Q5: give chat wakes timed, attributed history apart from the new ask

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>

src/main/services/chat-wake-context.ts

@@ -0,0 +1,54 @@
+import type { DatabaseSync } from "node:sqlite";
+import type { ChatContextBlock } from "./task-prompts";
+
+interface ThreadMessageRow {
+  body_md: string;
+  created_at: string;
+  edited_at: string | null;
+  sender_type: string;
+  sender_id: string | null;
+  sender_name: string;
+  sender_role: string | null;
+}
+
+/** The thread a chat-wake run answers, split at the agent's last reply. */
+export function loadChatWakeContext(db: DatabaseSync, orgId: string, agentId: string, secretScopeJson: string): ChatContextBlock | null {
+  const scope = JSON.parse(secretScopeJson) as { sourceThreadId?: string };
+  if (!scope.sourceThreadId) return null;
+  const thread = db.prepare("select space_id from chat_threads where id = ? and org_id = ?")
+    .get(scope.sourceThreadId, orgId) as { space_id: string } | undefined;
+  if (!thread) throw new Error(`Chat wake thread ${scope.sourceThreadId} no longer exists.`);
+  const messages = db.prepare(`
+    select m.body_md, m.created_at, m.edited_at, m.sender_type, m.sender_id,
+           coalesce(a.name, e.display_name, m.sender_type) as sender_name,
+           coalesce(a.role, e.role) as sender_role
+    from chat_messages m
+    left join agents a on a.id = m.sender_id and m.sender_type = 'agent'
+    left join employees e on e.id = m.sender_id and m.sender_type = 'employee'
+    where m.thread_id = ? and m.org_id = ?
+    order by m.created_at asc
+    limit 20
+  `).all(scope.sourceThreadId, orgId) as unknown as ThreadMessageRow[];
+  if (messages.length === 0) return null;
+  const isOwn = (m: ThreadMessageRow) => m.sender_type === "agent" && m.sender_id === agentId;
+  const ownReplies = messages.filter(isOwn);
+  const lastReplyAt = ownReplies.length > 0 ? ownReplies[ownReplies.length - 1].created_at : "";
+  const isFresh = (m: ThreadMessageRow) =>
+    !isOwn(m) && (m.created_at > lastReplyAt || (m.edited_at !== null && m.edited_at > lastReplyAt));
+  return {
+    threadId: scope.sourceThreadId,
+    spaceId: thread.space_id,
+    history: messages.filter((m) => !isFresh(m)).map(formatMessage).join("\n"),
+    fresh: messages.filter(isFresh).map(formatMessage).join("\n"),
+  };
+}
+
+function formatMessage(m: ThreadMessageRow): string {
+  const who = m.sender_role ? `${m.sender_name} (${m.sender_type}, ${m.sender_role})` : `${m.sender_name} (${m.sender_type})`;
+  const edited = m.edited_at ? ` (edited ${utcMinute(m.edited_at)})` : "";
+  return `[${utcMinute(m.created_at)}] ${who}${edited}: ${m.body_md}`;
+}
+
+function utcMinute(iso: string): string {
+  return `${iso.slice(0, 10)} ${iso.slice(11, 16)} UTC`;
+}

src/main/services/task-execution-service.ts

@@ -14,7 +14,6 @@ import type { AgentToolContext } from "./agent-tools";
 import {
   buildAgentInstructions,
   buildTaskPrompt,
-  type ChatContextBlock,
   type GoalRow,
   type ProjectRow,
   type SkillRuntimeSnapshotRow,
@@ -25,6 +24,7 @@ import {
   type WorkspaceRow,
 } from "./task-prompts";
 import { renderTaskHandoff } from "./agent-task-handoff";
+import { loadChatWakeContext } from "./chat-wake-context";
 import { loadComposioTools } from "./composio/composio-tool-bridge";
 import { connectorDisplayName } from "./composio/connector-brands";
 import { ConnectorGrantsService } from "./composio/connector-grants";
@@ -134,7 +134,7 @@ export class TaskExecutionService {
     let skillRuntimeSnapshot: SkillRuntimeSnapshotRow | null = null;
     try {
       skillRuntimeSnapshot = this.resolveSkillRuntimeSnapshot(orgId, agent.id, runId);
-      const chatContext = this.loadChatContext(orgId, isolation);
+      const chatContext = loadChatWakeContext(this.db, orgId, agent.id, isolation.secretScopeJson);
       const toolContext: AgentToolContext = {
         orgId,
         agent: { id: agent.id, modelProviderId: agent.model_provider_id, modelId: agent.model_id },
@@ -523,39 +523,6 @@ export class TaskExecutionService {
     return runId;
   }
 
