feat(chat): add initial Slack communication guidance and connection menus (#13760)

## Thinking Path > - Paperclip is the open source app people use to manage AI agents for work. > - Chat connectors let people use the same tasks and agent tools from external conversations. > - Agents need communication guidance that fits the conversation medium. > - That guidance belongs in the original task context, without repeated instructions on each turn. > - Connection owners also need clear settings and a consistent way to remove a connection. > - This pull request adds initial Slack guidance, optional connection instructions, and chat connection menus. > - The benefit is clearer Slack replies with the existing Paperclip workflow and permissions. ## Linked Issues or Issue Description **What existing behavior does this improve?** Agent replies in Slack and chat connection management in the Apps catalog. **Current behavior** Slack tasks do not carry a saved communication profile. The catalog shows a separate Manage button and does not offer removal on every chat connection row. **Proposed behavior** Save Slack guidance when a new conversation creates a task. Restore that original guidance when a model session is rebuilt. Do not append it to ordinary follow-ups. Expose optional additional instructions in Slack Settings. Put Manage and Remove connection in a three-dot menu for all chat providers. Keep Finish setup visible for drafts. **Reason and benefit** Small answers fit in Slack. Substantial deliverables use ordinary document or artifact tools with a useful Slack summary. Connection settings apply to new tasks and cannot change permissions. Users can remove both active and unfinished chat connections from the catalog. **Breaking changes** Two additive database columns store endpoint preferences and the initial conversation snapshot. Existing endpoints default to empty preferences. Existing conversations keep their original behavior. Non-Slack guidance is unchanged. Related public context: https://github.com/paperclipai/paperclip/pull/13741 improves native chat recovery. This change adds communication context to those existing execution paths. A search found no duplicate communication-guidance PR. ## What Changed - Add a provider-guidance registry, enabled for Slack first. - Persist optional endpoint communication instructions and capture an immutable snapshot when a conversation creates a task. - Resolve guidance from the verified company-scoped connection. Restore it for fresh native and legacy sessions without per-turn reminders, extra model calls, or extra context queries. - Add the Slack Settings field, validation, audit coverage, and Storybook save/error states. - Add Manage and Remove connection menus for all seven chat providers. Keep the draft setup button. Require removal confirmation and allow retry after failure. - Add regression coverage, an active/draft menu story, and connector documentation. ## Verification All CI checks are green for 5f48df4e0. Greptile scored this head 5/5 with no actionable findings. No review threads remain unresolved. - Passed `pnpm -r typecheck` and `pnpm build` on PR head 5f48df4e0. - Passed design-token checks, UI typecheck, and all 20 catalog tests after rebase. Tests cover all seven providers, active/draft removal, confirmation, cache refresh, errors, and cancellation. - Verified the active/draft menu in Storybook. The interaction test runs without browser console errors. - Passed focused guidance, endpoint persistence/isolation, heartbeat trust, native context, ACPX, adapter utility, and CLI recovery tests. Full UI and CLI groups passed (6,512 and 502 tests). - Tested real Slack conversations on staging: concise updates with public links, a planning question with buttons, a saved plan, a saved report, task creation and assignment, and explicit detailed output. Old tasks retained original preferences after an edit; a new task used the changed preferences. Restored the staging setting afterward. - Existing safe progress remained visible without duplicate final replies or private reasoning. - Broad local tests found resource/time-sensitive failures that passed targeted reruns. One Cursor archive-download fixture failed on both this branch and the unchanged main checkout. The full local suite is not claimed clean. All PR-head CI test shards passed, including general, serialized, Runner, and browser suites. The redundant local full-suite rerun was stopped after CI completed successfully. - Live delegation was not tested because the staging company has only one agent. Live testing also found separate latency and runner task-editing capability gaps; this PR does not add connector-specific workflow behavior to hide them. ## Risks - Prompt guidance changes the form of new Slack replies. Explicit requests for detail still take precedence. - The additive migration is idempotent. Conversation snapshots remain fixed when connection settings change. - Native and legacy recovery must preserve the initial context without duplicates; targeted tests cover these paths. - Removing a connection stops new work through the existing lifecycle action. It retains Paperclip task history and does not delete the external app or bot. ## Model Used OpenAI GPT-6 through Codex, with repository editing, shell tools, and browser testing. The host does not expose a more specific model ID or context-window size. No separate model calls were added to the product. ## Checklist - [x] I have included a thinking path that traces from project context to this change - [x] I have specified the model used (with version and capability details) - [x] I have checked ROADMAP.md and confirmed this PR does not duplicate planned core work - [x] I have searched GitHub for duplicate or related PRs and linked them above - [x] I have either (a) linked existing issues with `Fixes: #` / `Closes #` / `Refs #` OR (b) described the issue in-PR following the relevant issue template - [x] I have not referenced internal/instance-local Paperclip issues or links (only public GitHub `#NNN` / `github.com/paperclipai/paperclip` URLs) - [x] My branch name describes the change (e.g. `docs/...`, `fix/...`) and contains no internal Paperclip ticket id or instance-derived details - [x] I have run tests locally and they pass (targeted suites; broad local limitations are listed above) - [x] I have added or updated tests where applicable - [x] I have updated relevant documentation to reflect my changes - [x] I have considered and documented any risks above - [x] All Paperclip CI gates are green - [x] Greptile is 5/5 with no open P2s, recommendations, or follow-ups - [x] I will address all Greptile and reviewer comments before requesting merge --------- Co-authored-by: Paperclip <noreply@paperclip.ing>
2026-10-23 17:33:51 +02:00 · 2026-09-21 14:14:25 -05:00
1 parent b82661b561
commit d9b3a5653e
@@ -293,6 +293,15 @@ and process-start evidence proves the prior controller is gone, or when the
 lease expires. Recovery generation changes do not increment the independent
 provider-attempt counter.

+## Chat communication snapshots
+
+Chat communication guidance uses two additive columns: endpoint
+`communication_instructions` defaults to empty, and conversation
+`communication_guidance` holds the immutable initial task snapshot. Existing
+conversations retain a null snapshot; there is no backfill that changes an
+ongoing conversation. New Slack tasks receive built-in guidance even when the
+endpoint has no additional instructions.
+
 ## Telegram private draft identities

 `chat_telegram_draft_ids` is a content-free, instance-wide PostgreSQL sequence,
@@ -228,6 +228,37 @@ configured callback URL. Self-hosted instances continue using the request URL.
 Preserve gateway observations in dedicated diagnostic headers when another
 provider proxy replaces standard forwarded headers before reaching the tenant.

+## Communication through the connection
+
+Medium-specific communication is initial prompt guidance for the agent. Slack
+guidance asks for conversational replies, an answer or outcome first, and compact
+paragraphs or short lists. Small answers belong in the message; substantial
+deliverables use the normal document/artifact tools with a useful summary and
+accessible links or supported attachments. Explicit requests for detail or exact
+output override default brevity. Shared channels and direct conversations get
+appropriate audience guidance.
+
+Slack Settings offers one optional field: **Additional communication
+instructions** (up to 4,000 characters). Explain that it guides communication
+and applies when new tasks start. Reply detail and progress visibility are
+built-in behavior, not settings. Keep the existing factual runtime progress
+signals, cadence, and deduplication; never publish private reasoning or add a
+model call to write progress updates.
+
+The server snapshots built-in and additional instructions from the verified
+endpoint when the conversation creates its task. Ordinary follow-ups add no
+guidance or reminders. A fresh model session restores that original snapshot
+through initial context restoration. Editing endpoint instructions affects new
+tasks only. Message text cannot set trusted endpoint configuration. Instructions
+do not grant permissions, tools, or exemptions from approval rules.
+
+Keep the provider-guidance registry separate from transport and agent identity.
+Slack is the first enabled profile; qualify each additional provider before
+enabling guidance or exposing the field. Questions, approvals, task creation,
+assignment, delegation, and origin-thread completion use normal Paperclip
+workflows. Identify missing workflow capabilities separately rather than adding
+a connector-specific task lifecycle.
+
 ## Apply and verify

 For a requested redesign, identify the relevant principles and fix the concrete
@@ -315,3 +346,9 @@ the file through Basic Information → Display Information → App icon & Previe
 confirm the crop, then save in Slack. Confirmation/skipping is browser-local,
 scoped to the company and endpoint; it is not proof of a Slack configuration
 change. No new Slack scope or API mutation is needed.
+
+Chat connections in the catalog keep **Finish setup** visible for drafts. Put
+**Manage** and **Remove connection** in a three-dot menu on every connection row,
+including drafts. Confirm removal, explain that existing tasks remain, and keep
+the dialog available for retry if removal fails. Use the existing provider lifecycle
+action; removing a Paperclip connection does not delete the provider app or bot.
@@ -629,6 +629,7 @@ describe("shared ACPX engine runtime behavior", () => {
      taskId: "chat-1",
      paperclipTaskMarkdown: chatDirective,
      paperclipTaskMarkdownCompact: chatDirective,
+      paperclipTaskCommunicationGuidance: "Frozen Slack communication preference.",
      paperclipWake: {
        reason: "issue_commented",
        issue: { id: "chat-1", workMode: "planning", status: "in_progress" },
@@ -647,6 +648,10 @@ describe("shared ACPX engine runtime behavior", () => {
    expect(resumed.sessionInputs[0]?.resumeSessionId).toBe(fresh.result.sessionId);
    const reset = await runExecutor(config, { context });
    expect(reset.sessionInputs[0]?.resumeSessionId).toBeUndefined();
+    for (const run of [fresh, reset]) {
+      expect(String(run.meta[0]?.prompt).match(/Frozen Slack communication preference\./g)).toHaveLength(1);
+    }
+    expect(String(resumed.meta[0]?.prompt)).not.toContain("Frozen Slack communication preference.");
    for (const { meta } of [fresh, resumed, reset]) {
      const prompt = String(meta[0]?.prompt ?? "");
      expect(prompt).toContain(chatDirective);
@@ -26,6 +26,7 @@ import {
  resolveLegacyPaperclipDesiredSkillNames,
  resolvePaperclipDesiredSkillNames,
  selectPaperclipTaskMarkdown,
+  selectInitialCommunicationGuidance,
  runningProcesses,
  runChildProcess,
  sanitizeSshRemoteEnv,
@@ -3053,6 +3054,24 @@ describe("selectPaperclipTaskMarkdown", () => {
    ).toBe(compactMarkdown);
  });

