@openchambery/web 1.19.13-beta.1 → 1.19.13-beta.3

package/server/lib/assistants/contact-store.js

@@ -1,5 +1,10 @@
+import crypto from 'node:crypto';
+import { decodeDataUrlStrict } from '../fs/prompt-attachment-store.js';
 import { parseContactCard, parseContactPart, serializeContactPart } from './cards.js';
 
+/** Keep in sync with CONTACT_ATTACHMENT_HISTORICAL_MAX_BYTES in contact-attachments.js */
+const FINGERPRINT_DATA_URL_MAX_BYTES = 56 * 1024 * 1024;
+
 const json = (value) => JSON.stringify(value);
 const parse = (value) => JSON.parse(value);
 
@@ -45,6 +50,12 @@ export const CONTACT_SCHEMA_SQL = `
     after_ordinal INTEGER NOT NULL,
     updated_at INTEGER NOT NULL
   );
+  -- Contact transcript generation: bumps only on clear_chat_history / resetContact.
+  -- clear memory (context boundary) must not change this. Cursor keyset embeds it.
+  CREATE TABLE IF NOT EXISTS assistant_contact_generation (
+    assistant_id TEXT PRIMARY KEY,
+    generation INTEGER NOT NULL DEFAULT 0
+  );
 `;
 
 export const CONTACT_SETTLE_TEXT = Object.freeze({
@@ -53,23 +64,107 @@ export const CONTACT_SETTLE_TEXT = Object.freeze({
   question: 'oc.settle.question',
 });
 
+/** List-card preview body bound (plain text only; no base64 / tool traces). */
+export const CONTACT_PREVIEW_MAX_CHARS = 500;
+/** How many newest contact rows to scan per assistant for a visible preview. */
+export const CONTACT_PREVIEW_CANDIDATE_LIMIT = 24;
+
+/** Frozen UI page contract defaults. */
+export const CONTACT_PAGE_DEFAULT_LIMIT = 20;
+export const CONTACT_PAGE_MAX_LIMIT = 100;
+export const CONTACT_CURSOR_VERSION = 1;
+
 const IN_FLIGHT_WATCH = new Set(['busy', 'question']);
 
+const contactStoreError = (code, message) => {
+  const error = new Error(typeof message === 'string' && message.trim() ? message.trim() : code);
+  error.code = code;
+  return error;
+};
+
 export function ensureContactSchema(db) {
   db.exec(CONTACT_SCHEMA_SQL);
   const columns = new Set(db.prepare("SELECT name FROM pragma_table_info('assistant_contact_message')").all().map((column) => column.name));
   if (!columns.has('from_assistant_id')) db.exec('ALTER TABLE assistant_contact_message ADD COLUMN from_assistant_id TEXT');
   if (!columns.has('from_assistant_name')) db.exec('ALTER TABLE assistant_contact_message ADD COLUMN from_assistant_name TEXT');
+  // Attachment table ownership lives in contact-attachments.ensureContactAttachmentSchema.
+}
+
+/** Current contact transcript generation for one assistant (default 0). */
+export function getContactGeneration(db, assistantID) {
+  if (typeof assistantID !== 'string' || !assistantID) return 0;
+  const row = db.prepare(
+    'SELECT generation FROM assistant_contact_generation WHERE assistant_id=?',
+  ).get(assistantID);
+  if (!row || !Number.isSafeInteger(Number(row.generation)) || Number(row.generation) < 0) return 0;
+  return Number(row.generation);
+}
+
+/**
+ * Atomically bump contact generation (clear chat history / reset only).
+ * Returns the new generation. clearContactMemory must never call this.
+ */
+export function bumpContactGeneration(db, assistantID) {
+  if (typeof assistantID !== 'string' || !assistantID) {
+    throw contactStoreError('validation_error', 'assistantID required');
+  }
+  db.prepare(
+    'INSERT INTO assistant_contact_generation(assistant_id, generation) VALUES (?, 1) ON CONFLICT(assistant_id) DO UPDATE SET generation=generation+1',
+  ).run(assistantID);
+  return getContactGeneration(db, assistantID);
 }
 
