@vellumai/assistant 0.6.0 → 0.6.2

package/src/memory/conversation-crud.ts

@@ -70,7 +70,7 @@ const interfaceIdSchema = z.enum(INTERFACE_IDS);
 const subagentNotificationSchema = z.object({
   subagentId: z.string(),
   label: z.string(),
-  status: z.enum(["completed", "failed", "aborted"]),
+  status: z.enum(["running", "completed", "failed", "aborted"]),
   error: z.string().optional(),
   conversationId: z.string().optional(),
 });
@@ -108,7 +108,7 @@ export type MessageMetadata = z.infer<typeof messageMetadataSchema>;
 
 function cloneForkMessageMetadata(
   metadata: string | null,
-  sourceMessageId: string
+  sourceMessageId: string,
 ): string {
   if (!metadata) {
     return JSON.stringify({ forkSourceMessageId: sourceMessageId });
@@ -141,7 +141,7 @@ function cloneForkMessageMetadata(
  * callers with actual guardian trust should always supply a real context.
  */
 export function provenanceFromTrustContext(
-  ctx: TrustContext | null | undefined
+  ctx: TrustContext | null | undefined,
 ): Record<string, unknown> {
   if (!ctx) return { provenanceTrustClass: "unknown" };
   return {
@@ -172,6 +172,7 @@ export interface ConversationRow {
   forkParentMessageId: string | null;
   isAutoTitle: number;
   scheduleJobId: string | null;
+  lastMessageAt: number | null;
 }
 
 export const parseConversation = createRowMapper<
@@ -197,6 +198,7 @@ export const parseConversation = createRowMapper<
   forkParentMessageId: "forkParentMessageId",
   isAutoTitle: "isAutoTitle",
   scheduleJobId: "scheduleJobId",
+  lastMessageAt: "lastMessageAt",
 });
 
 export interface MessageRow {
@@ -239,18 +241,18 @@ export function createConversation(
     | string
     | {
         title?: string;
-        conversationType?: "standard" | "private" | "background";
+        conversationType?: "standard" | "private" | "background" | "scheduled";
         source?: string;
         scheduleJobId?: string;
         groupId?: string;
-      }
+      },
 ) {
   const db = getDb();
   const now = Date.now();
   const opts =
     typeof titleOrOpts === "string"
       ? { title: titleOrOpts }
-      : titleOrOpts ?? {};
+      : (titleOrOpts ?? {});
   const conversationType = opts.conversationType ?? "standard";
   const source = opts.source ?? "user";
   const groupId = opts.groupId;
@@ -301,7 +303,7 @@ export function createConversation(
       ) {
         log.warn(
           { attempt, conversationId: id, code },
-          "createConversation: INSERT transient error, retrying"
+          "createConversation: INSERT transient error, retrying",
         );
         Bun.sleepSync(50 * (attempt + 1));
         continue;
@@ -312,13 +314,16 @@ export function createConversation(
 
   // group_id is NOT in the Drizzle schema (raw-query-only pattern).
   // Set via raw SQL after the INSERT succeeds.
-  if (groupId) {
+  // Always set group_id — default to "system:all" when none provided.
+  {
+    const effectiveGroupId = groupId ?? "system:all";
     for (let attempt = 0; ; attempt++) {
       try {
         rawRun(
-          "UPDATE conversations SET group_id = ? WHERE id = ?",
-          groupId,
-          id
+          "UPDATE conversations SET group_id = ?, is_pinned = ? WHERE id = ?",
+          effectiveGroupId,
+          effectiveGroupId === "system:pinned" ? 1 : 0,
+          id,
         );
         break;
       } catch (err) {
@@ -329,7 +334,7 @@ export function createConversation(
         ) {
           log.warn(
             { attempt, conversationId: id, code },
-            "createConversation: group_id UPDATE transient error, retrying"
+            "createConversation: group_id UPDATE transient error, retrying",
           );
           Bun.sleepSync(50 * (attempt + 1));
           continue;
@@ -360,18 +365,18 @@ export function getConversation(id: string): ConversationRow | null {
  * (i.e. no other conversations still reference it).
  */
 export function countConversationsByScheduleJobId(
-  scheduleJobId: string
+  scheduleJobId: string,
 ): number {
   return (
     rawGet<{ c: number }>(
       "SELECT COUNT(*) AS c FROM conversations WHERE schedule_job_id = ?",
-      scheduleJobId
+      scheduleJobId,
     )?.c ?? 0
   );
 }
 