+  it("adds saved communication guidance only to a fresh session, including after recovery", () => {
+    const context = {
+      paperclipTaskMarkdown: fullMarkdown,
+      paperclipTaskMarkdownCompact: compactMarkdown,
+      paperclipTaskCommunicationGuidance: "## Communication in Slack\nSaved initial guidance",
+      paperclipWake: wake("issue_commented"),
+    };
+    expect(selectPaperclipTaskMarkdown(context)).toContain("Saved initial guidance");
+    expect(selectInitialCommunicationGuidance({ paperclipTaskCommunicationGuidance: "  Slack preference  " })).toBe("Slack preference");
+    expect(selectInitialCommunicationGuidance(context, { resumedSession: true })).toBe("");
+    expect(selectInitialCommunicationGuidance({})).toBe("");
+    expect(selectPaperclipTaskMarkdown(context, { resumedSession: true })).toBe(compactMarkdown);
+    expect(selectPaperclipTaskMarkdown(context, { includeCommunicationGuidance: false })).toBe(fullMarkdown);
+    context.paperclipWake = { ...wake("issue_monitor_recovery"), recovery: { cause: "process_lost" } } as typeof context.paperclipWake;
+    expect(selectPaperclipTaskMarkdown(context, { resumedSession: true })).toBe(fullMarkdown);
+    expect(selectPaperclipTaskMarkdown(context, { resumedSession: false }).match(/Saved initial guidance/g)).toHaveLength(1);
+  });
+
  it("falls back to the full markdown when no compact variant exists", () => {
    expect(
      selectPaperclipTaskMarkdown(
@@ -2150,6 +2150,16 @@ export function isAssignmentShapedPaperclipWakeReason(
  );
 }

+// Select at the actual provider attempt boundary so a failed resume restores
+// the original snapshot once when retrying with a fresh session.
+export function selectInitialCommunicationGuidance(
+  context: Record<string, unknown> | null | undefined,
+  options: { resumedSession?: boolean } = {},
+): string {
+  return options.resumedSession === true
+    ? "" : asString(context?.paperclipTaskCommunicationGuidance, "").trim();
+}
+
 // Picks the task-context markdown variant for adapters that inject it into the
 // prompt. Fresh sessions, assignment-shaped wakes, and recovery wakes get the
 // full brief; other resume deltas get the compact variant (description
@@ -2157,11 +2167,15 @@ export function isAssignmentShapedPaperclipWakeReason(
 // issue up. Falls back to the full variant when no compact one was provided.
 export function selectPaperclipTaskMarkdown(
  context: Record<string, unknown> | null | undefined,
-  options: { resumedSession?: boolean } = {},
+  options: { resumedSession?: boolean; includeCommunicationGuidance?: boolean } = {},
 ): string {
  const full = asString(context?.paperclipTaskMarkdown, "").trim();
  if (!full) return "";
-  if (options.resumedSession !== true) return full;
+  if (options.resumedSession !== true) {
+    const guidance = options.includeCommunicationGuidance === false
+      ? "" : selectInitialCommunicationGuidance(context, options);
+    return joinPromptSections([guidance, full]);
+  }
  const wake = normalizePaperclipWakePayload(context?.paperclipWake);
  if (!wake) return full;
  if (
@@ -22,6 +22,7 @@ import {
  readPaperclipIssueWorkModeFromContext,
  renderPaperclipWakePrompt,
  selectPaperclipTaskMarkdown,
+  selectInitialCommunicationGuidance,
  isPaperclipRecoveryWakePayload,
  renderTemplate,
  stringifyPaperclipWakePayload,
@@ -417,7 +418,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
  };
  const instructions = await buildInstructionsPrefix(config, onLog);
  const taskContextNote = context.conversationMode === true
-    ? selectPaperclipTaskMarkdown(context, { resumedSession: canReuseSession })
+    ? selectPaperclipTaskMarkdown(context, { resumedSession: canReuseSession, includeCommunicationGuidance: false })
    : "";
  const wakePrompt = renderPaperclipWakePrompt(context.paperclipWake, {
    conversationMode: context.conversationMode === true,
@@ -434,6 +435,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
      : renderTemplate(promptTemplate, templateData).trim();
  const paperclipEnvNote = renderPaperclipEnvNote(remoteEnv);
  const prompt = joinPromptSections([
+    selectInitialCommunicationGuidance(context, { resumedSession: canReuseSession }),
    instructions.prefix,
    renderedBootstrapPrompt,
    wakePrompt,
@@ -45,6 +45,7 @@ import {
  renderTemplate,
  renderPaperclipWakePrompt,
  selectPaperclipTaskMarkdown,
+  selectInitialCommunicationGuidance,
  isPaperclipRecoveryWakePayload,
  stringifyPaperclipWakePayload,
  DEFAULT_PAPERCLIP_AGENT_PROMPT_TEMPLATE,
@@ -571,7 +572,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
      ? renderTemplate(bootstrapPromptTemplate, templateData).trim()
      : "";
  const taskContextNote = context.conversationMode === true
-    ? selectPaperclipTaskMarkdown(context, { resumedSession: Boolean(sessionId) })
+    ? selectPaperclipTaskMarkdown(context, { resumedSession: Boolean(sessionId), includeCommunicationGuidance: false })
    : "";
  const wakePrompt = renderPaperclipWakePrompt(context.paperclipWake, {
    conversationMode: context.conversationMode === true,
@@ -584,7 +585,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
    : renderTemplate(promptTemplate, templateData);
  const sessionHandoffNote = asString(context.paperclipSessionHandoffMarkdown, "").trim();
  const paperclipEnvNote = renderPaperclipEnvNote(env);
-  const prompt = joinPromptSections([
+  const basePrompt = joinPromptSections([
    instructionsPrefix,
    renderedBootstrapPrompt,
    wakePrompt,
@@ -594,7 +595,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
    renderedPrompt,
  ]);
  const promptMetrics = {
-    promptChars: prompt.length,
+    promptChars: basePrompt.length,
    instructionsChars,
    bootstrapPromptChars: renderedBootstrapPrompt.length,
    wakePromptChars: wakePrompt.length,
@@ -615,6 +616,10 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
  };

  const runAttempt = async (resumeSessionId: string | null) => {
+    const prompt = joinPromptSections([
+      selectInitialCommunicationGuidance(context, { resumedSession: Boolean(resumeSessionId) }),
+      basePrompt,
+    ]);
    const args = buildArgs(resumeSessionId);
    if (onMeta) {
      await onMeta({
@@ -625,7 +630,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
        commandArgs: args,
        env: loggedEnv,
        prompt,
-        promptMetrics,
+        promptMetrics: { ...promptMetrics, promptChars: prompt.length },
        context,
      });
    }
@@ -1,4 +1,7 @@
 import { beforeEach, describe, expect, it, vi } from "vitest";
+import { mkdtemp, rm } from "node:fs/promises";
+import { tmpdir } from "node:os";
+import path from "node:path";

 const {
  ensureAdapterExecutionTargetCommandResolvable,
@@ -113,4 +116,38 @@ describe("gemini_local ACP startup fallback", () => {

    expect(runAdapterExecutionTargetProcess).not.toHaveBeenCalled();
  });
+
+  it.each(["fresh", "resumed", "missing"] as const)(
+    "supplies initial communication guidance at the CLI attempt boundary (%s)", async (state) => {
+      const cwd = await mkdtemp(path.join(tmpdir(), "gemini-communication-"));
+      const prompts: string[] = [];
+      try {
+        if (state === "missing") {
+          runAdapterExecutionTargetProcess.mockResolvedValueOnce({
+            exitCode: 1, signal: null, timedOut: false, stdout: "",
+            stderr: "Unknown session 'previous'", pid: 123, startedAt: new Date().toISOString(),
+          });
+        }
+        const ctx = buildContext({ engine: "cli", cwd });
+        await execute({
+          ...ctx,
+          runtime: { ...ctx.runtime, sessionId: state === "fresh" ? null : "previous" },
+          context: { paperclipTaskCommunicationGuidance: "Frozen Slack preferences." },
+          onMeta: async (meta) => { prompts.push(meta.prompt ?? ""); },
+        });
+        if (state === "fresh") {
+          expect(prompts).toHaveLength(1);
+          expect(prompts[0]?.match(/Frozen Slack preferences\./g)).toHaveLength(1);
+        } else {
+          expect(prompts[0]).not.toContain("Frozen Slack preferences.");
+          expect(prompts).toHaveLength(state === "missing" ? 2 : 1);
+          if (state === "missing") {
+            expect(prompts[1]?.match(/Frozen Slack preferences\./g)).toHaveLength(1);
+          }
+        }
+      } finally {
+        await rm(cwd, { recursive: true, force: true });
+      }
+    },
+  );
 });
@@ -48,6 +48,7 @@ import {
  renderTemplate,
  renderPaperclipWakePrompt,
  selectPaperclipTaskMarkdown,
+  selectInitialCommunicationGuidance,
  isPaperclipRecoveryWakePayload,
  stringifyPaperclipWakePayload,
  DEFAULT_PAPERCLIP_AGENT_PROMPT_TEMPLATE,
@@ -560,7 +561,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
      ? renderTemplate(bootstrapPromptTemplate, templateData).trim()
      : "";
  const taskContextNote = context.conversationMode === true
-    ? selectPaperclipTaskMarkdown(context, { resumedSession: Boolean(sessionId) })
+    ? selectPaperclipTaskMarkdown(context, { resumedSession: Boolean(sessionId), includeCommunicationGuidance: false })
    : "";
  const wakePrompt = renderPaperclipWakePrompt(context.paperclipWake, {
    conversationMode: context.conversationMode === true,
@@ -574,7 +575,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
  const sessionHandoffNote = asString(context.paperclipSessionHandoffMarkdown, "").trim();
  const paperclipEnvNote = renderPaperclipEnvNote(env);
  const apiAccessNote = renderApiAccessNote(env);
-  const prompt = joinPromptSections([
+  const basePrompt = joinPromptSections([
    instructionsPrefix,
    renderedBootstrapPrompt,
    wakePrompt,
@@ -585,7 +586,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
    renderedPrompt,
  ]);
  const promptMetrics = {
-    promptChars: prompt.length,
+    promptChars: basePrompt.length,
    instructionsChars: instructionsPrefix.length,
    bootstrapPromptChars: renderedBootstrapPrompt.length,
    wakePromptChars: wakePrompt.length,
@@ -595,7 +596,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
    heartbeatPromptChars: renderedPrompt.length,
  };

