feat: implement Context-Faithful Prompting — make LLMs use retrieved context (#667)

Resolves #667. Addresses R@5 vs E2E accuracy gap by forcing the
LLM to ground in retrieved context instead of parametric knowledge.

agent/context_faithful.py (293 lines):
- build_context_faithful_prompt(): context-before-question structure,
  explicit use-context instruction, I-dont-know escape hatch,
  passage numbering for citations, confidence calibration (1-5)
- build_summarization_prompt(): context-faithful version for session search
- build_answer_prompt(): context-faithful for direct Q&A
- assess_context_faithfulness(): heuristic faithfulness scoring
  (citation count, grounding ratio, honest-unknown detection)

tools/session_search_tool.py:
- Replaced hardcoded summarization prompt with build_summarization_prompt()
- LLM now forced to cite transcript passages and ground in context

tests/test_context_faithful_prompting.py (18 tests):
- Prompt structure, context-before-question, passage numbering
- Citation/confidence toggles, empty passages
- Summarization integration, answer generation
- Faithfulness assessment: citations, grounding ratio, honest unknown

agent/context_faithful.py

@@ -0,0 +1,293 @@
+"""Context-Faithful Prompting — Make LLMs Use Retrieved Context.
+
+Addresses the R@5 vs E2E accuracy gap by prompting the LLM to actually
+use the retrieved context instead of relying on parametric knowledge.
+
+Research: Context-faithful prompting achieves +5-15 E2E accuracy gains.
+
+Key patterns:
+1. Context-before-question structure (attention bias)
+2. Explicit "use the context" instruction
+3. Citation requirement (which passage used)
+4. Confidence calibration
+5. "I don't know" escape hatch
+
+Usage:
+    from agent.context_faithful import build_context_faithful_prompt
+    prompt = build_context_faithful_prompt(passages, query)
+"""
+
+from __future__ import annotations
+
+import os
+from typing import Any, Dict, List, Optional
+
+# Configuration
+CFAITHFUL_ENABLED = os.getenv("CFAITHFUL_ENABLED", "true").lower() not in ("false", "0", "no")
+CFAITHFUL_REQUIRE_CITATION = os.getenv("CFAITHFUL_REQUIRE_CITATION", "true").lower() not in ("false", "0", "no")
+CFAITHFUL_CONFIDENCE = os.getenv("CFAITHFUL_CONFIDENCE", "true").lower() not in ("false", "0", "no")
+CFAITHFUL_MAX_CONTEXT_CHARS = int(os.getenv("CFAITHFUL_MAX_CONTEXT_CHARS", "8000"))
+
+
+# ---------------------------------------------------------------------------
+# Prompt Templates
+# ---------------------------------------------------------------------------
+
+# Core instruction: forces the LLM to ground in context
+CONTEXT_FAITHFUL_INSTRUCTION = (
+    "You must answer based ONLY on the provided context below. "
+    "Do not use any prior knowledge or make assumptions beyond what is stated in the context. "
+    "If the context does not contain enough information to answer the question, "
+    "you MUST say: \"I don't know based on the provided context.\" "
+    "Do not guess. Do not fill in gaps with your training data."
+)
+
+# Citation instruction: forces the LLM to cite which passage it used
+CITATION_INSTRUCTION = (
+    "For each claim in your answer, cite the specific passage number "
+    "(e.g., [Passage 1], [Passage 3]) that supports it. "
+    "If you cannot cite a passage for a claim, do not include that claim."
+)
+
+# Confidence instruction: calibrates the LLM's certainty
+CONFIDENCE_INSTRUCTION = (
+    "After your answer, rate your confidence on a scale of 1-5:\n"
+    "1 = The context barely addresses the question\n"
+    "2 = Some relevant information but incomplete\n"
+    "3 = The context provides a partial answer\n"
+    "4 = The context provides a clear answer with minor gaps\n"
+    "5 = The context fully answers the question\n"
+    "Format: Confidence: N/5"
+)
+
+
+def build_context_faithful_prompt(
+    passages: List[Dict[str, Any]],
+    query: str,
+    require_citation: Optional[bool] = None,
+    include_confidence: Optional[bool] = None,
+    max_context_chars: int = CFAITHFUL_MAX_CONTEXT_CHARS,
+) -> Dict[str, str]:
+    """Build a context-faithful prompt with context-before-question structure.
+
+    Args:
+        passages: List of passage dicts with 'content' or 'text' key.
+            May have 'session_id', 'snippet', 'summary', etc.
+        query: The user's question.
+        require_citation: Override citation requirement.
+        include_confidence: Override confidence calibration.
+        max_context_chars: Max total context to include.
+
+    Returns:
+        Dict with 'system' and 'user' prompt strings.
+    """
+    if not CFAITHFUL_ENABLED:
+        return _fallback_prompt(passages, query)
+
+    if require_citation is None:
+        require_citation = CFAITHFUL_REQUIRE_CITATION
+    if include_confidence is None:
+        include_confidence = CFAITHFUL_CONFIDENCE
+
+    # Format passages with numbering for citation
+    context_block = _format_passages(passages, max_context_chars)
+
+    # Build system prompt
+    system_parts = [CONTEXT_FAITHFUL_INSTRUCTION]
+    if require_citation:
+        system_parts.append(CITATION_INSTRUCTION)
+    if include_confidence:
+        system_parts.append(CONFIDENCE_INSTRUCTION)
+
+    system_prompt = "\n\n".join(system_parts)
+
+    # Build user prompt: CONTEXT BEFORE QUESTION (attention bias)
+    user_prompt = (
+        f"CONTEXT:\n{context_block}\n\n"
+        f"---\n\n"
+        f"QUESTION: {query}\n\n"
+        f"Answer the question using ONLY the context above."
+    )
+
+    return {
+        "system": system_prompt,
+        "user": user_prompt,
+    }
+
+
+def _format_passages(
+    passages: List[Dict[str, Any]],
+    max_chars: int,
+) -> str:
+    """Format passages with numbering for citation reference."""
+    lines = []
+    total_chars = 0
+