-const decodeCursor = (value) => {
+/**
+ * Decode an opaque contact page cursor.
+ * v1: { v:1, assistantID, generation, ordinal, messageID }
+ * Legacy (pre-pagination clients): { ordinal, messageID } — treated as generation 0.
+ */
+export function decodeContactCursor(value) {
   if (value == null || value === '') return null;
-  const parsed = JSON.parse(Buffer.from(String(value), 'base64url').toString('utf8'));
-  if (!Number.isSafeInteger(parsed?.ordinal) || typeof parsed?.messageID !== 'string') return null;
-  return parsed;
-};
+  let parsed;
+  try {
+    parsed = JSON.parse(Buffer.from(String(value), 'base64url').toString('utf8'));
+  } catch {
+    return null;
+  }
+  if (!parsed || typeof parsed !== 'object' || Array.isArray(parsed)) return null;
+  if (!Number.isSafeInteger(parsed.ordinal) || typeof parsed.messageID !== 'string' || !parsed.messageID) {
+    return null;
+  }
+  const hasVersion = parsed.v != null;
+  if (hasVersion) {
+    if (parsed.v !== CONTACT_CURSOR_VERSION) return null;
+    if (typeof parsed.assistantID !== 'string' || !parsed.assistantID.trim()) return null;
+    if (!Number.isSafeInteger(parsed.generation) || parsed.generation < 0) return null;
+    return {
+      v: CONTACT_CURSOR_VERSION,
+      assistantID: parsed.assistantID.trim(),
+      generation: parsed.generation,
+      ordinal: parsed.ordinal,
+      messageID: parsed.messageID,
+      legacy: false,
+    };
+  }
+  // Legacy keyset without generation/assistant — only valid while generation is still 0.
+  return {
+    v: CONTACT_CURSOR_VERSION,
+    assistantID: null,
+    generation: 0,
+    ordinal: parsed.ordinal,
+    messageID: parsed.messageID,
+    legacy: true,
+  };
+}
 
-const encodeCursor = (row) => Buffer.from(json({ ordinal: row.ordinal, messageID: row.message_id })).toString('base64url');
+export function encodeContactCursor({ assistantID, generation, ordinal, messageID }) {
+  return Buffer.from(json({
+    v: CONTACT_CURSOR_VERSION,
+    assistantID,
+    generation,
+    ordinal,
+    messageID,
+  })).toString('base64url');
+}
 
 const hydrateMessage = (db, row) => {
   const parts = db.prepare(
@@ -116,19 +211,292 @@ export function getContactMessage(db, messageID) {
   return hydrateMessage(db, row);
 }
 