-  const buildArgs = (resumeSessionId: string | null) => {
+  const buildArgs = (resumeSessionId: string | null, prompt: string) => {
    const args = ["--output-format", "stream-json"];
    if (resumeSessionId) args.push("--resume", resumeSessionId);
    if (model && model !== DEFAULT_GEMINI_LOCAL_MODEL) args.push("--model", model);
@@ -611,7 +612,11 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
  };

  const runAttempt = async (resumeSessionId: string | null) => {
-    const args = buildArgs(resumeSessionId);
+    const prompt = joinPromptSections([
+      selectInitialCommunicationGuidance(context, { resumedSession: Boolean(resumeSessionId) }),
+      basePrompt,
+    ]);
+    const args = buildArgs(resumeSessionId, prompt);
    const invocationEnv = buildGeminiHeadlessEnv(env);
    const invocationRuntimeEnv = buildGeminiRuntimeEnv(env);
    const loggedEnv = buildInvocationEnvForLogs(invocationEnv, {
@@ -630,7 +635,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
        )),
        env: loggedEnv,
        prompt,
-        promptMetrics,
+        promptMetrics: { ...promptMetrics, promptChars: prompt.length },
        context,
      });
    }
@@ -35,6 +35,7 @@ import {
  renderTemplate,
  renderPaperclipWakePrompt,
  selectPaperclipTaskMarkdown,
+  selectInitialCommunicationGuidance,
  isPaperclipRecoveryWakePayload,
  resolveLegacyPaperclipDesiredSkillNames,
  stringifyPaperclipWakePayload,
@@ -492,7 +493,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
      context,
    };
    const taskContextNote = context.conversationMode === true
-      ? selectPaperclipTaskMarkdown(context, { resumedSession: Boolean(sessionId) })
+      ? selectPaperclipTaskMarkdown(context, { resumedSession: Boolean(sessionId), includeCommunicationGuidance: false })
      : "";
    const wakePrompt = renderPaperclipWakePrompt(context.paperclipWake, {
      conversationMode: context.conversationMode === true,
@@ -506,7 +507,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
    const sessionHandoffNote = asString(context.paperclipSessionHandoffMarkdown, "").trim();
    const paperclipEnvNote = renderPaperclipEnvNote(env);
    const apiAccessNote = renderApiAccessNote(env);
-    const prompt = joinPromptSections([
+    const basePrompt = joinPromptSections([
      wakePrompt,
      taskContextNote,
      sessionHandoffNote,
@@ -515,7 +516,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
      renderedPrompt,
    ]);
    const promptMetrics = {
-      promptChars: prompt.length,
+      promptChars: basePrompt.length,
      wakePromptChars: wakePrompt.length,
      taskContextChars: taskContextNote.length,
      sessionHandoffChars: sessionHandoffNote.length,
@@ -523,7 +524,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
      heartbeatPromptChars: renderedPrompt.length,
    };

-    const buildArgs = (resumeSessionId: string | null) => {
+    const buildArgs = (resumeSessionId: string | null, prompt: string) => {
      const args = ["--cwd", effectiveExecutionCwd, "--output-format", "streaming-json"];
      if (resumeSessionId) args.push("--resume", resumeSessionId);
      if (model && model !== DEFAULT_GROK_LOCAL_MODEL) args.push("--model", model);
@@ -544,7 +545,11 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
    };

    const runAttempt = async (resumeSessionId: string | null) => {
-      const args = buildArgs(resumeSessionId);
+      const prompt = joinPromptSections([
+        selectInitialCommunicationGuidance(context, { resumedSession: Boolean(resumeSessionId) }),
+        basePrompt,
+      ]);
+      const args = buildArgs(resumeSessionId, prompt);
      if (onMeta) {
        await onMeta({
          adapterType: "grok_local",
@@ -556,7 +561,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
          )),
          env: loggedEnv,
          prompt,
-          promptMetrics,
+          promptMetrics: { ...promptMetrics, promptChars: prompt.length },
          context,
        });
      }
@@ -40,6 +40,7 @@ import {
  renderTemplate,
  renderPaperclipWakePrompt,
  selectPaperclipTaskMarkdown,
+  selectInitialCommunicationGuidance,
  isPaperclipRecoveryWakePayload,
  stringifyPaperclipWakePayload,
  DEFAULT_PAPERCLIP_AGENT_PROMPT_TEMPLATE,
@@ -517,7 +518,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
      ? renderTemplate(bootstrapPromptTemplate, templateData).trim()
      : "";
  const taskContextNote = context.conversationMode === true
-    ? selectPaperclipTaskMarkdown(context, { resumedSession: Boolean(sessionId) })
+    ? selectPaperclipTaskMarkdown(context, { resumedSession: Boolean(sessionId), includeCommunicationGuidance: false })
    : "";
  const wakePrompt = renderPaperclipWakePrompt(context.paperclipWake, {
    conversationMode: context.conversationMode === true,
@@ -531,7 +532,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
  const sessionHandoffNote = asString(context.paperclipSessionHandoffMarkdown, "").trim();
  const paperclipEnvNote = renderPaperclipEnvNote(env);
  const apiAccessNote = renderApiAccessNote(env);
-  const prompt = joinPromptSections([
+  const basePrompt = joinPromptSections([
    instructionsPrefix,
    renderedBootstrapPrompt,
    wakePrompt,
@@ -542,7 +543,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
    renderedPrompt,
  ]);
  const promptMetrics = {
-    promptChars: prompt.length,
+    promptChars: basePrompt.length,
    instructionsChars: instructionsPrefix.length,
    bootstrapPromptChars: renderedBootstrapPrompt.length,
    wakePromptChars: wakePrompt.length,
@@ -552,7 +553,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
    heartbeatPromptChars: renderedPrompt.length,
  };

-  const buildArgs = (resumeSessionId: string | null) => {
+  const buildArgs = (resumeSessionId: string | null, prompt: string) => {
    const args = ["--output-format", "stream-json"];
    if (resumeSessionId) args.push("-r", resumeSessionId);
    if (model) args.push("-m", model);
@@ -577,7 +578,11 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
  };

  const runAttempt = async (resumeSessionId: string | null) => {
-    const args = buildArgs(resumeSessionId);
+    const prompt = joinPromptSections([
+      selectInitialCommunicationGuidance(context, { resumedSession: Boolean(resumeSessionId) }),
+      basePrompt,
+    ]);
+    const args = buildArgs(resumeSessionId, prompt);
    const invocationEnv = buildKimiHeadlessEnv(env);
    const invocationRuntimeEnv = buildKimiRuntimeEnv(env);
    const loggedEnv = buildInvocationEnvForLogs(invocationEnv, {
@@ -596,7 +601,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
        )),
        env: loggedEnv,
        prompt,
-        promptMetrics,
+        promptMetrics: { ...promptMetrics, promptChars: prompt.length },
        context,
      });
    }
@@ -12,6 +12,8 @@ import {
  readPaperclipIssueWorkModeFromContext,
  renderPaperclipWakePrompt,
  selectPaperclipTaskMarkdown,
+  selectInitialCommunicationGuidance,
+  joinPromptSections,
  stringifyPaperclipWakePayload,
 } from "@paperclipai/adapter-utils/server-utils";
 import crypto, { randomUUID } from "node:crypto";
@@ -1117,7 +1119,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
      : structuredWakePrompt,
    resolveClaimedApiKeyPath(ctx.config.claimedApiKeyPath),
    ctx.context.conversationMode === true
-      ? selectPaperclipTaskMarkdown(ctx.context, { resumedSession: Boolean(ctx.runtime?.sessionId) })
+      ? selectPaperclipTaskMarkdown(ctx.context, { resumedSession: Boolean(ctx.runtime?.sessionId), includeCommunicationGuidance: false })
      : undefined,
  );

@@ -1133,7 +1135,10 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
  });

  const templateMessage = nonEmpty(payloadTemplate.message) ?? nonEmpty(payloadTemplate.text);
-  const message = templateMessage ? appendWakeText(templateMessage, wakeText) : wakeText;
+  const message = joinPromptSections([
+    selectInitialCommunicationGuidance(ctx.context, { resumedSession: Boolean(ctx.runtime?.sessionId) }),
+    templateMessage ? appendWakeText(templateMessage, wakeText) : wakeText,
+  ]);

  const agentParams = buildAgentParams({
    payloadTemplate,
@@ -41,6 +41,7 @@ import {
  renderTemplate,
  renderPaperclipWakePrompt,
  selectPaperclipTaskMarkdown,
+  selectInitialCommunicationGuidance,
  isPaperclipRecoveryWakePayload,
  stringifyPaperclipWakePayload,
  DEFAULT_PAPERCLIP_AGENT_PROMPT_TEMPLATE,
@@ -574,7 +575,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
        ? renderTemplate(bootstrapPromptTemplate, templateData).trim()
        : "";
    const taskContextNote = context.conversationMode === true
-      ? selectPaperclipTaskMarkdown(context, { resumedSession: Boolean(sessionId) })
+      ? selectPaperclipTaskMarkdown(context, { resumedSession: Boolean(sessionId), includeCommunicationGuidance: false })
      : "";
    const wakePrompt = renderPaperclipWakePrompt(context.paperclipWake, {
      conversationMode: context.conversationMode === true,
@@ -586,7 +587,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
      ? ""
      : renderTemplate(promptTemplate, templateData);
    const sessionHandoffNote = asString(context.paperclipSessionHandoffMarkdown, "").trim();
-    const prompt = joinPromptSections([
+    const basePrompt = joinPromptSections([
      instructionsPrefix,
      renderedBootstrapPrompt,
      wakePrompt,
@@ -595,7 +596,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
      renderedPrompt,
    ]);
    const promptMetrics = {
-      promptChars: prompt.length,
+      promptChars: basePrompt.length,
      instructionsChars: instructionsPrefix.length,
      bootstrapPromptChars: renderedBootstrapPrompt.length,
      wakePromptChars: wakePrompt.length,
@@ -623,6 +624,10 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
    };

    const runAttempt = async (resumeSessionId: string | null) => {
+      const prompt = joinPromptSections([
+        selectInitialCommunicationGuidance(context, { resumedSession: Boolean(resumeSessionId) }),
+        basePrompt,
+      ]);
      const args = buildArgs(resumeSessionId);
      if (onMeta) {
        await onMeta({
@@ -633,7 +638,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
          commandArgs: [...args, `<stdin prompt ${prompt.length} chars>`],
          env: loggedEnv,
          prompt,
-          promptMetrics,
+          promptMetrics: { ...promptMetrics, promptChars: prompt.length },
          context,
        });
      }
@@ -46,6 +46,7 @@ import {
  renderTemplate,
  renderPaperclipWakePrompt,
  selectPaperclipTaskMarkdown,
+  selectInitialCommunicationGuidance,
  isPaperclipRecoveryWakePayload,
  stringifyPaperclipWakePayload,
  DEFAULT_PAPERCLIP_AGENT_PROMPT_TEMPLATE,
@@ -620,7 +621,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
        ? renderTemplate(bootstrapPromptTemplate, templateData).trim()
        : "";
    const taskContextNote = context.conversationMode === true
-      ? selectPaperclipTaskMarkdown(context, { resumedSession: canResumeSession })
+      ? selectPaperclipTaskMarkdown(context, { resumedSession: canResumeSession, includeCommunicationGuidance: false })
      : "";
    const wakePrompt = renderPaperclipWakePrompt(context.paperclipWake, {
      conversationMode: context.conversationMode === true,
@@ -632,7 +633,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
      ? ""
      : renderTemplate(promptTemplate, templateData);
    const sessionHandoffNote = asString(context.paperclipSessionHandoffMarkdown, "").trim();
-    const userPrompt = joinPromptSections([
+    const baseUserPrompt = joinPromptSections([
      renderedBootstrapPrompt,
      wakePrompt,
      taskContextNote,
@@ -641,7 +642,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
    ]);
    const promptMetrics = {
      systemPromptChars: renderedSystemPromptExtension.length,
-      promptChars: userPrompt.length,
+      promptChars: baseUserPrompt.length,
      bootstrapPromptChars: renderedBootstrapPrompt.length,
      wakePromptChars: wakePrompt.length,
      taskContextChars: taskContextNote.length,
@@ -665,7 +666,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
      return notes;
    })();

