"""Honcho-based session management for conversation history."""

from __future__ import annotations

import hashlib
import queue
import re
import logging
import threading
from dataclasses import dataclass, field
from datetime import datetime
from typing import Any, TYPE_CHECKING

from plugins.memory.honcho.client import get_honcho_client

if TYPE_CHECKING:
    from honcho import Honcho

logger = logging.getLogger(__name__)

# Sentinel to signal the async writer thread to shut down
_ASYNC_SHUTDOWN = object()
_PEER_ID_HASH_LEN = 8
_PEER_ID_HASH_ESCALATION_LENGTHS = (_PEER_ID_HASH_LEN, 12, 16, 24, 32, 64)


@dataclass
class HonchoSession:
    """
    A conversation session backed by Honcho.

    Provides a local message cache that syncs to Honcho's
    AI-native memory system for user modeling.
    """

    key: str  # channel:chat_id
    user_peer_id: str  # Honcho peer ID for the user
    assistant_peer_id: str  # Honcho peer ID for the assistant
    honcho_session_id: str  # Honcho session ID
    messages: list[dict[str, Any]] = field(default_factory=list)
    created_at: datetime = field(default_factory=datetime.now)
    updated_at: datetime = field(default_factory=datetime.now)
    metadata: dict[str, Any] = field(default_factory=dict)

    def add_message(self, role: str, content: str, **kwargs: Any) -> None:
        """Add a message to the local cache."""
        msg = {
            "role": role,
            "content": content,
            "timestamp": datetime.now().isoformat(),
            **kwargs,
        }
        self.messages.append(msg)
        self.updated_at = datetime.now()

    def get_history(self, max_messages: int = 50) -> list[dict[str, Any]]:
        """Get message history for LLM context."""
        recent = (
            self.messages[-max_messages:]
            if len(self.messages) > max_messages
            else self.messages
        )
        return [{"role": m["role"], "content": m["content"]} for m in recent]

    def clear(self) -> None:
        """Clear all messages in the session."""
        self.messages = []
        self.updated_at = datetime.now()


class HonchoSessionManager:
    """
    Manages conversation sessions using Honcho.

    Runs alongside hermes' existing SQLite state and file-based memory,
    adding persistent cross-session user modeling via Honcho's AI-native memory.
    """

    def __init__(
        self,
        honcho: Honcho | None = None,
        context_tokens: int | None = None,
        config: Any | None = None,
        runtime_user_peer_name: str | None = None,
        runtime_user_peer_name_alt: str | None = None,
    ):
        """
        Initialize the session manager.

        Args:
            honcho: Optional Honcho client. If not provided, uses the singleton.
            context_tokens: Max tokens for context() calls (None = Honcho default).
            config: HonchoClientConfig from global config (provides peer_name, ai_peer,
                    write_frequency, observation, etc.).
            runtime_user_peer_name: Gateway user identity for per-user memory scoping.
            runtime_user_peer_name_alt: Optional stable alternate gateway identity.
        """
        self._honcho = honcho
        self._context_tokens = context_tokens
        self._config = config
        self._runtime_user_peer_name = runtime_user_peer_name
        self._runtime_user_peer_name_alt = runtime_user_peer_name_alt
        self._cache: dict[str, HonchoSession] = {}
        self._cache_lock = threading.RLock()
        self._peers_cache: dict[str, Any] = {}
        self._sessions_cache: dict[str, Any] = {}

        # Write frequency state
        write_frequency = (config.write_frequency if config else "async")
        self._write_frequency = write_frequency
        self._turn_counter: int = 0

        # Prefetch cache: session_key → last context result (consumed once per turn).
        # Dialectic results are cached on the plugin side (HonchoMemoryProvider
        # ._prefetch_result) so session-start prewarm and turn-driven fires share
        # one source of truth; see __init__.py _do_session_init for the prewarm.
        self._context_cache: dict[str, dict] = {}
        self._prefetch_cache_lock = threading.Lock()
        self._dialectic_reasoning_level: str = (
            config.dialectic_reasoning_level if config else "low"
        )
        self._dialectic_dynamic: bool = (
            config.dialectic_dynamic if config else True
        )
        self._dialectic_max_chars: int = (
            config.dialectic_max_chars if config else 600
        )
        self._observation_mode: str = (
            config.observation_mode if config else "directional"
        )
        # Per-peer observation booleans (granular, from config)
        self._user_observe_me: bool = config.user_observe_me if config else True
        self._user_observe_others: bool = config.user_observe_others if config else True
        self._ai_observe_me: bool = config.ai_observe_me if config else True
        self._ai_observe_others: bool = config.ai_observe_others if config else True
        self._message_max_chars: int = (
            config.message_max_chars if config else 25000
        )
        self._dialectic_max_input_chars: int = (
            config.dialectic_max_input_chars if config else 10000
        )

        # Async write queue — started lazily on first enqueue
        self._async_queue: queue.Queue | None = None
        self._async_thread: threading.Thread | None = None
        if write_frequency == "async":
            self._async_queue = queue.Queue()
            self._async_thread = threading.Thread(
                target=self._async_writer_loop,
                name="honcho-async-writer",
                daemon=True,
            )
            self._async_thread.start()

    @property
    def honcho(self) -> Honcho:
        """Get the Honcho client, initializing if needed."""
        if self._honcho is None:
            self._honcho = get_honcho_client()
        return self._honcho

    def _get_or_create_peer(self, peer_id: str) -> Any:
        """
        Get or create a Honcho peer.