+    for idx, passage in enumerate(passages, 1):
+        content = (
+            passage.get("content")
+            or passage.get("text")
+            or passage.get("snippet")
+            or passage.get("summary", "")
+        )
+        if not content:
+            continue
+
+        # Truncate individual passage if needed
+        remaining = max_chars - total_chars
+        if remaining <= 0:
+            break
+        if len(content) > remaining:
+            content = content[:remaining] + "..."
+
+        source = passage.get("session_id") or passage.get("source", "")
+        header = f"[Passage {idx}"
+        if source:
+            header += f" — {source}"
+        header += "]"
+
+        lines.append(f"{header}\n{content}\n")
+        total_chars += len(content)
+
+    if not lines:
+        return "[No relevant context found]"
+
+    return "\n".join(lines)
+
+
+def _fallback_prompt(
+    passages: List[Dict[str, Any]],
+    query: str,
+) -> Dict[str, str]:
+    """Simple prompt without context-faithful patterns (when disabled)."""
+    context = _format_passages(passages, CFAITHFUL_MAX_CONTEXT_CHARS)
+    return {
+        "system": "Answer the user's question based on the provided context.",
+        "user": f"Context:\n{context}\n\nQuestion: {query}",
+    }
+
+
+# ---------------------------------------------------------------------------
+# Summarization Integration
+# ---------------------------------------------------------------------------
+
+def build_summarization_prompt(
+    conversation_text: str,
+    query: str,
+    session_meta: Dict[str, Any],
+) -> Dict[str, str]:
+    """Build a context-faithful summarization prompt for session search.
+
+    This is designed to replace the existing _summarize_session prompt
+    in session_search_tool.py with a context-faithful version.
+    """
+    source = session_meta.get("source", "unknown")
+    started = session_meta.get("started_at", "unknown")
+
+    system = (
+        "You are reviewing a past conversation transcript. "
+        + CONTEXT_FAITHFUL_INSTRUCTION + "\n\n"
+        "Summarize the conversation with focus on the search topic. Include:\n"
+        "1. What the user asked about or wanted to accomplish\n"
+        "2. What actions were taken and what the outcomes were\n"
+        "3. Key decisions, solutions found, or conclusions reached\n"
+        "4. Specific commands, files, URLs, or technical details\n"
+        "5. Anything left unresolved\n\n"
+        "Cite specific parts of the transcript (e.g., 'In the conversation, the user...'). "
+        "If the transcript doesn't contain information relevant to the search topic, "
+        "say so explicitly rather than inventing details."
+    )
+
+    user = (
+        f"CONTEXT (conversation transcript):\n{conversation_text}\n\n"
+        f"---\n\n"
+        f"SEARCH TOPIC: {query}\n"
+        f"Session source: {source}\n"
+        f"Session date: {started}\n\n"
+        f"Summarize this conversation with focus on: {query}"
+    )
+
+    return {"system": system, "user": user}
+
+
+# ---------------------------------------------------------------------------
+# Answer Generation
+# ---------------------------------------------------------------------------
+
+def build_answer_prompt(
+    passages: List[Dict[str, Any]],
+    query: str,
+    conversation_context: Optional[str] = None,
+) -> Dict[str, str]:
+    """Build a context-faithful answer generation prompt.
+
+    For direct question answering (not summarization).
+    """
+    context_block = _format_passages(passages, CFAITHFUL_MAX_CONTEXT_CHARS)
+
+    system = "\n\n".join([
+        CONTEXT_FAITHFUL_INSTRUCTION,
+        CITATION_INSTRUCTION,
+        CONFIDENCE_INSTRUCTION,
+    ])
+
+    user_parts = []
+    user_parts.append(f"CONTEXT:\n{context_block}")
+
+    if conversation_context:
+        user_parts.append(f"RECENT CONVERSATION:\n{conversation_context[:2000]}")
+
+    user_parts.append(f"---\n\nQUESTION: {query}")
+    user_parts.append("\nAnswer based ONLY on the context above.")
+
+    return {
+        "system": system,
+        "user": "\n\n".join(user_parts),
+    }
+
+
+# ---------------------------------------------------------------------------
+# Quality Metrics
+# ---------------------------------------------------------------------------
+
+def assess_context_faithfulness(
+    answer: str,
+    passages: List[Dict[str, Any]],
+) -> Dict[str, Any]:
+    """Assess how faithfully an answer uses the provided context.
+
+    Heuristic analysis (no LLM call):
+    - Citation count: how many [Passage N] references
+    - Grounding ratio: answer terms present in context
+    - "I don't know" detection
+    """
+    if not answer:
+        return {"faithful": False, "reason": "empty_answer"}
+
+    answer_lower = answer.lower()
+
+    # Check for "I don't know" escape hatch
+    if "don't know" in answer_lower or "does not contain" in answer_lower:
+        return {"faithful": True, "reason": "honest_unknown", "citations": 0}
+
+    # Count citations
+    import re
+    citations = re.findall(r'\[Passage \d+\]', answer)
+    citation_count = len(citations)
+
+    # Grounding ratio: how many answer words appear in context
+    context_text = " ".join(
+        (p.get("content") or p.get("text") or p.get("snippet") or "").lower()
+        for p in passages
+    )
+    answer_words = set(answer_lower.split())
+    context_words = set(context_text.split())
+    overlap = len(answer_words & context_words)
+    grounding_ratio = overlap / len(answer_words) if answer_words else 0
+
+    return {
+        "faithful": grounding_ratio > 0.3 or citation_count > 0,
+        "citations": citation_count,
+        "grounding_ratio": round(grounding_ratio, 3),
+        "reason": "grounded" if grounding_ratio > 0.3 else "weak_grounding",
+    }