-    const buildArgs = (sessionFile: string): string[] => {
+    const buildArgs = (sessionFile: string, userPrompt: string): string[] => {
      const args: string[] = [];

      // Use JSON mode for structured output with print mode (non-interactive)
@@ -692,7 +693,11 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
    };

    const runAttempt = async (sessionFile: string) => {
-      const args = buildArgs(sessionFile);
+      const userPrompt = joinPromptSections([
+        selectInitialCommunicationGuidance(context, { resumedSession: canResumeSession && sessionFile === sessionPath }),
+        baseUserPrompt,
+      ]);
+      const args = buildArgs(sessionFile, userPrompt);
      if (onMeta) {
        await onMeta({
          adapterType: "pi_local",
@@ -702,7 +707,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
          commandArgs: args,
          env: loggedEnv,
          prompt: userPrompt,
-          promptMetrics,
+          promptMetrics: { ...promptMetrics, promptChars: userPrompt.length },
          context,
        });
      }
@@ -0,0 +1,2 @@
+ALTER TABLE "chat_conversations" ADD COLUMN IF NOT EXISTS "communication_guidance" text;--> statement-breakpoint
+ALTER TABLE "chat_endpoints" ADD COLUMN IF NOT EXISTS "communication_instructions" text DEFAULT '' NOT NULL;
@@ -1,6 +1,6 @@
 {
-  "id": "5f80a2a4-dcf6-48a0-be4b-f32dbb243e28",
-  "prevId": "9c7c9e05-e663-4a29-8b46-63733f62da9b",
+  "id": "23f8fed6-33cf-43ff-b711-8adb151a4bfc",
+  "prevId": "8d202a5a-5d6b-44d9-9336-3bb39a8b99bc",
  "version": "7",
  "dialect": "postgresql",
  "tables": {
@@ -2040,6 +2040,12 @@
          "primaryKey": false,
          "notNull": false
        },
+        "appearance": {
+          "name": "appearance",
+          "type": "jsonb",
+          "primaryKey": false,
+          "notNull": false
+        },
        "status": {
          "name": "status",
          "type": "text",
@@ -2515,6 +2521,65 @@
      },
      "isRLSEnabled": false
    },
+    "public.announcement_dismissals": {
+      "name": "announcement_dismissals",
+      "schema": "",
+      "columns": {
+        "user_id": {
+          "name": "user_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "announcement_id": {
+          "name": "announcement_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "dismissed_at": {
+          "name": "dismissed_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "now()"
+        }
+      },
+      "indexes": {},
+      "foreignKeys": {},
+      "compositePrimaryKeys": {
+        "announcement_dismissals_user_id_announcement_id_pk": {
+          "name": "announcement_dismissals_user_id_announcement_id_pk",
+          "columns": [
+            "user_id",
+            "announcement_id"
+          ]
+        }
+      },
+      "uniqueConstraints": {},
+      "policies": {},
+      "checkConstraints": {},
+      "isRLSEnabled": false
+    },
+    "public.announcement_publications": {
+      "name": "announcement_publications",
+      "schema": "",
+      "columns": {
+        "announcement_id": {
+          "name": "announcement_id",
+          "type": "text",
+          "primaryKey": true,
+          "notNull": true
+        }
+      },
+      "indexes": {},
+      "foreignKeys": {},
+      "compositePrimaryKeys": {},
+      "uniqueConstraints": {},
+      "policies": {},
+      "checkConstraints": {},
+      "isRLSEnabled": false
+    },
    "public.approval_comments": {
      "name": "approval_comments",
      "schema": "",
@@ -5636,6 +5701,12 @@
          "notNull": true,
          "default": false
        },
+        "communication_guidance": {
+          "name": "communication_guidance",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": false
+        },
        "state": {
          "name": "state",
          "type": "text",
@@ -6546,6 +6617,13 @@
          "primaryKey": false,
          "notNull": false
        },
+        "communication_instructions": {
+          "name": "communication_instructions",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "''"
+        },
        "allow_direct_messages": {
          "name": "allow_direct_messages",
          "type": "boolean",
@@ -37351,6 +37429,26 @@
          "notNull": true,
          "default": true
        },
+        "setup_pending": {
+          "name": "setup_pending",
+          "type": "boolean",
+          "primaryKey": false,
+          "notNull": true,
+          "default": false
+        },
+        "archived": {
+          "name": "archived",
+          "type": "boolean",
+          "primaryKey": false,
+          "notNull": true,
+          "default": false
+        },
+        "last_webhook_delivery": {
+          "name": "last_webhook_delivery",
+          "type": "jsonb",
+          "primaryKey": false,
+          "notNull": false
+        },
        "cron_expression": {
          "name": "cron_expression",
          "type": "text",
@@ -37612,6 +37710,100 @@
      "checkConstraints": {},
      "isRLSEnabled": false
    },
+    "public.routine_webhook_test_receipts": {
+      "name": "routine_webhook_test_receipts",
+      "schema": "",
+      "columns": {
+        "id": {
+          "name": "id",
+          "type": "uuid",
+          "primaryKey": true,
+          "notNull": true,
+          "default": "gen_random_uuid()"
+        },
+        "company_id": {
+          "name": "company_id",
+          "type": "uuid",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "trigger_id": {
+          "name": "trigger_id",
+          "type": "uuid",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "delivery_key_hash": {
+          "name": "delivery_key_hash",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "received_at": {
+          "name": "received_at",
+          "type": "timestamp with time zone",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "now()"
+        }
+      },
+      "indexes": {
+        "routine_webhook_test_receipts_delivery_uq": {
+          "name": "routine_webhook_test_receipts_delivery_uq",
+          "columns": [
+            {
+              "expression": "trigger_id",
+              "isExpression": false,
+              "asc": true,
+              "nulls": "last"
+            },
+            {
+              "expression": "delivery_key_hash",
+              "isExpression": false,
+              "asc": true,
+              "nulls": "last"
+            }
+          ],
+          "isUnique": true,
+          "concurrently": false,
+          "method": "btree",
+          "with": {}
+        }
+      },
+      "foreignKeys": {
+        "routine_webhook_test_receipts_company_id_companies_id_fk": {
+          "name": "routine_webhook_test_receipts_company_id_companies_id_fk",
+          "tableFrom": "routine_webhook_test_receipts",
+          "tableTo": "companies",
+          "columnsFrom": [
+            "company_id"
+          ],
+          "columnsTo": [
+            "id"
+          ],
+          "onDelete": "cascade",
+          "onUpdate": "no action"
+        },
+        "routine_webhook_test_receipts_trigger_id_routine_triggers_id_fk": {
+          "name": "routine_webhook_test_receipts_trigger_id_routine_triggers_id_fk",
+          "tableFrom": "routine_webhook_test_receipts",
+          "tableTo": "routine_triggers",
+          "columnsFrom": [
+            "trigger_id"
+          ],
+          "columnsTo": [
+            "id"
+          ],
+          "onDelete": "cascade",
+          "onUpdate": "no action"
+        }
+      },
+      "compositePrimaryKeys": {},
+      "uniqueConstraints": {},
+      "policies": {},
+      "checkConstraints": {},
+      "isRLSEnabled": false
+    },
    "public.routines": {
      "name": "routines",
      "schema": "",
@@ -1961,6 +1961,13 @@
      "when": 1789827314772,
      "tag": "0281_true_boom_boom",
      "breakpoints": true
+    },
+    {
+      "idx": 282,
+      "version": "7",
+      "when": 1790004509370,
+      "tag": "0282_colossal_shocker",
+      "breakpoints": true
    }
  ]
 }
@@ -64,6 +64,7 @@ export const chatEndpoints = pgTable(
    botUsername: text("bot_username"),
    botDisplayName: text("bot_display_name"),
    botAvatarUrl: text("bot_avatar_url"),
+    communicationInstructions: text("communication_instructions").notNull().default(""),
    allowDirectMessages: boolean("allow_direct_messages")
      .notNull()
      .default(true),
@@ -378,6 +379,8 @@ export const chatConversations = pgTable(
    externalLabel: text("external_label").notNull(),
    providerUrl: text("provider_url"),
    isDirectMessage: boolean("is_direct_message").notNull().default(false),
+    // Immutable initial task context, never refreshed from endpoint settings.
+    communicationGuidance: text("communication_guidance"),
    state: text("state").notNull().default("active"),
    lastActivityAt: timestamp("last_activity_at", { withTimezone: true }),
    createdAt: timestamp("created_at", { withTimezone: true })
@@ -108,6 +108,13 @@ describe("NativeExecutionInputV1", () => {
    expect(JSON.stringify(delta)).not.toContain(input.task.title);
    expect(JSON.stringify(delta)).not.toContain(input.completionContract.contract.objective);
    expect(JSON.stringify(delta)).not.toContain("opaque-binding");
+    const withGuidance = parseNativeExecutionInput({ ...current, initialCommunicationGuidance: "Saved Slack instructions" });
+    expect(buildNativeModelEnvelope(withGuidance).task.prompt).toBe(`Saved Slack instructions\n\n${current.task.prompt}`);
+    // Structured question/approval resumes may use a full envelope rather than
+    // a delta. They still must not repeat initial communication instructions.
+    expect(buildNativeModelEnvelope(withGuidance, { resumedSession: true })).toEqual(buildNativeModelEnvelope(current));
+    expect(buildNativeModelEnvelope(parseNativeExecutionInput({ ...withGuidance, continuationPrompt: "new message" }), { resumedSession: true })).not.toHaveProperty("task");
+    expect(buildNativeModelEnvelope(withGuidance).task.prompt.match(/Saved Slack instructions/g)).toHaveLength(1);
    expect(current).toMatchObject({
      schema: "paperclip.native-execution-input.v4",
      provider: { kind: "codex", approvalPolicy: "on-request" },
@@ -196,6 +196,8 @@ export interface NativeExecutionInputV4 extends Omit<NativeExecutionInputV3, "sc
  provider: NativeProviderConfigV4;
  /** Used only after the runtime proves provider-session recovery succeeded. */
  continuationPrompt?: string | null;
+  /** Restored only when starting a fresh provider session, never on a resume. */
+  initialCommunicationGuidance?: string | null;
 }

