diff --git a/packages/api-client/src/posthog-client.ts b/packages/api-client/src/posthog-client.ts
index 18a2aa6da6..4ac94adb1b 100644
--- a/packages/api-client/src/posthog-client.ts
+++ b/packages/api-client/src/posthog-client.ts
@@ -52,6 +52,8 @@ import type {
   ActionabilityJudgmentArtefact,
   AvailableSuggestedReviewer,
   AvailableSuggestedReviewersResponse,
+  ChannelFeedMessage,
+  ChannelFeedMessageEvent,
   CodeReferenceArtefact,
   CommitArtefact,
   CommitDiffResponse,
@@ -2467,6 +2469,56 @@ export class PostHogAPIClient {
     return (await response.json()) as TaskChannel;
   }
 
+  // A channel's system-announcement feed (context created, CONTEXT.md being
+  // built), chronological. Durable + team-visible, rendered alongside task cards.
+  async getChannelFeed(channelId: string): Promise<ChannelFeedMessage[]> {
+    const teamId = await this.getTeamId();
+    const urlPath = `/api/projects/${teamId}/task_channels/${channelId}/feed/`;
+    const response = await this.api.fetcher.fetch({
+      method: "get",
+      url: new URL(`${this.api.baseUrl}${urlPath}`),
+      path: urlPath,
+    });
+    if (!response.ok) {
+      throw new Error(`Failed to fetch channel feed: ${response.statusText}`);
+    }
+    return (await response.json()) as ChannelFeedMessage[];
+  }
+
+  // Post a system announcement into a channel's feed. The row is authored by the
+  // system; the server records the requester as `author` for "Adam …" rendering.
+  async postChannelFeedMessage(
+    channelId: string,
+    input: {
+      event: ChannelFeedMessageEvent;
+      payload?: Record<string, unknown>;
+      // Optional explicit timestamp (ISO) so a burst of announcements orders
+      // deterministically instead of racing on server insert time.
+      createdAt?: string;
+    },
+  ): Promise<ChannelFeedMessage> {
+    const teamId = await this.getTeamId();
+    const urlPath = `/api/projects/${teamId}/task_channels/${channelId}/feed/`;
+    const response = await this.api.fetcher.fetch({
+      method: "post",
+      url: new URL(`${this.api.baseUrl}${urlPath}`),
+      path: urlPath,
+      overrides: {
+        body: JSON.stringify({
+          event: input.event,
+          payload: input.payload ?? {},
+          ...(input.createdAt ? { created_at: input.createdAt } : {}),
+        }),
+      },
+    });
+    if (!response.ok) {
+      throw new Error(
+        `Failed to post channel feed message: ${response.statusText}`,
+      );
+    }
+    return (await response.json()) as ChannelFeedMessage;
+  }
+
   // Mentions of the current user across task threads, newest first.
   async getTaskMentions(options?: { since?: string }): Promise<TaskMention[]> {
     const teamId = await this.getTeamId();
diff --git a/packages/shared/src/domain-types.ts b/packages/shared/src/domain-types.ts
index 358fa23864..5e46d7f947 100644
--- a/packages/shared/src/domain-types.ts
+++ b/packages/shared/src/domain-types.ts
@@ -79,6 +79,27 @@ export interface TaskChannel {
   created_by?: UserBasic | null;
 }
 
+/** Lifecycle events a client may post into a channel's feed. */
+export type ChannelFeedMessageEvent = "context_md_building";
+
+/**
+ * A durable, team-visible "PostHog agent" announcement in a channel's feed —
+ * rendered alongside task cards (e.g. "Adam created this context"). `author` is
+ * the user whose action produced the row; `author_kind` says who authored it.
+ * `payload` carries structured event data (e.g. `{ context_name }`) so rendering
+ * survives renames.
+ */
+export interface ChannelFeedMessage {
+  id: string;
+  channel: string;
+  author?: UserBasic | null;
+  author_kind: "human" | "system" | "agent";
+  event: ChannelFeedMessageEvent | string;
+  payload: Record<string, unknown>;
+  content: string;
+  created_at: string;
+}
+
 /**
  * One human message in a task's thread. Thread messages never reach the agent
  * unless the task author forwards one, which stamps the forwarded_* fields.
diff --git a/packages/ui/src/features/browser-tabs/BrowserTabStrip.tsx b/packages/ui/src/features/browser-tabs/BrowserTabStrip.tsx
index 8b42382a4c..d9c0a55844 100644
--- a/packages/ui/src/features/browser-tabs/BrowserTabStrip.tsx
+++ b/packages/ui/src/features/browser-tabs/BrowserTabStrip.tsx
@@ -1,6 +1,5 @@
 import {
   BrainIcon,
-  HashIcon,
   HouseIcon,
   PlugsConnectedIcon,
   RobotIcon,
@@ -50,6 +49,7 @@ import {
   useRouter,
   useRouterState,
 } from "@tanstack/react-router";
+import { SquircleDashed } from "lucide-react";
 import { type ReactNode, useEffect, useMemo } from "react";
 import { useHotkeys } from "react-hotkeys-hook";
 import {
@@ -519,8 +519,8 @@ export function BrowserTabStrip() {
           const meta = channelSectionFor(section);
           return {
             id: t.id,
-            label: meta?.label ?? channel ?? "Channel",
-            icon: <HashIcon size={14} />,
+            label: meta?.label ?? channel ?? "Context",
+            icon: <SquircleDashed size={14} />,
             channelName: channel,
             // No section meta → the channel's index page.
             isChannelHome: !meta,
diff --git a/packages/ui/src/features/browser-tabs/TabStrip.tsx b/packages/ui/src/features/browser-tabs/TabStrip.tsx
index 0d389d8d6b..718ad8045c 100644
--- a/packages/ui/src/features/browser-tabs/TabStrip.tsx
+++ b/packages/ui/src/features/browser-tabs/TabStrip.tsx
@@ -231,7 +231,7 @@ function SortableTabPill({
               repeat the channel-home name already shown above. */}
           {tab.channelName ? (
             <div className="text-muted">
-              #{tab.channelName}
+              {tab.channelName}
               {tab.isChannelHome ? " / home" : null}
             </div>
           ) : null}
diff --git a/packages/ui/src/features/canvas/components/ActivityView.tsx b/packages/ui/src/features/canvas/components/ActivityView.tsx
index 905360c757..e3323ae71c 100644
--- a/packages/ui/src/features/canvas/components/ActivityView.tsx
+++ b/packages/ui/src/features/canvas/components/ActivityView.tsx
@@ -89,7 +89,7 @@ function ActivityRow({
                 <>
                   {" in "}
                   <Text as="span" size="1" weight="medium">
-                    #{item.channelName}
+                    {item.channelName}
                   </Text>
                 </>
               )}
@@ -176,7 +176,7 @@ export function ActivityView() {
           Activity
         </Text>
         <Text size="2" className="block text-muted-foreground">
-          Mentions of you across channel threads.
+          Mentions of you across contexts.
         </Text>
         <div className="mt-4">
           {isLoading && items.length === 0 ? (
diff --git a/packages/ui/src/features/canvas/components/ChannelBreadcrumb.tsx b/packages/ui/src/features/canvas/components/ChannelBreadcrumb.tsx
index 9bd0adaa1f..86bd34fbfa 100644
--- a/packages/ui/src/features/canvas/components/ChannelBreadcrumb.tsx
+++ b/packages/ui/src/features/canvas/components/ChannelBreadcrumb.tsx
@@ -1,4 +1,3 @@
-import { HashIcon } from "@phosphor-icons/react";
 import {
   Button,
   Tooltip,
@@ -8,6 +7,7 @@ import {
 import { HeaderTitleEditor } from "@posthog/ui/features/task-detail/HeaderTitleEditor";
 import { Flex, Text } from "@radix-ui/themes";
 import { useNavigate } from "@tanstack/react-router";
+import { SquircleDashed } from "lucide-react";
 import { type ReactNode, useState } from "react";
 
 interface ChannelBreadcrumbProps {
@@ -48,7 +48,10 @@ export function ChannelBreadcrumb({
 
   const channelSegment = (
     <>
-      <HashIcon size={12} className="mt-px shrink-0 text-muted-foreground/80" />
+      <SquircleDashed
+        size={12}
+        className="mt-px shrink-0 text-muted-foreground/80"
+      />
       <Text
         className="min-w-0 truncate whitespace-nowrap font-medium text-[13px]"
         title={channelName}
diff --git a/packages/ui/src/features/canvas/components/ChannelContextPanel.test.tsx b/packages/ui/src/features/canvas/components/ChannelContextPanel.test.tsx
index 4c3dc65efd..b9d1b7e40e 100644
--- a/packages/ui/src/features/canvas/components/ChannelContextPanel.test.tsx
+++ b/packages/ui/src/features/canvas/components/ChannelContextPanel.test.tsx
@@ -34,7 +34,7 @@ describe("ChannelContextPanel", () => {
   it.each([
     {
       channelName: "project-bluebird",
-      expectedTitle: "#project-bluebird CONTEXT.md",
+      expectedTitle: "project-bluebird CONTEXT.md",
     },
     { channelName: undefined, expectedTitle: "CONTEXT.md" },
   ])(
diff --git a/packages/ui/src/features/canvas/components/ChannelContextPanel.tsx b/packages/ui/src/features/canvas/components/ChannelContextPanel.tsx
index 7b6397e0a8..b5ad42ac86 100644
--- a/packages/ui/src/features/canvas/components/ChannelContextPanel.tsx
+++ b/packages/ui/src/features/canvas/components/ChannelContextPanel.tsx
@@ -29,7 +29,7 @@ export function ChannelContextPanel({
           weight="medium"
           className="min-w-0 truncate text-gray-12"
         >
-          {channelName ? `#${channelName} ` : ""}CONTEXT.md
+          {channelName ? `${channelName} ` : ""}CONTEXT.md
         </Text>
         <Tooltip content="Close">
           <button
diff --git a/packages/ui/src/features/canvas/components/ChannelFeedView.tsx b/packages/ui/src/features/canvas/components/ChannelFeedView.tsx
index fd5a38f871..c3c25749dd 100644
--- a/packages/ui/src/features/canvas/components/ChannelFeedView.tsx
+++ b/packages/ui/src/features/canvas/components/ChannelFeedView.tsx
@@ -40,6 +40,7 @@ import { isTerminalStatus } from "@posthog/shared/domain-types";
 import { getUserInitials } from "@posthog/ui/features/auth/userInitials";
 import { TaskTabIcon } from "@posthog/ui/features/browser-tabs/TaskTabIcon";
 import { mentionChipClass } from "@posthog/ui/features/canvas/components/MentionText";
+import type { ChannelFeedSystemMessage } from "@posthog/ui/features/canvas/hooks/useChannelFeedMessages";
 import { useChannelTaskData } from "@posthog/ui/features/canvas/hooks/useChannelTaskData";
 import { useTaskThread } from "@posthog/ui/features/canvas/hooks/useTaskThread";
 import { userDisplayName } from "@posthog/ui/features/canvas/utils/userDisplay";
@@ -472,23 +473,89 @@ function FeedRow({
   );
 }
 