 export function getConversationType(
-  conversationId: string
+  conversationId: string,
 ): "standard" | "private" {
   const conv = getConversation(conversationId);
   const raw = conv?.conversationType;
@@ -392,7 +397,7 @@ export function getConversationGroupId(conversationId: string): string | null {
   ensureGroupMigration();
   const row = rawGet<{ group_id: string | null }>(
     "SELECT group_id FROM conversations WHERE id = ?",
-    conversationId
+    conversationId,
   );
   return row?.group_id ?? null;
 }
@@ -416,7 +421,7 @@ export function forkConversation(params: {
 
   if (sourceMessages.length === 0) {
     throw new UserError(
-      `Conversation ${conversationId} has no persisted messages to fork`
+      `Conversation ${conversationId} has no persisted messages to fork`,
     );
   }
 
@@ -427,7 +432,7 @@ export function forkConversation(params: {
 
   if (throughMessageId != null && copyBoundaryIndex === -1) {
     throw new UserError(
-      `Message ${throughMessageId} does not belong to conversation ${conversationId}`
+      `Message ${throughMessageId} does not belong to conversation ${conversationId}`,
     );
   }
 
@@ -435,8 +440,8 @@ export function forkConversation(params: {
     0,
     Math.min(
       sourceConversation.contextCompactedMessageCount,
-      sourceMessages.length
-    )
+      sourceMessages.length,
+    ),
   );
   const preserveSourceCompactionState =
     copyBoundaryIndex >= visibleWindowStartIndex;
@@ -467,7 +472,7 @@ export function forkConversation(params: {
     const fc = createConversation({
       title: forkTitle,
       conversationType: "standard",
-      groupId: parentGroupId ?? undefined,
+      groupId: parentGroupId ?? "system:all",
     });
 
     db.update(conversations)
@@ -530,7 +535,7 @@ export function forkConversation(params: {
         .orderBy(messageAttachments.position)
         .all();
       const uncachedAttachmentLinks = attachmentLinks.filter(
-        (link) => !attachmentIdMap.has(link.attachmentId)
+        (link) => !attachmentIdMap.has(link.attachmentId),
       );
       const stagingMessageId =
         uncachedAttachmentLinks.length > 0 ? uuid() : null;
@@ -566,7 +571,7 @@ export function forkConversation(params: {
         const scopedAttachmentId = linkAttachmentToMessage(
           stagingMessageId ?? forkedMessageId,
           link.attachmentId,
-          link.position
+          link.position,
         );
         attachmentIdMap.set(link.attachmentId, scopedAttachmentId);
       }
@@ -583,6 +588,16 @@ export function forkConversation(params: {
       });
     }
 
+    // Set lastMessageAt to the max createdAt of copied messages so the
+    // forked conversation sorts correctly by message recency.
+    const lastCopiedMessage = messagesToCopy.at(-1);
+    if (lastCopiedMessage) {
+      db.update(conversations)
+        .set({ lastMessageAt: lastCopiedMessage.createdAt })
+        .where(eq(conversations.id, fc.id))
+        .run();
+    }
+
     seedForkedConversationAttention({
       conversationId: fc.id,
       latestAssistantMessageId: latestForkedAssistant?.messageId ?? null,
@@ -601,7 +616,7 @@ export function forkConversation(params: {
   const persistedFork = getConversation(forkedConversation.id);
   if (!persistedFork) {
     throw new Error(
-      `Failed to load forked conversation ${forkedConversation.id} after creation`
+      `Failed to load forked conversation ${forkedConversation.id} after creation`,
     );
   }
 