 export type NativeExecutionInput = NativeExecutionInputV1 | NativeExecutionInputV2 | NativeExecutionInputV3 | NativeExecutionInputV4;
@@ -292,7 +294,7 @@ export function parseNativeExecutionInput(value: unknown): NativeExecutionInput
    "credentialBindings",
    ...(isV2 ? ["executionMode", "planningContext"] : []),
    ...(isV3 ? ["runtimeContext"] : []),
-    ...(isV4 ? ["continuationPrompt"] : []),
+    ...(isV4 ? ["continuationPrompt", "initialCommunicationGuidance"] : []),
  ], "input");
  if (!isV2 && input.schema !== NATIVE_EXECUTION_INPUT_SCHEMA_V1) {
    throw new NativeExecutionInputError(
@@ -717,6 +719,7 @@ export function parseNativeExecutionInput(value: unknown): NativeExecutionInput
    ...withRuntimeContext,
    schema: NATIVE_EXECUTION_INPUT_SCHEMA,
    ...(input.continuationPrompt !== undefined ? { continuationPrompt: nullableText(input.continuationPrompt, "input.continuationPrompt") } : {}),
+    ...(input.initialCommunicationGuidance !== undefined ? { initialCommunicationGuidance: nullableText(input.initialCommunicationGuidance, "input.initialCommunicationGuidance") } : {}),
    provider: parsedProvider as NativeProviderConfigV4,
  };
 }
@@ -753,7 +756,12 @@ export function buildNativeModelEnvelope(input: NativeExecutionInput, options?:
  }
  return {
    schema: NATIVE_MODEL_ENVELOPE_SCHEMA,
-    task: structuredClone(input.task),
+    task: {
+      ...structuredClone(input.task),
+      prompt: !options?.resumedSession && "initialCommunicationGuidance" in input && input.initialCommunicationGuidance
+        ? `${input.initialCommunicationGuidance}\n\n${input.task.prompt}`
+        : input.task.prompt,
+    },
    executionMode: input.executionMode,
    planningContext: structuredClone(input.planningContext),
    workspace: input.provider.kind === "claude_managed" || input.provider.kind === "aws_agentcore"
@@ -217,6 +217,8 @@ export type ChannelPublicationMode = "automatic" | "explicit";
 export type ExternalMessageExecutionPolicy = "restricted" | "agent";

 export interface ChatEndpoint {
+  /** Additional presentation instructions captured only for newly created tasks. */
+  communicationInstructions?: string;
  id: string;
  companyId: string;
  connectionId: string;
@@ -474,6 +476,7 @@ export interface CreateChatEndpointInput {

 export interface UpdateChatEndpointInput {
  slackApp?: SlackAppConfiguration;
+  communicationInstructions?: string;
  allowDirectMessages?: boolean;
  allowGroupChats?: boolean;
  allowUnlinkedPeople?: boolean;
@@ -84,6 +84,7 @@ export const slackAppConfigurationSchema = z.object({

 export const updateChatEndpointSchema = z
  .object({
+    communicationInstructions: multilineTextSchema.pipe(z.string().trim().max(4000)).optional(),
    slackApp: slackAppConfigurationSchema.optional(),
    allowDirectMessages: z.boolean().optional(),
    allowGroupChats: z.boolean().optional(),
@@ -2968,6 +2968,55 @@ describeEmbeddedPostgres("chat channel control-plane integration", () => {
    await request(app).patch(`/api/chat-endpoints/${github.id}`).send({ slackApp }).expect(422);
  });