+// A card-less feed row for a synthetic "PostHog agent" announcement (context
+// created, CONTEXT.md being built). Same chrome as a task row — Robot avatar,
+// "PostHog / Agent" — minus the task card and reply footer.
+function SystemFeedRow({ message }: { message: ChannelFeedSystemMessage }) {
+  return (
+    <ChatMessageScrollerItem messageId={message.id}>
+      <ThreadItem className="rounded-none py-4 pr-8">
+        <ThreadItemGutter>
+          <Avatar>
+            <AvatarFallback>
+              <RobotIcon size={16} />
+            </AvatarFallback>
+          </Avatar>
+        </ThreadItemGutter>
+        <ThreadItemContent className="min-w-0">
+          <ThreadItemHeader>
+            <ThreadItemAuthor>PostHog</ThreadItemAuthor>
+            <Badge variant="info">Agent</Badge>
+            <ThreadItemTimestamp dateTime={message.createdAt}>
+              {formatRelativeTimeShort(message.createdAt)}
+            </ThreadItemTimestamp>
+          </ThreadItemHeader>
+          <ThreadItemBody className="wrap-break-word text-muted-foreground">
+            {message.text}
+          </ThreadItemBody>
+        </ThreadItemContent>
+      </ThreadItem>
+    </ChatMessageScrollerItem>
+  );
+}
+
+// A single feed entry, either a real task card or a synthetic system row, tagged
+// with the timestamp used to interleave the two.
+type FeedEntry =
+  | { kind: "task"; id: string; createdAt: string; task: Task }
+  | {
+      kind: "system";
+      id: string;
+      createdAt: string;
+      message: ChannelFeedSystemMessage;
+    };
+
 // The Slack-style channel feed: every task kicked off in the channel, oldest
 // first, rendered as a kickoff message + task card. Multiplayer — the list is
-// team-visible and polls for teammates' cards and status flips.
+// team-visible and polls for teammates' cards and status flips. Synthetic
+// "PostHog agent" system rows (context lifecycle) are interleaved by timestamp.
 export function ChannelFeedView({
   tasks,
+  systemMessages,
   isLoading,
   emptyState,
   onOpenTask,
   onOpenThread,
 }: {
   tasks: Task[];
+  systemMessages?: ChannelFeedSystemMessage[];
   isLoading: boolean;
   emptyState?: React.ReactNode;
   onOpenTask: (task: Task) => void;
   onOpenThread: (task: Task) => void;
 }) {
-  if (isLoading && tasks.length === 0) {
+  // Merge tasks + system rows into one chronological list. ISO timestamps sort
+  // lexically, so a plain string compare is chronological.
+  const entries = useMemo<FeedEntry[]>(() => {
+    const merged: FeedEntry[] = [
+      ...tasks.map((task) => ({
+        kind: "task" as const,
+        id: task.id,
+        createdAt: task.created_at,
+        task,
+      })),
+      ...(systemMessages ?? []).map((message) => ({
+        kind: "system" as const,
+        id: message.id,
+        createdAt: message.createdAt,
+        message,
+      })),
+    ];
+    merged.sort((a, b) => a.createdAt.localeCompare(b.createdAt));
+    return merged;
+  }, [tasks, systemMessages]);
+
+  if (isLoading && entries.length === 0) {
     return (
       <div className="flex flex-1 items-center justify-center">
         <Spinner />
@@ -496,7 +563,7 @@ export function ChannelFeedView({
     );
   }
 
-  if (tasks.length === 0) {
+  if (entries.length === 0) {
     return <div className="flex-1 overflow-y-auto">{emptyState}</div>;
   }
 
@@ -510,25 +577,29 @@ export function ChannelFeedView({
               the row's top-right corner (absolute, past the row edge). Without a
               gutter they hug the scroll container and get clipped. */}
           <ChatMessageScrollerContent className="mx-auto w-full gap-0 py-4">
-            {tasks.map((task, index) => {
-              const previous = tasks[index - 1];
+            {entries.map((entry, index) => {
+              const previous = entries[index - 1];
               const showDayMarker =
                 !previous ||
-                dayKey(previous.created_at) !== dayKey(task.created_at);
+                dayKey(previous.createdAt) !== dayKey(entry.createdAt);
               return (
-                <Fragment key={task.id}>
+                <Fragment key={entry.id}>
                   {showDayMarker && (
                     <ChatMarker variant="separator">
                       <ChatMarkerContent>
-                        {dayLabel(task.created_at, now)}
+                        {dayLabel(entry.createdAt, now)}
                       </ChatMarkerContent>
                     </ChatMarker>
                   )}
-                  <FeedRow
-                    task={task}
-                    onOpenTask={onOpenTask}
-                    onOpenThread={onOpenThread}
-                  />
+                  {entry.kind === "task" ? (
+                    <FeedRow
+                      task={entry.task}
+                      onOpenTask={onOpenTask}
+                      onOpenThread={onOpenThread}
+                    />
+                  ) : (
+                    <SystemFeedRow message={entry.message} />
+                  )}
                 </Fragment>
               );
             })}
diff --git a/packages/ui/src/features/canvas/components/ChannelHeader.tsx b/packages/ui/src/features/canvas/components/ChannelHeader.tsx
index d7a9ed3878..d41bd2b299 100644
--- a/packages/ui/src/features/canvas/components/ChannelHeader.tsx
+++ b/packages/ui/src/features/canvas/components/ChannelHeader.tsx
@@ -1,9 +1,9 @@
-import { HashIcon } from "@phosphor-icons/react";
 import { Button, cn } from "@posthog/quill";
 import { ChannelTabs } from "@posthog/ui/features/canvas/components/ChannelTabs";
 import { useChannels } from "@posthog/ui/features/canvas/hooks/useChannels";
 import { Text } from "@radix-ui/themes";
 import { useNavigate, useRouterState } from "@tanstack/react-router";
+import { SquircleDashed } from "lucide-react";
 
 // The shared channel header: a clickable "# channel" that doubles as the Home
 // item — it routes to the channel home (`/website/$channelId`, like the sidebar
@@ -29,15 +29,12 @@ export function ChannelHeader({ channelId }: { channelId: string }) {
         size="sm"
         className={cn("min-w-0", isHome ? "bg-fill-selected" : "")}
       >
-        <HashIcon
-          size={12}
-          className="mt-px shrink-0 text-muted-foreground/80"
+        <SquircleDashed
+          size={20}
+          className="shrink-0 text-muted-foreground/80"
         />
-        <Text
-          className="min-w-0 truncate font-medium text-[13px]"
-          title={channelName}
-        >
-          {channelName ?? "Channel"}
+        <Text className="min-w-0 truncate font-medium" title={channelName}>
+          {channelName ?? "Context"}
         </Text>
       </Button>
       <ChannelTabs channelId={channelId} />
diff --git a/packages/ui/src/features/canvas/components/ChannelsList.tsx b/packages/ui/src/features/canvas/components/ChannelsList.tsx
index d6bc3e269e..a228e5dca1 100644
--- a/packages/ui/src/features/canvas/components/ChannelsList.tsx
+++ b/packages/ui/src/features/canvas/components/ChannelsList.tsx
@@ -2,7 +2,6 @@ import {
   ChartBarIcon,
   DotsThreeIcon,
   FileTextIcon,
-  HashIcon,
   LinkIcon,
   LockSimpleIcon,
   PencilSimpleIcon,
@@ -60,6 +59,7 @@ import { toast } from "@posthog/ui/primitives/toast";
 import { track } from "@posthog/ui/shell/analytics";
 import { Box, Flex, Text } from "@radix-ui/themes";
 import { useNavigate, useRouterState } from "@tanstack/react-router";
+import { SquircleDashed } from "lucide-react";
 import { Fragment, type ReactNode, useEffect, useRef, useState } from "react";
 import { hostClient } from "../hostClient";
 