        Peers are lazy -- no API call until first use.
        Observation settings are controlled per-session via SessionPeerConfig.
        """
        with self._cache_lock:
            if peer_id in self._peers_cache:
                return self._peers_cache[peer_id]

        peer = self.honcho.peer(peer_id)
        with self._cache_lock:
            self._peers_cache[peer_id] = peer
        return peer

    def _get_or_create_honcho_session(
        self, session_id: str, user_peer: Any, assistant_peer: Any
    ) -> tuple[Any, list]:
        """
        Get or create a Honcho session with peers configured.

        Returns:
            Tuple of (honcho_session, existing_messages).
        """
        with self._cache_lock:
            if session_id in self._sessions_cache:
                logger.debug("Honcho session '%s' retrieved from cache", session_id)
                return self._sessions_cache[session_id], []

        session = self.honcho.session(session_id)

        # Configure per-peer observation from granular booleans.
        # These map 1:1 to Honcho's SessionPeerConfig toggles.
        try:
            from honcho.session import SessionPeerConfig
            user_config = SessionPeerConfig(
                observe_me=self._user_observe_me,
                observe_others=self._user_observe_others,
            )
            ai_config = SessionPeerConfig(
                observe_me=self._ai_observe_me,
                observe_others=self._ai_observe_others,
            )

            session.add_peers([(user_peer, user_config), (assistant_peer, ai_config)])

            # Sync back: server-side config (set via Honcho UI) wins over
            # local defaults. Read the effective config after add_peers.
            # Note: observation booleans are manager-scoped, not per-session.
            # Last session init wins. Fine for CLI; gateway should scope per-session.
            try:
                server_user = session.get_peer_configuration(user_peer)
                server_ai = session.get_peer_configuration(assistant_peer)
                if server_user.observe_me is not None:
                    self._user_observe_me = server_user.observe_me
                if server_user.observe_others is not None:
                    self._user_observe_others = server_user.observe_others
                if server_ai.observe_me is not None:
                    self._ai_observe_me = server_ai.observe_me
                if server_ai.observe_others is not None:
                    self._ai_observe_others = server_ai.observe_others
                logger.debug(
                    "Honcho observation synced from server: user(me=%s,others=%s) ai(me=%s,others=%s)",
                    self._user_observe_me, self._user_observe_others,
                    self._ai_observe_me, self._ai_observe_others,
                )
            except Exception as e:
                logger.debug("Honcho get_peer_configuration failed (using local config): %s", e)
        except Exception as e:
            logger.warning(
                "Honcho session '%s' add_peers failed (non-fatal): %s",
                session_id, e,
            )

        # Load existing messages via context() - single call for messages + metadata
        existing_messages = []
        try:
            ctx = session.context(summary=True, tokens=self._context_tokens)
            existing_messages = ctx.messages or []

            # Verify chronological ordering
            if existing_messages and len(existing_messages) > 1:
                timestamps = [m.created_at for m in existing_messages if m.created_at]
                if timestamps and timestamps != sorted(timestamps):
                    logger.warning(
                        "Honcho messages not chronologically ordered for session '%s', sorting",
                        session_id,
                    )
                    existing_messages = sorted(
                        existing_messages,
                        key=lambda m: m.created_at or datetime.min,
                    )

            if existing_messages:
                logger.info(
                    "Honcho session '%s' retrieved (%d existing messages)",
                    session_id, len(existing_messages),
                )
            else:
                logger.info("Honcho session '%s' created (new)", session_id)
        except Exception as e:
            logger.warning(
                "Honcho session '%s' loaded (failed to fetch context: %s)",
                session_id, e,
            )

        self._sessions_cache[session_id] = session
        return session, existing_messages

    def _sanitize_id(self, id_str: str) -> str:
        """Sanitize an ID to match Honcho's pattern: ^[a-zA-Z0-9_-]+"""
        return re.sub(r'[^a-zA-Z0-9_-]', '-', id_str)

    def _runtime_user_ids(self) -> list[str]:
        """Return runtime identity candidates in lookup order."""
        candidates: list[str] = []
        for value in (self._runtime_user_peer_name, self._runtime_user_peer_name_alt):
            if value is None:
                continue
            candidate = str(value).strip()
            if candidate and candidate not in candidates:
                candidates.append(candidate)
        return candidates

    def _session_key_fallback_peer_id(self, key: str) -> str:
        parts = key.split(":", 1)
        channel = parts[0] if len(parts) > 1 else "default"
        chat_id = parts[1] if len(parts) > 1 else key
        return self._sanitize_id(f"user-{channel}-{chat_id}")

    def _explicit_user_peer_ids(self) -> set[str]:
        """Return sanitized user peer IDs that came from explicit config."""
        if self._config is None:
            return set()

        explicit_ids: set[str] = set()
        peer_name = getattr(self._config, "peer_name", None)
        if peer_name:
            explicit_ids.add(self._sanitize_id(str(peer_name).strip()))

        aliases = getattr(self._config, "user_peer_aliases", {})
        if isinstance(aliases, dict):
            for alias in aliases.values():
                if isinstance(alias, str) and alias.strip():
                    explicit_ids.add(self._sanitize_id(alias.strip()))