+const isSettleOnlyText = (text) => {
+  const trimmed = typeof text === 'string' ? text.trim() : '';
+  return trimmed.startsWith('oc.settle.');
+};
+
+/** Strip data-URLs / dense base64 so list previews never carry attachment bodies. */
+export function sanitizeContactPreviewText(text, maxChars = CONTACT_PREVIEW_MAX_CHARS) {
+  const raw = typeof text === 'string' ? text : '';
+  const cleaned = raw
+    .replace(/data:[^\s]+/giu, ' ')
+    .replace(/(?:[A-Za-z0-9+/]{48,}={0,2})/g, ' ')
+    .replace(/\s+/gu, ' ')
+    .trim();
+  const limit = Number.isFinite(maxChars) && maxChars > 0 ? Math.floor(maxChars) : CONTACT_PREVIEW_MAX_CHARS;
+  return cleaned.length > limit ? cleaned.slice(0, limit) : cleaned;
+}
+
+/**
+ * Build AssistantDTO.latestMessagePreview from one hydrated contact message.
+ * Returns null when the row is not list-visible (internal settle-only, empty,
+ * unsupported role). Peer inbox rows map to role `user` (user-visible DM).
+ * Visible error bubbles keep real body text. Cards/files set fallbackKind.
+ */
+export function buildContactMessagePreview(message) {
+  if (!message || typeof message !== 'object') return null;
+  const sourceRole = message.role;
+  if (sourceRole !== 'user' && sourceRole !== 'assistant' && sourceRole !== 'peer') return null;
+  const parts = Array.isArray(message.parts) ? message.parts : [];
+  const textFromParts = parts
+    .filter((part) => part?.type === 'text' && typeof part.text === 'string')
+    .map((part) => part.text)
+    .join('');
+  const rawText = (typeof message.text === 'string' && message.text) || textFromParts || '';
+  const trimmed = rawText.trim();
+  const files = parts.filter((part) => part?.type === 'file');
+  const cards = parts.filter((part) => part?.type === 'card');
+  // Assigned-session settle notices are internal transcript markers, not list copy.
+  if (isSettleOnlyText(trimmed) && files.length === 0 && cards.length === 0) return null;
+
+  let text = '';
+  let fallbackKind = null;
+  if (trimmed && !isSettleOnlyText(trimmed)) {
+    text = sanitizeContactPreviewText(trimmed);
+  }
+  if (!text && files.length > 0) {
+    const file = files[0];
+    const mime = typeof file.mime === 'string' ? file.mime : '';
+    fallbackKind = mime.startsWith('image/') ? 'image' : 'file';
+    const filename = typeof file.filename === 'string' ? file.filename.trim() : '';
+    text = sanitizeContactPreviewText(filename);
+  }
+  if (!text && !fallbackKind && cards.length > 0) {
+    const card = cards[0];
+    const cardType = card.cardType;
+    if (cardType === 'session' || cardType === 'assistant' || cardType === 'schedule') {
+      fallbackKind = cardType;
+    }
+    const label = typeof card.title === 'string' && card.title.trim()
+      ? card.title
+      : (typeof card.name === 'string' ? card.name : '');
+    text = sanitizeContactPreviewText(label);
+  }
+  // Empty pure-card without title still surfaces the card kind for the list icon.
+  if (!text && !fallbackKind) return null;
+  if (!text && fallbackKind && cards.length > 0 && files.length === 0 && !trimmed) {
+    // keep empty text + fallbackKind
+  } else if (!text && !fallbackKind) {
+    return null;
+  }
+
+  const messageID = typeof message.messageID === 'string' ? message.messageID : '';
+  const ordinal = Number(message.ordinal);
+  if (!messageID || !Number.isFinite(ordinal)) return null;
+
+  return {
+    messageID,
+    ordinal,
+    // Peer DMs are user-visible inbox rows; list language is user|assistant only.
+    role: sourceRole === 'assistant' ? 'assistant' : 'user',
+    text: text || '',
+    fallbackKind,
+  };
+}
+
+const loadContactPartsByMessageIDs = (db, messageIDs) => {
+  const map = new Map();
+  const ids = (Array.isArray(messageIDs) ? messageIDs : [])
+    .filter((id) => typeof id === 'string' && id);
+  if (ids.length === 0) return map;
+  const placeholders = ids.map(() => '?').join(',');
+  const rows = db.prepare(
+    `SELECT message_id, part_json FROM assistant_contact_part
+     WHERE message_id IN (${placeholders})
+     ORDER BY message_id ASC, ordinal ASC, part_id ASC`,
+  ).all(...ids);
+  for (const row of rows) {
+    const part = parseContactPart(parse(row.part_json));
+    if (!part) continue;
+    const list = map.get(row.message_id);
+    if (list) list.push(part);
+    else map.set(row.message_id, [part]);
+  }
+  return map;
+};
+
+const messageFromPreviewRow = (row, parts) => {
+  const list = Array.isArray(parts) ? parts : [];
+  return {
+    messageID: row.message_id,
+    assistantID: row.assistant_id,
+    role: row.role,
+    ordinal: row.ordinal,
+    status: row.status,
+    parts: list,
+    text: list.filter((part) => part.type === 'text').map((part) => part.text).join(''),
+  };
+};
+
+const pickPreviewFromCandidateRows = (rows, partsByMessage) => {
+  for (const row of rows) {
+    const preview = buildContactMessagePreview(
+      messageFromPreviewRow(row, partsByMessage.get(row.message_id) || []),
+    );
+    if (preview) return preview;
+  }
+  return null;
+};
+
+/**
+ * Indexed newest-first probe for list-visible contact rows.
+ *
+ * - Uses `assistant_contact_message_page` (assistant_id, ordinal, message_id).
+ * - Limits to `candidateLimit` rows per assistant (no full-history sort).
+ * - Restricts to user/assistant/peer (preview-visible roles).
+ * - Drops pure internal settle markers (`oc.settle.*` text-only parts) in SQL
+ *   so a long tail of settle rows cannot exhaust the LIMIT and hide the real
+ *   latest user/assistant bubble. File/card settle hybrids still pass through
+ *   for buildContactMessagePreview. Other empty/non-preview rows may still
+ *   occupy a slot and force a deeper probe only within the same LIMIT.
+ */
+const CONTACT_PREVIEW_CANDIDATE_SQL = `
+  SELECT message_id, assistant_id, role, ordinal, status
+  FROM assistant_contact_message m
+  WHERE m.assistant_id = ?
+    AND m.role IN ('user', 'assistant', 'peer')
+    AND NOT (