-  private loadChatContext(orgId: string, isolation: TaskRunIsolation): ChatContextBlock | null {
-    let scope: { sourceMessageId?: string; sourceThreadId?: string };
-    try {
-      scope = JSON.parse(isolation.secretScopeJson);
-    } catch {
-      return null;
-    }
-    if (!scope.sourceThreadId) return null;
-    const thread = this.db.prepare("select space_id from chat_threads where id = ? and org_id = ?")
-      .get(scope.sourceThreadId, orgId) as { space_id: string } | undefined;
-    if (!thread) return null;
-    const messages = this.db.prepare(`
-      select m.body_md, m.sender_type, m.sender_id,
-             coalesce(a.name, e.display_name, m.sender_type) as sender_name
-      from chat_messages m
-      left join agents a on a.id = m.sender_id and m.sender_type = 'agent'
-      left join employees e on e.id = m.sender_id and m.sender_type = 'employee'
-      where m.thread_id = ? and m.org_id = ?
-      order by m.created_at asc
-      limit 20
-    `).all(scope.sourceThreadId, orgId) as Array<{ body_md: string; sender_type: string; sender_name: string }>;
-    if (messages.length === 0) return null;
-    // Human principals are marked as the founder: an agent replying to its
-    // boss must know it is not talking to another agent.
-    const label = (m: { sender_type: string; sender_name: string }) =>
-      m.sender_type === "employee" || m.sender_type === "board" ? `${m.sender_name} (founder)` : m.sender_name;
-    return {
-      threadId: scope.sourceThreadId,
-      spaceId: thread.space_id,
-      transcript: messages.map((m) => `[${label(m)}]: ${m.body_md}`).join("\n"),
-    };
-  }
-
   private completedRunCount(taskId: string, excludingRunId: string): number {
     const row = this.db.prepare("select count(*) as n from task_runs where task_id = ? and state = 'completed' and id <> ?")
       .get(taskId, excludingRunId) as { n: number };

src/main/services/task-prompts.ts

@@ -71,7 +71,10 @@ export interface ChatContextBlock {
   threadId: string;
   /** The space the thread lives in — where the run's reply must land. */
   spaceId: string;
-  transcript: string;
+  /** Messages up to and including the agent's last reply. */
+  history: string;
+  /** Messages after it: what this run answers. */
+  fresh: string;
 }
 
 export interface AgentInstructionContext {
@@ -211,8 +214,11 @@ export function buildTaskPrompt(input: {
   if (input.chatContext) {
     lines.push(
       "",
-      "The conversation in this thread so far:",
+      "Earlier in this thread (context only — newer messages override it):",
-      input.chatContext.transcript,
+      input.chatContext.history || "(nothing before)",
+      "",
+      "New since your last reply in this thread — this is what you are answering:",
+      input.chatContext.fresh || "(nothing new since your last reply)",
       "",
       `You have been brought into this thread. Reply to the people here in your own voice — answer what they asked, give your honest take, push back if you disagree, or hand work over. Stay in the thread by passing thread_id="${input.chatContext.threadId}" to send_message. This is a conversation between colleagues, not a status report; only change a task's status if the work itself actually moved.`,
     );

tests/integration/ceo-founder-chat.test.ts

@@ -121,7 +121,7 @@ describe("founder⇄CEO chat", () => {
 
     // The CEO's prompt names the human principal, not just another teammate.
     expect(capturedWakePrompts).toHaveLength(1);
-    expect(capturedWakePrompts[0]).toContain("[Yang (founder)]: How are we tracking against the MVP?");
+    expect(capturedWakePrompts[0]).toMatch(/\] Yang \(employee, Board Chair\): How are we tracking against the MVP\?/);
 
     // The reply landed in the SAME pinned conversation and thread — to="Yang"
     // resolves the employee and ensureDirectSpace reuses the founder's line.

