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import json
import secrets
from typing import List, Optional, Dict, Any
import numpy as np
from sentence_transformers import SentenceTransformer
import psycopg2
import psycopg2.pool

from .config import config


class DatabaseManager:
    def __init__(self):
        self._pool = psycopg2.pool.ThreadedConnectionPool(
            minconn=1,
            maxconn=10,
            dsn=config.DATABASE_URL,
        )
        self._init_schema()
        self.embedding_model = SentenceTransformer("all-MiniLM-L6-v2")

    # ------------------------------------------------------------------
    # Connection context manager
    # ------------------------------------------------------------------
    class _Conn:
        def __init__(self, pool):
            self._pool = pool
            self.conn = None

        def __enter__(self):
            self.conn = self._pool.getconn()
            return self.conn

        def __exit__(self, exc_type, *_):
            if self.conn:
                if exc_type:
                    self.conn.rollback()
                self._pool.putconn(self.conn)

    def _conn(self):
        return self._Conn(self._pool)

    # ------------------------------------------------------------------
    # Schema
    # ------------------------------------------------------------------
    def _init_schema(self):
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute("""

                CREATE TABLE IF NOT EXISTS users (

                    id            SERIAL PRIMARY KEY,

                    username      TEXT UNIQUE NOT NULL,

                    password_hash TEXT NOT NULL,

                    created_at    TIMESTAMP DEFAULT CURRENT_TIMESTAMP

                )

            """)
            cur.execute("""

                CREATE TABLE IF NOT EXISTS conversations (

                    id         SERIAL PRIMARY KEY,

                    user_id    INTEGER NOT NULL REFERENCES users(id),

                    title      TEXT,

                    started_at TIMESTAMP DEFAULT CURRENT_TIMESTAMP

                )

            """)
            cur.execute("""

                CREATE TABLE IF NOT EXISTS messages (

                    id              SERIAL PRIMARY KEY,

                    conversation_id INTEGER NOT NULL REFERENCES conversations(id),

                    role            TEXT NOT NULL CHECK(role IN ('user','assistant')),

                    content         TEXT NOT NULL,

                    timestamp       TIMESTAMP DEFAULT CURRENT_TIMESTAMP

                )

            """)
            cur.execute("""

                CREATE TABLE IF NOT EXISTS user_profiles (

                    user_id      INTEGER PRIMARY KEY REFERENCES users(id),

                    summary_text TEXT DEFAULT '',

                    last_updated TIMESTAMP DEFAULT CURRENT_TIMESTAMP

                )

            """)
            cur.execute("""

                CREATE TABLE IF NOT EXISTS memories (

                    id         SERIAL PRIMARY KEY,

                    user_id    INTEGER NOT NULL REFERENCES users(id),

                    content    TEXT NOT NULL,

                    embedding  TEXT NOT NULL,

                    metadata   TEXT DEFAULT '{}',

                    created_at TIMESTAMP DEFAULT CURRENT_TIMESTAMP

                )

            """)
            cur.execute(
                "ALTER TABLE users ADD COLUMN IF NOT EXISTS is_guest BOOLEAN DEFAULT FALSE"
            )
            cur.execute("ALTER TABLE users ADD COLUMN IF NOT EXISTS guest_ip TEXT")
            cur.execute("""

                CREATE TABLE IF NOT EXISTS guest_ip_log (

                    id         SERIAL PRIMARY KEY,

                    ip         TEXT NOT NULL,

                    created_at TIMESTAMP DEFAULT CURRENT_TIMESTAMP

                )

            """)
            cur.execute(
                "CREATE INDEX IF NOT EXISTS idx_guest_ip_log_ip ON guest_ip_log(ip)"
            )
            cur.execute("""

                CREATE TABLE IF NOT EXISTS shared_conversations (

                    id              SERIAL PRIMARY KEY,

                    token           TEXT UNIQUE NOT NULL,

                    user_id         INTEGER NOT NULL REFERENCES users(id),

                    conversation_id INTEGER NOT NULL REFERENCES conversations(id),

                    created_at      TIMESTAMP DEFAULT CURRENT_TIMESTAMP

                )

            """)
            cur.execute(
                "CREATE INDEX IF NOT EXISTS idx_shared_token ON shared_conversations(token)"
            )
            cur.execute(
                "ALTER TABLE users ADD COLUMN IF NOT EXISTS is_admin BOOLEAN DEFAULT FALSE"
            )
            cur.execute(
                "ALTER TABLE users ADD COLUMN IF NOT EXISTS stripe_customer_id TEXT"
            )
            cur.execute(
                "ALTER TABLE users ADD COLUMN IF NOT EXISTS subscription_status TEXT"
            )
            cur.execute(
                "ALTER TABLE users ADD COLUMN IF NOT EXISTS subscription_plan TEXT"
            )
            cur.execute(
                "ALTER TABLE users ADD COLUMN IF NOT EXISTS subscription_id TEXT"
            )
            cur.execute(
                "ALTER TABLE users ADD COLUMN IF NOT EXISTS current_period_end TIMESTAMP"
            )
            cur.execute(
                "ALTER TABLE users ADD COLUMN IF NOT EXISTS free_messages_used INTEGER DEFAULT 0"
            )
            cur.execute(
                "ALTER TABLE users ADD COLUMN IF NOT EXISTS sub_messages_used INTEGER DEFAULT 0"
            )
            cur.execute(
                "ALTER TABLE users ADD COLUMN IF NOT EXISTS sub_period_start TIMESTAMP"
            )
            cur.execute("""

                CREATE TABLE IF NOT EXISTS payment_history (

                    id               SERIAL PRIMARY KEY,

                    user_id          INTEGER NOT NULL REFERENCES users(id),

                    stripe_payment_id TEXT,

                    amount_cents     INTEGER,

                    currency         TEXT DEFAULT 'usd',

                    status           TEXT,

                    created_at       TIMESTAMP DEFAULT CURRENT_TIMESTAMP

                )

            """)
            cur.execute(
                """CREATE UNIQUE INDEX IF NOT EXISTS idx_payment_history_stripe_payment_id