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_approval_tiers.py

@@ -0,0 +1,122 @@
+"""
+Tests for approval tier system
+
+Issue: #670
+"""
+
+import unittest
+from tools.approval_tiers import (
+    ApprovalTier,
+    detect_tier,
+    requires_human_approval,
+    requires_llm_approval,
+    get_timeout,
+    should_auto_approve,
+    create_approval_request,
+    is_crisis_bypass,
+    TIER_INFO,
+)
+
+
+class TestApprovalTier(unittest.TestCase):
+    
+    def test_tier_values(self):
+        self.assertEqual(ApprovalTier.SAFE, 0)
+        self.assertEqual(ApprovalTier.LOW, 1)
+        self.assertEqual(ApprovalTier.MEDIUM, 2)
+        self.assertEqual(ApprovalTier.HIGH, 3)
+        self.assertEqual(ApprovalTier.CRITICAL, 4)
+
+
+class TestTierDetection(unittest.TestCase):
+    
+    def test_safe_actions(self):
+        self.assertEqual(detect_tier("read_file"), ApprovalTier.SAFE)
+        self.assertEqual(detect_tier("web_search"), ApprovalTier.SAFE)
+        self.assertEqual(detect_tier("session_search"), ApprovalTier.SAFE)
+    
+    def test_low_actions(self):
+        self.assertEqual(detect_tier("write_file"), ApprovalTier.LOW)
+        self.assertEqual(detect_tier("terminal"), ApprovalTier.LOW)
+        self.assertEqual(detect_tier("execute_code"), ApprovalTier.LOW)
+    
+    def test_medium_actions(self):
+        self.assertEqual(detect_tier("send_message"), ApprovalTier.MEDIUM)
+        self.assertEqual(detect_tier("git_push"), ApprovalTier.MEDIUM)
+    
+    def test_high_actions(self):
+        self.assertEqual(detect_tier("config_change"), ApprovalTier.HIGH)
+        self.assertEqual(detect_tier("key_rotation"), ApprovalTier.HIGH)
+    
+    def test_critical_actions(self):
+        self.assertEqual(detect_tier("kill_process"), ApprovalTier.CRITICAL)
+        self.assertEqual(detect_tier("shutdown"), ApprovalTier.CRITICAL)
+    
+    def test_pattern_detection(self):
+        tier = detect_tier("unknown", "rm -rf /")
+        self.assertEqual(tier, ApprovalTier.CRITICAL)
+        
+        tier = detect_tier("unknown", "sudo apt install")
+        self.assertEqual(tier, ApprovalTier.MEDIUM)
+
+
+class TestTierInfo(unittest.TestCase):
+    
+    def test_safe_no_approval(self):
+        self.assertFalse(requires_human_approval(ApprovalTier.SAFE))
+        self.assertFalse(requires_llm_approval(ApprovalTier.SAFE))
+        self.assertIsNone(get_timeout(ApprovalTier.SAFE))
+    
+    def test_medium_requires_both(self):
+        self.assertTrue(requires_human_approval(ApprovalTier.MEDIUM))
+        self.assertTrue(requires_llm_approval(ApprovalTier.MEDIUM))
+        self.assertEqual(get_timeout(ApprovalTier.MEDIUM), 60)
+    
+    def test_critical_fast_timeout(self):
+        self.assertEqual(get_timeout(ApprovalTier.CRITICAL), 10)
+
+
+class TestAutoApprove(unittest.TestCase):
+    
+    def test_safe_auto_approves(self):
+        self.assertTrue(should_auto_approve("read_file"))
+        self.assertTrue(should_auto_approve("web_search"))
+    
+    def test_write_doesnt_auto_approve(self):
+        self.assertFalse(should_auto_approve("write_file"))
+
+
+class TestApprovalRequest(unittest.TestCase):
+    
+    def test_create_request(self):
+        req = create_approval_request(
+            "send_message",
+            "Hello world",
+            "User requested",
+            "session_123"
+        )
+        self.assertEqual(req.tier, ApprovalTier.MEDIUM)
+        self.assertEqual(req.timeout_seconds, 60)
+    
+    def test_to_dict(self):
+        req = create_approval_request("read_file", "cat file.txt", "test", "s1")
+        d = req.to_dict()
+        self.assertEqual(d["tier"], 0)
+        self.assertEqual(d["tier_name"], "Safe")
+
+
+class TestCrisisBypass(unittest.TestCase):
+    
+    def test_send_message_bypass(self):
+        self.assertTrue(is_crisis_bypass("send_message"))
+    
+    def test_crisis_context_bypass(self):
+        self.assertTrue(is_crisis_bypass("unknown", "call 988 lifeline"))
+        self.assertTrue(is_crisis_bypass("unknown", "crisis resources"))
+    
+    def test_normal_no_bypass(self):
+        self.assertFalse(is_crisis_bypass("read_file"))
+
+
+if __name__ == "__main__":
+    unittest.main()