+      EXISTS (
+        SELECT 1 FROM assistant_contact_part p
+        WHERE p.message_id = m.message_id
+          AND (
+            p.part_json LIKE '%"text":"oc.settle.complete"%'
+            OR p.part_json LIKE '%"text":"oc.settle.error"%'
+            OR p.part_json LIKE '%"text":"oc.settle.question"%'
+          )
+      )
+      AND NOT EXISTS (
+        SELECT 1 FROM assistant_contact_part p2
+        WHERE p2.message_id = m.message_id
+          AND (
+            p2.part_json LIKE '%"type":"file"%'
+            OR p2.part_json LIKE '%"type":"card"%'
+          )
+      )
+    )
+  ORDER BY m.ordinal DESC, m.message_id DESC
+  LIMIT ?
+`;
+
+const boundPreviewCandidateLimit = (candidateLimit) => {
+  if (Number.isFinite(candidateLimit) && candidateLimit > 0) {
+    return Math.min(Math.floor(candidateLimit), 100);
+  }
+  return CONTACT_PREVIEW_CANDIDATE_LIMIT;
+};
+
+/**
+ * Authoritative list preview for one assistant: newest visible contact row by
+ * (ordinal DESC, message_id DESC). One indexed probe + parts for those IDs only.
+ */
+export function getLatestContactMessagePreview(db, assistantID, {
+  candidateLimit = CONTACT_PREVIEW_CANDIDATE_LIMIT,
+} = {}) {
+  if (typeof assistantID !== 'string' || !assistantID) return null;
+  const limit = boundPreviewCandidateLimit(candidateLimit);
+  const rows = db.prepare(CONTACT_PREVIEW_CANDIDATE_SQL).all(assistantID, limit);
+  if (rows.length === 0) return null;
+  const partsByMessage = loadContactPartsByMessageIDs(db, rows.map((row) => row.message_id));
+  return pickPreviewFromCandidateRows(rows, partsByMessage);
+}
+
+/**
+ * Batch previews for snapshot (catalog size ≤100).
+ *
+ * Reuses **one** prepared statement: per assistant_id, indexed
+ * `ORDER BY ordinal DESC, message_id DESC LIMIT candidateLimit` (not a window
+ * over the full multi-assistant history). Collects bounded candidate IDs, then
+ * **one** parts IN-query for all of them. No HTTP N+1; no full-table rank sort.
+ *
+ * Returns Map(assistantID → preview | null). Missing / empty assistants → null.
+ */
+export function getLatestContactMessagePreviews(db, assistantIDs, {
+  candidateLimit = CONTACT_PREVIEW_CANDIDATE_LIMIT,
+} = {}) {
+  const result = new Map();
+  const ids = [...new Set(
+    (Array.isArray(assistantIDs) ? assistantIDs : [])
+      .filter((id) => typeof id === 'string' && id),
+  )];
+  for (const id of ids) result.set(id, null);
+  if (ids.length === 0) return result;
+
+  const limit = boundPreviewCandidateLimit(candidateLimit);
+  const probe = db.prepare(CONTACT_PREVIEW_CANDIDATE_SQL);
+  const candidates = [];
+  for (const assistantID of ids) {
+    const rows = probe.all(assistantID, limit);
+    for (const row of rows) candidates.push(row);
+  }
+  if (candidates.length === 0) return result;
+
+  const partsByMessage = loadContactPartsByMessageIDs(
+    db,
+    candidates.map((row) => row.message_id),
+  );
+  const byAssistant = new Map();
+  for (const row of candidates) {
+    const list = byAssistant.get(row.assistant_id);
+    if (list) list.push(row);
+    else byAssistant.set(row.assistant_id, [row]);
+  }
+  for (const [assistantID, rows] of byAssistant) {
+    result.set(assistantID, pickPreviewFromCandidateRows(rows, partsByMessage));
+  }
+  return result;
+}
+
 /** Stable fingerprint for idempotent contact admission replay. */
+/**
+ * Canonical fingerprint for idempotent admission.
+ * File parts prefer sha256+size+mime+filename (stable across attachmentID/url forms).
+ * Legacy data URLs are normalized by decoded content hash when possible.
+ */
 export function contactPartsFingerprint(parts) {
   const list = Array.isArray(parts) ? parts : [];
   return json(list.map((part) => {
     if (!part || typeof part !== 'object') return null;
     if (part.type === 'text') return { type: 'text', text: typeof part.text === 'string' ? part.text : '' };
     if (part.type === 'file') {
-      return {
-        type: 'file',
-        mime: typeof part.mime === 'string' ? part.mime : '',
-        url: typeof part.url === 'string' ? part.url : '',
-        ...(typeof part.filename === 'string' && part.filename ? { filename: part.filename } : {}),
-      };
+      const mime = typeof part.mime === 'string' ? part.mime : '';
+      const filename = typeof part.filename === 'string' ? part.filename : '';
+      const sha256 = typeof part.sha256 === 'string' ? part.sha256.toLowerCase() : '';
+      const size = Number.isSafeInteger(part.size) ? part.size : null;
+      // Content identity only when hash/size known — attachmentID is ownership, not replay key.
+      if (sha256 || size != null) {
+        return {
+          type: 'file',
+          mime,
+          filename,
+          sha256,
+          size,
+        };
+      }
+      const url = typeof part.url === 'string' ? part.url : '';
+      if (url.startsWith('data:')) {
+        try {
+          // Reuse fs-store strict decoder (same alphabet / padding / charset rules).
+          const decoded = decodeDataUrlStrict(url, {
+            mode: 'migration',
+            maxBytes: FINGERPRINT_DATA_URL_MAX_BYTES,
+          });
+          return {
+            type: 'file',
+            mime: mime || decoded.mime,
+            filename,
+            sha256: crypto.createHash('sha256').update(decoded.buffer).digest('hex'),
+            size: decoded.buffer.length,
+          };
+        } catch {
+          return { type: 'file', mime, filename, sha256: '', size: null, urlLen: url.length };
+        }
+      }
+      // Ref without hash/size: ownership id is not content identity (cannot key replay alone).
+      if (typeof part.attachmentID === 'string' && part.attachmentID) {
+        return { type: 'file', mime, filename, sha256: '', size: null, refOnly: true };
+      }
+      return { type: 'file', mime, filename, sha256: '', size: null };
     }
     return part;
   }));
@@ -158,35 +526,136 @@ export function insertContactMessage(db, {
   });
 }
 