@@ -138,7 +138,7 @@ function useChannelActions(channel: Channel): {
         channel_id: channel.id,
         success: false,
       });
-      toast.error("Couldn't delete channel", {
+      toast.error("Couldn't delete context", {
         description: error instanceof Error ? error.message : String(error),
       });
       return false;
@@ -148,7 +148,7 @@ function useChannelActions(channel: Channel): {
   const actions: ChannelActionItem[] = [
     {
       key: "star",
-      label: isStarred ? "Unstar channel" : "Star channel",
+      label: isStarred ? "Unstar context" : "Star context",
       icon: <StarIcon size={14} weight={isStarred ? "fill" : "regular"} />,
       onSelect: () => {
         track(ANALYTICS_EVENTS.CHANNEL_ACTION, {
@@ -167,14 +167,14 @@ function useChannelActions(channel: Channel): {
     },
     {
       key: "rename",
-      label: "Rename channel…",
+      label: "Rename context…",
       icon: <PencilSimpleIcon size={14} />,
       separatorBefore: true,
       onSelect: () => setRenameOpen(true),
     },
     {
       key: "delete",
-      label: "Delete channel…",
+      label: "Delete context…",
       icon: <TrashIcon size={14} />,
       variant: "destructive",
       onSelect: () => setConfirmDeleteOpen(true),
@@ -334,7 +334,7 @@ function ChannelSection({ channel }: { channel: Channel }) {
               }}
               className="w-full min-w-0 justify-start gap-2 data-selected:bg-fill-selected data-selected:text-gray-12"
             >
-              <HashIcon size={14} className="shrink-0 text-gray-9" />
+              <SquircleDashed size={14} className="shrink-0 text-gray-9" />
               <span
                 className={cn(
                   "truncate font-medium text-[13px] text-gray-12 group-hover/chan:pr-8",
@@ -439,19 +439,19 @@ function ChannelSection({ channel }: { channel: Channel }) {
       >
         <AlertDialogContent className="max-w-md">
           <AlertDialogHeader>
-            <AlertDialogTitle>Delete #{channel.name}?</AlertDialogTitle>
+            <AlertDialogTitle>Delete {channel.name}?</AlertDialogTitle>
             <AlertDialogDescription>
-              This permanently deletes the channel and can’t be undone.
+              This permanently deletes the context and can’t be undone.
               <ul className="list-disc ps-4">
                 <li>
-                  The channel and its{" "}
+                  The context and its{" "}
                   <span className="font-medium">CONTEXT.md</span> are deleted.
                 </li>
                 <li>
-                  Every canvas saved in this channel is permanently deleted.
+                  Every canvas saved in this context is permanently deleted.
                 </li>
                 <li>
-                  Filed tasks are removed from the channel, but the tasks
+                  Filed tasks are removed from the context, but the tasks
                   themselves are not deleted.
                 </li>
               </ul>
@@ -470,7 +470,7 @@ function ChannelSection({ channel }: { channel: Channel }) {
                 })
               }
             >
-              Delete channel
+              Delete context
             </Button>
           </AlertDialogFooter>
         </AlertDialogContent>
@@ -505,7 +505,7 @@ function PersonalChannelRow() {
         params: { channelId: folder.id },
       });
     } catch (error) {
-      toast.error("Couldn't open #me", {
+      toast.error("Couldn't open me", {
         description: error instanceof Error ? error.message : String(error),
       });
     }
@@ -521,7 +521,7 @@ function PersonalChannelRow() {
       onClick={() => void open()}
       className="w-full min-w-0 justify-start gap-2 data-selected:bg-fill-selected data-selected:text-gray-12"
     >
-      <HashIcon size={14} className="shrink-0 text-gray-9" />
+      <SquircleDashed size={14} className="shrink-0 text-gray-9" />
       <span className="truncate font-medium text-[13px] text-gray-12">
         {PERSONAL_CHANNEL_NAME}
       </span>
@@ -583,8 +583,8 @@ export function ChannelsList() {
         <Box className={cn(starred.length > 0 && "mt-3")}>
           <MenuLabel className="group flex items-center justify-between uppercase">
             <span className="flex items-center gap-2">
-              <HashIcon size={14} className="text-gray-9" />
-              Channels
+              <SquircleDashed size={14} className="text-gray-9" />
+              Contexts
             </span>
             <Button
               variant="outline"
@@ -599,7 +599,7 @@ export function ChannelsList() {
 
         {!isLoading && channels.length === 0 && (
           <Text size="1" className="px-2 text-gray-9">
-            No channels yet. Create one to get started.
+            No contexts yet. Create one to get started.
           </Text>
         )}
 
diff --git a/packages/ui/src/features/canvas/components/CreateChannelModal.tsx b/packages/ui/src/features/canvas/components/CreateChannelModal.tsx
index 2622386528..ca380cea00 100644
--- a/packages/ui/src/features/canvas/components/CreateChannelModal.tsx
+++ b/packages/ui/src/features/canvas/components/CreateChannelModal.tsx
@@ -1,152 +1,254 @@
-import { HashIcon, XIcon } from "@phosphor-icons/react";
 import { validateChannelName } from "@posthog/core/canvas/channelName";
-import { Button } from "@posthog/quill";
+import {
+  Button,
+  Dialog,
+  DialogBody,
+  DialogClose,
+  DialogContent,
+  DialogDescription,
+  DialogFooter,
+  DialogHeader,
+  DialogTitle,
+  Field,
+  FieldError,
+  FieldLabel,
+  Input,
+  Textarea,
+} from "@posthog/quill";
 import { ANALYTICS_EVENTS } from "@posthog/shared/analytics-events";
 import { useChannelMutations } from "@posthog/ui/features/canvas/hooks/useChannels";
+import { useGenerateContext } from "@posthog/ui/features/canvas/hooks/useGenerateContext";
 import { toast } from "@posthog/ui/primitives/toast";
 import { track } from "@posthog/ui/shell/analytics";
-import { Dialog, Flex, IconButton, Text, TextField } from "@radix-ui/themes";
 import { useNavigate } from "@tanstack/react-router";
 import { useState } from "react";
 
 // Matches Slack's "Create a channel" naming constraint.
-const MAX_CHANNEL_NAME_LENGTH = 80;
+const MAX_CONTEXT_NAME_LENGTH = 80;
+
+const DESCRIPTION_PLACEHOLDER = "Tell me about what this context will be about";
+
+// When a create attempt creates the context but fails to launch the session, we
+// stash the description here so reopening the create dialog restores it instead
+// of losing what the user typed. Module-scoped so it survives the dialog (and
+// its host) unmounting; consumed and cleared on the next create-dialog open.
+let stashedDescription = "";
 
 interface CreateChannelModalProps {
   open: boolean;
   onOpenChange: (open: boolean) => void;
+  // When set, the context already exists (e.g. the CONTEXT.md empty state): the
+  // name field is skipped and submitting just launches the planning session.
+  existingContext?: { channelId: string; channelName: string };
 }
 
+// Create-a-context dialog. Asks for a name and a short description of what the
+// context is about, then launches a plan-mode session that investigates and
+// builds the context's CONTEXT.md with the user. Reused from the CONTEXT.md
+// empty state via `existingContext` to describe-and-plan an existing context.
 export function CreateChannelModal({
   open,
   onOpenChange,
+  existingContext,
 }: CreateChannelModalProps) {
+  const isDescribeMode = !!existingContext;
   const { createChannel, isCreating } = useChannelMutations();
+  const { generate, isStarting } = useGenerateContext();
   const navigate = useNavigate();
   const [name, setName] = useState("");
+  const [description, setDescription] = useState("");
 
-  // Reset the field each time the modal opens so a previous draft never lingers.
-  // Adjusted inline during render (prev-prop comparison) rather than in an
-  // effect, which would flash a stale value for one commit.
+  // Reset the fields each time the modal opens so a previous draft never
+  // lingers. Adjusted inline during render (prev-prop comparison) rather than in
+  // an effect, which would flash a stale value for one commit.
   const [wasOpen, setWasOpen] = useState(open);
   if (open !== wasOpen) {
     setWasOpen(open);
-    if (open) setName("");
+    if (open) {
+      setName("");
+      // Restore a description stashed by a prior failed launch (create mode
+      // only), otherwise start blank. Only create mode consumes the stash — a
+      // describe-mode open (e.g. the CONTEXT.md empty state the failed flow
+      // lands on) must not wipe a draft it doesn't use.
+      setDescription(isDescribeMode ? "" : stashedDescription);
+      if (!isDescribeMode) stashedDescription = "";
+    }
   }
 
-  const trimmed = name.trim();
-  const remaining = MAX_CHANNEL_NAME_LENGTH - name.length;
-  const validationError = validateChannelName(trimmed);
+  const trimmedName = name.trim();
+  const trimmedDescription = description.trim();
+  const remaining = MAX_CONTEXT_NAME_LENGTH - name.length;
+  const nameError = isDescribeMode ? null : validateChannelName(trimmedName);
+
+  const busy = isCreating || isStarting;
+  const canSubmit =
+    !busy &&
+    !!trimmedDescription &&
+    (isDescribeMode || (!!trimmedName && !nameError));
 
   const submit = async () => {
-    if (!trimmed || validationError || isCreating) return;
-    let channel: Awaited<ReturnType<typeof createChannel>>;
-    try {
-      channel = await createChannel(trimmed);
-      track(ANALYTICS_EVENTS.CHANNEL_ACTION, {
-        action_type: "create",
-        surface: "sidebar",
-        channel_id: channel.id,
-        success: true,
-      });
-    } catch (error) {
-      track(ANALYTICS_EVENTS.CHANNEL_ACTION, {
-        action_type: "create",
-        surface: "sidebar",
-        success: false,
-      });
-      toast.error("Couldn't create channel", {
-        description: error instanceof Error ? error.message : String(error),
-      });
+    if (!canSubmit) return;
+
+    // Resolve the target context: an existing one, or create it now. The
+    // context must exist before we can seed a session against its id.
+    let contextId: string;
+    let contextName: string;
+    if (existingContext) {
+      contextId = existingContext.channelId;
+      contextName = existingContext.channelName;
+    } else {
+      try {
+        const channel = await createChannel(trimmedName);
+        track(ANALYTICS_EVENTS.CHANNEL_ACTION, {
+          action_type: "create",
+          surface: "sidebar",
+          channel_id: channel.id,
+          success: true,
+        });
+        contextId = channel.id;
+        contextName = trimmedName;
+      } catch (error) {
+        track(ANALYTICS_EVENTS.CHANNEL_ACTION, {
+          action_type: "create",
+          surface: "sidebar",
+          success: false,
+        });
+        toast.error("Couldn't create context", {
+          description: error instanceof Error ? error.message : String(error),
+        });
+        return;
+      }
+    }
+
+    track(ANALYTICS_EVENTS.CONTEXT_ACTION, {
+      action_type: "generate_started",
+      channel_id: contextId,
+    });
+    const task = await generate({
+      channelId: contextId,
+      channelName: contextName,
+      description: trimmedDescription,
+    });
+
+    if (!task) {
+      // The session failed to start (generate() already toasted the details).
+      // In create mode the context was still created — close and drop the user
+      // on its home so they can retry from the empty state. Stash the typed
+      // description so reopening the create dialog restores it. In describe mode
+      // the context already existed; keep the dialog open (state intact) for a
+      // clean retry.
+      if (!existingContext) {
+        stashedDescription = trimmedDescription;
+        onOpenChange(false);
+        void navigate({
+          to: "/website/$channelId",
+          params: { channelId: contextId },
+        });
+      }
       return;
     }
+
+    // Launch succeeded. The feed announcements ("created this context", derived
+    // from the channel row; context_md_building, posted by generate against the
+    // backend channel) are handled where the channel is known — the dialog just
+    // navigates.
+    //
+    // Land on the context index (its feed), where the announcements and the plan
+    // task card show. The user clicks the card to open the session.
     onOpenChange(false);
-    // Open the new channel's static homepage.
     void navigate({
       to: "/website/$channelId",
-      params: { channelId: channel.id },
+      params: { channelId: contextId },
     });
   };
 