tests/test_context_faithful_prompting.py

@@ -0,0 +1,133 @@
+"""Tests for Context-Faithful Prompting — issue #667."""
+
+import pytest
+from agent.context_faithful import (
+    build_context_faithful_prompt,
+    build_summarization_prompt,
+    build_answer_prompt,
+    assess_context_faithfulness,
+    CONTEXT_FAITHFUL_INSTRUCTION,
+    CITATION_INSTRUCTION,
+    CONFIDENCE_INSTRUCTION,
+)
+
+
+class TestBuildContextFaithfulPrompt:
+    def test_returns_system_and_user(self):
+        passages = [{"content": "Paris is the capital of France.", "session_id": "s1"}]
+        result = build_context_faithful_prompt(passages, "What is the capital of France?")
+        assert "system" in result
+        assert "user" in result
+
+    def test_system_has_use_context_instruction(self):
+        passages = [{"content": "test content", "session_id": "s1"}]
+        result = build_context_faithful_prompt(passages, "test query")
+        assert "provided context" in result["system"].lower() or "context" in result["system"].lower()
+
+    def test_system_has_dont_know_escape(self):
+        passages = [{"content": "test", "session_id": "s1"}]
+        result = build_context_faithful_prompt(passages, "q")
+        assert "don't know" in result["system"].lower() or "I don't know" in result["system"]
+
+    def test_user_has_context_before_question(self):
+        passages = [{"content": "Test content here.", "session_id": "s1"}]
+        result = build_context_faithful_prompt(passages, "What is this?")
+        # Context should appear before the question
+        context_pos = result["user"].find("CONTEXT")
+        question_pos = result["user"].find("QUESTION")
+        assert context_pos < question_pos
+
+    def test_passages_are_numbered(self):
+        passages = [
+            {"content": "First passage.", "session_id": "s1"},
+            {"content": "Second passage.", "session_id": "s2"},
+        ]
+        result = build_context_faithful_prompt(passages, "q")
+        assert "Passage 1" in result["user"]
+        assert "Passage 2" in result["user"]
+
+    def test_citation_instruction_included_by_default(self):
+        passages = [{"content": "test", "session_id": "s1"}]
+        result = build_context_faithful_prompt(passages, "q")
+        assert "cite" in result["system"].lower() or "[Passage" in result["system"]
+
+    def test_confidence_calibration_included_by_default(self):
+        passages = [{"content": "test", "session_id": "s1"}]
+        result = build_context_faithful_prompt(passages, "q")
+        assert "confidence" in result["system"].lower() or "1-5" in result["system"]
+
+    def test_can_disable_citation(self):
+        passages = [{"content": "test", "session_id": "s1"}]
+        result = build_context_faithful_prompt(passages, "q", require_citation=False)
+        # Should not have citation instruction
+        assert "cite" not in result["system"].lower() or "citation" not in result["system"].lower()
+
+    def test_empty_passages_handled(self):
+        result = build_context_faithful_prompt([], "test query")
+        assert "system" in result
+        assert "user" in result
+
+
+class TestBuildSummarizationPrompt:
+    def test_includes_transcript(self):
+        prompts = build_summarization_prompt(
+            "User: Hello\nAssistant: Hi",
+            "greeting",
+            {"source": "cli", "started_at": "2024-01-01"},
+        )
+        assert "Hello" in prompts["user"]
+        assert "greeting" in prompts["user"]
+
+    def test_has_context_faithful_instruction(self):
+        prompts = build_summarization_prompt("text", "q", {})
+        assert "provided context" in prompts["system"].lower() or "context" in prompts["system"].lower()
+
+
+class TestBuildAnswerPrompt:
+    def test_returns_prompts(self):
+        passages = [{"content": "Answer is 42.", "session_id": "s1"}]
+        result = build_answer_prompt(passages, "What is the answer?")
+        assert "system" in result
+        assert "user" in result
+        assert "42" in result["user"]
+
+    def test_includes_conversation_context(self):
+        passages = [{"content": "info", "session_id": "s1"}]
+        result = build_answer_prompt(passages, "q", conversation_context="Previous message")
+        assert "Previous message" in result["user"]
+
+
+class TestAssessContextFaithfulness:
+    def test_empty_answer_not_faithful(self):
+        result = assess_context_faithfulness("", [])
+        assert result["faithful"] is False
+
+    def test_honest_unknown_is_faithful(self):
+        result = assess_context_faithfulness(
+            "I don't know based on the provided context.",
+            [{"content": "unrelated", "session_id": "s1"}],
+        )
+        assert result["faithful"] is True
+
+    def test_cited_answer_is_faithful(self):
+        result = assess_context_faithfulness(
+            "The capital is Paris [Passage 1].",
+            [{"content": "Paris is the capital.", "session_id": "s1"}],
+        )
+        assert result["faithful"] is True
+        assert result["citations"] >= 1
+
+    def test_grounded_answer_is_faithful(self):
+        result = assess_context_faithfulness(
+            "The system uses SQLite for storage with FTS5 indexing.",
+            [{"content": "The system uses SQLite for persistent storage with FTS5 indexing.", "session_id": "s1"}],
+        )
+        assert result["faithful"] is True
+        assert result["grounding_ratio"] > 0.3
+
+    def test_ungrounded_answer_not_faithful(self):
+        result = assess_context_faithfulness(
+            "The system uses PostgreSQL with MongoDB sharding.",
+            [{"content": "SQLite storage with FTS5.", "session_id": "s1"}],
+        )
+        assert result["grounding_ratio"] < 0.3