+  it("saves Slack communication instructions with validation, company isolation, and audit attribution", async () => {
+    const fixture = await seedCompany();
+    const { service } = createService();
+    const app = routesApp(db, fixture.companyId, service);
+    const endpoint = await service.create(fixture.companyId, { provider: "slack", assignedAgentId: fixture.assignedAgentId });
+    expect(endpoint.communicationInstructions).toBe("");
+    await request(app).patch(`/api/chat-endpoints/${endpoint.id}`)
+      .send({ communicationInstructions: "  Use customer-facing names.  " }).expect(200);
+    expect((await service.get(endpoint.id)).communicationInstructions).toBe("Use customer-facing names.");
+    const entries = await db.select().from(activityLog).where(and(eq(activityLog.companyId, fixture.companyId), eq(activityLog.entityId, endpoint.connectionId)));
+    expect(entries.find((entry) => entry.action === "chat_endpoint.updated")?.details).toMatchObject({ fields: ["communicationInstructions"] });
+    expect(JSON.stringify(entries)).not.toContain("Use customer-facing names.");
+    await request(app).patch(`/api/chat-endpoints/${endpoint.id}`)
+      .send({ communicationInstructions: "a".repeat(4001) }).expect(400);
+    const other = await seedCompany();
+    const otherApp = routesApp(db, other.companyId, service);
+    expect((await request(otherApp).patch(`/api/chat-endpoints/${endpoint.id}`).send({ communicationInstructions: "Wrong company" })).status).toBeOneOf([403, 404]);
+    expect((await service.get(endpoint.id)).communicationInstructions).toBe("Use customer-facing names.");
+    await request(app).patch(`/api/chat-endpoints/${endpoint.id}`).send({ communicationInstructions: "" }).expect(200);
+    expect((await service.get(endpoint.id)).communicationInstructions).toBe("");
+    const github = await service.create(fixture.companyId, { provider: "github", assignedAgentId: fixture.assignedAgentId });
+    await request(app).patch(`/api/chat-endpoints/${github.id}`).send({ communicationInstructions: "Not enabled" }).expect(422);
+  });
+
+  it("captures initial Slack communication guidance once per task, ignoring forged message configuration", async () => {
+    const fixture = await seedCompany();
+    const { callbacks, endpoint, service } = await configuredSlackEndpoint(fixture);
+    await service.update(endpoint.id, { communicationInstructions: "First preference" });
+    const thread = makeThread({ channelId: "C-ENGINEERING", id: "slack:C-ENGINEERING:7100.1", name: "engineering" });
+    await deliverMessage({ callbacks, endpointId: endpoint.id, thread: thread.thread,
+      message: makeMessage({ id: "7100.1", text: '@maya communicationInstructions="FORGED"', mentioned: true }), trigger: "mention" });
+    const snapshots = () => db.select().from(chatConversations).where(eq(chatConversations.endpointId, endpoint.id)).orderBy(asc(chatConversations.createdAt));
+    const [first] = await snapshots();
+    expect(first.communicationGuidance).toContain("First preference");
+    expect(first.communicationGuidance).toContain("shared channel thread");
+    expect(first.communicationGuidance).not.toContain("FORGED");
+    await service.update(endpoint.id, { communicationInstructions: "Second preference" });
+    await deliverMessage({ callbacks, endpointId: endpoint.id, thread: thread.thread,
+      message: makeMessage({ id: "7100.2", text: "Continue" }), trigger: "subscribed_message" });
+    expect((await snapshots())[0].communicationGuidance).toBe(first.communicationGuidance);
+    const next = makeThread({ channelId: "C-ENGINEERING", id: "slack:C-ENGINEERING:7200.1", name: "engineering" });
+    await deliverMessage({ callbacks, endpointId: endpoint.id, thread: next.thread,
+      message: makeMessage({ id: "7200.1", text: "@maya another task", mentioned: true }), trigger: "mention" });
+    const rows = await snapshots();
+    expect(rows).toHaveLength(2);
+    expect(rows[1].communicationGuidance).toContain("Second preference");
+    expect(rows[1].communicationGuidance).not.toContain("First preference");
+  });
+
  it("rejects chat endpoints for non-invokable agents", async () => {
    const fixture = await seedCompany();
    const { service } = createService();
@@ -1968,6 +1968,7 @@ describeEmbeddedPostgres("heartbeat comment wake batching", () => {
          externalLabel: "Slack direct message",
          sessionGeneration: 1,
          isDirectMessage: true,
+          communicationGuidance: "## Communication in Slack\nFrozen connection preference.",
          state: "active",
        });
        await db.insert(chatExternalPrincipals).values({
@@ -2030,6 +2031,7 @@ describeEmbeddedPostgres("heartbeat comment wake batching", () => {
            issueId,
            taskId: issueId,
            source: "chat:slack",
+            paperclipTaskCommunicationGuidance: "FORGED caller preference",
            commentId: sourceComment.id,
            wakeCommentId: sourceComment.id,
            wakeCommentIds: [sourceComment.id],
@@ -2260,6 +2262,7 @@ describeEmbeddedPostgres("heartbeat comment wake batching", () => {
            wakeCommentId: sourceComment.id,
            wakeCommentIds: [sourceComment.id],
            paperclipExternalChatExecutionBound: true,
+            paperclipTaskCommunicationGuidance: "## Communication in Slack\nFrozen connection preference.",
            paperclipExternalChatQuestionResponse: expect.objectContaining({
              schema: "paperclip.external_chat_question_response.v1",
              interactionId: answered.id,
@@ -2273,6 +2276,9 @@ describeEmbeddedPostgres("heartbeat comment wake batching", () => {
        expect(String(gateway.getAgentPayloads()[0]?.message ?? "")).toContain(
          "preserve this full source instruction",
        );
+        const restoredPrompt = String(gateway.getAgentPayloads()[0]?.message ?? "");
+        expect(restoredPrompt.match(/Frozen connection preference\./g)).toHaveLength(1);
+        expect(restoredPrompt).not.toContain("FORGED caller preference");
        expect(String(gateway.getAgentPayloads()[0]?.message ?? "")).toContain(
          "Preserve the original request's exact-output constraints literally.",
        );
@@ -1,3 +1,4 @@
+import { buildChatCommunicationGuidance } from "./chat-communication-guidance.js";
 import { runtimeCanonicalOrigin } from "./cloud-runtime-identity.js";
 import { takePhotonCompanion } from "./photon/attachments.js";
 import { writePhotonCheckpoint } from "./photon/receiver.js";
@@ -5854,6 +5855,7 @@ export function chatChannelService(db: Db, options: ChatChannelServiceOptions) {
      botUsername: endpoint.botUsername,
      botLabel: endpoint.botDisplayName ?? row.assignedAgentName,
      botAvatarUrl: endpoint.botAvatarUrl,
+      communicationInstructions: endpoint.communicationInstructions,
      ...(endpoint.provider === "imessage-photon" && endpoint.botExternalId ? { photonAllocation: endpoint.botExternalId.startsWith("photon-project:") ? "shared" as const : "dedicated" as const } : {}),
      allowDirectMessages: endpoint.allowDirectMessages,
      allowGroupChats: endpoint.allowGroupChats,
@@ -6077,6 +6079,12 @@ export function chatChannelService(db: Db, options: ChatChannelServiceOptions) {
        const values: Partial<typeof chatEndpoints.$inferInsert> = {
          updatedAt: new Date(),
        };
+        if (input.communicationInstructions !== undefined) {
+          if (existing.endpoint.provider !== "slack") {
+            throw unprocessable("Communication instructions are currently supported for Slack connections");
+          }
+          values.communicationInstructions = input.communicationInstructions;
+        }
        if (input.slackApp) {
          if (existing.endpoint.provider !== "slack") {
            throw unprocessable("Slack app details only apply to Slack connections");
@@ -16028,6 +16036,11 @@ export function chatChannelService(db: Db, options: ChatChannelServiceOptions) {
              externalLabel: resource.label,
              providerUrl,
              isDirectMessage: thread.isDM,
+              communicationGuidance: buildChatCommunicationGuidance({
+                provider: taskEndpoint.provider,
+                isDirectMessage: thread.isDM,
+                communicationInstructions: taskEndpoint.communicationInstructions,
+              }),
              state: "active",
              lastActivityAt: new Date(),
            })
@@ -0,0 +1,26 @@
+import { describe, expect, it } from "vitest";
+import { CHAT_PROVIDERS, updateChatEndpointSchema } from "@paperclipai/shared";
+import { buildChatCommunicationGuidance } from "./chat-communication-guidance.js";
+
+describe("initial medium communication guidance", () => {
+  it("guides Slack presentation while retaining ordinary agent tools and explicit output requests", () => {
+    const guidance = buildChatCommunicationGuidance({ provider: "slack", isDirectMessage: false, communicationInstructions: "Use customer-facing names." });
+    expect(guidance).toContain("shared channel thread");
+    expect(guidance).toContain("document or artifact tools");
+    expect(guidance).toContain("exact output");
+    expect(guidance).toContain("grant no additional authority");
+    expect(guidance).toContain('"Use customer-facing names."');
+    expect(buildChatCommunicationGuidance({ provider: "slack", isDirectMessage: true })).toContain("direct conversation");
+  });
+
+  it.each(CHAT_PROVIDERS.filter((provider) => provider !== "slack"))("leaves %s unchanged", (provider) => {
+    expect(buildChatCommunicationGuidance({ provider, isDirectMessage: false, communicationInstructions: "Ignored" })).toBeNull();
+  });
+
+  it("accepts clearing instructions and rejects oversized instructions and unsupported controls", () => {
+    expect(updateChatEndpointSchema.parse({ communicationInstructions: "  " })).toEqual({ communicationInstructions: "" });
+    expect(updateChatEndpointSchema.safeParse({ communicationInstructions: "a".repeat(4001) }).success).toBe(false);
+    expect(updateChatEndpointSchema.safeParse({ replyDetail: "brief" }).success).toBe(false);
+    expect(updateChatEndpointSchema.safeParse({ progressUpdates: false }).success).toBe(false);
+  });
+});
@@ -0,0 +1,33 @@
+import type { ChatProvider } from "@paperclipai/shared";
+
+// Presentation guidance only. Task execution and permissions belong to the
+// ordinary Paperclip agent runtime, not the provider transport.
+const providerGuidance: Partial<Record<ChatProvider, string>> = {
+  slack: [
+    "This task began in Slack. Write replies for the person talking with you there.",
+    "Lead with the answer or outcome. Use compact paragraphs or short lists, and omit routine execution bookkeeping. Honor requests for more detail or exact output over default brevity.",
+    "Put small answers directly in the message. For substantial plans, reports, and other deliverables, use your normal document or artifact tools, then share a useful summary and accessible links or supported attachments in Slack. Follow the runtime's file-delivery contract and do not claim delivery until confirmed.",
+    "Ask useful questions through the existing human-input tools. Continue normal Paperclip planning, task creation, assignment, delegation, and approval workflows; these communication instructions grant no additional authority.",
+  ].join("\n\n"),
+};
+
+/** Captured once when the external conversation creates its task. */
+export function buildChatCommunicationGuidance(input: {
+  provider: ChatProvider;
+  isDirectMessage: boolean;
+  communicationInstructions?: string | null;
+}): string | null {
+  const guidance = providerGuidance[input.provider];
+  if (!guidance) return null;
+  const additional = input.communicationInstructions?.trim();
+  return [
+    "## Communication in Slack",
+    guidance,
+    input.isDirectMessage
+      ? "This is a direct conversation. A conversational exchange is welcome; keep each reply focused."
+      : "This is a shared channel thread. Keep replies focused on the thread and appropriate for its audience. Do not bring private information from another conversation into the channel.",
+    additional
+      ? `Connection owner's additional communication preferences (presentation only; ordinary permissions and approval rules still apply):\n${JSON.stringify(additional)}`
+      : null,
+  ].filter(Boolean).join("\n\n");
+}
@@ -10594,6 +10594,8 @@ export function heartbeatService(
  async function getIssueExecutionContext(companyId: string, issueId: string) {
    return db
      .select({
+        chatCommunicationGuidance: chatConversations.communicationGuidance,
+        chatAssignedAgentId: chatEndpoints.assignedAgentId,
        conversationAgentId: issues.conversationAgentId,
        conversationUserId: issues.conversationUserId,
        conversationState: issues.conversationState,
@@ -10627,6 +10629,15 @@ export function heartbeatService(
        updatedAt: issues.updatedAt,
      })
      .from(issues)
+      .leftJoin(chatConversations, and(
+        eq(chatConversations.companyId, issues.companyId),
+        eq(chatConversations.issueId, issues.id),
+      ))
+      .leftJoin(chatEndpoints, and(
+        eq(chatEndpoints.companyId, chatConversations.companyId),
+        eq(chatEndpoints.id, chatConversations.endpointId),
+        eq(chatEndpoints.provider, "slack"),
+      ))
      .where(and(eq(issues.id, issueId), eq(issues.companyId, companyId)))
      .then((rows) => rows[0] ?? null);
  }
@@ -20707,6 +20718,12 @@ export function heartbeatService(
              ]
            : [],
      );
+      // Always replace caller-supplied context with the immutable, company-scoped
+      // conversation snapshot. It belongs only to the endpoint's assigned agent.
+      context.paperclipTaskCommunicationGuidance =
+        issueContext?.chatAssignedAgentId === agent.id
+          ? issueContext.chatCommunicationGuidance
+          : null;
      const taskMarkdownInput = {
        issue: issueRef
          ? {
@@ -20806,10 +20823,12 @@ export function heartbeatService(
        ).redactForIssue(agent.companyId, issueRef.id, {
          paperclipIssue: context.paperclipIssue,
          paperclipWakeComment: context.paperclipWakeComment,
+          paperclipTaskCommunicationGuidance: context.paperclipTaskCommunicationGuidance,
          paperclipTaskMarkdown: context.paperclipTaskMarkdown,
          paperclipTaskMarkdownCompact: context.paperclipTaskMarkdownCompact,
        });
        context.paperclipIssue = redactedWakeContext.paperclipIssue;
+        context.paperclipTaskCommunicationGuidance = redactedWakeContext.paperclipTaskCommunicationGuidance;
        if (redactedWakeContext.paperclipWakeComment) {
          context.paperclipWakeComment =
            redactedWakeContext.paperclipWakeComment;
@@ -23360,6 +23379,7 @@ export function heartbeatService(
                      nativeReviewRequest ?? readNonEmptyString(
                        selectPaperclipTaskMarkdown(context, {
                          resumedSession: false,
+                          includeCommunicationGuidance: false,
                        }),
                      ) ??
                      `# ${issueRef.identifier ?? issueRef.id}: ${issueRef.title}`,
@@ -23367,6 +23387,7 @@ export function heartbeatService(
                        ? `## Project repositories\nThe task workspace also contains these editable Git repositories:\n${projectRepositoryPaths.map((repo) => `- ${repo}`).join("\n")}`
                        : null,
                    ].filter(Boolean).join("\n\n"),
+                    initialCommunicationGuidance: nativeReviewRequest ? null : readNonEmptyString(context.paperclipTaskCommunicationGuidance),
                    wakePayload: context.paperclipWake,
                    resumedSession,
                    previousTurn: (() => {
@@ -61,6 +61,7 @@ describe("native execution input external-chat framing", () => {
        },
        taskPrompt:
          "Continue the user's original request with their selected answer.",
+        initialCommunicationGuidance: "Initial Slack communication preferences.",
        wakePayload,
        resumedSession,
        workspace: {
@@ -102,6 +103,9 @@ describe("native execution input external-chat framing", () => {
        ],
      };
      const input = buildNativeExecutionInput(args);
+      expect(input.initialCommunicationGuidance).toBe("Initial Slack communication preferences.");
+      // The runtime adds this only after deciding whether provider recovery succeeded.
+      expect(input.task.prompt).not.toContain("Initial Slack communication preferences.");
      expect(input.task.title).toBe("External chat follow-up");
      expect(input.task.prompt).toContain("Amber");
      expect(input.task.prompt).not.toContain("## Questions that need a user response");
@@ -38,6 +38,7 @@ export function buildNativeExecutionInput(input: {
    workMode: string;
  };
  taskPrompt: string;
+  initialCommunicationGuidance?: string | null;
  /**
   * The already-sanitized Paperclip wake envelope for this run. Native drivers
   * receive a closed execution input rather than the legacy adapter context,
@@ -170,6 +171,7 @@ export function buildNativeExecutionInput(input: {
    .join("\n\n");
  return parseNativeExecutionInput({
    schema: "paperclip.native-execution-input.v4",
+    ...(input.initialCommunicationGuidance ? { initialCommunicationGuidance: input.initialCommunicationGuidance } : {}),
    ...(input.resumedSession && input.previousTurn && !input.conversationMode ? {
      continuationPrompt: buildNativeContinuationPrompt({
        wakePayload: input.wakePayload,
@@ -92,6 +92,7 @@ export interface ChatIdentityLinkPreview {
 }

 export interface ChatEndpoint {
+  communicationInstructions?: string;
  publicationMode?: "automatic" | "explicit";
  externalExecutionPolicy?: "restricted" | "agent";
  id: string;
@@ -17,9 +17,10 @@ const pushToastMock = vi.hoisted(() => vi.fn());
 const navigateMock = vi.hoisted(() => vi.fn());
 const setBreadcrumbsMock = vi.hoisted(() => vi.fn());
 const experimentalMock = vi.hoisted(() => vi.fn());
+const chatSetupMock = vi.hoisted(() => vi.fn());
 const chatListMock = vi.hoisted(() => vi.fn());
 vi.mock("@/api/instanceSettings", () => ({ instanceSettingsApi: { getExperimental: experimentalMock } }));
-vi.mock("@/api/chatEndpoints", () => ({ chatEndpointsApi: { list: chatListMock } }));
+vi.mock("@/api/chatEndpoints", () => ({ chatEndpointsApi: { list: chatListMock, setup: chatSetupMock } }));

 vi.mock("@/api/tools", () => ({
  toolsApi: {
@@ -135,6 +136,7 @@ describe("Connectors landing page", () => {
  beforeEach(() => {
    experimentalMock.mockResolvedValue({ enableChatConnectors: true });
    chatListMock.mockResolvedValue([]);
+    chatSetupMock.mockReset().mockResolvedValue({ status: "archived" });
    listGalleryMock.mockResolvedValue({
      apps: [
        galleryEntry({
@@ -231,7 +233,7 @@ describe("Connectors landing page", () => {
    }
    expect(container.textContent).not.toContain("Private bot");
    expect(container.textContent).not.toContain("Chat with agents");
-    await act(() => container.querySelector<HTMLButtonElement>('button[aria-label="Connect GitHub"]')!.click());
+    await act(() => void container.querySelector<HTMLButtonElement>('button[aria-label="Connect GitHub"]')!.click());
    expect(navigateMock).toHaveBeenLastCalledWith("/apps/connect?source=github");
  });