        return explicit_ids

    def _generated_runtime_peer_id(self, prefix: str, runtime_id: str) -> str:
        """Return a stable peer ID for an unknown prefixed runtime user."""
        raw_peer_id = f"{prefix}{runtime_id}"
        sanitized_peer_id = self._sanitize_id(raw_peer_id)
        explicit_ids = self._explicit_user_peer_ids()
        if (
            sanitized_peer_id != raw_peer_id
            or sanitized_peer_id in explicit_ids
        ):
            digest = hashlib.sha256(raw_peer_id.encode("utf-8")).hexdigest()
            for hash_len in _PEER_ID_HASH_ESCALATION_LENGTHS:
                candidate = f"{sanitized_peer_id}-{digest[:hash_len]}"
                if candidate not in explicit_ids:
                    return candidate
            return f"{sanitized_peer_id}-{digest}"
        return sanitized_peer_id

    def _resolve_user_peer_id(self, key: str) -> str:
        """Resolve the Honcho user peer ID for this manager/session."""
        pin_peer_name = (
            self._config is not None
            and bool(getattr(self._config, "peer_name", None))
            and getattr(self._config, "pin_peer_name", False) is True
        )
        if pin_peer_name:
            return self._sanitize_id(self._config.peer_name)

        runtime_ids = self._runtime_user_ids()
        if runtime_ids:
            aliases = getattr(self._config, "user_peer_aliases", {}) if self._config else {}
            if not isinstance(aliases, dict):
                aliases = {}
            for runtime_id in runtime_ids:
                alias = aliases.get(runtime_id)
                if isinstance(alias, str) and alias.strip():
                    return self._sanitize_id(alias.strip())

            primary_runtime_id = runtime_ids[0]
            prefix = getattr(self._config, "runtime_peer_prefix", "") if self._config else ""
            prefix = prefix.strip() if isinstance(prefix, str) else ""
            if prefix:
                return self._generated_runtime_peer_id(prefix, primary_runtime_id)
            return self._sanitize_id(primary_runtime_id)

        if self._config and self._config.peer_name:
            return self._sanitize_id(self._config.peer_name)

        return self._session_key_fallback_peer_id(key)

    def get_or_create(self, key: str) -> HonchoSession:
        """
        Get an existing session or create a new one.

        Args:
            key: Session key (usually channel:chat_id).

        Returns:
            The session.
        """
        with self._cache_lock:
            if key in self._cache:
                logger.debug("Local session cache hit: %s", key)
                return self._cache[key]

        # Determine peer IDs — no lock needed (read-only, no shared state mutation).
        # Gateway sessions normally use the runtime user identity (the
        # platform-native ID: Telegram UID, Discord snowflake, Slack user,
        # etc.) so multi-user bots scope memory per user.  Config can alias
        # known runtime IDs or prefix unknown IDs.  For a single-user
        # deployment, ``pinPeerName`` still pins all runtime identities to
        # ``peerName`` (see #14984).
        user_peer_id = self._resolve_user_peer_id(key)

        assistant_peer_id = self._sanitize_id(
            self._config.ai_peer if self._config else "hermes-assistant"
        )

        # All expensive I/O outside the lock — Honcho's persistence is source of truth
        honcho_session_id = self._sanitize_id(key)
        user_peer = self._get_or_create_peer(user_peer_id)
        assistant_peer = self._get_or_create_peer(assistant_peer_id)
        honcho_session, existing_messages = self._get_or_create_honcho_session(
            honcho_session_id, user_peer, assistant_peer
        )

        local_messages = []
        for msg in existing_messages:
            role = "assistant" if msg.peer_id == assistant_peer_id else "user"
            local_messages.append({
                "role": role,
                "content": msg.content,
                "timestamp": msg.created_at.isoformat() if msg.created_at else "",
                "_synced": True,
            })

        session = HonchoSession(
            key=key,
            user_peer_id=user_peer_id,
            assistant_peer_id=assistant_peer_id,
            honcho_session_id=honcho_session_id,
            messages=local_messages,
        )

        # Write to cache under lock — only one writer wins
        with self._cache_lock:
            self._cache[key] = session
        return session

    def _flush_session(self, session: HonchoSession) -> bool:
        """Internal: write unsynced messages to Honcho synchronously."""
        if not session.messages:
            return True

        user_peer = self._get_or_create_peer(session.user_peer_id)
        assistant_peer = self._get_or_create_peer(session.assistant_peer_id)
        honcho_session = self._sessions_cache.get(session.honcho_session_id)

        if not honcho_session:
            honcho_session, _ = self._get_or_create_honcho_session(
                session.honcho_session_id, user_peer, assistant_peer
            )

        new_messages = [m for m in session.messages if not m.get("_synced")]
        if not new_messages:
            return True

        honcho_messages = []
        for msg in new_messages:
            peer = user_peer if msg["role"] == "user" else assistant_peer
            honcho_messages.append(peer.message(msg["content"]))

        try:
            honcho_session.add_messages(honcho_messages)
            for msg in new_messages:
                msg["_synced"] = True
            logger.debug("Synced %d messages to Honcho for %s", len(honcho_messages), session.key)
            with self._cache_lock:
                self._cache[session.key] = session
            return True
        except Exception as e:
            for msg in new_messages:
                msg["_synced"] = False
            logger.error("Failed to sync messages to Honcho: %s", e)
            with self._cache_lock:
                self._cache[session.key] = session
            return False

    def _async_writer_loop(self) -> None:
        """Background daemon thread: drains the async write queue."""
        while True:
            try:
                item = self._async_queue.get(timeout=5)
                if item is _ASYNC_SHUTDOWN:
                    break

                first_error: Exception | None = None
                try:
                    success = self._flush_session(item)
                except Exception as e:
                    success = False
                    first_error = e

                if success:
                    continue

                if first_error is not None:
                    logger.warning("Honcho async write failed, retrying once: %s", first_error)
                else:
                    logger.warning("Honcho async write failed, retrying once")

                import time as _time
                _time.sleep(2)

                try:
                    retry_success = self._flush_session(item)
                except Exception as e2:
                    logger.error("Honcho async write retry failed, dropping batch: %s", e2)
                    continue

                if not retry_success:
                    logger.error("Honcho async write retry failed, dropping batch")
            except queue.Empty:
                continue
            except Exception as e:
                logger.error("Honcho async writer error: %s", e)

    def save(self, session: HonchoSession) -> None:
        """Save messages to Honcho, respecting write_frequency.