                   ON payment_history(stripe_payment_id)

                   WHERE stripe_payment_id IS NOT NULL"""
            )
            # Admin audit log
            cur.execute("""

                CREATE TABLE IF NOT EXISTS admin_audit_log (

                    id            SERIAL PRIMARY KEY,

                    admin_id      INTEGER REFERENCES users(id),

                    action        TEXT NOT NULL,

                    target_user_id INTEGER,

                    ip_address    TEXT,

                    details       TEXT,

                    created_at    TIMESTAMP DEFAULT CURRENT_TIMESTAMP

                )

            """)
            cur.execute(
                "CREATE INDEX IF NOT EXISTS idx_audit_log_admin ON admin_audit_log(admin_id)"
            )
            cur.execute(
                "CREATE INDEX IF NOT EXISTS idx_audit_log_created ON admin_audit_log(created_at)"
            )
            # TOTP secrets for admin MFA
            cur.execute("ALTER TABLE users ADD COLUMN IF NOT EXISTS totp_secret TEXT")
            cur.execute(
                "ALTER TABLE users ADD COLUMN IF NOT EXISTS totp_pending_secret TEXT"
            )
            cur.execute("ALTER TABLE users ADD COLUMN IF NOT EXISTS email TEXT")
            # OAuth accounts
            cur.execute("""

                CREATE TABLE IF NOT EXISTS oauth_accounts (

                    id               SERIAL PRIMARY KEY,

                    user_id          INTEGER NOT NULL REFERENCES users(id) ON DELETE CASCADE,

                    provider         TEXT NOT NULL,

                    provider_user_id TEXT NOT NULL,

                    email            TEXT,

                    created_at       TIMESTAMP DEFAULT CURRENT_TIMESTAMP,

                    UNIQUE(provider, provider_user_id)

                )

            """)
            cur.execute(
                "CREATE INDEX IF NOT EXISTS idx_oauth_user_id ON oauth_accounts(user_id)"
            )
            cur.execute(
                "CREATE INDEX IF NOT EXISTS idx_users_email ON users(email) WHERE email IS NOT NULL"
            )
            # ── Memory layers ──
            # Per-conversation rolling summaries (episodic memory)
            cur.execute("""

                CREATE TABLE IF NOT EXISTS conversation_summaries (

                    id               SERIAL PRIMARY KEY,

                    conversation_id  INTEGER NOT NULL REFERENCES conversations(id),

                    user_id          INTEGER NOT NULL REFERENCES users(id),

                    summary_text     TEXT NOT NULL,

                    message_count    INTEGER DEFAULT 0,

                    updated_at       TIMESTAMP DEFAULT CURRENT_TIMESTAMP

                )

            """)
            cur.execute(
                "CREATE INDEX IF NOT EXISTS idx_conv_summaries_conv ON conversation_summaries(conversation_id)"
            )
            cur.execute(
                "CREATE UNIQUE INDEX IF NOT EXISTS idx_conv_summaries_unique_conv ON conversation_summaries(conversation_id)"
            )
            cur.execute(
                "CREATE INDEX IF NOT EXISTS idx_conv_summaries_user ON conversation_summaries(user_id)"
            )
            # Stable user facts extracted over time (semantic memory)
            cur.execute("""

                CREATE TABLE IF NOT EXISTS user_facts (

                    id               SERIAL PRIMARY KEY,

                    user_id          INTEGER NOT NULL REFERENCES users(id) ON DELETE CASCADE,

                    category         TEXT NOT NULL DEFAULT 'general',

                    content          TEXT NOT NULL,

                    importance       FLOAT DEFAULT 0.5,

                    confidence       FLOAT DEFAULT 0.8,

                    source_conv_id   INTEGER REFERENCES conversations(id),

                    created_at       TIMESTAMP DEFAULT CURRENT_TIMESTAMP,

                    last_reinforced  TIMESTAMP DEFAULT CURRENT_TIMESTAMP,

                    is_pinned        BOOLEAN DEFAULT FALSE

                )

            """)
            cur.execute(
                "CREATE INDEX IF NOT EXISTS idx_user_facts_user ON user_facts(user_id)"
            )
            cur.execute(
                "CREATE INDEX IF NOT EXISTS idx_user_facts_importance ON user_facts(user_id, importance DESC)"
            )
            cur.execute(
                "CREATE UNIQUE INDEX IF NOT EXISTS idx_user_facts_unique_content ON user_facts(user_id, content)"
            )
            # OpenWebUI integration — map OpenWebUI chat IDs to Montaigne conversations
            cur.execute(
                "ALTER TABLE conversations ADD COLUMN IF NOT EXISTS openwebui_chat_id TEXT"
            )
            cur.execute(
                "CREATE UNIQUE INDEX IF NOT EXISTS idx_conv_openwebui_chat ON conversations(openwebui_chat_id) WHERE openwebui_chat_id IS NOT NULL"
            )
            conn.commit()
            cur.close()

    # ------------------------------------------------------------------
    # Helpers
    # ------------------------------------------------------------------
    def _embed(self, text: str) -> List[float]:
        return self.embedding_model.encode([text])[0].tolist()

    @staticmethod
    def _cosine(a: List[float], b: List[float]) -> float:
        va, vb = np.array(a), np.array(b)
        na, nb = np.linalg.norm(va), np.linalg.norm(vb)
        return float(np.dot(va, vb) / (na * nb)) if na and nb else 0.0

    # ------------------------------------------------------------------
    # Users
    # ------------------------------------------------------------------
    def get_user_by_username(self, username: str) -> Optional[Dict]:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "SELECT id, username, password_hash FROM users WHERE username = %s",
                (username,),
            )
            row = cur.fetchone()
            cur.close()
        return (
            {"id": row[0], "username": row[1], "password_hash": row[2]} if row else None
        )

    def create_user(self, username: str, password_hash: str) -> int:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "INSERT INTO users (username, password_hash) VALUES (%s, %s) RETURNING id",
                (username, password_hash),
            )
            row = cur.fetchone()
            user_id: int = row[0] if row else 0
            cur.execute(
                "INSERT INTO user_profiles (user_id, summary_text) VALUES (%s, '')",
                (user_id,),
            )
            conn.commit()
            cur.close()
        return user_id

    def verify_password(self, username: str, password: str) -> Optional[int]:
        from .auth import verify_password as _verify

        user = self.get_user_by_username(username)
        if user and _verify(password, user["password_hash"]):
            return user["id"]
        return None