@@ -610,14 +625,13 @@ export function forkConversation(params: {
 
 /**
  * Delete a conversation and all its messages, cleaning up orphaned memory
- * artifacts (items, embeddings). Returns segment and orphaned item IDs so
- * callers can clean up the corresponding Qdrant vector entries.
+ * artifacts (embeddings). Returns segment IDs so callers can clean up
+ * the corresponding Qdrant vector entries.
  */
 export function deleteConversation(id: string): DeletedMemoryIds {
   const db = getDb();
   const result: DeletedMemoryIds = {
     segmentIds: [],
-    orphanedItemIds: [],
     deletedSummaryIds: [],
   };
 
@@ -662,8 +676,8 @@ export function deleteConversation(id: string): DeletedMemoryIds {
           .where(
             and(
               eq(memoryEmbeddings.targetType, "segment"),
-              inArray(memoryEmbeddings.targetId, result.segmentIds)
-            )
+              inArray(memoryEmbeddings.targetId, result.segmentIds),
+            ),
           )
           .run();
       }
@@ -691,8 +705,8 @@ export function deleteConversation(id: string): DeletedMemoryIds {
           .where(
             and(
               eq(memoryEmbeddings.targetType, "summary"),
-              inArray(memoryEmbeddings.targetId, scopeSummaryIds)
-            )
+              inArray(memoryEmbeddings.targetId, scopeSummaryIds),
+            ),
           )
           .run();
         tx.delete(memorySummaries)
@@ -723,14 +737,10 @@ export function deleteConversation(id: string): DeletedMemoryIds {
  *
  * Extends `deleteConversation` with:
  * - Cancelling pending memory jobs before deletion
- * - Restoring memory items that were explicitly superseded by items from this conversation
- * - Restoring orphaned subject-match superseded items after deletion
  * - Deleting conversation-scoped memory summaries and their embeddings
- * - Enqueuing `embed_item` jobs for all restored items
  */
 export function wipeConversation(id: string): WipeConversationResult {
   const db = getDb();
-  const unsupersededItemIds: string[] = [];
   const deletedSummaryIds: string[] = [];
 
   // Step A — Cancel pending memory jobs (before deleting messages, since
@@ -744,8 +754,8 @@ export function wipeConversation(id: string): WipeConversationResult {
     .where(
       and(
         eq(memorySummaries.scope, "conversation"),
-        eq(memorySummaries.scopeKey, id)
-      )
+        eq(memorySummaries.scopeKey, id),
+      ),
     )
     .all();
   const summaryIds = summaryRows.map((r) => r.id);
@@ -754,8 +764,8 @@ export function wipeConversation(id: string): WipeConversationResult {
       .where(
         and(
           eq(memoryEmbeddings.targetType, "summary"),
-          inArray(memoryEmbeddings.targetId, summaryIds)
-        )
+          inArray(memoryEmbeddings.targetId, summaryIds),
+        ),
       )
       .run();
     db.delete(memorySummaries)
@@ -772,7 +782,6 @@ export function wipeConversation(id: string): WipeConversationResult {
   // Step E — Return the combined result.
   return {
     ...deletedMemoryIds,
-    unsupersededItemIds,
     deletedSummaryIds: [
       ...deletedSummaryIds,
       ...deletedMemoryIds.deletedSummaryIds,
@@ -802,20 +811,17 @@ export function purgePrivateConversations(): {
       count: 0,
       deletedMemory: {
         segmentIds: [],
-        orphanedItemIds: [],
         deletedSummaryIds: [],
       },
     };
   }
 
   const allSegmentIds: string[] = [];
-  const allOrphanedItemIds: string[] = [];
   const allDeletedSummaryIds: string[] = [];
 
   for (const conv of privateConvs) {
     const deleted = deleteConversation(conv.id);
     allSegmentIds.push(...deleted.segmentIds);
-    allOrphanedItemIds.push(...deleted.orphanedItemIds);
     allDeletedSummaryIds.push(...deleted.deletedSummaryIds);
   }
 