tests/test_error_classifier.py

@@ -0,0 +1,55 @@
+"""
+Tests for error classification (#752).
+"""
+
+import pytest
+from tools.error_classifier import classify_error, ErrorCategory, ErrorClassification
+
+
+class TestErrorClassification:
+    def test_timeout_is_retryable(self):
+        err = Exception("Connection timed out")
+        result = classify_error(err)
+        assert result.category == ErrorCategory.RETRYABLE
+        assert result.should_retry is True
+    
+    def test_429_is_retryable(self):
+        err = Exception("Rate limit exceeded")
+        result = classify_error(err, response_code=429)
+        assert result.category == ErrorCategory.RETRYABLE
+        assert result.should_retry is True
+    
+    def test_404_is_permanent(self):
+        err = Exception("Not found")
+        result = classify_error(err, response_code=404)
+        assert result.category == ErrorCategory.PERMANENT
+        assert result.should_retry is False
+    
+    def test_403_is_permanent(self):
+        err = Exception("Forbidden")
+        result = classify_error(err, response_code=403)
+        assert result.category == ErrorCategory.PERMANENT
+        assert result.should_retry is False
+    
+    def test_500_is_retryable(self):
+        err = Exception("Internal server error")
+        result = classify_error(err, response_code=500)
+        assert result.category == ErrorCategory.RETRYABLE
+        assert result.should_retry is True
+    
+    def test_schema_error_is_permanent(self):
+        err = Exception("Schema validation failed")
+        result = classify_error(err)
+        assert result.category == ErrorCategory.PERMANENT
+        assert result.should_retry is False
+    
+    def test_unknown_is_retryable_with_caution(self):
+        err = Exception("Some unknown error")
+        result = classify_error(err)
+        assert result.category == ErrorCategory.UNKNOWN
+        assert result.should_retry is True
+        assert result.max_retries == 1
+
+
+if __name__ == "__main__":
+    pytest.main([__file__])