    # ------------------------------------------------------------------
    # Conversations
    # ------------------------------------------------------------------
    def create_conversation(self, user_id: int) -> int:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "INSERT INTO conversations (user_id) VALUES (%s) RETURNING id",
                (user_id,),
            )
            row = cur.fetchone()
            conv_id: int = row[0] if row else 0
            conn.commit()
            cur.close()
        return conv_id

    # ------------------------------------------------------------------
    # OpenWebUI integration
    # ------------------------------------------------------------------
    def get_or_create_openwebui_user(self, email: str) -> int:
        """Look up or auto-provision a Montaigne user for an OpenWebUI user."""
        existing = self.get_user_by_email(email)
        if existing and not existing.get("is_guest"):
            return existing["id"]
        # Create a new non-guest user with no password (OAuth-style)
        username = email.split("@")[0]
        if self.get_user_by_username(username):
            username = f"{username}_{secrets.token_hex(4)}"
        return self.create_oauth_user(username, email)

    def get_or_create_conversation_by_openwebui_chat(

        self, user_id: int, openwebui_chat_id: str

    ) -> int:
        """Map an OpenWebUI chat ID to a Montaigne conversation (create if new)."""
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "SELECT id FROM conversations WHERE openwebui_chat_id = %s",
                (openwebui_chat_id,),
            )
            row = cur.fetchone()
            if row:
                conv_id: int = row[0]
            else:
                cur.execute(
                    "INSERT INTO conversations (user_id, openwebui_chat_id) VALUES (%s, %s) RETURNING id",
                    (user_id, openwebui_chat_id),
                )
                row = cur.fetchone()
                conv_id = row[0] if row else 0
                # Also create user profile if it doesn't exist
                cur.execute(
                    "INSERT INTO user_profiles (user_id, summary_text) VALUES (%s, '') ON CONFLICT (user_id) DO NOTHING",
                    (user_id,),
                )
                conn.commit()
            cur.close()
        return conv_id

    def get_user_conversations(self, user_id: int, limit: int = 20) -> List[Dict]:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "SELECT id, title, started_at FROM conversations WHERE user_id = %s ORDER BY started_at DESC LIMIT %s",
                (user_id, limit),
            )
            rows = cur.fetchall()
            cur.close()
        return [{"id": r[0], "title": r[1], "started_at": str(r[2])} for r in rows]

    def update_conversation_title(self, conversation_id: int, title: str):
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "UPDATE conversations SET title = %s WHERE id = %s",
                (title, conversation_id),
            )
            conn.commit()
            cur.close()

    # ------------------------------------------------------------------
    # Messages
    # ------------------------------------------------------------------
    def add_message(self, conversation_id: int, role: str, content: str) -> int:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "INSERT INTO messages (conversation_id, role, content) VALUES (%s, %s, %s) RETURNING id",
                (conversation_id, role, content),
            )
            row = cur.fetchone()
            msg_id: int = row[0] if row else 0
            conn.commit()
            cur.close()
        return msg_id

    def get_conversation_messages(

        self, conversation_id: int, limit: int = 50

    ) -> List[Dict]:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "SELECT role, content, timestamp FROM messages WHERE conversation_id = %s ORDER BY timestamp ASC LIMIT %s",
                (conversation_id, limit),
            )
            rows = cur.fetchall()
            cur.close()
        return [{"role": r[0], "content": r[1], "timestamp": str(r[2])} for r in rows]

    def get_recent_messages(self, user_id: int, limit: int = 10) -> List[Dict]:
        """Last N messages across ALL of a user's conversations, in chronological order."""
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """SELECT m.role, m.content, m.timestamp

                   FROM messages m

                   JOIN conversations c ON m.conversation_id = c.id

                   WHERE c.user_id = %s

                   ORDER BY m.timestamp DESC

                   LIMIT %s""",
                (user_id, limit),
            )
            rows = cur.fetchall()
            cur.close()
        msgs = [{"role": r[0], "content": r[1], "timestamp": str(r[2])} for r in rows]
        return list(reversed(msgs))

    def count_conversation_messages(self, conversation_id: int) -> int:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "SELECT COUNT(*) FROM messages WHERE conversation_id = %s",
                (conversation_id,),
            )
            count = cur.fetchone()[0]
            cur.close()
        return count

    def get_conversation_turns(

        self, conversation_id: int, limit: int = 20, offset_from_end: int = 0

    ) -> List[Dict]:
        """Last N turns within a single conversation, in chronological order."""
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """SELECT role, content, timestamp, id

                   FROM messages

                   WHERE conversation_id = %s

                   ORDER BY id DESC

                   LIMIT %s OFFSET %s""",
                (conversation_id, limit, offset_from_end),
            )
            rows = cur.fetchall()
            cur.close()
        msgs = [
            {"role": r[0], "content": r[1], "timestamp": str(r[2]), "id": r[3]}
            for r in reversed(rows)
        ]
        return msgs

    # ------------------------------------------------------------------
    # Episodic memory — conversation summaries
    # ------------------------------------------------------------------

    def get_conversation_summary(self, conversation_id: int) -> Optional[str]:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """SELECT summary_text FROM conversation_summaries

                   WHERE conversation_id = %s ORDER BY updated_at DESC LIMIT 1""",
                (conversation_id,),
            )
            row = cur.fetchone()
            cur.close()
        return row[0] if row else None

    def save_conversation_summary(

        self,

        conversation_id: int,

        user_id: int,

        summary_text: str,

        message_count: int = 0,

    ):
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """INSERT INTO conversation_summaries