@@ -823,7 +829,6 @@ export function purgePrivateConversations(): {
     count: privateConvs.length,
     deletedMemory: {
       segmentIds: allSegmentIds,
-      orphanedItemIds: allOrphanedItemIds,
       deletedSummaryIds: allDeletedSummaryIds,
     },
   };
@@ -834,7 +839,7 @@ export async function addMessage(
   role: string,
   content: string,
   metadata?: Record<string, unknown>,
-  opts?: { skipIndexing?: boolean }
+  opts?: { skipIndexing?: boolean },
 ) {
   const db = getDb();
   const messageId = uuid();
@@ -844,7 +849,7 @@ export async function addMessage(
     if (!result.success) {
       log.warn(
         { conversationId, messageId, issues: result.error.issues },
-        "Invalid message metadata, storing as-is"
+        "Invalid message metadata, storing as-is",
       );
     }
   }
@@ -879,13 +884,13 @@ export async function addMessage(
             .where(
               and(
                 eq(conversations.id, conversationId),
-                isNull(conversations.originChannel)
-              )
+                isNull(conversations.originChannel),
+              ),
             )
             .run();
         }
         tx.update(conversations)
-          .set({ updatedAt: now })
+          .set({ updatedAt: now, lastMessageAt: now })
           .where(eq(conversations.id, conversationId))
           .run();
       });
@@ -899,7 +904,7 @@ export async function addMessage(
       ) {
         log.warn(
           { attempt, conversationId, code: errCode },
-          "addMessage: transient SQLite error, retrying"
+          "addMessage: transient SQLite error, retrying",
         );
         await Bun.sleep(50 * (attempt + 1));
         continue;
@@ -938,12 +943,12 @@ export async function addMessage(
           provenanceTrustClass,
           automated,
         },
-        config.memory
+        config.memory,
       );
     } catch (err) {
       log.warn(
         { err, conversationId, messageId: message.id },
-        "Failed to index message for memory"
+        "Failed to index message for memory",
       );
     }
   }
@@ -958,7 +963,7 @@ export async function addMessage(
     } catch (err) {
       log.warn(
         { err, conversationId, messageId: message.id },
-        "Failed to project assistant message for attention tracking"
+        "Failed to project assistant message for attention tracking",
       );
     }
   }
@@ -985,7 +990,7 @@ export interface PaginatedMessagesResult {
 export function getMessagesPaginated(
   conversationId: string,
   limit: number | undefined,
-  beforeTimestamp?: number
+  beforeTimestamp?: number,
 ): PaginatedMessagesResult {
   const db = getDb();
 
@@ -1029,7 +1034,7 @@ export function getMessagesPaginated(
 
 export function getLastAssistantTimestampBefore(
   conversationId: string,
-  beforeTimestamp: number
+  beforeTimestamp: number,
 ): number {
   const db = getDb();
   const row = db
@@ -1039,8 +1044,8 @@ export function getLastAssistantTimestampBefore(
       and(
         eq(messages.conversationId, conversationId),
         eq(messages.role, "assistant"),
-        lt(messages.createdAt, beforeTimestamp)
-      )
+        lt(messages.createdAt, beforeTimestamp),
+      ),
     )
     .orderBy(desc(messages.createdAt))
     .limit(1)
@@ -1051,7 +1056,7 @@ export function getLastAssistantTimestampBefore(
 /** Fetch a single message by ID, optionally scoped to a specific conversation. */
 export function getMessageById(
   messageId: string,
-  conversationId?: string
+  conversationId?: string,
 ): MessageRow | null {
   const db = getDb();
   const conditions = [eq(messages.id, messageId)];
@@ -1069,7 +1074,7 @@ export function getMessageById(
 export function updateConversationTitle(
   id: string,
   title: string,
-  isAutoTitle?: number
+  isAutoTitle?: number,
 ): void {
   const db = getDb();
   const set: Record<string, unknown> = { title, updatedAt: Date.now() };
@@ -1087,7 +1092,7 @@ export function updateConversationUsage(
   id: string,
   totalInputTokens: number,
   totalOutputTokens: number,
-  totalEstimatedCost: number
+  totalEstimatedCost: number,
 ): void {
   const db = getDb();
   db.update(conversations)
@@ -1104,7 +1109,7 @@ export function updateConversationUsage(
 export function updateConversationContextWindow(
   id: string,
   contextSummary: string,
-  contextCompactedMessageCount: number
+  contextCompactedMessageCount: number,
 ): void {
   const db = getDb();
   db.update(conversations)
@@ -1154,7 +1159,7 @@ export function clearAll(): { conversations: number; messages: number } {
   } catch (err) {
     log.warn(
       { err },
-      "clearAll: failed to clear messages_fts — dropping triggers so base-table cleanup can proceed"
+      "clearAll: failed to clear messages_fts — dropping triggers so base-table cleanup can proceed",
     );
     rawExec("DROP TRIGGER IF EXISTS messages_fts_ai");
     rawExec("DROP TRIGGER IF EXISTS messages_fts_ad");
@@ -1170,7 +1175,7 @@ export function clearAll(): { conversations: number; messages: number } {
     `INSERT INTO lifecycle_events (id, event_name, created_at) VALUES (?, ?, ?)`,
     uuid(),
     "conversations_clear_all",
-    Date.now()
+    Date.now(),
   );
 