        write_frequency modes:
          "async"   — enqueue for background thread (zero blocking, zero token cost)
          "turn"    — flush synchronously every turn
          "session" — defer until flush_session() is called explicitly
          N (int)   — flush every N turns
        """
        self._turn_counter += 1
        wf = self._write_frequency

        if wf == "async":
            if self._async_queue is not None:
                self._async_queue.put(session)
        elif wf == "turn":
            self._flush_session(session)
        elif wf == "session":
            # Accumulate; caller must call flush_all() at session end
            pass
        elif isinstance(wf, int) and wf > 0:
            if self._turn_counter % wf == 0:
                self._flush_session(session)

    def flush_all(self) -> None:
        """Flush all pending unsynced messages for all cached sessions.

        Called at session end for "session" write_frequency, or to force
        a sync before process exit regardless of mode.
        """
        with self._cache_lock:
            sessions = list(self._cache.values())
        for session in sessions:
            try:
                self._flush_session(session)
            except Exception as e:
                logger.error("Honcho flush_all error for %s: %s", session.key, e)

        # Drain async queue synchronously if it exists
        if self._async_queue is not None:
            while not self._async_queue.empty():
                try:
                    item = self._async_queue.get_nowait()
                    if item is not _ASYNC_SHUTDOWN:
                        self._flush_session(item)
                except queue.Empty:
                    break

    def shutdown(self) -> None:
        """Gracefully shut down the async writer thread."""
        if self._async_queue is not None and self._async_thread is not None:
            self.flush_all()
            self._async_queue.put(_ASYNC_SHUTDOWN)
            self._async_thread.join(timeout=10)

    def delete(self, key: str) -> bool:
        """Delete a session from local cache."""
        with self._cache_lock:
            if key in self._cache:
                del self._cache[key]
                return True
        return False

    def new_session(self, key: str) -> HonchoSession:
        """
        Create a new session, preserving the old one for user modeling.

        Creates a fresh session with a new ID while keeping the old
        session's data in Honcho for continued user modeling.
        """
        import time

        # Hold the reentrant lock across get_or_create so a concurrent caller
        # can't observe the (old-popped, new-not-yet-inserted) gap and create
        # its own session under the raw key.  `_cache_lock` is an RLock so
        # nested reacquisition inside get_or_create is safe.
        with self._cache_lock:
            # Remove old session from caches (but don't delete from Honcho)
            old_session = self._cache.pop(key, None)
            if old_session:
                self._sessions_cache.pop(old_session.honcho_session_id, None)

            # Create new session with timestamp suffix
            timestamp = int(time.time())
            new_key = f"{key}:{timestamp}"

            # get_or_create will create a fresh session
            session = self.get_or_create(new_key)

            # Cache under the original key so callers find it by the expected name
            self._cache[key] = session

        logger.info("Created new session for %s (honcho: %s)", key, session.honcho_session_id)
        return session

    _REASONING_LEVELS = ("minimal", "low", "medium", "high", "max")

    def _default_reasoning_level(self) -> str:
        """Return the configured default reasoning level."""
        return self._dialectic_reasoning_level

    def dialectic_query(
        self, session_key: str, query: str,
        reasoning_level: str | None = None,
        peer: str = "user",
    ) -> str:
        """
        Query Honcho's dialectic endpoint about a peer.

        Runs an LLM on Honcho's backend against the target peer's full
        representation. Higher latency than context() — callers run this in
        a background thread (see HonchoMemoryProvider) to avoid blocking.

        Args:
            session_key: The session key to query against.
            query: Natural language question.
            reasoning_level: Override the configured default (dialecticReasoningLevel).
                             Only honored when dialecticDynamic is true.
                             If None or dialecticDynamic is false, uses the configured default.
            peer: Which peer to query — "user" (default) or "ai".

        Returns:
            Honcho's synthesized answer, or empty string on failure.
        """
        session = self._cache.get(session_key)
        if not session:
            return ""

        target_peer_id = self._resolve_peer_id(session, peer)
        if target_peer_id is None:
            return ""

        # Guard: truncate query to Honcho's dialectic input limit
        if len(query) > self._dialectic_max_input_chars:
            query = query[:self._dialectic_max_input_chars].rsplit(" ", 1)[0]

        if self._dialectic_dynamic and reasoning_level:
            level = reasoning_level
        else:
            level = self._default_reasoning_level()

        try:
            if self._ai_observe_others:
                # AI peer can observe other peers — use assistant as observer.
                ai_peer_obj = self._get_or_create_peer(session.assistant_peer_id)
                if target_peer_id == session.assistant_peer_id:
                    result = ai_peer_obj.chat(query, reasoning_level=level) or ""
                else:
                    result = ai_peer_obj.chat(
                        query,
                        target=target_peer_id,
                        reasoning_level=level,
                    ) or ""
            else:
                # Without cross-observation, each peer queries its own context.
                target_peer = self._get_or_create_peer(target_peer_id)
                result = target_peer.chat(query, reasoning_level=level) or ""

            # Apply Hermes-side char cap before caching
            if result and self._dialectic_max_chars and len(result) > self._dialectic_max_chars:
                result = result[:self._dialectic_max_chars].rsplit(" ", 1)[0] + " …"
            return result
        except Exception as e:
            logger.warning("Honcho dialectic query failed: %s", e)
            return ""

    def prefetch_context(self, session_key: str, user_message: str | None = None) -> None:
        """
        Fire get_prefetch_context in a background thread, caching the result.