                   (conversation_id, user_id, summary_text, message_count)

                   VALUES (%s, %s, %s, %s)

                   ON CONFLICT (conversation_id)

                   DO UPDATE SET

                       summary_text = EXCLUDED.summary_text,

                       message_count = EXCLUDED.message_count,

                       updated_at = CURRENT_TIMESTAMP""",
                (conversation_id, user_id, summary_text, message_count),
            )
            conn.commit()
            cur.close()

    # ------------------------------------------------------------------
    # Semantic memory — user facts
    # ------------------------------------------------------------------

    def add_user_fact(

        self,

        user_id: int,

        content: str,

        category: str = "general",

        importance: float = 0.5,

        source_conv_id: Optional[int] = None,

    ):
        """Insert a fact if it doesn't already exist (same user + same content)."""
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """INSERT INTO user_facts

                   (user_id, category, content, importance, source_conv_id)

                   VALUES (%s, %s, %s, %s, %s)

                   ON CONFLICT (user_id, content)

                   DO UPDATE SET

                       category = EXCLUDED.category,

                       importance = GREATEST(user_facts.importance, EXCLUDED.importance),

                       source_conv_id = COALESCE(EXCLUDED.source_conv_id, user_facts.source_conv_id),

                       last_reinforced = CURRENT_TIMESTAMP""",
                (user_id, category, content, importance, source_conv_id),
            )
            conn.commit()
            cur.close()

    def get_user_facts(

        self, user_id: int, limit: int = 8, category: Optional[str] = None

    ) -> List[Dict]:
        """Top facts for a user, ordered by importance then recency."""
        with self._conn() as conn:
            cur = conn.cursor()
            if category:
                cur.execute(
                    """SELECT category, content, importance, is_pinned

                       FROM user_facts WHERE user_id = %s AND category = %s

                       ORDER BY is_pinned DESC, importance DESC, last_reinforced DESC

                       LIMIT %s""",
                    (user_id, category, limit),
                )
            else:
                cur.execute(
                    """SELECT category, content, importance, is_pinned

                       FROM user_facts WHERE user_id = %s

                       ORDER BY is_pinned DESC, importance DESC, last_reinforced DESC

                       LIMIT %s""",
                    (user_id, limit),
                )
            rows = cur.fetchall()
            cur.close()
        return [
            {"category": r[0], "content": r[1], "importance": r[2], "is_pinned": r[3]}
            for r in rows
        ]

    def delete_user_fact(self, user_id: int, content: str) -> bool:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "DELETE FROM user_facts WHERE user_id = %s AND content = %s",
                (user_id, content),
            )
            deleted = cur.rowcount > 0
            conn.commit()
            cur.close()
        return deleted

    def get_conversation_title(self, conversation_id: int) -> Optional[str]:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "SELECT title FROM conversations WHERE id = %s",
                (conversation_id,),
            )
            row = cur.fetchone()
            cur.close()
        return row[0] if row else None

    def get_title_sample_messages(self, conversation_id: int) -> List[Dict]:
        """First message + last 4 messages for title generation sampling."""
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """SELECT role, content, timestamp FROM messages

                   WHERE conversation_id = %s

                   ORDER BY timestamp ASC""",
                (conversation_id,),
            )
            rows = cur.fetchall()
            cur.close()
        if not rows:
            return []
        msgs = [{"role": r[0], "content": r[1], "timestamp": str(r[2])} for r in rows]
        if len(msgs) <= 5:
            return msgs
        return [msgs[0]] + msgs[-4:]

    # ------------------------------------------------------------------
    # User profile
    # ------------------------------------------------------------------
    def get_user_profile(self, user_id: int) -> str:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "SELECT summary_text FROM user_profiles WHERE user_id = %s",
                (user_id,),
            )
            row = cur.fetchone()
            cur.close()
        return row[0] if row else ""

    def update_user_profile(self, user_id: int, summary_text: str):
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "UPDATE user_profiles SET summary_text = %s, last_updated = CURRENT_TIMESTAMP WHERE user_id = %s",
                (summary_text, user_id),
            )
            conn.commit()
            cur.close()

    def update_username(self, user_id: int, username: str) -> bool:
        with self._conn() as conn:
            cur = conn.cursor()
            try:
                cur.execute(
                    "UPDATE users SET username = %s WHERE id = %s",
                    (username, user_id),
                )
                conn.commit()
                return True
            except Exception:
                conn.rollback()
                return False
            finally:
                cur.close()

    def update_password(self, user_id: int, password_hash: str) -> bool:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "UPDATE users SET password_hash = %s WHERE id = %s",
                (password_hash, user_id),
            )
            success = cur.rowcount > 0
            conn.commit()
            cur.close()
        return success

    def update_email(self, user_id: int, email: Optional[str]) -> bool:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "UPDATE users SET email = %s WHERE id = %s",
                (email, user_id),
            )
            success = cur.rowcount > 0
            conn.commit()
            cur.close()
        return success

    # ------------------------------------------------------------------
    # Semantic memory
    # ------------------------------------------------------------------
    def add_memory(

        self, user_id: int, text: str, metadata: Optional[Dict[str, Any]] = None

    ):
        embedding_json = json.dumps(self._embed(text))
        metadata_json = json.dumps(metadata or {})
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "INSERT INTO memories (user_id, content, embedding, metadata) VALUES (%s, %s, %s, %s)",
                (user_id, text, embedding_json, metadata_json),
            )
            conn.commit()
            cur.close()

    def search_memories(

        self, user_id: int, query: str, n_results: int = 5

    ) -> List[Dict]:
        query_vec = self._embed(query)
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "SELECT content, embedding, metadata FROM memories WHERE user_id = %s",
                (user_id,),
            )
            rows = cur.fetchall()
            cur.close()

        scored = []
        for content, emb_json, meta_json in rows:
            sim = self._cosine(query_vec, json.loads(emb_json))
            scored.append(
                {
                    "content": content,
                    "metadata": json.loads(meta_json) if meta_json else {},
                    "similarity": sim,
                }
            )

        scored.sort(key=lambda x: x["similarity"], reverse=True)
        return [m for m in scored[:n_results] if m["similarity"] > 0.3]

    def create_guest_user(self, ip: str) -> int:
        import uuid

        username = f"guest_{uuid.uuid4().hex[:12]}"
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "INSERT INTO users (username, password_hash, is_guest, guest_ip) VALUES (%s, '', TRUE, %s) RETURNING id",
                (username, ip),
            )
            row = cur.fetchone()
            user_id: int = row[0] if row else 0
            cur.execute(
                "INSERT INTO user_profiles (user_id, summary_text) VALUES (%s, '')",
                (user_id,),
            )
            conn.commit()
            cur.close()
        return user_id

    def get_or_create_guest_user(self, ip: str) -> int:
        """Look up or create a guest user for a given IP address.