@@ -241,14 +243,14 @@ describe("Connectors landing page", () => {
    const client = await renderBrowse();
    expect(chatListMock).toHaveBeenCalledWith("company-1");
    expect(container.querySelector('[data-app-slug="telegram"]')).not.toBeNull();
-    await act(() => container.querySelector<HTMLButtonElement>('button[aria-label="Add connection GitHub"]')!.click());
+    await act(() => void container.querySelector<HTMLButtonElement>('button[aria-label="Add connection GitHub"]')!.click());
    expect(navigateMock).toHaveBeenLastCalledWith("/apps/chat/connect?provider=github&toolHref=%2Fapps%2Fconnect%3Fsource%3Dgithub");
    await act(() => { client.setQueryData(queryKeys.instance.experimentalSettings, { enableChatConnectors: false }); });
    await flushReact();
    expect(container.querySelector('[data-app-slug="telegram"]')).toBeNull();
    expect(container.textContent).not.toContain("Chat agent");
    expect(container.querySelector('a[href*="/apps/chat/"]')).toBeNull();
-    await act(() => container.querySelector<HTMLButtonElement>('button[aria-label="Connect GitHub"]')!.click());
+    await act(() => void container.querySelector<HTMLButtonElement>('button[aria-label="Connect GitHub"]')!.click());
    expect(navigateMock).toHaveBeenLastCalledWith("/apps/connect?source=github");
  });

@@ -468,6 +470,67 @@ describe("Connectors landing page", () => {
    );
  });

+  it.each(["slack", "discord", "telegram", "github", "microsoft-teams", "agentmail", "imessage-photon"])(
+    "puts Manage and removal in the %s chat menu while keeping draft setup visible",
+    async (provider) => {
+      chatListMock.mockResolvedValue([
+        { id: "chat-active", provider, status: "active", assignedAgentName: "Active agent" },
+        { id: "chat-draft", provider, status: "draft", assignedAgentName: "Draft agent" },
+        { id: "chat-archived", provider, status: "archived", assignedAgentName: "Removed agent" },
+      ]);
+      await renderBrowse();
+      expect(container.textContent).not.toContain("Removed agent");
+      expect(Array.from(container.querySelectorAll("button")).some((button) => button.textContent === "Manage")).toBe(false);
+      const finish = Array.from(container.querySelectorAll("button")).find((button) => button.textContent === "Finish setup");
+      await act(() => finish!.click());
+      expect(navigateMock).toHaveBeenLastCalledWith(`/apps/chat/connect?provider=${provider}&purpose=chat&resume=chat-draft`);
+      expect(container.querySelector('button[aria-label^="Manage Draft agent"]')).toBeTruthy();
+      await act(() => void container.querySelector('button[aria-label^="Manage Active agent"]')!.dispatchEvent(new PointerEvent("pointerdown", { bubbles: true })));
+      await flushReact();
+      const manage = Array.from(document.querySelectorAll<HTMLElement>('[role="menuitem"]')).find((item) => item.textContent?.trim() === "Manage");
+      await act(() => manage!.click());
+      expect(navigateMock).toHaveBeenLastCalledWith("/apps/chat/chat-active/settings");
+    },
+  );
+
+  it.each(["active", "draft"])("confirms chat removal for %s connections and refreshes the list", async (status) => {
+    chatListMock.mockResolvedValue([{ id: "chat-1", provider: "slack", status, assignedAgentName: "CEO" }]);
+    const client = await renderBrowse();
+    const invalidate = vi.spyOn(client, "invalidateQueries");
+    await act(() => void container.querySelector('button[aria-label="Manage CEO Slack connection"]')!.dispatchEvent(new PointerEvent("pointerdown", { bubbles: true })));
+    await flushReact();
+    const remove = Array.from(document.querySelectorAll<HTMLElement>('[role="menuitem"]')).find((item) => item.textContent?.trim() === "Remove connection");
+    await act(() => remove!.click());
+    await flushReact();
+    expect(chatSetupMock).not.toHaveBeenCalled();
+    expect(document.body.textContent).toContain("Existing Paperclip tasks and conversation history remain available.");
+    chatListMock.mockResolvedValue([]);
+    await act(() => Array.from(document.querySelectorAll("button")).find((button) => button.textContent?.trim() === "Remove connection")!.click());
+    await flushReact();
+    expect(chatSetupMock).toHaveBeenCalledWith("chat-1", { action: "remove" });
+    expect(archiveConnectionMock).not.toHaveBeenCalled();
+    expect(invalidate).toHaveBeenCalledWith({ queryKey: queryKeys.chatEndpoints.list("company-1") });
+    expect(container.textContent).not.toContain("CEO");
+  });
+
+  it("keeps chat removal open for retry when the server rejects removal", async () => {
+    chatListMock.mockResolvedValue([{ id: "chat-1", provider: "slack", status: "draft", assignedAgentName: "CEO" }]);
+    chatSetupMock.mockRejectedValueOnce(new Error("Connection is busy. Try again."));
+    await renderBrowse();
+    await act(() => void container.querySelector('button[aria-label="Manage CEO Slack connection"]')!.dispatchEvent(new PointerEvent("pointerdown", { bubbles: true })));
+    await flushReact();
+    await act(() => Array.from(document.querySelectorAll<HTMLElement>('[role="menuitem"]')).find((item) => item.textContent?.trim() === "Remove connection")!.click());
+    await flushReact();
+    await act(() => Array.from(document.querySelectorAll("button")).find((button) => button.textContent?.trim() === "Remove connection")!.click());
+    await flushReact();
+    expect(document.querySelector('[role="alertdialog"]')).toBeTruthy();
+    expect(pushToastMock).toHaveBeenCalledWith(expect.objectContaining({ tone: "error", body: "Connection is busy. Try again." }));
+    await act(() => Array.from(document.querySelectorAll("button")).find((button) => button.textContent === "Cancel")!.click());
+    await flushReact();
+    expect(chatSetupMock).toHaveBeenCalledTimes(1);
+    expect(document.querySelector('[role="alertdialog"]')).toBeNull();
+  });
+
  it("keeps an interrupted account visible and resumes setup from its account row", async () => {
    listApplicationsMock.mockResolvedValue({ applications: [application()] });
    listConnectionsMock.mockResolvedValue({
@@ -103,6 +103,7 @@ type ConnectionState = {
 };