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/approval_tiers.py

@@ -0,0 +1,261 @@
+"""
+Approval Tier System — Graduated safety based on risk level
+
+Extends approval.py with 5-tier system for command approval.
+
+| Tier | Action          | Human | LLM | Timeout |
+|------|-----------------|-------|-----|---------|
+| 0    | Read, search    | No    | No  | N/A     |
+| 1    | Write, scripts  | No    | Yes | N/A     |
+| 2    | Messages, API   | Yes   | Yes | 60s     |
+| 3    | Crypto, config  | Yes   | Yes | 30s     |
+| 4    | Crisis          | Yes   | Yes | 10s     |
+
+Issue: #670
+"""
+
+import re
+from dataclasses import dataclass
+from enum import IntEnum
+from typing import Any, Dict, List, Optional, Tuple
+
+
+class ApprovalTier(IntEnum):
+    """Approval tiers based on risk level."""
+    SAFE = 0      # Read, search — no approval needed
+    LOW = 1       # Write, scripts — LLM approval
+    MEDIUM = 2    # Messages, API — human + LLM, 60s timeout
+    HIGH = 3      # Crypto, config — human + LLM, 30s timeout
+    CRITICAL = 4  # Crisis — human + LLM, 10s timeout
+
+
+# Tier metadata
+TIER_INFO = {
+    ApprovalTier.SAFE: {
+        "name": "Safe",
+        "human_required": False,
+        "llm_required": False,
+        "timeout_seconds": None,
+        "description": "Read-only operations, no approval needed"
+    },
+    ApprovalTier.LOW: {
+        "name": "Low",
+        "human_required": False,
+        "llm_required": True,
+        "timeout_seconds": None,
+        "description": "Write operations, LLM approval sufficient"
+    },
+    ApprovalTier.MEDIUM: {
+        "name": "Medium",
+        "human_required": True,
+        "llm_required": True,
+        "timeout_seconds": 60,
+        "description": "External actions, human confirmation required"
+    },
+    ApprovalTier.HIGH: {
+        "name": "High",
+        "human_required": True,
+        "llm_required": True,
+        "timeout_seconds": 30,
+        "description": "Sensitive operations, quick timeout"
+    },
+    ApprovalTier.CRITICAL: {
+        "name": "Critical",
+        "human_required": True,
+        "llm_required": True,
+        "timeout_seconds": 10,
+        "description": "Crisis or dangerous operations, fastest timeout"
+    },
+}
+
+
+# Action-to-tier mapping
+ACTION_TIERS: Dict[str, ApprovalTier] = {
+    # Tier 0: Safe (read-only)
+    "read_file": ApprovalTier.SAFE,
+    "search_files": ApprovalTier.SAFE,
+    "web_search": ApprovalTier.SAFE,
+    "session_search": ApprovalTier.SAFE,
+    "list_files": ApprovalTier.SAFE,
+    "get_file_content": ApprovalTier.SAFE,
+    "memory_search": ApprovalTier.SAFE,
+    "skills_list": ApprovalTier.SAFE,
+    "skills_search": ApprovalTier.SAFE,
+    
+    # Tier 1: Low (write operations)
+    "write_file": ApprovalTier.LOW,
+    "create_file": ApprovalTier.LOW,
+    "patch_file": ApprovalTier.LOW,
+    "delete_file": ApprovalTier.LOW,
+    "execute_code": ApprovalTier.LOW,
+    "terminal": ApprovalTier.LOW,
+    "run_script": ApprovalTier.LOW,
+    "skill_install": ApprovalTier.LOW,
+    
+    # Tier 2: Medium (external actions)
+    "send_message": ApprovalTier.MEDIUM,
+    "web_fetch": ApprovalTier.MEDIUM,
+    "browser_navigate": ApprovalTier.MEDIUM,
+    "api_call": ApprovalTier.MEDIUM,
+    "gitea_create_issue": ApprovalTier.MEDIUM,
+    "gitea_create_pr": ApprovalTier.MEDIUM,
+    "git_push": ApprovalTier.MEDIUM,
+    "deploy": ApprovalTier.MEDIUM,
+    
+    # Tier 3: High (sensitive operations)
+    "config_change": ApprovalTier.HIGH,
+    "env_change": ApprovalTier.HIGH,
+    "key_rotation": ApprovalTier.HIGH,
+    "access_grant": ApprovalTier.HIGH,
+    "permission_change": ApprovalTier.HIGH,
+    "backup_restore": ApprovalTier.HIGH,
+    
+    # Tier 4: Critical (crisis/dangerous)
+    "kill_process": ApprovalTier.CRITICAL,
+    "rm_rf": ApprovalTier.CRITICAL,
+    "format_disk": ApprovalTier.CRITICAL,
+    "shutdown": ApprovalTier.CRITICAL,
+    "crisis_override": ApprovalTier.CRITICAL,
+}
+
+
+# Dangerous command patterns (from existing approval.py)
+_DANGEROUS_PATTERNS = [
+    (r"rm\s+-rf\s+/", ApprovalTier.CRITICAL),
+    (r"mkfs\.", ApprovalTier.CRITICAL),
+    (r"dd\s+if=.*of=/dev/", ApprovalTier.CRITICAL),
+    (r"shutdown|reboot|halt", ApprovalTier.CRITICAL),
+    (r"chmod\s+777", ApprovalTier.HIGH),
+    (r"curl.*\|\s*bash", ApprovalTier.HIGH),
+    (r"wget.*\|\s*sh", ApprovalTier.HIGH),
+    (r"eval\s*\(", ApprovalTier.HIGH),
+    (r"sudo\s+", ApprovalTier.MEDIUM),
+    (r"git\s+push.*--force", ApprovalTier.HIGH),
+    (r"docker\s+rm.*-f", ApprovalTier.MEDIUM),
+    (r"kubectl\s+delete", ApprovalTier.HIGH),
+]
+
+
+@dataclass
+class ApprovalRequest:
+    """A request for approval."""
+    action: str
+    tier: ApprovalTier
+    command: str
+    reason: str
+    session_key: str
+    timeout_seconds: Optional[int] = None
+    
+    def to_dict(self) -> Dict[str, Any]:
+        return {
+            "action": self.action,
+            "tier": self.tier.value,
+            "tier_name": TIER_INFO[self.tier]["name"],
+            "command": self.command,
+            "reason": self.reason,
+            "session_key": self.session_key,
+            "timeout": self.timeout_seconds,
+            "human_required": TIER_INFO[self.tier]["human_required"],
+            "llm_required": TIER_INFO[self.tier]["llm_required"],
+        }
+
+
+def detect_tier(action: str, command: str = "") -> ApprovalTier:
+    """
+    Detect the approval tier for an action.
+    
+    Checks action name first, then falls back to pattern matching.
+    """
+    # Direct action mapping
+    if action in ACTION_TIERS:
+        return ACTION_TIERS[action]
+    
+    # Pattern matching on command
+    if command:
+        for pattern, tier in _DANGEROUS_PATTERNS:
+            if re.search(pattern, command, re.IGNORECASE):
+                return tier
+    
+    # Default to LOW for unknown actions
+    return ApprovalTier.LOW
+
+
+def requires_human_approval(tier: ApprovalTier) -> bool:
+    """Check if tier requires human approval."""
+    return TIER_INFO[tier]["human_required"]
+
+
+def requires_llm_approval(tier: ApprovalTier) -> bool:
+    """Check if tier requires LLM approval."""
+    return TIER_INFO[tier]["llm_required"]
+
+
+def get_timeout(tier: ApprovalTier) -> Optional[int]:
+    """Get timeout in seconds for a tier."""
+    return TIER_INFO[tier]["timeout_seconds"]
+
+
+def should_auto_approve(action: str, command: str = "") -> bool:
+    """Check if action should be auto-approved (tier 0)."""
+    tier = detect_tier(action, command)
+    return tier == ApprovalTier.SAFE
+
+
+def format_approval_prompt(request: ApprovalRequest) -> str:
+    """Format an approval request for display."""
+    info = TIER_INFO[request.tier]
+    lines = []
+    lines.append(f"⚠️ Approval Required (Tier {request.tier.value}: {info['name']})")
+    lines.append(f"")
+    lines.append(f"Action: {request.action}")
+    lines.append(f"Command: {request.command[:100]}{'...' if len(request.command) > 100 else ''}")
+    lines.append(f"Reason: {request.reason}")
+    lines.append(f"")
+    
+    if info["human_required"]:
+        lines.append(f"👤 Human approval required")
+    if info["llm_required"]:
+        lines.append(f"🤖 LLM approval required")
+    if info["timeout_seconds"]:
+        lines.append(f"⏱️ Timeout: {info['timeout_seconds']}s")
+    
+    return "\n".join(lines)
+
+
+def create_approval_request(
+    action: str,
+    command: str,
+    reason: str,
+    session_key: str
+) -> ApprovalRequest:
+    """Create an approval request for an action."""
+    tier = detect_tier(action, command)
+    timeout = get_timeout(tier)
+    
+    return ApprovalRequest(
+        action=action,
+        tier=tier,
+        command=command,
+        reason=reason,
+        session_key=session_key,
+        timeout_seconds=timeout
+    )
+
+
+# Crisis bypass rules
+CRISIS_BYPASS_ACTIONS = frozenset([
+    "send_message",  # Always allow sending crisis resources
+    "check_crisis",
+    "notify_crisis",
+])
+
+
+def is_crisis_bypass(action: str, context: str = "") -> bool:
+    """Check if action should bypass approval during crisis."""
+    if action in CRISIS_BYPASS_ACTIONS:
+        return True
+    
+    # Check if context indicates crisis
+    crisis_indicators = ["988", "crisis", "suicide", "self-harm", "lifeline"]
+    context_lower = context.lower()
+    return any(indicator in context_lower for indicator in crisis_indicators)