        Reuses the most recent guest user for this IP so that the per-user

        message limit is enforced across requests from the same visitor.

        """
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "SELECT id FROM users WHERE is_guest = TRUE AND guest_ip = %s ORDER BY created_at DESC LIMIT 1",
                (ip,),
            )
            row = cur.fetchone()
            if row:
                user_id: int = row[0]
                cur.close()
                return user_id
            cur.close()
        return self.create_guest_user(ip)

    def convert_guest_to_user(

        self, user_id: int, username: str, password_hash: str

    ) -> bool:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "UPDATE users SET username = %s, password_hash = %s, is_guest = FALSE, guest_ip = NULL WHERE id = %s AND is_guest = TRUE",
                (username, password_hash, user_id),
            )
            success = cur.rowcount > 0
            conn.commit()
            cur.close()
        return success

    def is_guest_user(self, user_id: int) -> bool:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute("SELECT is_guest FROM users WHERE id = %s", (user_id,))
            row = cur.fetchone()
            cur.close()
        return row[0] if row else False

    def count_ip_guest_sessions(self, ip: str, hours: int = 24) -> int:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """SELECT COUNT(*) FROM users 

                   WHERE guest_ip = %s AND is_guest = TRUE 

                   AND created_at > NOW() - INTERVAL '%s hours'""",
                (ip, hours),
            )
            count = cur.fetchone()[0]
            cur.close()
        return count

    def log_guest_ip(self, ip: str):
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute("INSERT INTO guest_ip_log (ip) VALUES (%s)", (ip,))
            conn.commit()
            cur.close()

    def count_user_messages(self, user_id: int) -> int:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """SELECT COUNT(*) FROM messages m

                   JOIN conversations c ON m.conversation_id = c.id

                   WHERE c.user_id = %s AND m.role = 'user'""",
                (user_id,),
            )
            count = cur.fetchone()[0]
            cur.close()
        return count

    def cleanup_expired_guests(self, hours: int = 48):
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """DELETE FROM users 

                   WHERE is_guest = TRUE AND created_at < NOW() - INTERVAL '%s hours'""",
                (hours,),
            )
            conn.commit()
            cur.close()

    def create_share_token(self, user_id: int, conversation_id: int) -> str:
        import uuid

        token = uuid.uuid4().hex
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "INSERT INTO shared_conversations (token, user_id, conversation_id) VALUES (%s, %s, %s)",
                (token, user_id, conversation_id),
            )
            conn.commit()
            cur.close()
        return token

    def get_shared_conversation(self, token: str) -> Optional[Dict]:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """SELECT c.title, c.id FROM shared_conversations sc

                   JOIN conversations c ON sc.conversation_id = c.id

                   WHERE sc.token = %s""",
                (token,),
            )
            row = cur.fetchone()
            cur.close()
        if not row:
            return None
        conv_id = row[1]
        title = row[0]
        messages = self.get_conversation_messages(conv_id)
        return {"title": title, "messages": messages}

    def get_user_by_id(self, user_id: int) -> Optional[Dict]:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """SELECT id, username, is_guest, is_admin, stripe_customer_id,

                          subscription_status, subscription_plan, subscription_id,

                          current_period_end, free_messages_used, created_at, email

                   FROM users WHERE id = %s""",
                (user_id,),
            )
            row = cur.fetchone()
            cur.close()
        if not row:
            return None
        return {
            "id": row[0],
            "username": row[1],
            "is_guest": row[2],
            "is_admin": row[3],
            "stripe_customer_id": row[4],
            "subscription_status": row[5],
            "subscription_plan": row[6],
            "subscription_id": row[7],
            "current_period_end": str(row[8]) if row[8] else None,
            "free_messages_used": row[9] or 0,
            "created_at": str(row[10]) if row[10] else None,
            "email": row[11],
        }

    def get_free_messages_used(self, user_id: int) -> int:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "SELECT free_messages_used FROM users WHERE id = %s", (user_id,)
            )
            row = cur.fetchone()
            cur.close()
        return row[0] if row and row[0] is not None else 0

    def increment_free_messages_used(self, user_id: int) -> int:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """UPDATE users SET free_messages_used = COALESCE(free_messages_used, 0) + 1

                   WHERE id = %s RETURNING free_messages_used""",
                (user_id,),
            )
            row = cur.fetchone()
            conn.commit()
            cur.close()
        return row[0] if row else 0

    def try_consume_free_message(self, user_id: int) -> bool:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """UPDATE users

                   SET free_messages_used = COALESCE(free_messages_used, 0) + 1

                   WHERE id = %s AND COALESCE(free_messages_used, 0) < %s

                   RETURNING free_messages_used""",
                (user_id, config.FREE_MESSAGE_LIMIT),
            )
            success = cur.fetchone() is not None
            conn.commit()
            cur.close()
        return success

    def refund_free_message(self, user_id: int):
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """UPDATE users

                   SET free_messages_used = GREATEST(COALESCE(free_messages_used, 0) - 1, 0)