   return (
-    <Dialog.Root
+    <Dialog
       open={open}
       onOpenChange={(next) => {
-        if (!isCreating) onOpenChange(next);
+        if (!busy) onOpenChange(next);
       }}
     >
-      <Dialog.Content maxWidth="560px">
-        <Flex align="start" justify="between" gap="3">
-          <Dialog.Title>
-            <Text className="font-bold text-lg">Create a channel</Text>
-          </Dialog.Title>
-          <Dialog.Close>
-            <IconButton
-              variant="ghost"
-              color="gray"
-              size="2"
-              aria-label="Close"
-              disabled={isCreating}
-            >
-              <XIcon size={18} />
-            </IconButton>
-          </Dialog.Close>
-        </Flex>
-
-        <Flex direction="column" gap="2" mt="4">
-          <Text
-            as="label"
-            htmlFor="channel-name"
-            className="font-medium text-sm"
-          >
-            Name
-          </Text>
-          <TextField.Root
-            id="channel-name"
-            autoFocus
-            size="3"
-            value={name}
-            placeholder="e.g. mobile"
-            maxLength={MAX_CHANNEL_NAME_LENGTH}
-            disabled={isCreating}
-            onChange={(e) => setName(e.target.value)}
-            onKeyDown={(e) => {
-              if (e.key === "Enter") {
-                e.preventDefault();
-                void submit();
-              }
-            }}
-          >
-            <TextField.Slot>
-              <HashIcon size={16} className="text-gray-10" />
-            </TextField.Slot>
-            <TextField.Slot side="right">
-              <Text className="text-gray-9 text-sm tabular-nums">
-                {remaining}
-              </Text>
-            </TextField.Slot>
-          </TextField.Root>
-          {validationError && (
-            <Text color="red" className="text-sm">
-              {validationError}
-            </Text>
+      <DialogContent showCloseButton={false} className="sm:max-w-lg">
+        <DialogHeader>
+          <DialogTitle>
+            {isDescribeMode ? "Build this context" : "Create a context"}
+          </DialogTitle>
+          <DialogDescription>
+            {isDescribeMode
+              ? `Describe what ${existingContext.channelName} is about — an agent plans and builds its CONTEXT.md with you.`
+              : "Name it and describe what it's about — an agent plans and builds its CONTEXT.md with you."}
+          </DialogDescription>
+        </DialogHeader>
+
+        <DialogBody className="flex flex-col gap-4">
+          {!isDescribeMode && (
+            <Field>
+              <FieldLabel htmlFor="context-name">Name</FieldLabel>
+              <Input
+                id="context-name"
+                autoFocus
+                value={name}
+                placeholder="e.g. mobile"
+                maxLength={MAX_CONTEXT_NAME_LENGTH}
+                disabled={busy}
+                onChange={(e) => setName(e.target.value)}
+                onKeyDown={(e) => {
+                  if (e.key === "Enter") {
+                    e.preventDefault();
+                    void submit();
+                  }
+                }}
+              />
+              {nameError ? (
+                <FieldError>{nameError}</FieldError>
+              ) : (
+                <span className="text-gray-9 text-xs tabular-nums">
+                  {remaining} left
+                </span>
+              )}
+            </Field>
           )}
-          <Text className="text-gray-10 text-sm">
-            Each channel gets its own dashboards, tasks, and settings. Use a
-            name that's easy to find.
-          </Text>
-        </Flex>
 
-        <Flex gap="3" mt="5" justify="end">
+          <Field>
+            <FieldLabel htmlFor="context-description">Description</FieldLabel>
+            <Textarea
+              id="context-description"
+              autoFocus={isDescribeMode}
+              rows={4}
+              value={description}
+              placeholder={DESCRIPTION_PLACEHOLDER}
+              disabled={busy}
+              onChange={(e) => setDescription(e.target.value)}
+              onKeyDown={(e) => {
+                // ⌘/Ctrl+Enter submits; a bare Enter stays a newline.
+                if (e.key === "Enter" && (e.metaKey || e.ctrlKey)) {
+                  e.preventDefault();
+                  void submit();
+                }
+              }}
+            />
+          </Field>
+        </DialogBody>
+
+        <DialogFooter>
+          <DialogClose
+            render={
+              <Button variant="outline" disabled={busy}>
+                Cancel
+              </Button>
+            }
+          />
           <Button
             variant="primary"
-            disabled={!trimmed || !!validationError || isCreating}
+            disabled={!canSubmit}
+            loading={busy}
             onClick={submit}
           >
-            Create
+            {isDescribeMode ? "Start planning" : "Create & plan"}
           </Button>
-        </Flex>
-      </Dialog.Content>
-    </Dialog.Root>
+        </DialogFooter>
+      </DialogContent>
+    </Dialog>
   );
 }
diff --git a/packages/ui/src/features/canvas/components/RenameChannelModal.tsx b/packages/ui/src/features/canvas/components/RenameChannelModal.tsx
index 2384d5369b..12ef4df1cd 100644
--- a/packages/ui/src/features/canvas/components/RenameChannelModal.tsx
+++ b/packages/ui/src/features/canvas/components/RenameChannelModal.tsx
@@ -1,4 +1,4 @@
-import { HashIcon, XIcon } from "@phosphor-icons/react";
+import { XIcon } from "@phosphor-icons/react";
 import { validateChannelName } from "@posthog/core/canvas/channelName";
 import { Button } from "@posthog/quill";
 import { ANALYTICS_EVENTS } from "@posthog/shared/analytics-events";
@@ -7,6 +7,7 @@ import { useChannelMutations } from "@posthog/ui/features/canvas/hooks/useChanne
 import { toast } from "@posthog/ui/primitives/toast";
 import { track } from "@posthog/ui/shell/analytics";
 import { Dialog, Flex, IconButton, Text, TextField } from "@radix-ui/themes";
+import { SquircleDashed } from "lucide-react";
 import { useEffect, useState } from "react";
 
 // Matches the create-channel naming constraint.
@@ -54,7 +55,7 @@ export function RenameChannelModal({
         channel_id: channel.id,
         success: false,
       });
-      toast.error("Couldn't rename channel", {
+      toast.error("Couldn't rename context", {
         description: error instanceof Error ? error.message : String(error),
       });
     }
@@ -70,7 +71,7 @@ export function RenameChannelModal({
       <Dialog.Content maxWidth="560px">
         <Flex align="start" justify="between" gap="3">
           <Dialog.Title>
-            <Text className="font-bold text-lg">Rename channel</Text>
+            <Text className="font-bold text-lg">Rename context</Text>
           </Dialog.Title>
           <Dialog.Close>
             <IconButton
@@ -110,7 +111,7 @@ export function RenameChannelModal({
             }}
           >
             <TextField.Slot>
-              <HashIcon size={16} className="text-gray-10" />
+              <SquircleDashed size={16} className="text-gray-10" />
             </TextField.Slot>
             <TextField.Slot side="right">
               <Text className="text-gray-9 text-sm tabular-nums">
diff --git a/packages/ui/src/features/canvas/components/WebsiteChannelHome.tsx b/packages/ui/src/features/canvas/components/WebsiteChannelHome.tsx
index 1f7e217988..78d0eeccf2 100644
--- a/packages/ui/src/features/canvas/components/WebsiteChannelHome.tsx
+++ b/packages/ui/src/features/canvas/components/WebsiteChannelHome.tsx
@@ -12,17 +12,24 @@ import {
   channelFeedQueryKey,
   useChannelFeed,
 } from "@posthog/ui/features/canvas/hooks/useChannelFeed";
+import {
+  channelCreationMessage,
+  useChannelFeedMessages,
+} from "@posthog/ui/features/canvas/hooks/useChannelFeedMessages";
 import { useChannels } from "@posthog/ui/features/canvas/hooks/useChannels";
 import { useChannelTaskMutations } from "@posthog/ui/features/canvas/hooks/useChannelTasks";
 import { useFolderInstructions } from "@posthog/ui/features/canvas/hooks/useFolderInstructions";
-import { useBackendChannel } from "@posthog/ui/features/canvas/hooks/useTaskChannels";
+import {
+  PERSONAL_CHANNEL_NAME,
+  useBackendChannel,
+} from "@posthog/ui/features/canvas/hooks/useTaskChannels";
 import { useThreadPanelStore } from "@posthog/ui/features/canvas/stores/threadPanelStore";
 import { SuggestedPromptCard } from "@posthog/ui/features/task-detail/components/SuggestedPromptCard";
 import { taskDetailQuery } from "@posthog/ui/features/tasks/queries";
 import { useSetHeaderContent } from "@posthog/ui/hooks/useSetHeaderContent";
 import { toast } from "@posthog/ui/primitives/toast";
 import { track } from "@posthog/ui/shell/analytics";
-import { Text } from "@radix-ui/themes";
+import { Heading, Text } from "@radix-ui/themes";
 import { useQueryClient } from "@tanstack/react-query";
 import { useNavigate } from "@tanstack/react-router";
 import { useCallback, useEffect, useMemo, useRef } from "react";
@@ -45,6 +52,20 @@ export function WebsiteChannelHome({ channelId }: { channelId: string }) {
   // personal channel), which owns the task feed and threads.
   const { channel: backendChannel } = useBackendChannel(channelName);
   const { tasks, isLoading } = useChannelFeed(backendChannel?.id);
+  // Durable "PostHog agent" rows (CONTEXT.md being built, …) live on the
+  // backend channel — the same id the feed tasks use, not the folder id.
+  const { messages: feedMessages } = useChannelFeedMessages(backendChannel?.id);
+  // "Ann created this context" opens the feed, derived from the channel row so
+  // it renders (and sorts first) even where the feed endpoint isn't deployed.
+  // Suppressed while it would be the feed's only entry — an untouched context
+  // shows the welcome empty state instead.
+  const systemMessages = useMemo(() => {
+    const creation = channelCreationMessage(backendChannel);
+    if (!creation || (tasks.length === 0 && feedMessages.length === 0)) {
+      return feedMessages;
+    }
+    return [creation, ...feedMessages];
+  }, [backendChannel, tasks.length, feedMessages]);
 
   useSetHeaderContent(
     useMemo(() => <ChannelHeader channelId={channelId} />, [channelId]),
@@ -100,7 +121,7 @@ export function WebsiteChannelHome({ channelId }: { channelId: string }) {
             task_id: task.id,
             success: false,
           });
-          toast.error("Couldn't file task to channel", {
+          toast.error("Couldn't file task to context", {
             description: error instanceof Error ? error.message : String(error),
           });
         });
@@ -131,12 +152,17 @@ export function WebsiteChannelHome({ channelId }: { channelId: string }) {
 