        Non-blocking. Consumed next turn via pop_context_result(). This avoids
        a synchronous HTTP round-trip blocking every response.
        """
        def _run():
            result = self.get_prefetch_context(session_key, user_message)
            if result:
                self.set_context_result(session_key, result)

        t = threading.Thread(target=_run, name="honcho-context-prefetch", daemon=True)
        t.start()

    def set_context_result(self, session_key: str, result: dict[str, str]) -> None:
        """Store a prefetched context result in a thread-safe way."""
        if not result:
            return
        with self._prefetch_cache_lock:
            self._context_cache[session_key] = result

    def pop_context_result(self, session_key: str) -> dict[str, str]:
        """
        Return and clear the cached context result for this session.

        Returns empty dict if no result is ready yet (first turn).
        """
        with self._prefetch_cache_lock:
            return self._context_cache.pop(session_key, {})

    def get_prefetch_context(self, session_key: str, user_message: str | None = None) -> dict[str, str]:
        """
        Pre-fetch user and AI peer context from Honcho.

        Fetches peer_representation and peer_card for both peers, plus the
        session summary when available. When user_message is provided, it is
        passed as search_query to the peer context call so Honcho returns
        conclusions relevant to the session topic rather than the full
        observation dump.

        Args:
            session_key: The session key to get context for.
            user_message: Optional first user message used as search_query for
                          topic-relevant context retrieval.

        Returns:
            Dictionary with 'representation', 'card', 'ai_representation',
            'ai_card', and optionally 'summary' keys.
        """
        session = self._cache.get(session_key)
        if not session:
            return {}

        result: dict[str, str] = {}

        # Session summary — provides session-scoped context.
        # Fresh sessions (per-session cold start, or first-ever per-directory)
        # return null summary — the guard below handles that gracefully.
        # Per-directory returning sessions get their accumulated summary.
        try:
            honcho_session = self._sessions_cache.get(session.honcho_session_id)
            if honcho_session:
                ctx = honcho_session.context(summary=True)
                if ctx.summary and getattr(ctx.summary, "content", None):
                    result["summary"] = ctx.summary.content
        except Exception as e:
            logger.debug("Failed to fetch session summary from Honcho: %s", e)

        try:
            user_ctx = self._fetch_peer_context(session.user_peer_id, search_query=user_message or None, target=session.user_peer_id)
            result["representation"] = user_ctx["representation"]
            result["card"] = "\n".join(user_ctx["card"])
        except Exception as e:
            logger.warning("Failed to fetch user context from Honcho: %s", e)

        # Also fetch AI peer's own representation so Hermes knows itself.
        try:
            ai_ctx = self._fetch_peer_context(session.assistant_peer_id, target=session.assistant_peer_id)
            result["ai_representation"] = ai_ctx["representation"]
            result["ai_card"] = "\n".join(ai_ctx["card"])
        except Exception as e:
            logger.debug("Failed to fetch AI peer context from Honcho: %s", e)

        return result

    def migrate_local_history(self, session_key: str, messages: list[dict[str, Any]]) -> bool:
        """
        Upload local session history to Honcho as a file.

        Used when Honcho activates mid-conversation to preserve prior context.

        Args:
            session_key: The session key (e.g., "telegram:123456").
            messages: Local messages (dicts with role, content, timestamp).

        Returns:
            True if upload succeeded, False otherwise.
        """
        session = self._cache.get(session_key)
        if not session:
            logger.warning("No local session cached for '%s', skipping migration", session_key)
            return False

        honcho_session = self._sessions_cache.get(session.honcho_session_id)
        if not honcho_session:
            logger.warning("No Honcho session cached for '%s', skipping migration", session_key)
            return False

        user_peer = self._get_or_create_peer(session.user_peer_id)

        content_bytes = self._format_migration_transcript(session_key, messages)
        first_ts = messages[0].get("timestamp") if messages else None

        try:
            honcho_session.upload_file(
                file=("prior_history.txt", content_bytes, "text/plain"),
                peer=user_peer,
                metadata={"source": "local_jsonl", "count": len(messages)},
                created_at=first_ts,
            )
            logger.info("Migrated %d local messages to Honcho for %s", len(messages), session_key)
            return True
        except Exception as e:
            logger.error("Failed to upload local history to Honcho for %s: %s", session_key, e)
            return False

    @staticmethod
    def _format_migration_transcript(session_key: str, messages: list[dict[str, Any]]) -> bytes:
        """Format local messages as an XML transcript for Honcho file upload."""
        timestamps = [m.get("timestamp", "") for m in messages]
        time_range = f"{timestamps[0]} to {timestamps[-1]}" if timestamps else "unknown"

        lines = [
            "<prior_conversation_history>",
            "<context>",
            "This conversation history occurred BEFORE the Honcho memory system was activated.",
            "These messages are the preceding elements of this conversation session and should",
            "be treated as foundational context for all subsequent interactions. The user and",
            "assistant have already established rapport through these exchanges.",
            "</context>",
            "",
            f'<transcript session_key="{session_key}" message_count="{len(messages)}"',
            f'           time_range="{time_range}">',
            "",
        ]
        for msg in messages:
            ts = msg.get("timestamp", "?")
            role = msg.get("role", "unknown")
            content = msg.get("content") or ""
            lines.append(f"[{ts}] {role}: {content}")

        lines.append("")
        lines.append("</transcript>")
        lines.append("</prior_conversation_history>")

        return "\n".join(lines).encode("utf-8")

    def migrate_memory_files(self, session_key: str, memory_dir: str) -> bool:
        """
        Upload MEMORY.md and USER.md to Honcho as files.