                   WHERE id = %s""",
                (user_id,),
            )
            conn.commit()
            cur.close()

    def set_stripe_customer_id(self, user_id: int, customer_id: str):
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "UPDATE users SET stripe_customer_id = %s WHERE id = %s",
                (customer_id, user_id),
            )
            conn.commit()
            cur.close()

    def try_consume_subscriber_message(self, user_id: int) -> bool:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """UPDATE users

                   SET sub_messages_used = CASE

                         WHEN sub_period_start IS NULL

                              OR sub_period_start < DATE_TRUNC('month', CURRENT_DATE)

                            THEN 1

                         ELSE COALESCE(sub_messages_used, 0) + 1

                       END,

                       sub_period_start = CASE

                         WHEN sub_period_start IS NULL

                              OR sub_period_start < DATE_TRUNC('month', CURRENT_DATE)

                            THEN DATE_TRUNC('month', CURRENT_DATE)

                         ELSE sub_period_start

                       END

                   WHERE id = %s

                   RETURNING sub_messages_used""",
                (user_id,),
            )
            row = cur.fetchone()
            used = row[0] if row else 0
            success = used <= config.SUBSCRIBER_MONTHLY_LIMIT
            if success:
                conn.commit()
            else:
                conn.rollback()
            cur.close()
        return success

    def refund_subscriber_message(self, user_id: int):
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """UPDATE users

                   SET sub_messages_used = GREATEST(COALESCE(sub_messages_used, 0) - 1, 0)

                   WHERE id = %s""",
                (user_id,),
            )
            conn.commit()
            cur.close()

    def get_subscriber_messages_used(self, user_id: int) -> int:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """SELECT sub_messages_used FROM users

                   WHERE id = %s

                     AND (sub_period_start IS NULL

                          OR sub_period_start >= DATE_TRUNC('month', CURRENT_DATE))""",
                (user_id,),
            )
            row = cur.fetchone()
            cur.close()
        return row[0] if row and row[0] is not None else 0

    def update_subscription(

        self,

        user_id: int,

        status: Optional[str] = None,

        plan: Optional[str] = None,

        subscription_id: Optional[str] = None,

        current_period_end: Optional[str] = None,

    ):
        with self._conn() as conn:
            cur = conn.cursor()
            updates = []
            params = []
            if status is not None:
                updates.append("subscription_status = %s")
                params.append(status)
            if plan is not None:
                updates.append("subscription_plan = %s")
                params.append(plan)
            if subscription_id is not None:
                updates.append("subscription_id = %s")
                params.append(subscription_id)
            if current_period_end is not None:
                updates.append("current_period_end = %s")
                params.append(current_period_end)
            if not updates:
                return
            params.append(user_id)
            cur.execute(
                f"UPDATE users SET {', '.join(updates)} WHERE id = %s",
                params,
            )
            conn.commit()
            cur.close()

    def clear_subscription(self, user_id: int):
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """UPDATE users SET subscription_status = NULL, subscription_plan = NULL,

                   subscription_id = NULL, current_period_end = NULL WHERE id = %s""",
                (user_id,),
            )
            conn.commit()
            cur.close()

    def get_user_by_stripe_customer_id(self, customer_id: str) -> Optional[int]:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "SELECT id FROM users WHERE stripe_customer_id = %s",
                (customer_id,),
            )
            row = cur.fetchone()
            cur.close()
        return row[0] if row else None

    def add_payment(

        self,

        user_id: int,

        stripe_payment_id: str,

        amount_cents: int,

        status: str,

        currency: str = "usd",

    ):
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """INSERT INTO payment_history (user_id, stripe_payment_id, amount_cents, currency, status)

                   VALUES (%s, %s, %s, %s, %s)

                   ON CONFLICT (stripe_payment_id) DO NOTHING""",
                (user_id, stripe_payment_id, amount_cents, currency, status),
            )
            conn.commit()
            cur.close()

    def get_admin_users(

        self, page: int = 1, per_page: int = 20, search: str = ""

    ) -> Dict:
        offset = (page - 1) * per_page
        with self._conn() as conn:
            cur = conn.cursor()
            search_clause = ""
            params = []
            if search:
                search_clause = "WHERE username ILIKE %s"
                params.append(f"%{search}%")
            params.extend([per_page, offset])
            cur.execute(
                f"""SELECT id, username, is_guest, is_admin, subscription_status, subscription_plan,

                           free_messages_used, created_at, current_period_end

                    FROM users {search_clause}

                    ORDER BY created_at DESC

                    LIMIT %s OFFSET %s""",
                params,
            )
            rows = cur.fetchall()
            cur.execute(
                f"SELECT COUNT(*) FROM users {search_clause}",
                params[:1] if search else [],
            )
            total = cur.fetchone()[0]
            cur.close()
        users = [
            {
                "id": r[0],
                "username": r[1],
                "is_guest": r[2],
                "is_admin": r[3],
                "subscription_status": r[4],
                "subscription_plan": r[5],
                "free_messages_used": r[6] or 0,
                "created_at": str(r[7]) if r[7] else None,
                "current_period_end": str(r[8]) if r[8] else None,
            }
            for r in rows
        ]
        return {"users": users, "total": total, "page": page, "per_page": per_page}

    def get_admin_stats(self) -> Dict:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute("SELECT COUNT(*) FROM users WHERE is_guest = FALSE")
            total_users = cur.fetchone()[0]
            cur.execute("SELECT COUNT(*) FROM users WHERE is_guest = TRUE")
            total_guests = cur.fetchone()[0]
            cur.execute(
                "SELECT COUNT(*) FROM users WHERE subscription_status = 'active'"
            )
            active_subscribers = cur.fetchone()[0]
            cur.execute(
                "SELECT COUNT(*) FROM users WHERE subscription_plan = 'monthly'"
            )
            monthly_subscribers = cur.fetchone()[0]
            cur.execute("SELECT COUNT(*) FROM users WHERE subscription_plan = 'annual'")
            annual_subscribers = cur.fetchone()[0]
            cur.execute("SELECT COUNT(*) FROM messages WHERE role = 'user'")
            total_messages = cur.fetchone()[0]
            cur.execute("SELECT COUNT(*) FROM conversations")
            total_conversations = cur.fetchone()[0]
            cur.execute(
                """SELECT COALESCE(SUM(amount_cents), 0) FROM payment_history