   const emptyState = (
     <div className="mx-auto flex min-h-full w-full max-w-[680px] flex-col justify-center gap-6 px-4 py-10">
-      <div className="text-center">
-        <h1 className="font-semibold text-2xl text-gray-12 tracking-tight">
-          {channelName ? `Welcome to #${channelName}` : "Welcome"}
-        </h1>
-        <Text className="mt-2 block text-[13px] text-gray-10">
-          Every message kicks off a task the whole channel can follow.
+      <div className="flex flex-col items-center gap-2 text-center">
+        <Heading className="font-bold text-2xl">
+          {channelName === PERSONAL_CHANNEL_NAME
+            ? "Welcome to your own personal context"
+            : channelName
+              ? `Welcome to ${channelName}`
+              : "Welcome"}
+        </Heading>
+        <Text>
+          Contexts are for areas of work. Context.md is self-updating, so start
+          some work and the context file will update itself.
         </Text>
       </div>
       <div className="flex flex-col gap-2">
@@ -163,6 +189,7 @@ export function WebsiteChannelHome({ channelId }: { channelId: string }) {
       <div className="flex min-w-0 flex-1 flex-col">
         <ChannelFeedView
           tasks={tasks}
+          systemMessages={systemMessages}
           isLoading={isLoading}
           emptyState={emptyState}
           onOpenTask={handleOpenTask}
diff --git a/packages/ui/src/features/canvas/components/WebsiteContext.tsx b/packages/ui/src/features/canvas/components/WebsiteContext.tsx
index 78f0ca5487..34e27071bc 100644
--- a/packages/ui/src/features/canvas/components/WebsiteContext.tsx
+++ b/packages/ui/src/features/canvas/components/WebsiteContext.tsx
@@ -1,8 +1,4 @@
-import {
-  FileTextIcon,
-  SparkleIcon,
-  SpinnerGapIcon,
-} from "@phosphor-icons/react";
+import { FileTextIcon, SparkleIcon } from "@phosphor-icons/react";
 import { FolderInstructionsConflictError } from "@posthog/api-client/posthog-client";
 import { buildContextSaveProps } from "@posthog/core/canvas/canvasAnalytics";
 import {
@@ -13,31 +9,17 @@ import {
   EmptyMedia,
   EmptyTitle,
   Button as QuillButton,
-  Tooltip,
-  TooltipContent,
-  TooltipTrigger,
 } from "@posthog/quill";
 import { ANALYTICS_EVENTS } from "@posthog/shared/analytics-events";
-import { isTerminalStatus } from "@posthog/shared/domain-types";
 import { ChannelHeader } from "@posthog/ui/features/canvas/components/ChannelHeader";
+import { CreateChannelModal } from "@posthog/ui/features/canvas/components/CreateChannelModal";
 import { useChannels } from "@posthog/ui/features/canvas/hooks/useChannels";
-import {
-  useFolderGenerationTask,
-  useFolderGenerationTaskMutation,
-} from "@posthog/ui/features/canvas/hooks/useFolderGenerationTask";
 import {
   useFolderInstructions,
   useFolderInstructionsMutations,
   useFolderInstructionsVersions,
 } from "@posthog/ui/features/canvas/hooks/useFolderInstructions";
-import { useGenerateContext } from "@posthog/ui/features/canvas/hooks/useGenerateContext";
 import { MarkdownRenderer } from "@posthog/ui/features/editor/components/MarkdownRenderer";
-import { useSessionForTask } from "@posthog/ui/features/sessions/useSession";
-import {
-  type WorkspaceMode,
-  WorkspaceModeSelect,
-} from "@posthog/ui/features/task-detail/components/WorkspaceModeSelect";
-import { taskDetailQuery } from "@posthog/ui/features/tasks/queries";
 import { useSetHeaderContent } from "@posthog/ui/hooks/useSetHeaderContent";
 import { track } from "@posthog/ui/shell/analytics";
 import {
@@ -52,8 +34,6 @@ import {
   Text,
   TextArea,
 } from "@radix-ui/themes";
-import { useQuery } from "@tanstack/react-query";
-import { Link } from "@tanstack/react-router";
 import { useEffect, useMemo, useState } from "react";
 
 type Mode = "rendered" | "edit";
@@ -77,7 +57,6 @@ export function WebsiteContext({ channelId }: WebsiteContextProps) {
     isLoading: isLoadingLatest,
     isFetching: isFetchingLatest,
     error: latestError,
-    refetch: refetchLatest,
   } = useFolderInstructions(channelId);
 
   const { data: versions = [], isLoading: isLoadingVersions } =
@@ -92,66 +71,6 @@ export function WebsiteContext({ channelId }: WebsiteContextProps) {
 
   const hasInstructions = (latest?.content ?? "").trim().length > 0;
 
-  // CONTEXT.md generation runs as a normal task (local or cloud) in the
-  // channel's repo. The "which task" association is stored server-side (shared
-  // across the project) so any user sees an in-progress generation. We poll it
-  // and the file while there's no published content yet.
-  const pollGen = !hasInstructions;
-  const { data: genTaskId } = useFolderGenerationTask(channelId, {
-    refetchInterval: pollGen ? 5000 : false,
-  });
-  const { set: setGenerationTask } = useFolderGenerationTaskMutation(channelId);
-
-  const genTaskQuery = useQuery({
-    ...taskDetailQuery(genTaskId ?? ""),
-    enabled: !!genTaskId && pollGen,
-    refetchInterval: genTaskId && pollGen ? 5000 : false,
-  });
-  const genTask = genTaskQuery.data;
-  const genSession = useSessionForTask(genTaskId ?? undefined);
-
-  // Running is environment-aware: cloud runs report status via cloudStatus /
-  // latest_run.status (a cloud session stays "connected" while polling), while
-  // local runs are tied to the live ACP session. While the task record is still
-  // loading we assume running to avoid a flash of "stopped".
-  const running = (() => {
-    if (!genTaskId) return false;
-    if (genTaskQuery.isLoading) return true;
-    if (genTask?.latest_run?.environment === "cloud") {
-      const cloudStatus =
-        genSession?.cloudStatus ?? genTask?.latest_run?.status ?? null;
-      return !isTerminalStatus(cloudStatus);
-    }
-    return (
-      genSession?.status === "connecting" || genSession?.status === "connected"
-    );
-  })();
-  const isGenerating = !!genTaskId && pollGen && running;
-  const isStopped = !!genTaskId && pollGen && !running;
-
-  // While the agent runs, poll the published file so it shows up without a
-  // manual refresh once the agent publishes via the MCP.
-  useEffect(() => {
-    if (!isGenerating) return;
-    const id = setInterval(() => void refetchLatest(), 5000);
-    return () => clearInterval(id);
-  }, [isGenerating, refetchLatest]);
-
-  // The agent publishes mid-run, just before its run ends — so when the run
-  // stops, refetch once to catch a just-published file before concluding it
-  // stopped without producing one.
-  useEffect(() => {
-    if (isStopped) void refetchLatest();
-  }, [isStopped, refetchLatest]);
-
-  // Once the file exists, the generation task has served its purpose — clear the
-  // server association so everyone stops tracking it. (The backend should also
-  // auto-clear on publish; this covers clients that observe content first.)
-  useEffect(() => {
-    if (genTaskId && hasInstructions)
-      void setGenerationTask(null).catch(() => {});
-  }, [genTaskId, hasInstructions, setGenerationTask]);
-
   // Seed the editor draft from the latest content the first time we land on
   // edit mode (or whenever latest changes while we're not actively editing).
   // We don't blow away an in-flight edit just because the cache refetched.
@@ -346,9 +265,7 @@ export function WebsiteContext({ channelId }: WebsiteContextProps) {
         className="scroll-area-constrain-width min-h-0 flex-1"
       >
         <Box p="4">
-          {isGenerating && genTaskId ? (
-            <GeneratingState channelId={channelId} taskId={genTaskId} />
-          ) : selectedVersion ? (
+          {selectedVersion ? (
             <Callout.Root color="gray" size="1">
               <Callout.Text>
                 Viewing v{selectedVersion.version} metadata. Past content is not
@@ -365,7 +282,6 @@ export function WebsiteContext({ channelId }: WebsiteContextProps) {
               <EmptyState
                 channelId={channelId}
                 channelName={channelName}
-                stoppedTaskId={isStopped ? (genTaskId ?? null) : null}
                 onCreate={() => {
                   setDraft(EMPTY_TEMPLATE);
                   setHasDraft(true);
@@ -397,13 +313,10 @@ export function WebsiteContext({ channelId }: WebsiteContextProps) {
 function EmptyState({
   channelId,
   channelName,
-  stoppedTaskId,
   onCreate,
 }: {
   channelId: string;
   channelName: string;
-  /** A prior generation task that stopped without producing a file, if any. */
-  stoppedTaskId: string | null;
   onCreate: () => void;
 }) {
   return (
@@ -415,144 +328,54 @@ function EmptyState({
         <EmptyTitle>No CONTEXT.md yet</EmptyTitle>
         <EmptyDescription>
           CONTEXT.md tells agents the specific details they need to know when
-          working in <strong>#{channelName}</strong> — conventions, gotchas, key
+          working in <strong>{channelName}</strong> — conventions, gotchas, key
           files, and anything else that isn't obvious from the code.
         </EmptyDescription>
       </EmptyHeader>
       <EmptyContent>
-        {stoppedTaskId ? (
-          <Callout.Root color="amber" size="1" className="w-full text-left">
-            <Callout.Text>
-              The previous generation in task{" "}
-              <Link
-                to="/website/$channelId/tasks/$taskId"
-                params={{ channelId, taskId: stoppedTaskId }}
-                className="font-medium text-amber-11 underline"
-              >
-                {shortTaskId(stoppedTaskId)}
-              </Link>{" "}
-              stopped before writing a CONTEXT.md. You can generate again.
-            </Callout.Text>
-          </Callout.Root>
-        ) : null}
-
         <Flex align="center" gap="3">
           <QuillButton variant="primary" size="default" onClick={onCreate}>
-            Create
+            Write it myself
           </QuillButton>
-          <GenerateWithAgent
-            channelId={channelId}
-            channelName={channelName}
-            regenerate={!!stoppedTaskId}
-          />
+          <GenerateWithAgent channelId={channelId} channelName={channelName} />
         </Flex>
       </EmptyContent>
     </Empty>
   );
 }
 