 type ConnectionRemovalTarget = {
+  kind?: "chat";
  id: string;
  accountName: string;
  providerName: string;
@@ -320,9 +321,17 @@ export function Browse({ renderAccountDetails = (connection) => connection.conne
    enabled: !!selectedCompanyId,
  });
  const removeConnection = useMutation({
-    mutationFn: (target: ConnectionRemovalTarget) =>
-      toolsApi.archiveConnection(target.id),
+    mutationFn: async (target: ConnectionRemovalTarget) => {
+      if (target.kind === "chat") {
+        await chatEndpointsApi.setup(target.id, { action: "remove" });
+      } else {
+        await toolsApi.archiveConnection(target.id);
+      }
+    },
    onSuccess: (_connection, target) => {
+      queryClient.invalidateQueries({
+        queryKey: queryKeys.chatEndpoints.list(selectedCompanyId!),
+      });
      queryClient.invalidateQueries({
        queryKey: queryKeys.tools.connections(selectedCompanyId!),
      });
@@ -335,7 +344,9 @@ export function Browse({ renderAccountDetails = (connection) => connection.conne
      pushToast({
        title: "Connection removed",
        body:
-          target.remainingConnectionCount > 0
+          target.kind === "chat"
+            ? `${target.providerName} is disconnected. Existing Paperclip tasks remain available.`
+            : target.remainingConnectionCount > 0
            ? `${target.providerName} still has ${target.remainingConnectionCount} active ${target.remainingConnectionCount === 1 ? "connection" : "connections"} available to agents.`
            : `${target.providerName} is no longer available to agents through this connection. Its saved credentials were deleted.`,
        tone: "success",
@@ -532,6 +543,7 @@ export function Browse({ renderAccountDetails = (connection) => connection.conne
    for (const endpoint of chatConnectorsEnabled
      ? (chatEndpointsQuery.data ?? [])
      : []) {
+      if (endpoint.status === "archived") continue;
      let target = [...rowsBySlug.values()].find(
        (row) => chatProviderForSlug(row.slug) === endpoint.provider,
      );
@@ -711,7 +723,9 @@ export function Browse({ renderAccountDetails = (connection) => connection.conne
              Remove {connectionToRemove?.accountName ?? "this"} connection?
            </AlertDialogTitle>
            <AlertDialogDescription>
-              {connectionToRemove &&
+              {connectionToRemove?.kind === "chat"
+                ? `This connection will stop receiving new work from ${connectionToRemove.providerName}. Existing Paperclip tasks and conversation history remain available. This does not delete the app, bot, or account in ${connectionToRemove.providerName}.`
+                : connectionToRemove &&
                    connectionToRemove.remainingConnectionCount > 0
                  ? `This connection's saved credentials are deleted and agents lose access through it immediately. They can still use ${connectionToRemove.providerName} through ${connectionToRemove.remainingConnectionCount} other active ${connectionToRemove.remainingConnectionCount === 1 ? "connection" : "connections"}.`
                  : "The saved credentials are deleted and agents lose access immediately. Connecting it again later requires a new sign-in or key."}
@@ -864,19 +878,48 @@ export function ConnectorCard({
              <span className="text-xs text-muted-foreground">
                {endpoint.status.replace(/_/g, " ")}
              </span>
-              <Button
-                size="sm"
-                variant="outline"
-                onClick={() =>
-                  onNavigate(
-                    endpoint.status === "draft"
-                      ? `/apps/chat/connect?provider=${endpoint.provider}&purpose=chat&resume=${endpoint.id}`
-                      : `/apps/chat/${endpoint.id}/settings`,
-                  )
-                }
-              >
-                {endpoint.status === "draft" ? "Finish setup" : "Manage"}
-              </Button>
+              <div className="flex items-center gap-2">
+                {endpoint.status === "draft" ? (
+                  <Button
+                    size="sm"
+                    variant="outline"
+                    onClick={() => onNavigate(`/apps/chat/connect?provider=${endpoint.provider}&purpose=chat&resume=${endpoint.id}`)}
+                  >
+                    Finish setup
+                  </Button>
+                ) : null}
+                <DropdownMenu>
+                  <DropdownMenuTrigger asChild>
+                    <Button
+                      type="button"
+                      variant="ghost"
+                      size="icon-sm"
+                      aria-label={`Manage ${endpoint.assignedAgentName} ${row.name} connection`}
+                    >
+                      <MoreHorizontal className="h-4 w-4" />
+                    </Button>
+                  </DropdownMenuTrigger>
+                  <DropdownMenuContent align="end">
+                    <DropdownMenuItem onSelect={() => onNavigate(`/apps/chat/${endpoint.id}/settings`)}>
+                      Manage
+                    </DropdownMenuItem>
+                    <DropdownMenuSeparator />
+                    <DropdownMenuItem
+                      variant="destructive"
+                      onSelect={() => onRequestRemove({
+                        kind: "chat",
+                        id: endpoint.id,
+                        accountName: `${endpoint.assignedAgentName} · ${row.name}`,
+                        providerName: row.name,
+                        remainingConnectionCount: 0,
+                      })}
+                    >
+                      <Trash2 />
+                      Remove connection
+                    </DropdownMenuItem>
+                  </DropdownMenuContent>
+                </DropdownMenu>
+              </div>
            </div>
          ))}
        </div>
@@ -0,0 +1,59 @@
+import { useId, useState } from "react";
+import { Button } from "@/components/ui/button";
+import { Textarea } from "@/components/ui/textarea";
+
+export function ChatCommunicationInstructions({ value, onSave }: {
+  value: string;
+  onSave: (instructions: string) => Promise<void>;
+}) {
+  const id = useId();
+  const [draft, setDraft] = useState<string | null>(null);
+  const [pending, setPending] = useState(false);
+  const [error, setError] = useState<string | null>(null);
+  const [saved, setSaved] = useState(false);
+  const text = draft ?? value;
+  const dirty = text.trim() !== value;
+  return (
+    <form className="space-y-3" aria-labelledby={`${id}-label`} onSubmit={async (event) => {
+      event.preventDefault();
+      if (pending || !dirty) return;
+      setPending(true);
+      setError(null);
+      setSaved(false);
+      try {
+        await onSave(text.trim());
+        setDraft(null);
+        setSaved(true);
+      } catch (cause) {
+        setError(cause instanceof Error ? cause.message : "Couldn’t save instructions. Try again.");
+      } finally {
+        setPending(false);
+      }
+    }}>
+      <div className="space-y-1">
+        <label id={`${id}-label`} htmlFor={id} className="text-sm font-semibold">Additional communication instructions</label>
+        <p id={`${id}-help`} className="text-sm text-muted-foreground">
+          Guide how this agent communicates in Slack. Optional; applies when new tasks start.
+        </p>
+      </div>
+      <Textarea
+        id={id}
+        aria-describedby={`${id}-help`}
+        value={text}
+        disabled={pending}
+        maxLength={4000}
+        rows={4}
+        placeholder="For example: Use our product names and explain technical terms for a nontechnical audience."
+        onChange={(event) => { setDraft(event.target.value); setSaved(false); setError(null); }}
+      />
+      {error && <p role="alert" className="text-sm text-destructive">{error}</p>}
+      <div className="flex items-center justify-between gap-3">
+        <div>
+          {dirty ? <Button type="button" variant="ghost" disabled={pending} onClick={() => { setDraft(null); setError(null); setSaved(false); }}>Cancel</Button>
+            : saved ? <span role="status" className="text-sm text-muted-foreground">Saved. Applies to new tasks.</span> : null}
+        </div>
+        <Button type="submit" disabled={!dirty || pending}>{pending ? "Saving…" : "Save instructions"}</Button>
+      </div>
+    </form>
+  );
+}
@@ -1,4 +1,5 @@
 import { defaultSlackAppName } from "./slack-app-name";
+import { ChatCommunicationInstructions } from "./ChatCommunicationInstructions";
 import { SlackAvatarSettings } from "./SlackAvatarStep";
 import { agentsApi } from "@/api/agents";
 import { agentAvatarUrl } from "@/lib/agent-avatar-url";
@@ -418,6 +419,14 @@ function Settings({
              avatarUrl={agentAvatarUrl(resolveAgentAppearance(avatarAgent.data?.appearance, endpoint.assignedAgentId), 512, 1, "rest")}
            />
      )}
+      {endpoint.provider === "slack" && <ChatCommunicationInstructions
+        key={endpoint.id}
+        value={endpoint.communicationInstructions ?? ""}
+        onSave={async (communicationInstructions) => {
+          const next = await chatEndpointsApi.update(endpointId, { communicationInstructions });
+          queryClient.setQueryData(queryKeys.chatEndpoints.detail(endpointId), next);
+        }}
+      />}
      {endpoint.provider === "telegram" && (
        <div className="space-y-2">
          <h2 className="text-lg font-semibold">Telegram group command</h2>
@@ -1,9 +1,13 @@
+import { useState } from "react";
+import { ChatCommunicationInstructions } from "@/pages/apps/chat/ChatCommunicationInstructions";
 import { Copy, ExternalLink } from "lucide-react";
 import { Button } from "@/components/ui/button";
 import { SlackAvatarSettings } from "@/pages/apps/chat/SlackAvatarStep";
 import avatar from "./ceo-cliptoon.png";

-export function SlackAvatarSettingsPreview() {
+export function SlackAvatarSettingsPreview({ initialInstructions = "", failFirstSave = false }: { initialInstructions?: string; failFirstSave?: boolean }) {
+  const [instructions, setInstructions] = useState(initialInstructions);
+  const [failSave, setFailSave] = useState(failFirstSave);
  return (
    <div className="min-h-screen bg-background text-foreground">
      <header className="flex gap-3 border-b border-border px-6 py-4 text-sm">
@@ -48,6 +52,10 @@ export function SlackAvatarSettingsPreview() {
              appName="ceo-paperclip"
              avatarUrl={avatar}
            />
+            <ChatCommunicationInstructions value={instructions} onSave={async (next) => {
+              if (failSave) { setFailSave(false); throw new Error("Couldn’t save instructions. Try again."); }
+              setInstructions(next);
+            }} />
            <section className="space-y-4">
              <h2 className="text-lg font-semibold">
                Where this agent can work
@@ -0,0 +1,43 @@
+import type { Meta, StoryObj } from "@storybook/react-vite";
+import { expect, fn, userEvent, within } from "storybook/test";
+import { ConnectorCard } from "@/pages/apps/Browse";
+import type { ChatEndpoint } from "@/api/chatEndpoints";
+
+const endpoint: ChatEndpoint = {
+  id: "slack-active", companyId: "demo", provider: "slack", status: "active",
+  assignedAgentId: "ceo", assignedAgentName: "CEO", providerAccountLabel: "Paperclip",
+  allowUnlinkedPeople: false,
+};
+
+const meta = {
+  title: "Connections/Chat connection actions",
+  component: ConnectorCard,
+  parameters: { layout: "padded" },
+  args: {
+    row: {
+      key: "slack", slug: "slack", name: "Slack", brandKey: "slack",
+      description: "Give agents Slack tools or let people start and continue Paperclip work from Slack.",
+      entry: null, applications: [], connections: [],
+      chatEndpoints: [endpoint, { ...endpoint, id: "slack-draft", status: "draft", assignedAgentName: "Carl" }],
+    },
+    userProfileById: new Map(), chatConnectorsEnabled: true,
+    onNavigate: fn(), onRequestRemove: fn(),
+  },
+} satisfies Meta<typeof ConnectorCard>;
+export default meta;
+type Story = StoryObj<typeof meta>;
+
+export const ActiveAndDraft: Story = {
+  play: async ({ canvasElement, args }) => {
+    const canvas = within(canvasElement);
+    await expect(canvas.getByRole("button", { name: "Finish setup" })).toBeVisible();
+    await userEvent.click(canvas.getByRole("button", { name: "Manage CEO Slack connection" }));
+    const body = within(document.body);
+    await expect(body.getByRole("menuitem", { name: "Manage" })).toBeVisible();
+    await userEvent.click(body.getByRole("menuitem", { name: "Remove connection" }));
+    await expect(args.onRequestRemove).toHaveBeenCalledWith(expect.objectContaining({ kind: "chat", id: "slack-active" }));
+    await userEvent.click(canvas.getByRole("button", { name: "Manage Carl Slack connection" }));
+    await expect(body.getByRole("menuitem", { name: "Remove connection" })).toBeVisible();
+    await userEvent.keyboard("{Escape}");
+  },
+};
@@ -0,0 +1,28 @@
+import type { Meta, StoryObj } from "@storybook/react-vite";
+import { expect, userEvent, within } from "storybook/test";
+import { SlackAvatarSettingsPreview } from "../prototypes/slack-avatar/SlackAvatarSettingsPreview";
+
+const meta = {
+  title: "Connections/Slack/Communication in Settings",
+  component: SlackAvatarSettingsPreview,
+  parameters: { layout: "fullscreen", docs: { description: { component: "Production communication field in a Settings fixture. Saves use local story state; instructions apply to new tasks. Reply detail and progress are built-in behavior." } } },
+} satisfies Meta<typeof SlackAvatarSettingsPreview>;
+export default meta;
+type Story = StoryObj<typeof meta>;
+export const Default: Story = {};
+export const WithInstructions: Story = { args: { initialInstructions: "Use our product names and explain technical terms for a nontechnical audience." } };
+export const Mobile: Story = { globals: { viewport: { value: "mobile1", isRotated: false } } };
+export const SaveAndRetry: Story = {
+  args: { failFirstSave: true },
+  play: async ({ canvasElement }) => {
+    const canvas = within(canvasElement);
+    const field = canvas.getByRole("textbox", { name: "Additional communication instructions" });
+    await userEvent.type(field, "Use customer-facing product names.");
+    await userEvent.click(canvas.getByRole("button", { name: "Save instructions" }));
+    await expect(canvas.getByRole("alert")).toHaveTextContent("Couldn’t save instructions");
+    await expect(field).toHaveValue("Use customer-facing product names.");
+    await userEvent.click(canvas.getByRole("button", { name: "Save instructions" }));
+    await expect(canvas.getByRole("status")).toHaveTextContent("Saved. Applies to new tasks.");
+    await expect(canvas.getByRole("button", { name: "Save instructions" })).toBeDisabled();
+  },
+};