        Used when Honcho activates on an instance that already has locally
        consolidated memory. Backwards compatible -- skips if files don't exist.

        Args:
            session_key: The session key to associate files with.
            memory_dir: Path to the memories directory (~/.hermes/memories/).

        Returns:
            True if at least one file was uploaded, False otherwise.
        """
        from pathlib import Path
        memory_path = Path(memory_dir)

        if not memory_path.exists():
            return False

        session = self._cache.get(session_key)
        if not session:
            logger.warning("No local session cached for '%s', skipping memory migration", session_key)
            return False

        honcho_session = self._sessions_cache.get(session.honcho_session_id)
        if not honcho_session:
            logger.warning("No Honcho session cached for '%s', skipping memory migration", session_key)
            return False

        user_peer = self._get_or_create_peer(session.user_peer_id)
        assistant_peer = self._get_or_create_peer(session.assistant_peer_id)

        uploaded = False
        files = [
            (
                "MEMORY.md",
                "consolidated_memory.md",
                "Long-term agent notes and preferences",
                user_peer,
                "user",
            ),
            (
                "USER.md",
                "user_profile.md",
                "User profile and preferences",
                user_peer,
                "user",
            ),
            (
                "SOUL.md",
                "agent_soul.md",
                "Agent persona and identity configuration",
                assistant_peer,
                "ai",
            ),
        ]

        for filename, upload_name, description, target_peer, target_kind in files:
            filepath = memory_path / filename
            if not filepath.exists():
                continue
            content = filepath.read_text(encoding="utf-8").strip()
            if not content:
                continue

            wrapped = (
                f"<prior_memory_file>\n"
                f"<context>\n"
                f"This file was consolidated from local conversations BEFORE Honcho was activated.\n"
                f"{description}. Treat as foundational context for this user.\n"
                f"</context>\n"
                f"\n"
                f"{content}\n"
                f"</prior_memory_file>\n"
            )

            try:
                honcho_session.upload_file(
                    file=(upload_name, wrapped.encode("utf-8"), "text/plain"),
                    peer=target_peer,
                    metadata={
                        "source": "local_memory",
                        "original_file": filename,
                        "target_peer": target_kind,
                    },
                )
                logger.info(
                    "Uploaded %s to Honcho for %s (%s peer)",
                    filename,
                    session_key,
                    target_kind,
                )
                uploaded = True
            except Exception as e:
                logger.error("Failed to upload %s to Honcho: %s", filename, e)

        return uploaded

    @staticmethod
    def _normalize_card(card: Any) -> list[str]:
        """Normalize Honcho card payloads into a plain list of strings."""
        if not card:
            return []
        if isinstance(card, list):
            return [str(item) for item in card if item]
        return [str(card)]

    def _fetch_peer_card(self, peer_id: str, *, target: str | None = None) -> list[str]:
        """Fetch a peer card directly from the peer object.

        This avoids relying on session.context(), which can return an empty
        peer_card for per-session messaging sessions even when the peer itself
        has a populated card.
        """
        peer = self._get_or_create_peer(peer_id)
        getter = getattr(peer, "get_card", None)
        if callable(getter):
            return self._normalize_card(getter(target=target) if target is not None else getter())

        legacy_getter = getattr(peer, "card", None)
        if callable(legacy_getter):
            return self._normalize_card(legacy_getter(target=target) if target is not None else legacy_getter())

        return []

    def _fetch_peer_context(
        self,
        peer_id: str,
        search_query: str | None = None,
        *,
        target: str | None = None,
    ) -> dict[str, Any]:
        """Fetch representation + peer card directly from a peer object."""
        peer = self._get_or_create_peer(peer_id)
        representation = ""
        card: list[str] = []

        try:
            context_kwargs: dict[str, Any] = {}
            if target is not None:
                context_kwargs["target"] = target
            if search_query is not None:
                context_kwargs["search_query"] = search_query
            ctx = peer.context(**context_kwargs) if context_kwargs else peer.context()
            representation = (
                getattr(ctx, "representation", None)
                or getattr(ctx, "peer_representation", None)
                or ""
            )
            card = self._normalize_card(getattr(ctx, "peer_card", None))
        except Exception as e:
            logger.debug("Direct peer.context() failed for '%s': %s", peer_id, e)

        if not representation:
            try:
                representation = (
                    peer.representation(target=target) if target is not None else peer.representation()
                ) or ""
            except Exception as e:
                logger.debug("Direct peer.representation() failed for '%s': %s", peer_id, e)

        if not card:
            try:
                card = self._fetch_peer_card(peer_id, target=target)
            except Exception as e:
                logger.debug("Direct peer card fetch failed for '%s': %s", peer_id, e)

        return {"representation": representation, "card": card}

    def get_session_context(self, session_key: str, peer: str = "user") -> dict[str, Any]:
        """Fetch full session context from Honcho including summary.