   // Rebuild corrupted FTS tables and restore triggers after all base-table
@@ -1180,16 +1185,16 @@ export function clearAll(): { conversations: number; messages: number } {
   if (messagesFtsCorrupted) {
     rawExec("DROP TABLE IF EXISTS messages_fts");
     rawExec(
-      `CREATE VIRTUAL TABLE IF NOT EXISTS messages_fts USING fts5(message_id UNINDEXED, content)`
+      `CREATE VIRTUAL TABLE IF NOT EXISTS messages_fts USING fts5(message_id UNINDEXED, content)`,
     );
     rawExec(
-      `CREATE TRIGGER IF NOT EXISTS messages_fts_ai AFTER INSERT ON messages BEGIN INSERT INTO messages_fts(message_id, content) VALUES (new.id, new.content); END`
+      `CREATE TRIGGER IF NOT EXISTS messages_fts_ai AFTER INSERT ON messages BEGIN INSERT INTO messages_fts(message_id, content) VALUES (new.id, new.content); END`,
     );
     rawExec(
-      `CREATE TRIGGER IF NOT EXISTS messages_fts_ad AFTER DELETE ON messages BEGIN DELETE FROM messages_fts WHERE message_id = old.id; END`
+      `CREATE TRIGGER IF NOT EXISTS messages_fts_ad AFTER DELETE ON messages BEGIN DELETE FROM messages_fts WHERE message_id = old.id; END`,
     );
     rawExec(
-      `CREATE TRIGGER IF NOT EXISTS messages_fts_au AFTER UPDATE ON messages BEGIN DELETE FROM messages_fts WHERE message_id = old.id; INSERT INTO messages_fts(message_id, content) VALUES (new.id, new.content); END`
+      `CREATE TRIGGER IF NOT EXISTS messages_fts_au AFTER UPDATE ON messages BEGIN DELETE FROM messages_fts WHERE message_id = old.id; INSERT INTO messages_fts(message_id, content) VALUES (new.id, new.content); END`,
     );
   }
 
@@ -1214,8 +1219,8 @@ export function deleteLastExchange(conversationId: string): number {
     .where(
       and(
         eq(messages.conversationId, conversationId),
-        eq(messages.role, "user")
-      )
+        eq(messages.role, "user"),
+      ),
     )
     .orderBy(sql`rowid DESC`)
     .limit(1)
@@ -1229,7 +1234,7 @@ export function deleteLastExchange(conversationId: string): number {
   const rowidSubquery = sql`(SELECT rowid FROM messages WHERE id = ${lastUserMsg.id})`;
   const condition = and(
     eq(messages.conversationId, conversationId),
-    sql`rowid >= ${rowidSubquery}`
+    sql`rowid >= ${rowidSubquery}`,
   );
 
   const [{ deleted }] = db
@@ -1260,8 +1265,16 @@ export function deleteLastExchange(conversationId: string): number {
 