-export function listContactMessages(db, assistantID, { before, limit = 50 } = {}) {
-  const cursor = before == null || before === '' ? null : decodeCursor(before);
-  if (before && !cursor) {
-    const error = new Error('validation_error');
-    error.code = 'validation_error';
-    throw error;
+/**
+ * Page the contact transcript (UI contract).
+ * - Ascending messages on the page; keyset is (ordinal DESC, messageID DESC) for older pages.
+ * - Default limit 20, max 100.
+ * - `before` and `messageID` are mutually exclusive.
+ * - Exact `messageID` returns at most one row for this assistant, nextCursor null, complete true.
+ * - Stale generation in cursor → contact_generation_conflict.
+ */
+export function listContactMessages(db, assistantID, {
+  before,
+  limit = CONTACT_PAGE_DEFAULT_LIMIT,
+  messageID = null,
+} = {}) {
+  if (typeof assistantID !== 'string' || !assistantID) {
+    throw contactStoreError('validation_error', 'assistantID required');
+  }
+  const hasBefore = !(before == null || before === '');
+  const hasExact = !(messageID == null || messageID === '');
+  if (hasBefore && hasExact) {
+    throw contactStoreError('validation_error', 'before and messageID are mutually exclusive');
+  }
+
+  let parsedLimit = limit;
+  if (parsedLimit == null || parsedLimit === '') parsedLimit = CONTACT_PAGE_DEFAULT_LIMIT;
+  parsedLimit = typeof parsedLimit === 'number' ? parsedLimit : Number(String(parsedLimit).trim());
+  if (!Number.isInteger(parsedLimit) || parsedLimit < 1 || parsedLimit > CONTACT_PAGE_MAX_LIMIT) {
+    throw contactStoreError('validation_error', `limit must be an integer from 1 to ${CONTACT_PAGE_MAX_LIMIT}`);
+  }
+
+  const generation = getContactGeneration(db, assistantID);
+
+  if (hasExact) {
+    if (typeof messageID !== 'string' || !messageID.trim()) {
+      throw contactStoreError('validation_error', 'messageID must be a non-empty string');
+    }
+    const row = db.prepare(
+      'SELECT * FROM assistant_contact_message WHERE assistant_id=? AND message_id=?',
+    ).get(assistantID, messageID.trim());
+    return {
+      messages: row ? [hydrateMessage(db, row)] : [],
+      nextCursor: null,
+      complete: true,
+      generation,
+    };
+  }
+
+  let cursor = null;
+  if (hasBefore) {
+    cursor = decodeContactCursor(before);
+    if (!cursor) {
+      throw contactStoreError('validation_error', 'invalid contact messages cursor');
+    }
+    if (cursor.assistantID && cursor.assistantID !== assistantID) {
+      throw contactStoreError('validation_error', 'cursor assistantID does not match path');
+    }
+    if (cursor.generation !== generation) {
+      throw contactStoreError(
+        'contact_generation_conflict',
+        'Contact transcript generation changed; refetch from the start.',
+      );
+    }
   }
+
   const rows = cursor
     ? db.prepare(
       'SELECT * FROM assistant_contact_message WHERE assistant_id=? AND (ordinal<? OR (ordinal=? AND message_id<?)) ORDER BY ordinal DESC, message_id DESC LIMIT ?',
-    ).all(assistantID, cursor.ordinal, cursor.ordinal, cursor.messageID, limit + 1)
+    ).all(assistantID, cursor.ordinal, cursor.ordinal, cursor.messageID, parsedLimit + 1)
     : db.prepare(
       'SELECT * FROM assistant_contact_message WHERE assistant_id=? ORDER BY ordinal DESC, message_id DESC LIMIT ?',
-    ).all(assistantID, limit + 1);
-  const page = rows.slice(0, limit);
-  const nextCursor = rows.length > limit && page[page.length - 1] ? encodeCursor(page[page.length - 1]) : null;
+    ).all(assistantID, parsedLimit + 1);
+  const page = rows.slice(0, parsedLimit);
+  const oldest = page[page.length - 1];
+  const nextCursor = rows.length > parsedLimit && oldest
+    ? encodeContactCursor({
+      assistantID,
+      generation,
+      ordinal: oldest.ordinal,
+      messageID: oldest.message_id,
+    })
+    : null;
   return {
     messages: [...page].reverse().map((row) => hydrateMessage(db, row)),
     nextCursor,
     complete: nextCursor === null,
+    generation,
   };
 }
 