        Uses the session-level context() API which returns summary,
        peer_representation, peer_card, and messages.
        """
        session = self._cache.get(session_key)
        if not session:
            return {}

        honcho_session = self._sessions_cache.get(session.honcho_session_id)
        if not honcho_session:
            # Fall back to peer-level context, respecting the requested peer
            peer_id = self._resolve_peer_id(session, peer)
            if peer_id is None:
                peer_id = session.user_peer_id
            return self._fetch_peer_context(peer_id, target=peer_id)

        try:
            observer_peer_id, target_peer_id = self._resolve_observer_target(session, peer)
            ctx = honcho_session.context(
                summary=True,
                peer_target=target_peer_id or observer_peer_id,
                peer_perspective=observer_peer_id,
            )

            result: dict[str, Any] = {}

            # Summary
            if ctx.summary:
                result["summary"] = ctx.summary.content

            # Peer representation and card
            if ctx.peer_representation:
                result["representation"] = ctx.peer_representation
            if ctx.peer_card:
                result["card"] = "\n".join(ctx.peer_card)

            # Messages (last N for context)
            if ctx.messages:
                recent = ctx.messages[-10:]  # last 10 messages
                result["recent_messages"] = [
                    {"role": getattr(m, "peer_id", "unknown"), "content": (m.content or "")[:500]}
                    for m in recent
                ]

            return result
        except Exception as e:
            logger.debug("Session context fetch failed: %s", e)
            return {}

    def _resolve_peer_id(self, session: HonchoSession, peer: str | None) -> str:
        """Resolve a peer alias or explicit peer ID to a concrete Honcho peer ID.

        Always returns a non-empty string: either a known peer ID or a
        sanitized version of the caller-supplied alias/ID.
        """
        candidate = (peer or "user").strip()
        if not candidate:
            return session.user_peer_id

        normalized = self._sanitize_id(candidate)
        if normalized == self._sanitize_id("user"):
            return session.user_peer_id
        if normalized == self._sanitize_id("ai"):
            return session.assistant_peer_id

        return normalized

    def _resolve_observer_target(
        self,
        session: HonchoSession,
        peer: str | None,
    ) -> tuple[str, str | None]:
        """Resolve observer and target peer IDs for context/search/profile queries."""
        target_peer_id = self._resolve_peer_id(session, peer)

        if target_peer_id == session.assistant_peer_id:
            return session.assistant_peer_id, session.assistant_peer_id

        if self._ai_observe_others:
            return session.assistant_peer_id, target_peer_id

        return target_peer_id, None

    def get_peer_card(self, session_key: str, peer: str = "user") -> list[str]:
        """
        Fetch a peer card — a curated list of key facts.

        Fast, no LLM reasoning. Returns raw structured facts Honcho has
        inferred about the target peer (name, role, preferences, patterns).
        Empty list if unavailable.
        """
        session = self._cache.get(session_key)
        if not session:
            return []

        try:
            observer_peer_id, target_peer_id = self._resolve_observer_target(session, peer)
            card = self._fetch_peer_card(observer_peer_id, target=target_peer_id)
            if card:
                return card
            # Some backends store cards directly on the target peer, not the
            # observer-target slot. Fall back so honcho_profile still works.
            if target_peer_id:
                return self._fetch_peer_card(target_peer_id)
            return []
        except Exception as e:
            logger.debug("Failed to fetch peer card from Honcho: %s", e)
            return []

    def search_context(
        self,
        session_key: str,
        query: str,
        max_tokens: int = 800,
        peer: str = "user",
    ) -> str:
        """
        Semantic search over Honcho session context.

        Returns raw excerpts ranked by relevance to the query. No LLM
        reasoning — cheaper and faster than dialectic_query. Good for
        factual lookups where the model will do its own synthesis.

        Args:
            session_key: Session to search against.
            query: Search query for semantic matching.
            max_tokens: Token budget for returned content.
            peer: Peer alias or explicit peer ID to search about.

        Returns:
            Relevant context excerpts as a string, or empty string if none.
        """
        session = self._cache.get(session_key)
        if not session:
            return ""

        try:
            observer_peer_id, target = self._resolve_observer_target(session, peer)

            ctx = self._fetch_peer_context(
                observer_peer_id,
                search_query=query,
                target=target,
            )
            parts = []
            if ctx["representation"]:
                parts.append(ctx["representation"])
            card = ctx["card"] or []
            if card:
                parts.append("\n".join(f"- {f}" for f in card))
            return "\n\n".join(parts)
        except Exception as e:
            logger.debug("Honcho search_context failed: %s", e)
            return ""

    def create_conclusion(self, session_key: str, content: str, peer: str = "user") -> bool:
        """Write a conclusion about a target peer back to Honcho.

        Conclusions are facts a peer observes about another peer or itself —
        preferences, corrections, clarifications, and project context.
        They feed into the target peer's card and representation.

        Args:
            session_key: Session to associate the conclusion with.
            content: The conclusion text.
            peer: Peer alias or explicit peer ID. "user" is the default alias.