tools/error_classifier.py

@@ -0,0 +1,233 @@
+"""
+Tool Error Classification — Retryable vs Permanent.
+
+Classifies tool errors so the agent retries transient errors
+but gives up on permanent ones immediately.
+"""
+
+import logging
+import re
+import time
+from dataclasses import dataclass
+from enum import Enum
+from typing import Optional, Dict, Any
+
+logger = logging.getLogger(__name__)
+
+
+class ErrorCategory(Enum):
+    """Error category classification."""
+    RETRYABLE = "retryable"
+    PERMANENT = "permanent"
+    UNKNOWN = "unknown"
+
+
+@dataclass
+class ErrorClassification:
+    """Result of error classification."""
+    category: ErrorCategory
+    reason: str
+    should_retry: bool
+    max_retries: int
+    backoff_seconds: float
+    error_code: Optional[int] = None
+    error_type: Optional[str] = None
+
+
+# Retryable error patterns
+_RETRYABLE_PATTERNS = [
+    # HTTP status codes
+    (r"\b429\b", "rate limit", 3, 5.0),
+    (r"\b500\b", "server error", 3, 2.0),
+    (r"\b502\b", "bad gateway", 3, 2.0),
+    (r"\b503\b", "service unavailable", 3, 5.0),
+    (r"\b504\b", "gateway timeout", 3, 5.0),
+    
+    # Timeout patterns
+    (r"timeout", "timeout", 3, 2.0),
+    (r"timed out", "timeout", 3, 2.0),
+    (r"TimeoutExpired", "timeout", 3, 2.0),
+    
+    # Connection errors
+    (r"connection refused", "connection refused", 2, 5.0),
+    (r"connection reset", "connection reset", 2, 2.0),
+    (r"network unreachable", "network unreachable", 2, 10.0),
+    (r"DNS", "DNS error", 2, 5.0),
+    
+    # Transient errors
+    (r"temporary", "temporary error", 2, 2.0),
+    (r"transient", "transient error", 2, 2.0),
+    (r"retry", "retryable", 2, 2.0),
+]
+
+# Permanent error patterns
+_PERMANENT_PATTERNS = [
+    # HTTP status codes
+    (r"\b400\b", "bad request", "Invalid request parameters"),
+    (r"\b401\b", "unauthorized", "Authentication failed"),
+    (r"\b403\b", "forbidden", "Access denied"),
+    (r"\b404\b", "not found", "Resource not found"),
+    (r"\b405\b", "method not allowed", "HTTP method not supported"),
+    (r"\b409\b", "conflict", "Resource conflict"),
+    (r"\b422\b", "unprocessable", "Validation error"),
+    
+    # Schema/validation errors
+    (r"schema", "schema error", "Invalid data schema"),
+    (r"validation", "validation error", "Input validation failed"),
+    (r"invalid.*json", "JSON error", "Invalid JSON"),
+    (r"JSONDecodeError", "JSON error", "JSON parsing failed"),
+    
+    # Authentication
+    (r"api.?key", "API key error", "Invalid or missing API key"),
+    (r"token.*expir", "token expired", "Authentication token expired"),
+    (r"permission", "permission error", "Insufficient permissions"),
+    
+    # Not found patterns
+    (r"not found", "not found", "Resource does not exist"),
+    (r"does not exist", "not found", "Resource does not exist"),
+    (r"no such file", "file not found", "File does not exist"),
+    
+    # Quota/billing
+    (r"quota", "quota exceeded", "Usage quota exceeded"),
+    (r"billing", "billing error", "Billing issue"),
+    (r"insufficient.*funds", "billing error", "Insufficient funds"),
+]
+
+
+def classify_error(error: Exception, response_code: Optional[int] = None) -> ErrorClassification:
+    """
+    Classify an error as retryable or permanent.
+    
+    Args:
+        error: The exception that occurred
+        response_code: HTTP response code if available
+        
+    Returns:
+        ErrorClassification with retry guidance
+    """
+    error_str = str(error).lower()
+    error_type = type(error).__name__
+    
+    # Check response code first
+    if response_code:
+        if response_code in (429, 500, 502, 503, 504):
+            return ErrorClassification(
+                category=ErrorCategory.RETRYABLE,
+                reason=f"HTTP {response_code} - transient server error",
+                should_retry=True,
+                max_retries=3,
+                backoff_seconds=5.0 if response_code == 429 else 2.0,
+                error_code=response_code,
+                error_type=error_type,
+            )
+        elif response_code in (400, 401, 403, 404, 405, 409, 422):
+            return ErrorClassification(
+                category=ErrorCategory.PERMANENT,
+                reason=f"HTTP {response_code} - client error",
+                should_retry=False,
+                max_retries=0,
+                backoff_seconds=0,
+                error_code=response_code,
+                error_type=error_type,
+            )
+    
+    # Check retryable patterns
+    for pattern, reason, max_retries, backoff in _RETRYABLE_PATTERNS:
+        if re.search(pattern, error_str, re.IGNORECASE):
+            return ErrorClassification(
+                category=ErrorCategory.RETRYABLE,
+                reason=reason,
+                should_retry=True,
+                max_retries=max_retries,
+                backoff_seconds=backoff,
+                error_type=error_type,
+            )
+    
+    # Check permanent patterns
+    for pattern, error_code, reason in _PERMANENT_PATTERNS:
+        if re.search(pattern, error_str, re.IGNORECASE):
+            return ErrorClassification(
+                category=ErrorCategory.PERMANENT,
+                reason=reason,
+                should_retry=False,
+                max_retries=0,
+                backoff_seconds=0,
+                error_type=error_type,
+            )
+    
+    # Default: unknown, treat as retryable with caution
+    return ErrorClassification(
+        category=ErrorCategory.UNKNOWN,
+        reason=f"Unknown error type: {error_type}",
+        should_retry=True,
+        max_retries=1,
+        backoff_seconds=1.0,
+        error_type=error_type,
+    )
+
+
+def execute_with_retry(
+    func,
+    *args,
+    max_retries: int = 3,
+    backoff_base: float = 1.0,
+    **kwargs,
+) -> Any:
+    """
+    Execute a function with automatic retry on retryable errors.
+    
+    Args:
+        func: Function to execute
+        *args: Function arguments
+        max_retries: Maximum retry attempts
+        backoff_base: Base backoff time in seconds
+        **kwargs: Function keyword arguments
+        
+    Returns:
+        Function result
+        
+    Raises:
+        Exception: If permanent error or max retries exceeded
+    """
+    last_error = None
+    
+    for attempt in range(max_retries + 1):
+        try:
+            return func(*args, **kwargs)
+        except Exception as e:
+            last_error = e
+            
+            # Classify the error
+            classification = classify_error(e)
+            
+            logger.info(
+                "Attempt %d/%d failed: %s (%s, retryable: %s)",
+                attempt + 1, max_retries + 1,
+                classification.reason,
+                classification.category.value,
+                classification.should_retry,
+            )
+            
+            # If permanent error, fail immediately
+            if not classification.should_retry:
+                logger.error("Permanent error: %s", classification.reason)
+                raise
+            
+            # If this was the last attempt, raise
+            if attempt >= max_retries:
+                logger.error("Max retries (%d) exceeded", max_retries)
+                raise
+            
+            # Calculate backoff with exponential increase
+            backoff = backoff_base * (2 ** attempt)
+            logger.info("Retrying in %.1fs...", backoff)
+            time.sleep(backoff)
+    
+    # Should not reach here, but just in case
+    raise last_error
+
+
+def format_error_report(classification: ErrorClassification) -> str:
+    """Format error classification as a report string."""
+    icon = "🔄" if classification.should_retry else "❌"
+    return f"{icon} {classification.category.value}: {classification.reason}"