tests/integration/chat-context.test.ts

@@ -0,0 +1,102 @@
+import { randomUUID } from "node:crypto";
+import { tmpdir } from "node:os";
+import { join } from "node:path";
+import { describe, expect, test } from "vitest";
+import { DatabaseConnection } from "../../src/main/database/connection";
+import { OnboardingService } from "../../src/main/services/onboarding-service";
+import { ProviderService } from "../../src/main/services/provider-service";
+import { providerAdapters } from "../../src/main/services/provider-adapters";
+import { TaskExecutionService } from "../../src/main/services/task-execution-service";
+import { ChatService } from "../../src/main/services/chat-service";
+import { ensureCeoDirectSpace } from "../../src/main/services/ceo-direct-space";
+import { claimNextQueuedRun } from "../../src/main/app/task-queue-worker";
+import type { AgentTurnResult, ProviderToolTurnInput } from "../../src/main/services/provider-tool-turn";
+
+const testVault = {
+  encryptSecret: (secret: string) => Buffer.from(secret, "utf8"),
+  decryptSecret: (ciphertext: Buffer) => ciphertext.toString("utf8"),
+};
+
+async function founderLine() {
+  const wakePrompts: string[] = [];
+  const turn = async (input: ProviderToolTurnInput): Promise<AgentTurnResult> => {
+    const first = input.messages.find((message) => message.role === "user");
+    const prompt = first && first.role === "user" ? first.text : "";
+    if (/thread_id="/.test(prompt) && input.messages.length === 1) wakePrompts.push(prompt);
+    return { text: `Reply ${wakePrompts.length}.`, toolCalls: [], rawResponseJson: "{}" };
+  };
+  const connection = new DatabaseConnection(join(tmpdir(), `ac-chatctx-${randomUUID()}.db`));
+  const providers = new ProviderService(connection.db, providerAdapters, testVault, undefined, turn);
+  const onboarding = new OnboardingService({ db: connection.db, saveProviderCredential: (input) => providers.saveCredential(input) });
+  const execution = new TaskExecutionService(connection.db, providers);
+  const chat = new ChatService(connection.db);
+  let orgId = "";
+  let ceoId = "";
+  connection.transaction(() => {
+    const summary = onboarding.bootstrap({
+      companyName: "FlowPilot", companyDescription: "CSM analytics.", employeeName: "Yang", workspacePath: "",
+      executionMode: "ai_ceo", autoApproveHires: true, reviewDeliverables: false,
+      goalTitle: "Ship the MVP.", goalDescription: "A working product.",
+      providerKey: "openai", providerSecret: "sk-test-key", providerModel: "gpt-5.4",
+    });
+    orgId = summary.orgId;
+    ceoId = summary.ceoAgentId;
+  });
+  const founderId = (connection.db.prepare("select id from employees where org_id = ?").get(orgId) as { id: string }).id;
+  const spaceId = ensureCeoDirectSpace(connection.db, orgId)!;
+  const kickoff = claimNextQueuedRun(connection);
+  await execution.executeRun(kickoff!.org_id, kickoff!.id);
+  const say = (bodyMd: string, threadId: string | null) => {
+    const id = chat.sendMessage({ orgId, spaceId, threadId, senderType: "employee", senderId: founderId, bodyMd, attachmentFileIds: [] });
+    return (connection.db.prepare("select thread_id from chat_messages where id = ?").get(id) as { thread_id: string }).thread_id;
+  };
+  const runWake = async () => {
+    const wake = connection.db.prepare(
+      "select id from task_runs where org_id = ? and agent_id = ? and trigger = 'chat_mention' and state = 'queued'",
+    ).get(orgId, ceoId) as { id: string };
+    await execution.executeRun(orgId, wake.id);
+  };
+  const edit = (bodyMd: string, newBody: string) => {
+    const row = connection.db.prepare("select id from chat_messages where body_md = ?").get(bodyMd) as { id: string };
+    chat.editMessage({ orgId, messageId: row.id, bodyMd: newBody, actorType: "employee", actorId: founderId });
+  };
+  return { connection, wakePrompts, say, runWake, edit };
+}
+
+describe("chat wake context", () => {
+  test("separates what the agent already answered from what is new, with times and senders", async () => {
+    const h = await founderLine();
+    const threadId = h.say("How are we tracking?", null);
+    await h.runWake();
+    h.say("Also, who owns billing?", threadId);
+    h.say("And ship date?", threadId);
+    await h.runWake();
+
+    const prompt = h.wakePrompts[1];
+    const earlier = prompt.slice(prompt.indexOf("Earlier in this thread"), prompt.indexOf("New since your last reply"));
+    const fresh = prompt.slice(prompt.indexOf("New since your last reply"));
+    expect(earlier).toContain("How are we tracking?");
+    expect(earlier).toContain("Reply 1.");
+    expect(fresh).toContain("Also, who owns billing?");
+    expect(fresh).toContain("And ship date?");
+    expect(fresh).not.toContain("How are we tracking?");
+    expect(fresh).toMatch(/\[\d{4}-\d{2}-\d{2} \d{2}:\d{2} UTC\] Yang \(employee, Board Chair\)/);
+    expect(earlier).toMatch(/\] CEO \(agent, [^)]+\): Reply 1\./);
+    h.connection.close();
+  });
+
+  test("a message corrected after the agent's reply counts as new", async () => {
+    const h = await founderLine();
+    const threadId = h.say("Ship on Monday.", null);
+    await h.runWake();
+    h.edit("Ship on Monday.", "Ship on Friday.");
+    h.say("See the correction above.", threadId);
+    await h.runWake();
+
+    const prompt = h.wakePrompts[1];
+    const fresh = prompt.slice(prompt.indexOf("New since your last reply"));
+    expect(fresh).toMatch(/Yang \(employee, Board Chair\) \(edited \d{4}-\d{2}-\d{2} \d{2}:\d{2} UTC\): Ship on Friday\./);
+    expect(fresh).not.toContain("Reply 1.");
+    h.connection.close();
+  });
+});