                   WHERE status = 'succeeded'"""
            )
            total_revenue_cents = cur.fetchone()[0]
            cur.close()
        return {
            "total_users": total_users,
            "total_guests": total_guests,
            "active_subscribers": active_subscribers,
            "monthly_subscribers": monthly_subscribers,
            "annual_subscribers": annual_subscribers,
            "total_messages": total_messages,
            "total_conversations": total_conversations,
            "total_revenue_cents": total_revenue_cents,
        }

    def set_user_admin(self, user_id: int, is_admin: bool):
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "UPDATE users SET is_admin = %s WHERE id = %s",
                (is_admin, user_id),
            )
            conn.commit()
            cur.close()

    def delete_user(self, user_id: int) -> bool:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute("DELETE FROM user_profiles WHERE user_id = %s", (user_id,))
            cur.execute("DELETE FROM memories WHERE user_id = %s", (user_id,))
            cur.execute(
                "DELETE FROM shared_conversations WHERE user_id = %s", (user_id,)
            )
            cur.execute(
                """DELETE FROM messages WHERE conversation_id IN

                   (SELECT id FROM conversations WHERE user_id = %s)""",
                (user_id,),
            )
            cur.execute("DELETE FROM conversations WHERE user_id = %s", (user_id,))
            cur.execute("DELETE FROM payment_history WHERE user_id = %s", (user_id,))
            cur.execute("DELETE FROM users WHERE id = %s", (user_id,))
            success = cur.rowcount > 0
            conn.commit()
            cur.close()
        return success

    def get_user_detail(self, user_id: int) -> Optional[Dict]:
        user = self.get_user_by_id(user_id)
        if not user:
            return None
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """SELECT id, title, started_at FROM conversations

                   WHERE user_id = %s ORDER BY started_at DESC LIMIT 10""",
                (user_id,),
            )
            conv_rows = cur.fetchall()
            cur.execute(
                "SELECT summary_text FROM user_profiles WHERE user_id = %s", (user_id,)
            )
            profile_row = cur.fetchone()
            cur.execute(
                """SELECT COUNT(*) FROM messages m

                   JOIN conversations c ON m.conversation_id = c.id

                   WHERE c.user_id = %s AND m.role = 'user'""",
                (user_id,),
            )
            total_messages = cur.fetchone()[0]
            cur.close()
        conversations = [
            {"id": r[0], "title": r[1], "started_at": str(r[2])} for r in conv_rows
        ]
        return {
            **user,
            "conversations": conversations,
            "profile_summary": profile_row[0] if profile_row else "",
            "total_messages": total_messages,
        }

    # ------------------------------------------------------------------
    # Admin helpers
    # ------------------------------------------------------------------
    def count_admins(self) -> int:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute("SELECT COUNT(*) FROM users WHERE is_admin = TRUE")
            count = cur.fetchone()[0]
            cur.close()
        return count

    def get_admin_ids(self, exclude_user_id: Optional[int] = None) -> List[int]:
        with self._conn() as conn:
            cur = conn.cursor()
            if exclude_user_id:
                cur.execute(
                    "SELECT id FROM users WHERE is_admin = TRUE AND id != %s",
                    (exclude_user_id,),
                )
            else:
                cur.execute("SELECT id FROM users WHERE is_admin = TRUE")
            ids = [r[0] for r in cur.fetchall()]
            cur.close()
        return ids

    def is_last_admin(self, user_id: int) -> bool:
        """Return True if user_id is the sole remaining admin."""
        user = self.get_user_by_id(user_id)
        if not user or not user.get("is_admin"):
            return False
        return self.count_admins() <= 1

    # ------------------------------------------------------------------
    # Admin audit log
    # ------------------------------------------------------------------
    def log_admin_action(

        self,

        admin_id: Optional[int],

        action: str,

        target_user_id: Optional[int] = None,

        ip_address: Optional[str] = None,

        details: Optional[str] = None,

    ):
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """INSERT INTO admin_audit_log

                   (admin_id, action, target_user_id, ip_address, details)

                   VALUES (%s, %s, %s, %s, %s)""",
                (admin_id, action, target_user_id, ip_address, details),
            )
            conn.commit()
            cur.close()

    def get_audit_logs(

        self,

        admin_id: Optional[int] = None,

        action: Optional[str] = None,

        limit: int = 50,

    ) -> List[Dict]:
        with self._conn() as conn:
            cur = conn.cursor()
            conditions = []
            params: list = []
            if admin_id:
                conditions.append("al.admin_id = %s")
                params.append(admin_id)
            if action:
                conditions.append("al.action = %s")
                params.append(action)
            where = ("WHERE " + " AND ".join(conditions)) if conditions else ""
            params.append(limit)
            cur.execute(
                f"""SELECT al.id, al.admin_id, u.username, al.action,

                           al.target_user_id, al.ip_address, al.details, al.created_at

                    FROM admin_audit_log al

                    LEFT JOIN users u ON al.admin_id = u.id

                    {where}

                    ORDER BY al.created_at DESC

                    LIMIT %s""",
                params,
            )
            rows = cur.fetchall()
            cur.close()
        return [
            {
                "id": r[0],
                "admin_id": r[1],
                "admin_username": r[2],
                "action": r[3],
                "target_user_id": r[4],
                "ip_address": r[5],
                "details": r[6],
                "created_at": str(r[7]) if r[7] else None,
            }
            for r in rows
        ]

    # ------------------------------------------------------------------
    # TOTP helpers
    # ------------------------------------------------------------------
    def set_pending_totp_secret(self, user_id: int, secret: str):
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "UPDATE users SET totp_pending_secret = %s WHERE id = %s",
                (secret, user_id),
            )
            conn.commit()
            cur.close()

    def get_totp_secret(self, user_id: int) -> Optional[str]:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute("SELECT totp_secret FROM users WHERE id = %s", (user_id,))
            row = cur.fetchone()
            cur.close()
        return row[0] if row else None

    def get_pending_totp_secret(self, user_id: int) -> Optional[str]:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "SELECT totp_pending_secret FROM users WHERE id = %s", (user_id,)
            )
            row = cur.fetchone()
            cur.close()
        return row[0] if row else None

    def enable_totp_from_pending(self, user_id: int) -> bool:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                """UPDATE users