tools/session_search_tool.py

@@ -176,28 +176,11 @@ async def _summarize_session(
     conversation_text: str, query: str, session_meta: Dict[str, Any]
 ) -> Optional[str]:
     """Summarize a single session conversation focused on the search query."""
-    system_prompt = (
-        "You are reviewing a past conversation transcript to help recall what happened. "
-        "Summarize the conversation with a focus on the search topic. Include:\n"
-        "1. What the user asked about or wanted to accomplish\n"
-        "2. What actions were taken and what the outcomes were\n"
-        "3. Key decisions, solutions found, or conclusions reached\n"
-        "4. Any specific commands, files, URLs, or technical details that were important\n"
-        "5. Anything left unresolved or notable\n\n"
-        "Be thorough but concise. Preserve specific details (commands, paths, error messages) "
-        "that would be useful to recall. Write in past tense as a factual recap."
-    )
-
-    source = session_meta.get("source", "unknown")
-    started = _format_timestamp(session_meta.get("started_at"))
-
-    user_prompt = (
-        f"Search topic: {query}\n"
-        f"Session source: {source}\n"
-        f"Session date: {started}\n\n"
-        f"CONVERSATION TRANSCRIPT:\n{conversation_text}\n\n"
-        f"Summarize this conversation with focus on: {query}"
-    )
+    # Context-faithful prompting: force LLM to ground in transcript
+    from agent.context_faithful import build_summarization_prompt
+    prompts = build_summarization_prompt(conversation_text, query, session_meta)
+    system_prompt = prompts["system"]
+    user_prompt = prompts["user"]
 
     max_retries = 3
     for attempt in range(max_retries):
@@ -394,6 +377,23 @@ 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():