-// Kicks off a repo-less task that explores PostHog data (and a repo, if the
-// agent decides it needs one) and publishes CONTEXT.md via the MCP. The user no
-// longer picks a folder/repo up front — the agent attaches one lazily and asks
-// to clarify if it can't find the right one.
+// Opens the describe-and-plan dialog for this (already-existing) context, which
+// launches a plan-mode session that investigates PostHog + the repo and publishes
+// CONTEXT.md via the MCP once the user approves the plan. Same flow as creating a
+// context from scratch, minus the name field.
 function GenerateWithAgent({
   channelId,
   channelName,
-  regenerate,
 }: {
   channelId: string;
   channelName: string;
-  regenerate: boolean;
 }) {
-  const { generate, isStarting } = useGenerateContext(channelId, channelName);
-
-  // Generation always runs in the cloud, except the dev-only picker below lets a
-  // local build of these features be tested before it's merged to the cloud env.
-  const [workspaceMode, setWorkspaceMode] = useState<WorkspaceMode>("cloud");
-
-  const onGenerate = () => {
-    track(ANALYTICS_EVENTS.CONTEXT_ACTION, {
-      action_type: "generate_started",
-      channel_id: channelId,
-    });
-    void generate(workspaceMode);
-  };
+  const [dialogOpen, setDialogOpen] = useState(false);
 
   return (
-    <Flex align="center" gap="2">
+    <>
       <QuillButton
         variant="outline"
         size="default"
-        disabled={isStarting}
-        onClick={onGenerate}
+        onClick={() => setDialogOpen(true)}
       >
-        {isStarting ? <Spinner size="1" /> : <SparkleIcon size={14} />}
-        {regenerate ? "Generate again" : "Generate with agent"}
+        <SparkleIcon size={14} />
+        Build with agent
       </QuillButton>
-      {/* Dev-only: pick local vs cloud so a local build can be tested pre-merge. */}
-      {import.meta.env.DEV && (
-        <Tooltip>
-          <TooltipTrigger render={<div />}>
-            <WorkspaceModeSelect
-              value={workspaceMode}
-              onChange={setWorkspaceMode}
-              overrideModes={["local", "cloud"]}
-              disabled={isStarting}
-              size="1"
-            />
-          </TooltipTrigger>
-          <TooltipContent>
-            Dev mode only — generation always runs in the cloud in production.
-          </TooltipContent>
-        </Tooltip>
-      )}
-    </Flex>
+      <CreateChannelModal
+        open={dialogOpen}
+        onOpenChange={setDialogOpen}
+        existingContext={{ channelId, channelName }}
+      />
+    </>
   );
 }
 
-// Shown while the generation task is running: a centered status with a spinner
-// and a button to jump to the task that's doing the work.
-function GeneratingState({
-  channelId,
-  taskId,
-}: {
-  channelId: string;
-  taskId: string;
-}) {
-  return (
-    <Empty>
-      <EmptyHeader>
-        <EmptyMedia variant="icon">
-          <SpinnerGapIcon size={18} className="animate-spin text-accent-9" />
-        </EmptyMedia>
-        <EmptyTitle>Generating</EmptyTitle>
-        <EmptyDescription>
-          An agent is writing this CONTEXT.md.
-        </EmptyDescription>
-      </EmptyHeader>
-      <EmptyContent>
-        <QuillButton
-          variant="primary"
-          size="default"
-          render={
-            <Link
-              to="/website/$channelId/tasks/$taskId"
-              params={{ channelId, taskId }}
-            />
-          }
-        >
-          View task
-        </QuillButton>
-      </EmptyContent>
-    </Empty>
-  );
-}
-
-// A compact, readable handle for a task uuid in inline text.
-function shortTaskId(taskId: string): string {
-  return taskId.slice(0, 8);
-}
-
 // `created_at` is an ISO timestamp; we render it as a short local string for
 // the version dropdown. Falls back to the raw string if Date parsing fails.
 function formatTimestamp(iso: string): string {
diff --git a/packages/ui/src/features/canvas/components/WebsiteNewTask.test.tsx b/packages/ui/src/features/canvas/components/WebsiteNewTask.test.tsx
index 55250bc627..0ee1e45e2e 100644
--- a/packages/ui/src/features/canvas/components/WebsiteNewTask.test.tsx
+++ b/packages/ui/src/features/canvas/components/WebsiteNewTask.test.tsx
@@ -73,14 +73,12 @@ describe("WebsiteNewTask context panel", () => {
 
     // Panel starts closed.
     expect(
-      screen.queryByText("#project-bluebird CONTEXT.md"),
+      screen.queryByText("project-bluebird CONTEXT.md"),
     ).not.toBeInTheDocument();
 
     await user.click(screen.getByRole("button", { name: "context-chip" }));
 
-    expect(
-      screen.getByText("#project-bluebird CONTEXT.md"),
-    ).toBeInTheDocument();
+    expect(screen.getByText("project-bluebird CONTEXT.md")).toBeInTheDocument();
     const viewContextCalls = () =>
       track.mock.calls.filter(
         ([, props]) => props?.action_type === "view_context",
@@ -97,7 +95,7 @@ describe("WebsiteNewTask context panel", () => {
     // Clicking again closes the panel and must NOT re-track view_context.
     await user.click(screen.getByRole("button", { name: "context-chip" }));
     expect(
-      screen.queryByText("#project-bluebird CONTEXT.md"),
+      screen.queryByText("project-bluebird CONTEXT.md"),
     ).not.toBeInTheDocument();
     expect(viewContextCalls()).toHaveLength(1);
   });
diff --git a/packages/ui/src/features/canvas/components/WebsiteNewTask.tsx b/packages/ui/src/features/canvas/components/WebsiteNewTask.tsx
index 078e8dd1ca..786d6412eb 100644
--- a/packages/ui/src/features/canvas/components/WebsiteNewTask.tsx
+++ b/packages/ui/src/features/canvas/components/WebsiteNewTask.tsx
@@ -91,7 +91,7 @@ export function WebsiteNewTask({ channelId }: { channelId: string }) {
             task_id: task.id,
             success: false,
           });
-          toast.error("Couldn't file task to channel", {
+          toast.error("Couldn't file task to context", {
             description: error instanceof Error ? error.message : String(error),
           });
         });
diff --git a/packages/ui/src/features/canvas/contextPrompt.ts b/packages/ui/src/features/canvas/contextPrompt.ts
index 2b1c60284e..e602414a5d 100644
--- a/packages/ui/src/features/canvas/contextPrompt.ts
+++ b/packages/ui/src/features/canvas/contextPrompt.ts
@@ -1,20 +1,35 @@
-// Builds the prompt for the task that generates a channel's CONTEXT.md. The
+// Builds the prompt for the task that generates a context's CONTEXT.md. The
 // task runs as a normal repo-less agent task (no repo picked up front), so the
 // agent has full tools; this is the task's content (its first user message).
 // CONTEXT.md is not a file on disk — it lives in PostHog — so the agent must
 // publish the result via the PostHog MCP rather than writing a file.
+//
+// The task starts in plan mode: the agent investigates and proposes a plan for
+// the document, the user shapes it, and only once the plan is approved does the
+// agent publish. The user's own description of what the context is about seeds
+// that plan.
 export function buildContextGenerationPrompt(input: {
   channelName: string;
   channelId: string;
+  description?: string;
 }): string {
-  const { channelName, channelId } = input;
-  return `Generate a CONTEXT.md for the channel/folder "${channelName}".
-
+  const { channelName, channelId, description } = input;
+  const seed = description?.trim()
+    ? `\nThe user describes what this context is about:
+"""
+${description.trim()}
+"""
+Treat this as the primary guide for what CONTEXT.md should cover — start from it,
+then verify and fill it out against the sources below.\n`
+    : "";
+  return `Build a CONTEXT.md for the context/folder "${channelName}".
+${seed}
 CONTEXT.md tells future agents the specific, non-obvious details they need to
 work in "${channelName}": what it is, key files, conventions, gotchas, and the
 PostHog resources that relate to it.
 
-Investigate two sources:
+You are in plan mode. Investigate first, then propose a plan for the document and
+let the user refine it before you publish. Investigate two sources:
 1. The relevant repository — use Read, Grep, and Glob to find code, directories,
    and config related to "${channelName}" (conventions, key files, gotchas). No
    repo is attached up front: if one isn't already available and you can't infer
@@ -23,7 +38,7 @@ Investigate two sources:
    this project: feature flags, experiments, surveys, notebooks, insights, web
    analytics, and persons. Operate only on this project.
 