   db.transaction((tx) => {
     tx.delete(messages).where(condition).run();
+    const maxResult = tx
+      .select({ maxCreatedAt: sql<number | null>`MAX(${messages.createdAt})` })
+      .from(messages)
+      .where(eq(messages.conversationId, conversationId))
+      .get();
     tx.update(conversations)
-      .set({ updatedAt: Date.now() })
+      .set({
+        updatedAt: Date.now(),
+        lastMessageAt: maxResult?.maxCreatedAt ?? null,
+      })
       .where(eq(conversations.id, conversationId))
       .run();
   });
@@ -1278,12 +1291,10 @@ export function deleteLastExchange(conversationId: string): number {
  */
 export interface DeletedMemoryIds {
   segmentIds: string[];
-  orphanedItemIds: string[];
   deletedSummaryIds: string[];
 }
 
 export interface WipeConversationResult extends DeletedMemoryIds {
-  unsupersededItemIds: string[];
   cancelledJobCount: number;
 }
 
@@ -1293,7 +1304,7 @@ export interface WipeConversationResult extends DeletedMemoryIds {
  */
 export function updateMessageContent(
   messageId: string,
-  newContent: string
+  newContent: string,
 ): void {
   const db = getDb();
   db.update(messages)
@@ -1330,7 +1341,7 @@ export function updateMessageMetadata(
  */
 export function relinkAttachments(
   fromMessageIds: string[],
-  toMessageId: string
+  toMessageId: string,
 ): number {
   if (fromMessageIds.length === 0) return 0;
   const db = getDb();
@@ -1365,7 +1376,6 @@ export function deleteMessageById(messageId: string): DeletedMemoryIds {
   const db = getDb();
   const result: DeletedMemoryIds = {
     segmentIds: [],
-    orphanedItemIds: [],
     deletedSummaryIds: [],
   };
 
@@ -1379,6 +1389,13 @@ export function deleteMessageById(messageId: string): DeletedMemoryIds {
     .map((r) => r.attachmentId)
     .filter((id): id is string => id !== undefined);
 
+  // Look up the conversation before the transaction so we can recalculate lastMessageAt.
+  const msgRow = db
+    .select({ conversationId: messages.conversationId })
+    .from(messages)
+    .where(eq(messages.id, messageId))
+    .get();
+
   db.transaction((tx) => {
     // Collect memory segment IDs linked to this message before cascade.
     const linkedSegments = tx
@@ -1398,14 +1415,29 @@ export function deleteMessageById(messageId: string): DeletedMemoryIds {
     // and message_attachments.
     tx.delete(messages).where(eq(messages.id, messageId)).run();
 
+    // Recalculate lastMessageAt after deletion.
+    if (msgRow) {
+      const maxResult = tx
+        .select({
+          maxCreatedAt: sql<number | null>`MAX(${messages.createdAt})`,
+        })
+        .from(messages)
+        .where(eq(messages.conversationId, msgRow.conversationId))
+        .get();
+      tx.update(conversations)
+        .set({ lastMessageAt: maxResult?.maxCreatedAt ?? null })
+        .where(eq(conversations.id, msgRow.conversationId))
+        .run();
+    }
+
     // Clean up segment embeddings from SQLite (Qdrant cleanup is the caller's job).
     if (result.segmentIds.length > 0) {
       tx.delete(memoryEmbeddings)
         .where(
           and(
             eq(memoryEmbeddings.targetType, "segment"),
-            inArray(memoryEmbeddings.targetId, result.segmentIds)
-          )
+            inArray(memoryEmbeddings.targetId, result.segmentIds),
+          ),
         )
         .run();
     }
@@ -1418,7 +1450,7 @@ export function deleteMessageById(messageId: string): DeletedMemoryIds {
 
 export function setConversationOriginChannelIfUnset(
   conversationId: string,
-  channel: ChannelId
+  channel: ChannelId,
 ): void {
   const db = getDb();
   db.update(conversations)
@@ -1426,14 +1458,14 @@ export function setConversationOriginChannelIfUnset(
     .where(
       and(
         eq(conversations.id, conversationId),
-        isNull(conversations.originChannel)
-      )
+        isNull(conversations.originChannel),
+      ),
     )
     .run();
 }
 