-export function deleteContactMessages(db, assistantID) {
-  const ids = db.prepare('SELECT message_id FROM assistant_contact_message WHERE assistant_id=?').all(assistantID).map((row) => row.message_id);
+/**
+ * Wipe contact transcript rows for one assistant.
+ *
+ * Bounded tool wipe (`upToOrdinal` = wiping turn's user ordinal):
+ * - **Keep** only `role='user'` rows with `ordinal >= ceiling` (the wipe request
+ *   itself plus later-admitted queued users) and their parts / message IDs.
+ * - **Delete** every other row at any ordinal: prior users, and all
+ *   assistant / peer / error / card rows — including late writes from an
+ *   earlier still-running lane whose ordinal landed after the wipe user.
+ * Keeping the wipe user avoids delete+re-admit reordering queued users before it.
+ *
+ * Direct API callers without a turn ceiling omit `upToOrdinal` and delete every
+ * row (existing contract; concurrent in-flight admissions are not preserved).
+ * Watches and the LLM context boundary always clear on wipe.
+ */
+export function deleteContactMessages(db, assistantID, { upToOrdinal = null } = {}) {
+  const parsedCeiling = upToOrdinal == null || upToOrdinal === ''
+    ? NaN
+    : Number(upToOrdinal);
+  const bounded = Number.isFinite(parsedCeiling);
+  // Single delete set drives both parts and message rows.
+  const ids = bounded
+    ? db.prepare(
+      `SELECT message_id FROM assistant_contact_message
+       WHERE assistant_id=?
+         AND NOT (role = 'user' AND ordinal >= ?)`,
+    ).all(assistantID, parsedCeiling).map((row) => row.message_id)
+    : db.prepare(
+      'SELECT message_id FROM assistant_contact_message WHERE assistant_id=?',
+    ).all(assistantID).map((row) => row.message_id);
   for (const messageID of ids) {
     db.prepare('DELETE FROM assistant_contact_part WHERE message_id=?').run(messageID);
   }
-  db.prepare('DELETE FROM assistant_contact_message WHERE assistant_id=?').run(assistantID);
+  if (bounded) {
+    db.prepare(
+      `DELETE FROM assistant_contact_message
+       WHERE assistant_id=?
+         AND NOT (role = 'user' AND ordinal >= ?)`,
+    ).run(assistantID, parsedCeiling);
+  } else {
+    db.prepare('DELETE FROM assistant_contact_message WHERE assistant_id=?').run(assistantID);
+  }
   db.prepare('DELETE FROM assistant_contact_watch WHERE assistant_id=?').run(assistantID);
   db.prepare('DELETE FROM assistant_contact_context_boundary WHERE assistant_id=?').run(assistantID);
 }