-When you have gathered enough, PUBLISH the document by calling the PostHog MCP
+Once the plan is approved, PUBLISH the document by calling the PostHog MCP
 tool \`desktop-file-system-instructions-partial-update\` exactly once with:
 - id: "${channelId}"
 - content: the full CONTEXT.md markdown
diff --git a/packages/ui/src/features/canvas/hooks/useChannelFeedMessages.ts b/packages/ui/src/features/canvas/hooks/useChannelFeedMessages.ts
new file mode 100644
index 0000000000..91c20ddd14
--- /dev/null
+++ b/packages/ui/src/features/canvas/hooks/useChannelFeedMessages.ts
@@ -0,0 +1,100 @@
+import type {
+  ChannelFeedMessage,
+  TaskChannel,
+} from "@posthog/shared/domain-types";
+import { userDisplayName } from "@posthog/ui/features/canvas/utils/userDisplay";
+import { useAuthenticatedQuery } from "@posthog/ui/hooks/useAuthenticatedQuery";
+import { useMemo } from "react";
+
+// Multiplayer, like the task feed: poll so a teammate's announcement appears
+// without a dedicated push channel.
+const CHANNEL_FEED_MESSAGES_POLL_INTERVAL_MS = 5_000;
+
+// A channel-feed system message flattened to what the feed renders.
+export interface ChannelFeedSystemMessage {
+  id: string;
+  /** ISO; interleaved with task cards in the feed. */
+  createdAt: string;
+  text: string;
+}
+
+export function channelFeedMessagesQueryKey(channelId: string | undefined) {
+  return ["channel-feed-messages", channelId ?? "none"] as const;
+}
+
+// The "created this context" row is synthesized from the channel row itself
+// (below) — the canonical creation record, available even where the feed
+// endpoint isn't. Server-emitted channel_created (and its legacy client-posted
+// context_created twin) would duplicate it, so both are dropped from the feed.
+const CREATION_EVENTS = new Set(["channel_created", "context_created"]);
+
+// Render the announcement from its event + structured payload (rename-safe),
+// falling back to the freeform content.
+function messageText(message: ChannelFeedMessage): string {
+  const actor = userDisplayName(message.author ?? null);
+  const contextName =
+    typeof message.payload?.context_name === "string"
+      ? message.payload.context_name
+      : "";
+  switch (message.event) {
+    case "context_md_building":
+      return `${actor} is building CONTEXT.md${contextName ? ` for ${contextName}` : ""}`;
+    default:
+      return message.content || `${actor} posted an update`;
+  }
+}
+
+/**
+ * The feed's "Ann created this context" opener, derived from the channel row
+ * (creator + creation time) rather than a feed message: the channel predates
+ * everything in its feed, so it always sorts first, and it renders even before
+ * the feed-message endpoint is deployed. Personal channels are provisioned by
+ * the system, so they get no creation row.
+ */
+export function channelCreationMessage(
+  channel: TaskChannel | undefined,
+): ChannelFeedSystemMessage | undefined {
+  if (!channel || channel.channel_type !== "public") return undefined;
+  return {
+    id: `channel-created-${channel.id}`,
+    createdAt: channel.created_at,
+    text: `${userDisplayName(channel.created_by ?? null)} created this context`,
+  };
+}
+
+/**
+ * A channel's durable "PostHog agent" announcements (context created, CONTEXT.md
+ * being built), oldest first, flattened to display text.
+ */
+export function useChannelFeedMessages(channelId: string | undefined): {
+  messages: ChannelFeedSystemMessage[];
+  isLoading: boolean;
+} {
+  const query = useAuthenticatedQuery<ChannelFeedMessage[]>(
+    channelFeedMessagesQueryKey(channelId),
+    (client) => client.getChannelFeed(channelId as string),
+    {
+      enabled: !!channelId,
+      // The endpoint may not be deployed yet (posthog#70320): don't retry, and
+      // stop polling once the query errors — otherwise every open channel view
+      // streams 404s (poll tick × default retries) forever.
+      retry: false,
+      refetchInterval: (query) =>
+        query.state.status === "error"
+          ? false
+          : CHANNEL_FEED_MESSAGES_POLL_INTERVAL_MS,
+    },
+  );
+  const messages = useMemo(
+    () =>
+      (query.data ?? [])
+        .filter((m) => !CREATION_EVENTS.has(m.event))
+        .map((m) => ({
+          id: m.id,
+          createdAt: m.created_at,
+          text: messageText(m),
+        })),
+    [query.data],
+  );
+  return { messages, isLoading: query.isLoading };
+}
diff --git a/packages/ui/src/features/canvas/hooks/useDashboards.ts b/packages/ui/src/features/canvas/hooks/useDashboards.ts
index 184d45ed4c..213e3ed77b 100644
--- a/packages/ui/src/features/canvas/hooks/useDashboards.ts
+++ b/packages/ui/src/features/canvas/hooks/useDashboards.ts
@@ -193,7 +193,7 @@ export function useOpenHomeCanvas(): (channel: {
         });
       } catch (error) {
         log.error("Failed to open home canvas", { error });
-        toast.error("Couldn't open channel home", {
+        toast.error("Couldn't open context home", {
           description: error instanceof Error ? error.message : String(error),
         });
       }
diff --git a/packages/ui/src/features/canvas/hooks/useFolderGenerationTask.ts b/packages/ui/src/features/canvas/hooks/useFolderGenerationTask.ts
deleted file mode 100644
index 87bab52e11..0000000000
--- a/packages/ui/src/features/canvas/hooks/useFolderGenerationTask.ts
+++ /dev/null
@@ -1,60 +0,0 @@
-import { useOptionalAuthenticatedClient } from "@posthog/ui/features/auth/authClient";
-import { useAuthenticatedQuery } from "@posthog/ui/hooks/useAuthenticatedQuery";
-import { useMutation, useQueryClient } from "@tanstack/react-query";
-import { useCallback } from "react";
-
-// The task generating a channel's CONTEXT.md is stored server-side (keyed on the
-// folder), so it's shared across everyone in the project — any user sees an
-// in-progress generation and won't double-start it. Mirrors the
-// useFolderInstructions query/mutation shape.
-
-const GENERATION_TASK_QUERY_KEY = (folderId: string) =>
-  ["folder-generation-task", folderId] as const;
-
-export function useFolderGenerationTask(
-  folderId: string | null,
-  options?: { enabled?: boolean; refetchInterval?: number | false },
-) {
-  return useAuthenticatedQuery<string | null>(
-    folderId
-      ? GENERATION_TASK_QUERY_KEY(folderId)
-      : (["folder-generation-task", "none"] as const),
-    async (client) => {
-      if (!folderId) return null;
-      return client.getDesktopFolderGenerationTask(folderId);
-    },
-    {
-      enabled: Boolean(folderId) && (options?.enabled ?? true),
-      staleTime: 0,
-      refetchInterval: options?.refetchInterval ?? false,
-    },
-  );
-}
-
-// set(taskId) records the generating task; set(null) clears it. Best-effort:
-// callers should not block generation on this (the backend endpoint may not
-// exist yet, in which case the client no-ops on 404).
-export function useFolderGenerationTaskMutation(folderId: string | null) {
-  const client = useOptionalAuthenticatedClient();
-  const queryClient = useQueryClient();
-
-  const mutation = useMutation({
-    mutationFn: async (taskId: string | null) => {
-      if (!client || !folderId) return;
-      await client.setDesktopFolderGenerationTask(folderId, taskId);
-    },
-    onSuccess: () => {
-      if (!folderId) return;
-      void queryClient.invalidateQueries({
-        queryKey: GENERATION_TASK_QUERY_KEY(folderId),
-      });
-    },
-  });
-
-  const set = useCallback(
-    (taskId: string | null) => mutation.mutateAsync(taskId),
-    [mutation],
-  );
-
-  return { set };
-}
diff --git a/packages/ui/src/features/canvas/hooks/useGenerateContext.ts b/packages/ui/src/features/canvas/hooks/useGenerateContext.ts
index b868629eb3..7c6fd53676 100644
--- a/packages/ui/src/features/canvas/hooks/useGenerateContext.ts
+++ b/packages/ui/src/features/canvas/hooks/useGenerateContext.ts
@@ -1,67 +1,188 @@
+import type { PostHogAPIClient } from "@posthog/api-client/posthog-client";
+import {
+  REPORT_MODEL_RESOLVER,
+  type ReportModelResolver,
+} from "@posthog/core/inbox/identifiers";
 import {
   TASK_SERVICE,
   type TaskService,
 } from "@posthog/core/task-detail/taskService";
 import { useService } from "@posthog/di/react";
 import { useHostTRPC } from "@posthog/host-router/react";
-import type { WorkspaceMode } from "@posthog/shared";
+import { getCloudUrlFromRegion, type WorkspaceMode } from "@posthog/shared";
+import type { Task } from "@posthog/shared/domain-types";
+import { useOptionalAuthenticatedClient } from "@posthog/ui/features/auth/authClient";
+import { useAuthStateValue } from "@posthog/ui/features/auth/store";
 import { buildContextGenerationPrompt } from "@posthog/ui/features/canvas/contextPrompt";
+import { channelFeedQueryKey } from "@posthog/ui/features/canvas/hooks/useChannelFeed";
+import { channelFeedMessagesQueryKey } from "@posthog/ui/features/canvas/hooks/useChannelFeedMessages";
 import { useChannelTaskMutations } from "@posthog/ui/features/canvas/hooks/useChannelTasks";
-import { useFolderGenerationTaskMutation } from "@posthog/ui/features/canvas/hooks/useFolderGenerationTask";
+import {
+  normalizeChannelName,
+  PERSONAL_CHANNEL_NAME,
+} from "@posthog/ui/features/canvas/hooks/useTaskChannels";
 import { toastError } from "@posthog/ui/features/notifications/errorDetails";
+import { useSettingsStore } from "@posthog/ui/features/settings/settingsStore";
+import { usePreviewConfig } from "@posthog/ui/features/task-detail/hooks/usePreviewConfig";
 import { useCreateTask } from "@posthog/ui/features/tasks/useTaskCrudMutations";
 import { useQueryClient } from "@tanstack/react-query";
 import { useCallback, useState } from "react";
 
-// Kicks off CONTEXT.md generation as a repo-less task. The user no longer picks
-// a folder/repo up front — the agent decides at runtime whether it needs one and
-// asks the user to clarify if it can't find the right one. The task runs as a
-// cloud run (not a local agent) so generation proceeds server-side regardless of
-// which client kicked it off, is filed to the channel, and recorded server-side
-// as the channel's generation task so every user's CONTEXT.md view can track it.
-export function useGenerateContext(channelId: string, channelName: string) {
+interface GenerateContextInput {
+  /** The desktop folder/context id — also the /website route param. */
+  channelId: string;
+  channelName: string;
+  /** What the user says this context is about; seeds the plan. */
+  description: string;
+  workspaceMode?: WorkspaceMode;
+}
+
+// The task's backend channel is what the context feed queries (getTasks by
+// channel), while the folder id drives Recents/Artifacts. Resolve the folder's
+// display name onto its backend channel the way useBackendChannel does: the "me"
+// folder maps to the personal channel; any other name resolve-or-creates its
+// public channel. Without this the task only appears in Recents, not the feed.
+async function resolveBackendChannelId(
+  client: PostHogAPIClient | null,
+  channelName: string,
+): Promise<string | undefined> {
+  if (!client) return undefined;
+  const normalized = normalizeChannelName(channelName);
+  if (!normalized) return undefined;
+  if (normalized === PERSONAL_CHANNEL_NAME) {
+    const channels = await client.getTaskChannels();
+    return channels.find((c) => c.channel_type === "personal")?.id;
+  }
+  return (await client.resolveTaskChannel(normalized)).id;
+}
+
+// Launches the plan-mode session that builds a context's CONTEXT.md. The task
+// runs repo-less (the agent attaches a repo lazily and asks to clarify if it
+// can't find the right one) and starts in plan mode, seeded by the user's
+// description, so the user shapes the document before it publishes via the
+// PostHog MCP. Defaults to a cloud run so generation never ties up (or depends
+// on) the local machine. Returns the created task, or null on failure.
+//
+// Channel-agnostic on purpose: the create-context dialog calls this with a
+// freshly-created context's id (no bound hook possible before it exists), and
+// the CONTEXT.md empty state calls it with the existing context.
+export function useGenerateContext() {
   const taskService = useService<TaskService>(TASK_SERVICE);
+  const modelResolver = useService<ReportModelResolver>(REPORT_MODEL_RESOLVER);
+  const cloudRegion = useAuthStateValue((state) => state.cloudRegion);
   const trpc = useHostTRPC();
   const queryClient = useQueryClient();
   const { invalidateTasks } = useCreateTask();
   const { fileTask } = useChannelTaskMutations();
-  const { set: setGenerationTask } = useFolderGenerationTaskMutation(channelId);
+  const client = useOptionalAuthenticatedClient();
   const [isStarting, setIsStarting] = useState(false);
 