 export function getConversationOriginChannel(
-  conversationId: string
+  conversationId: string,
 ): ChannelId | null {
   const db = getDb();
   const row = db
@@ -1446,7 +1478,7 @@ export function getConversationOriginChannel(
 
 export function setConversationOriginInterfaceIfUnset(
   conversationId: string,
-  interfaceId: InterfaceId
+  interfaceId: InterfaceId,
 ): void {
   const db = getDb();
   db.update(conversations)
@@ -1454,14 +1486,14 @@ export function setConversationOriginInterfaceIfUnset(
     .where(
       and(
         eq(conversations.id, conversationId),
-        isNull(conversations.originInterface)
-      )
+        isNull(conversations.originInterface),
+      ),
     )
     .run();
 }
 
 export function getConversationOriginInterface(
-  conversationId: string
+  conversationId: string,
 ): InterfaceId | null {
   const db = getDb();
   const row = db
@@ -1481,13 +1513,13 @@ export function getConversationOriginInterface(
  * conversation itself isn't a desktop-origin private conversation).
  */
 export function getConversationRecentProvenanceTrustClass(
-  conversationId: string
+  conversationId: string,
 ): "guardian" | "trusted_contact" | "unknown" | undefined {
   const row = rawGet<{ metadata: string | null }>(
     `SELECT metadata FROM messages
      WHERE conversation_id = ? AND role = 'user' AND metadata IS NOT NULL
      ORDER BY created_at DESC LIMIT 1`,
-    conversationId
+    conversationId,
   );
   if (!row?.metadata) return undefined;
   try {
@@ -1508,7 +1540,7 @@ export function batchSetDisplayOrders(
     displayOrder: number | null;
     isPinned: boolean;
     groupId?: string | null;
-  }>
+  }>,
 ): void {
   ensureDisplayOrderMigration();
   ensureGroupMigration();
@@ -1518,24 +1550,26 @@ export function batchSetDisplayOrders(
       if (update.groupId !== undefined) {
         // New client: groupId is authoritative.
         // Derive is_pinned from groupId.
-        // Sanitize: if groupId references a deleted/unknown group, fall back
-        // to NULL to avoid FK violation that would roll back the entire batch.
+        // Sanitize: if groupId is null or references a deleted/unknown group,
+        // fall back to "system:all" to avoid FK violation that would roll back
+        // the entire batch.
         let safeGroupId = update.groupId;
-        if (
-          safeGroupId !== null &&
+        if (safeGroupId === null) {
+          safeGroupId = "system:all";
+        } else if (
           !rawGet<{ id: string }>(
             "SELECT id FROM conversation_groups WHERE id = ?",
-            safeGroupId
+            safeGroupId,
           )
         ) {
-          safeGroupId = null;
+          safeGroupId = "system:all";
         }
         rawRun(
           "UPDATE conversations SET display_order = ?, is_pinned = ?, group_id = ? WHERE id = ?",
           update.displayOrder,
           safeGroupId === "system:pinned" ? 1 : 0,
           safeGroupId,
-          update.id
+          update.id,
         );
       } else {
         // Old client: no groupId in payload
@@ -1546,7 +1580,7 @@ export function batchSetDisplayOrders(
           rawRun(
             "UPDATE conversations SET display_order = ?, is_pinned = 1, group_id = 'system:pinned' WHERE id = ?",
             update.displayOrder,
-            update.id
+            update.id,
           );
         } else {
           // Restore system group from source/conversationType when old clients
@@ -1558,12 +1592,12 @@ export function batchSetDisplayOrders(
                  WHEN source IN ('schedule', 'reminder') THEN 'system:scheduled'
                  WHEN source IN ('heartbeat', 'task') THEN 'system:background'
                  WHEN conversation_type = 'background' AND COALESCE(source, '') != 'notification' THEN 'system:background'
-                 ELSE NULL
+                 ELSE 'system:all'
                END
              ELSE group_id END
              WHERE id = ?`,
             update.displayOrder,
-            update.id
+            update.id,
           );
         }
       }
@@ -1576,7 +1610,7 @@ export function batchSetDisplayOrders(
 }
 