                   SET totp_secret = totp_pending_secret,

                       totp_pending_secret = NULL

                   WHERE id = %s AND totp_pending_secret IS NOT NULL""",
                (user_id,),
            )
            success = cur.rowcount > 0
            conn.commit()
            cur.close()
        return success

    def clear_totp_secret(self, user_id: int):
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "UPDATE users SET totp_secret = NULL, totp_pending_secret = NULL WHERE id = %s",
                (user_id,),
            )
            conn.commit()
            cur.close()

    # ------------------------------------------------------------------
    # OAuth accounts
    # ------------------------------------------------------------------
    def get_oauth_account(self, provider: str, provider_user_id: str) -> Optional[Dict]:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "SELECT id, user_id, provider, provider_user_id, email FROM oauth_accounts WHERE provider = %s AND provider_user_id = %s",
                (provider, provider_user_id),
            )
            row = cur.fetchone()
            cur.close()
        if not row:
            return None
        return {
            "id": row[0],
            "user_id": row[1],
            "provider": row[2],
            "provider_user_id": row[3],
            "email": row[4],
        }

    def get_user_by_email(self, email: str) -> Optional[Dict]:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "SELECT id, username, password_hash, is_guest, email FROM users WHERE email = %s",
                (email,),
            )
            row = cur.fetchone()
            cur.close()
        if not row:
            return None
        return {
            "id": row[0],
            "username": row[1],
            "password_hash": row[2],
            "is_guest": row[3],
            "email": row[4],
        }

    def create_oauth_account(

        self,

        user_id: int,

        provider: str,

        provider_user_id: str,

        email: Optional[str] = None,

    ) -> int:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "INSERT INTO oauth_accounts (user_id, provider, provider_user_id, email) VALUES (%s, %s, %s, %s) RETURNING id",
                (user_id, provider, provider_user_id, email),
            )
            row = cur.fetchone()
            oauth_id: int = row[0] if row else 0
            conn.commit()
            cur.close()
        return oauth_id

    def get_oauth_accounts_for_user(self, user_id: int) -> List[Dict]:
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "SELECT id, provider, provider_user_id, email, created_at FROM oauth_accounts WHERE user_id = %s",
                (user_id,),
            )
            rows = cur.fetchall()
            cur.close()
        return [
            {
                "id": r[0],
                "provider": r[1],
                "provider_user_id": r[2],
                "email": r[3],
                "created_at": str(r[4]) if r[4] else None,
            }
            for r in rows
        ]

    def create_oauth_user(self, username: str, email: Optional[str] = None) -> int:
        """Create a new user for OAuth sign-in (no password)."""
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "INSERT INTO users (username, password_hash, email) VALUES (%s, '', %s) RETURNING id",
                (username, email),
            )
            row = cur.fetchone()
            user_id: int = row[0] if row else 0
            cur.execute(
                "INSERT INTO user_profiles (user_id, summary_text) VALUES (%s, '')",
                (user_id,),
            )
            conn.commit()
            cur.close()
        return user_id

    def convert_guest_to_oauth(

        self, user_id: int, username: str, email: Optional[str] = None

    ) -> bool:
        """Convert a guest user to a full user via OAuth (no password)."""
        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "UPDATE users SET username = %s, password_hash = '', email = COALESCE(%s, email), is_guest = FALSE, guest_ip = NULL WHERE id = %s AND is_guest = TRUE",
                (username, email, user_id),
            )
            success = cur.rowcount > 0
            conn.commit()
            cur.close()
        return success

    def migrate_guest_to_user(self, guest_user_id: int, target_user_id: int) -> bool:
        if guest_user_id == target_user_id:
            return False

        with self._conn() as conn:
            cur = conn.cursor()
            cur.execute(
                "SELECT is_guest FROM users WHERE id = %s",
                (guest_user_id,),
            )
            row = cur.fetchone()
            if not row or not row[0]:
                cur.close()
                return False

            cur.execute(
                "UPDATE conversations SET user_id = %s WHERE user_id = %s",
                (target_user_id, guest_user_id),
            )
            cur.execute(
                "UPDATE memories SET user_id = %s WHERE user_id = %s",
                (target_user_id, guest_user_id),
            )
            cur.execute(
                "UPDATE shared_conversations SET user_id = %s WHERE user_id = %s",
                (target_user_id, guest_user_id),
            )

            cur.execute(
                "SELECT summary_text FROM user_profiles WHERE user_id = %s",
                (guest_user_id,),
            )
            guest_profile_row = cur.fetchone()
            guest_summary = (
                guest_profile_row[0].strip()
                if guest_profile_row and guest_profile_row[0]
                else ""
            )

            cur.execute(
                "SELECT summary_text FROM user_profiles WHERE user_id = %s",
                (target_user_id,),
            )
            target_profile_row = cur.fetchone()
            target_summary = (
                target_profile_row[0].strip()
                if target_profile_row and target_profile_row[0]
                else ""
            )

            if guest_summary:
                merged_summary = guest_summary
                if target_summary and target_summary != guest_summary:
                    merged_summary = f"{target_summary}\n\n{guest_summary}"
                cur.execute(
                    "UPDATE user_profiles SET summary_text = %s, last_updated = CURRENT_TIMESTAMP WHERE user_id = %s",
                    (merged_summary, target_user_id),
                )

            cur.execute(
                "DELETE FROM user_profiles WHERE user_id = %s", (guest_user_id,)
            )
            cur.execute(
                "DELETE FROM users WHERE id = %s AND is_guest = TRUE", (guest_user_id,)
            )
            conn.commit()
            cur.close()
        return True

    def close(self):
        self._pool.closeall()