())
+        passage_terms = set(passage_lower.split())
+        overlap = len(answer_terms & passage_terms)
+        if overlap > 3:
+            score += 0.15
+        elif overlap > 0:
+            score += 0.05
+
+        # Query relevance: does the answer address query terms?
+        query_terms = set(query.lower().split())
+        query_overlap = len(answer_terms & query_terms)
+        if query_overlap > 1:
+            score += 0.1
+
+        # Hedge penalty: hedging language suggests uncertainty
+        hedge_words = {"maybe", "possibly", "might", "could", "perhaps",
+                       "not sure", "unclear", "don't know", "cannot"}
+        if any(h in prediction.lower() for h in hedge_words):
+            score -= 0.2
+
+        # "I cannot" / "I don't" penalty (model refusing rather than answering)
+        if prediction.lower().startswith(("i cannot", "i don't", "i can't", "there is no")):
+            score -= 0.15
+
+        return max(0.0, min(1.0, score))
+
+
+def rerank_passages(
+    passages: List[Dict[str, Any]],
+    query: str,
+    top_n: int = RIDER_TOP_N,
+) -> List[Dict[str, Any]]:
+    """Convenience function for passage reranking."""
+    rider = RIDER()
+    return rider.rerank(passages, query, top_n)
+
+
+def is_rider_available() -> bool:
+    """Check if RIDER can run (auxiliary client available)."""
+    if not RIDER_ENABLED:
+        return False
+    try:
+        from agent.auxiliary_client import get_text_auxiliary_client
+        client, model = get_text_auxiliary_client(task="rider")
+        return client is not None and model is not None
+    except Exception:
+        return False

tests/test_reader_guided_reranking.py

@@ -0,0 +1,82 @@
+"""Tests for Reader-Guided Reranking (RIDER) — issue #666."""
+
+import pytest
+from unittest.mock import MagicMock, patch
+from agent.rider import RIDER, rerank_passages, is_rider_available
+
+
+class TestRIDERClass:
+    def test_init(self):
+        rider = RIDER()
+        assert rider._auxiliary_task == "rider"
+
+    def test_rerank_empty_passages(self):
+        rider = RIDER()
+        result = rider.rerank([], "test query")
+        assert result == []
+
+    def test_rerank_fewer_than_top_n(self):
+        """If passages <= top_n, return all (with scores if possible)."""
+        rider = RIDER()
+        passages = [{"content": "test content", "session_id": "s1"}]
+        result = rider.rerank(passages, "test query", top_n=3)
+        assert len(result) == 1
+
+    @patch("agent.rider.RIDER_ENABLED", False)
+    def test_rerank_disabled(self):
+        """When disabled, return original order."""
+        rider = RIDER()
+        passages = [
+            {"content": f"content {i}", "session_id": f"s{i}"}
+            for i in range(5)
+        ]
+        result = rider.rerank(passages, "test query", top_n=3)
+        assert result == passages[:3]
+
+
+class TestConfidenceCalculation:
+    @pytest.fixture
+    def rider(self):
+        return RIDER()
+
+    def test_short_specific_answer(self, rider):
+        score = rider._calculate_confidence("Paris", "What is the capital of France?", "Paris is the capital of France.")
+        assert score > 0.5
+
+    def test_hedged_answer(self, rider):
+        score = rider._calculate_confidence(
+            "Maybe it could be Paris, but I'm not sure",
+            "What is the capital of France?",
+            "Paris is the capital.",
+        )
+        assert score < 0.5
+
+    def test_passage_grounding(self, rider):
+        score = rider._calculate_confidence(
+            "The system uses SQLite for storage",
+            "What database is used?",
+            "The system uses SQLite for persistent storage with FTS5 indexing.",
+        )
+        assert score > 0.5
+
+    def test_refusal_penalty(self, rider):
+        score = rider._calculate_confidence(
+            "I cannot answer this from the given context",
+            "What is X?",
+            "Some unrelated content",
+        )
+        assert score < 0.5
+
+
+class TestRerankPassages:
+    def test_convenience_function(self):
+        """Test the module-level convenience function."""
+        passages = [{"content": "test", "session_id": "s1"}]
+        result = rerank_passages(passages, "query", top_n=1)
+        assert len(result) == 1
+
+
+class TestIsRiderAvailable:
+    def test_returns_bool(self):
+        result = is_rider_available()
+        assert isinstance(result, bool)

tools/session_search_tool.py

@@ -394,6 +394,23 @@ def session_search(
             if len(seen_sessions) >= limit:
                 break
 
+        # RIDER: Reader-guided reranking — sort sessions by LLM answerability
+        # This bridges the R@5 vs E2E accuracy gap by prioritizing passages
+        # the LLM can actually answer from, not just keyword matches.
+        try:
+            from agent.rider import rerank_passages, is_rider_available
+            if is_rider_available() and len(seen_sessions) > 1:
+                rider_passages = [
+                    {"session_id": sid, "content": info.get("snippet", ""), "rank": i + 1}
+                    for i, (sid, info) in enumerate(seen_sessions.items())
+                ]
+                reranked = rerank_passages(rider_passages, query, top_n=len(rider_passages))
+                # Reorder seen_sessions by RIDER score
+                reranked_sids = [p["session_id"] for p in reranked]
+                seen_sessions = {sid: seen_sessions[sid] for sid in reranked_sids if sid in seen_sessions}
+        except Exception as e:
+            logging.debug("RIDER reranking skipped: %s", e)
+
         # Prepare all sessions for parallel summarization
         tasks = []
         for session_id, match_info in seen_sessions.items():