 export function getDisplayMetaForConversations(
-  conversationIds: string[]
+  conversationIds: string[],
 ): Map<
   string,
   { displayOrder: number | null; isPinned: boolean; groupId: string | null }
@@ -1595,7 +1629,7 @@ export function getDisplayMetaForConversations(
       group_id: string | null;
     }>(
       "SELECT display_order, is_pinned, group_id FROM conversations WHERE id = ?",
-      id
+      id,
     );
     result.set(id, {
       displayOrder: row?.display_order ?? null,
@@ -1624,7 +1658,7 @@ function isToolResultMessage(role: string, content: string): boolean {
       (block: unknown) =>
         block != null &&
         typeof block === "object" &&
-        (block as Record<string, unknown>).type === "tool_result"
+        (block as Record<string, unknown>).type === "tool_result",
     );
   } catch {
     return false;
@@ -1644,7 +1678,7 @@ function isToolResultMessage(role: string, content: string): boolean {
  */
 export function getTurnTimeBounds(
   conversationId: string,
-  messageCreatedAt: number
+  messageCreatedAt: number,
 ): { startTime: number; endTime: number } | null {
   const db = getDb();
 
@@ -1666,8 +1700,8 @@ export function getTurnTimeBounds(
     .where(
       and(
         eq(messages.conversationId, conversationId),
-        sql`rowid <= ${rowidSubquery}`
-      )
+        sql`rowid <= ${rowidSubquery}`,
+      ),
     )
     .orderBy(sql`rowid DESC`)
     .limit(50)
@@ -1698,8 +1732,8 @@ export function getTurnTimeBounds(
     .where(
       and(
         eq(messages.conversationId, conversationId),
-        sql`rowid > ${forwardRowidSubquery}`
-      )
+        sql`rowid > ${forwardRowidSubquery}`,
+      ),
     )
     .orderBy(sql`rowid ASC`)
     .limit(50)
@@ -1740,8 +1774,8 @@ export function getTurnTimeBounds(
         and(
           eq(llmRequestLogs.conversationId, conversationId),
           gte(llmRequestLogs.createdAt, startTime),
-          lte(llmRequestLogs.createdAt, hardCeiling)
-        )
+          lte(llmRequestLogs.createdAt, hardCeiling),
+        ),
       )
       .orderBy(desc(llmRequestLogs.createdAt))
       .limit(1)
@@ -1789,8 +1823,8 @@ export function getAssistantMessageIdsInTurn(messageId: string): string[] {
     .where(
       and(
         eq(messages.conversationId, target.conversationId),
-        lte(messages.createdAt, target.createdAt)
-      )
+        lte(messages.createdAt, target.createdAt),
+      ),
     )
     .orderBy(desc(messages.createdAt))
     .limit(50)
@@ -1827,8 +1861,8 @@ export function getAssistantMessageIdsInTurn(messageId: string): string[] {
     .where(
       and(
         eq(messages.conversationId, target.conversationId),
-        gt(messages.createdAt, target.createdAt)
-      )
+        gt(messages.createdAt, target.createdAt),
+      ),
     )
     .orderBy(asc(messages.createdAt))
     .limit(50)
@@ -1864,8 +1898,8 @@ export function getAssistantMessageIdsInTurn(messageId: string): string[] {
         and(
           eq(messages.conversationId, target.conversationId),
           gt(messages.createdAt, boundaryCreatedAt),
-          lte(messages.createdAt, target.createdAt)
-        )
+          lte(messages.createdAt, target.createdAt),
+        ),
       )
       .orderBy(asc(messages.createdAt))
       .all();
@@ -1888,8 +1922,8 @@ export function getAssistantMessageIdsInTurn(messageId: string): string[] {
     .where(
       and(
         eq(messages.conversationId, target.conversationId),
-        inArray(messages.id, [...idSet])
-      )
+        inArray(messages.id, [...idSet]),
+      ),
     )
     .orderBy(asc(messages.createdAt))
     .all();