+  // Resolve adapter + model the same way the composer does. A cloud run rejects
+  // a task with no model ("required when selecting a cloud runtime"), so this
+  // headless launch must supply one rather than relying on a composer's picker.
+  const adapter = useSettingsStore((s) => s.lastUsedAdapter);
+  const { modelOption } = usePreviewConfig(adapter);
+  const currentModel =
+    modelOption?.type === "select" ? modelOption.currentValue : undefined;
+
   const generate = useCallback(
-    async (workspaceMode: WorkspaceMode = "cloud"): Promise<string | null> => {
+    async ({
+      channelId,
+      channelName,
+      description,
+      workspaceMode = "cloud",
+    }: GenerateContextInput): Promise<Task | null> => {
       setIsStarting(true);
       try {
+        // The composer's picker may not have resolved yet (or the user never
+        // used it), so fall back to the adapter's server default the way the
+        // inbox one-click flows do; the resolver validates against the gateway.
+        // Without a model a cloud run is rejected server-side after the context
+        // was already created — hard-stop with a clear toast instead.
+        let model = currentModel;
+        if (workspaceMode === "cloud") {
+          model = cloudRegion
+            ? await modelResolver.resolveDefaultModel(
+                getCloudUrlFromRegion(cloudRegion),
+                adapter ?? "claude",
+                currentModel,
+              )
+            : undefined;
+          if (!model) {
+            toastError(
+              "Couldn't start the planning session",
+              "No model is configured for cloud runs.",
+            );
+            return null;
+          }
+        }
+        // Own the task on the backend channel so it lands in the context feed
+        // (not just Recents). Best-effort: fall back to no channel on failure.
+        const backendChannelId = await resolveBackendChannelId(
+          client,
+          channelName,
+        ).catch(() => undefined);
+
         const result = await taskService.createTask(
           {
-            content: buildContextGenerationPrompt({ channelName, channelId }),
-            taskDescription: `Generate CONTEXT.md for #${channelName}`,
-            // Defaults to a cloud run — generation should never tie up (or
-            // depend on) the local machine, and it's never the sticky last-used
-            // workspace mode. The dev-only picker can override to "local" to
-            // test a local build of these features before merging.
+            content: buildContextGenerationPrompt({
+              channelName,
+              channelId,
+              description,
+            }),
+            taskDescription: `Build CONTEXT.md for ${channelName}`,
             workspaceMode,
+            adapter: adapter ?? "claude",
+            model,
+            channelId: backendChannelId,
+            // Plan mode: the agent proposes the document and waits for approval
+            // before publishing, so the user co-designs CONTEXT.md.
+            executionMode: "plan",
             allowNoRepo: true,
           },
           (output) => invalidateTasks(output.task),
         );
 
         if (!result.success) {
-          toastError("Couldn't start CONTEXT.md generation", result.error);
+          toastError("Couldn't start the planning session", result.error);
           return null;
         }
 
         const task = result.data.task;
-        // File into the channel + record as the (shared) generation task. Both
-        // are best-effort: a failure here shouldn't undo a started task.
+        // File into the context so its Recents/Artifacts tabs pick it up.
+        // Best-effort — a failure here shouldn't undo a started task.
         void fileTask(channelId, task.id, task.title).catch(() => {});
-        void setGenerationTask(task.id).catch(() => {});
+        if (backendChannelId) {
+          // Announce the CONTEXT.md build in the channel feed (durable, team-
+          // visible), keyed on the backend channel — the same id the task cards
+          // use. Timestamped just before the task so it sorts above the card.
+          // Best-effort.
+          const buildingAt = new Date(
+            new Date(task.created_at).getTime() - 1,
+          ).toISOString();
+          void client
+            ?.postChannelFeedMessage(backendChannelId, {
+              event: "context_md_building",
+              payload: { context_name: channelName },
+              createdAt: buildingAt,
+            })
+            .then(() =>
+              queryClient.invalidateQueries({
+                queryKey: channelFeedMessagesQueryKey(backendChannelId),
+              }),
+            )
+            .catch(() => {});
+          // Show the new card in the context feed without waiting for the poll.
+          void queryClient.invalidateQueries({
+            queryKey: channelFeedQueryKey(backendChannelId),
+          });
+        }
         // Refresh the workspace cache so the new cloud workspace row appears and
         // the task view resolves the cloud run instead of the repo-picker prompt.
         void queryClient.invalidateQueries({
           queryKey: trpc.workspace.getAll.queryKey(),
         });
-        return task.id;
+        return task;
       } finally {
         setIsStarting(false);
       }
@@ -72,9 +193,11 @@ export function useGenerateContext(channelId: string, channelName: string) {
       queryClient,
       invalidateTasks,
       fileTask,
-      setGenerationTask,
-      channelId,
-      channelName,
+      client,
+      adapter,
+      currentModel,
+      modelResolver,
+      cloudRegion,
     ],
   );
 
diff --git a/packages/ui/src/features/command/CommandMenu.tsx b/packages/ui/src/features/command/CommandMenu.tsx
index 92231d3a64..5a734c343c 100644
--- a/packages/ui/src/features/command/CommandMenu.tsx
+++ b/packages/ui/src/features/command/CommandMenu.tsx
@@ -3,7 +3,6 @@ import {
   CaretRightIcon,
   ChartLine,
   EnvelopeSimple,
-  HashIcon,
 } from "@phosphor-icons/react";
 import { resolveService } from "@posthog/di/container";
 import {
@@ -76,6 +75,7 @@ import {
   ZoomInIcon,
   ZoomOutIcon,
 } from "@radix-ui/react-icons";
+import { SquircleDashed } from "lucide-react";
 import { useCallback, useEffect, useMemo, useState } from "react";
 
 interface CommandMenuProps {
@@ -483,12 +483,12 @@ export function CommandMenu({ open, onOpenChange }: CommandMenuProps) {
     if (channels.length === 0) return [];
     return [
       {
-        label: "Channels",
+        label: "Contexts",
         items: channels.map((channel) => ({
           id: `channel-${channel.id}`,
           label: channel.name,
-          keywords: "channel",
-          icon: <HashIcon size={12} className="text-gray-11" />,
+          keywords: "context",
+          icon: <SquircleDashed size={12} className="text-gray-11" />,
           action: "open-channel" as CommandMenuAction,
           channelId: channel.id,
           onRun: () => {
diff --git a/packages/ui/src/features/sidebar/components/SidebarNavSection.tsx b/packages/ui/src/features/sidebar/components/SidebarNavSection.tsx
index 5dd3b59233..2097ee0555 100644
--- a/packages/ui/src/features/sidebar/components/SidebarNavSection.tsx
+++ b/packages/ui/src/features/sidebar/components/SidebarNavSection.tsx
@@ -1,4 +1,3 @@
-import { HashIcon } from "@phosphor-icons/react";
 import { Badge, Switch } from "@posthog/quill";
 import { PROJECT_BLUEBIRD_FLAG } from "@posthog/shared";
 import { ANALYTICS_EVENTS } from "@posthog/shared/analytics-events";
@@ -29,6 +28,7 @@ import { track } from "@posthog/ui/shell/analytics";
 import { useCommandMenuStore } from "@posthog/ui/shell/commandMenuStore";
 import { Box, Flex } from "@radix-ui/themes";
 import { useRouterState } from "@tanstack/react-router";
+import { SquircleDashed } from "lucide-react";
 import { ActivityItem } from "./items/ActivityItem";
 import { AgentsItem } from "./items/AgentsItem";
 import { CommandCenterItem } from "./items/CommandCenterItem";
@@ -199,9 +199,9 @@ export function SidebarNavSection({
           className="group flex w-full cursor-pointer items-center gap-2 rounded px-2 py-1 text-[13px] leading-snug transition-colors hover:bg-fill-secondary"
         >
           <span className="flex shrink-0 items-center opacity-80">
-            <HashIcon size={16} />
+            <SquircleDashed size={14} />
           </span>
-          <span className="min-w-0 truncate font-medium">Channels</span>
+          <span className="min-w-0 truncate font-medium">Contexts</span>
           <Badge variant="info">Alpha</Badge>
           <Switch
             id="channels-toggle"
diff --git a/packages/ui/src/features/task-detail/components/TaskInput.tsx b/packages/ui/src/features/task-detail/components/TaskInput.tsx
index c152024f96..11b35d10e4 100644
--- a/packages/ui/src/features/task-detail/components/TaskInput.tsx
+++ b/packages/ui/src/features/task-detail/components/TaskInput.tsx
@@ -1335,7 +1335,7 @@ export function TaskInput({
                         <button
                           type="button"
                           onClick={() => setChannelContextDismissed(true)}
-                          aria-label="Remove channel context from prompt"
+                          aria-label="Remove context from prompt"
                           className="ml-0.5 inline-flex size-3.5 items-center justify-center rounded text-gray-10 hover:bg-gray-5 hover:text-gray-12"
                         >
                           <X size={12} />
diff --git a/packages/ui/src/features/tasks/useTaskContextMenu.ts b/packages/ui/src/features/tasks/useTaskContextMenu.ts
index bafeb8270c..d7c9c29c81 100644
--- a/packages/ui/src/features/tasks/useTaskContextMenu.ts
+++ b/packages/ui/src/features/tasks/useTaskContextMenu.ts
@@ -124,7 +124,7 @@ export function useTaskContextMenu() {
             try {
               await fileTask(intent.channelId, task.id, task.title);
             } catch (error) {
-              toast.error("Couldn't file task to channel", {
+              toast.error("Couldn't file task to context", {
                 description:
                   error instanceof Error ? error.message : String(error),
               });