        Returns:
            True on success, False on failure.
        """
        if not content or not content.strip():
            return False

        session = self._cache.get(session_key)
        if not session:
            logger.warning("No session cached for '%s', skipping conclusion", session_key)
            return False

        try:
            target_peer_id = self._resolve_peer_id(session, peer)
            if target_peer_id is None:
                logger.warning("Could not resolve conclusion peer '%s' for session '%s'", peer, session_key)
                return False

            if target_peer_id == session.assistant_peer_id:
                assistant_peer = self._get_or_create_peer(session.assistant_peer_id)
                conclusions_scope = assistant_peer.conclusions_of(session.assistant_peer_id)
            elif self._ai_observe_others:
                assistant_peer = self._get_or_create_peer(session.assistant_peer_id)
                conclusions_scope = assistant_peer.conclusions_of(target_peer_id)
            else:
                target_peer = self._get_or_create_peer(target_peer_id)
                conclusions_scope = target_peer.conclusions_of(target_peer_id)

            conclusions_scope.create([{
                "content": content.strip(),
                "session_id": session.honcho_session_id,
            }])
            logger.info("Created conclusion about %s for %s: %s", target_peer_id, session_key, content[:80])
            return True
        except Exception as e:
            logger.error("Failed to create conclusion: %s", e)
            return False

    def delete_conclusion(self, session_key: str, conclusion_id: str, peer: str = "user") -> bool:
        """Delete a conclusion by ID. Use only for PII removal.

        Args:
            session_key: Session key for peer resolution.
            conclusion_id: The conclusion ID to delete.
            peer: Peer alias or explicit peer ID.

        Returns:
            True on success, False on failure.
        """
        session = self._cache.get(session_key)
        if not session:
            return False
        try:
            target_peer_id = self._resolve_peer_id(session, peer)
            if target_peer_id == session.assistant_peer_id:
                observer = self._get_or_create_peer(session.assistant_peer_id)
                scope = observer.conclusions_of(session.assistant_peer_id)
            elif self._ai_observe_others:
                observer = self._get_or_create_peer(session.assistant_peer_id)
                scope = observer.conclusions_of(target_peer_id)
            else:
                target_peer = self._get_or_create_peer(target_peer_id)
                scope = target_peer.conclusions_of(target_peer_id)
            scope.delete(conclusion_id)
            logger.info("Deleted conclusion %s for %s", conclusion_id, session_key)
            return True
        except Exception as e:
            logger.error("Failed to delete conclusion %s: %s", conclusion_id, e)
            return False

    def set_peer_card(self, session_key: str, card: list[str], peer: str = "user") -> list[str] | None:
        """Update a peer's card.

        Args:
            session_key: Session key for peer resolution.
            card: New peer card as list of fact strings.
            peer: Peer alias or explicit peer ID.

        Returns:
            Updated card on success, None on failure.
        """
        session = self._cache.get(session_key)
        if not session:
            return None
        try:
            observer_peer_id, target_peer_id = self._resolve_observer_target(session, peer)
            if observer_peer_id is None:
                logger.warning("Could not resolve peer '%s' for set_peer_card in session '%s'", peer, session_key)
                return None
            peer_obj = self._get_or_create_peer(observer_peer_id)
            result = (
                peer_obj.set_card(card, target=target_peer_id)
                if target_peer_id is not None
                else peer_obj.set_card(card)
            )
            logger.info(
                "Updated peer card observer=%s target=%s (%d facts)",
                observer_peer_id,
                target_peer_id or observer_peer_id,
                len(card),
            )
            return result
        except Exception as e:
            logger.error("Failed to set peer card: %s", e)
            return None

    def seed_ai_identity(self, session_key: str, content: str, source: str = "manual") -> bool:
        """
        Seed the AI peer's Honcho representation from text content.

        Useful for priming AI identity from SOUL.md, exported chats, or
        any structured description. The content is sent as an assistant
        peer message so Honcho's reasoning model can incorporate it.

        Args:
            session_key: The session key to associate with.
            content: The identity/persona content to seed.
            source: Metadata tag for the source (e.g. "soul_md", "export").

        Returns:
            True on success, False on failure.
        """
        if not content or not content.strip():
            return False

        session = self._cache.get(session_key)
        if not session:
            logger.warning("No session cached for '%s', skipping AI seed", session_key)
            return False

        assistant_peer = self._get_or_create_peer(session.assistant_peer_id)
        honcho_session = self._sessions_cache.get(session.honcho_session_id)
        if not honcho_session:
            logger.warning("No Honcho session cached for '%s', skipping AI seed", session_key)
            return False

        try:
            wrapped = (
                f"<ai_identity_seed>\n"
                f"<source>{source}</source>\n"
                f"\n"
                f"{content.strip()}\n"
                f"</ai_identity_seed>"
            )
            honcho_session.add_messages([assistant_peer.message(wrapped)])
            logger.info("Seeded AI identity from '%s' into %s", source, session_key)
            return True
        except Exception as e:
            logger.error("Failed to seed AI identity: %s", e)
            return False

    def get_ai_representation(self, session_key: str) -> dict[str, str]:
        """
        Fetch the AI peer's current Honcho representation.

        Returns:
            Dict with 'representation' and 'card' keys, empty strings if unavailable.
        """
        session = self._cache.get(session_key)
        if not session:
            return {"representation": "", "card": ""}

        try:
            ctx = self._fetch_peer_context(session.assistant_peer_id, target=session.assistant_peer_id)
            return {
                "representation": ctx["representation"] or "",
                "card": "\n".join(ctx["card"]),
            }
        except Exception as e:
            logger.debug("Failed to fetch AI representation: %s", e)
            return {"representation": "", "card": ""}

    def list_sessions(self) -> list[dict[str, Any]]:
        """List all cached sessions."""
        return [
            {
                "key": s.key,
                "created_at": s.created_at.isoformat(),
                "updated_at": s.updated_at.isoformat(),
                "message_count": len(s.messages),
            }
            for s in self._cache.values()
        ]
