diff --git a/apps/code/snapshots.yml b/apps/code/snapshots.yml
index e2fc980da7..fc8cd61bb6 100644
--- a/apps/code/snapshots.yml
+++ b/apps/code/snapshots.yml
@@ -680,6 +680,14 @@ snapshots:
         hash: v1.k4693efd2.e01a8a548c694761b9f2a575268f420f653ad7eb9d26c2e33dc245ab03415fcf.Z5Ut_gF62xXnxkDgBXxE3yk6UDIAEVX5Sw_rKBPsqps
     settings-personalizationsettings--synced-truncated--light:
         hash: v1.k4693efd2.3c9f0dfa759b8c174abd8754593f0db9fd1518ff5225cccdcf0c3e83d4cdbe77.BqdmyuIiYJuGmHCQiRVAaBMk-xgycYOgVfwuMqma4LY
+    sidebar-taskitem--in-repository-group--dark:
+        hash: v1.k4693efd2.601f072b55c719b74db2abf8e4aa7f268f7c2cf80a279590fe841198392b49ee.sL5RJdxs9Ur7fkB9J_SO2L9JXFEpW1l1fmmQpd_-hEA
+    sidebar-taskitem--in-repository-group--light:
+        hash: v1.k4693efd2.0ae532ca59c02e645355bb9f08af295fb0c2afcd2c8c3cc6acd178f276acb416.6sNqaOArOyd2Wns3UDl8uQyd4aiwAAncKTbYidsZ9yw
+    sidebar-taskitem--pinned--dark:
+        hash: v1.k4693efd2.fef3cdc0c8a5485cabbb7ac37830d119d8939e864e972ee7a9cbd5e8c1a99fa9.6r2emBachF9VHn2cz9a2ktly_0P6sGl1iKfoQt9Sxu4
+    sidebar-taskitem--pinned--light:
+        hash: v1.k4693efd2.8e36c4705d8650d806cf7c933684299aca5d751d1dbffd58e836e20015115bd5.gkDV3puY-rvStAc8WBaLWOOakDzZDYv8B3wTukt4QbQ
     skill-buttons-skillbuttonactionmessage--add-analytics--dark:
         hash: v1.k4693efd2.6d4ce4fac8e23a50efbbfaf24c2e11f8981f6778af2bfb2ca559749d7bda0eca.OnypKY5jyJSbQUZtTVcUy-eXC2euU-xQ2wFBYJOsKwI
     skill-buttons-skillbuttonactionmessage--add-analytics--light:
diff --git a/packages/core/src/sidebar/groupTasks.ts b/packages/core/src/sidebar/groupTasks.ts
index af674467d1..b1a4f33b87 100644
--- a/packages/core/src/sidebar/groupTasks.ts
+++ b/packages/core/src/sidebar/groupTasks.ts
@@ -16,7 +16,19 @@ export interface GroupableTask {
   originProduct?: string;
 }
 
+/** The registered-folder fields that decide which group a folder belongs to. */
+export interface GroupableFolder {
+  path: string;
+  remoteUrl: string | null;
+  /**
+   * Root of the main checkout when this folder is a linked git worktree, null
+   * or absent for a main clone.
+   */
+  mainRepoPath?: string | null;
+}
+
 export const CUSTOM_IMAGES_GROUP_ID = "custom-images";
+export const CUSTOM_IMAGES_GROUP_NAME = "Custom images";
 
 export interface TaskGroup<T extends GroupableTask> {
   id: string;
@@ -53,10 +65,9 @@ export function getRepositoryInfo(
   return null;
 }
 
-export function folderGroupId(folder: {
-  path: string;
-  remoteUrl: string | null;
-}): string {
+export function folderGroupId(
+  folder: Pick<GroupableFolder, "path" | "remoteUrl">,
+): string {
   if (folder.remoteUrl) {
     return normalizeRepoKey(folder.remoteUrl).toLowerCase();
   }
@@ -70,13 +81,10 @@ export function folderGroupId(folder: {
  * so prefer a folder that is not a linked worktree (`mainRepoPath` is set only
  * on linked worktrees).
  */
-export function findGroupFolder<
-  F extends {
-    path: string;
-    remoteUrl: string | null;
-    mainRepoPath?: string | null;
-  },
->(folders: F[], groupId: string): F | undefined {
+export function findGroupFolder<F extends GroupableFolder>(
+  folders: F[],
+  groupId: string,
+): F | undefined {
   const matches = folders.filter((f) => folderGroupId(f) === groupId);
   return matches.find((f) => !f.mainRepoPath) ?? matches[0];
 }
@@ -95,7 +103,7 @@ export function groupByRepository<T extends GroupableTask>(
       ? CUSTOM_IMAGES_GROUP_ID
       : (repository?.fullPath ?? "other");
     const groupName = isImageBuilder
-      ? "Custom images"
+      ? CUSTOM_IMAGES_GROUP_NAME
       : (repository?.name ?? "Other");
 
     let group = groupMap.get(groupId);
diff --git a/packages/core/src/sidebar/taskContext.test.ts b/packages/core/src/sidebar/taskContext.test.ts
new file mode 100644
index 0000000000..6ad6f27bea
--- /dev/null
+++ b/packages/core/src/sidebar/taskContext.test.ts
@@ -0,0 +1,119 @@
+import { describe, expect, it } from "vitest";
+import {
+  formatTaskContext,
+  type TaskContextFolder,
+  type TaskContextTask,
+} from "./taskContext";
+
+const CODE_REPO = {
+  fullPath: "posthog/code",
+  name: "code",
+  organization: "PostHog",
+};
+
+function task(overrides: Partial<TaskContextTask> = {}): TaskContextTask {
+  return {
+    repository: CODE_REPO,
+    workspaceMode: "local",
+    branchName: null,
+    linkedBranch: null,
+    ...overrides,
+  };
+}
+
+const mainClone: TaskContextFolder = {
+  name: "PostHog Desktop",
+  path: "/repos/code",
+  remoteUrl: "posthog/code",
+  mainRepoPath: null,
+};
+
+describe("formatTaskContext", () => {
+  it.each<{ name: string; task: TaskContextTask; expected: string | null }>([
+    {
+      name: "repository only when the task has no branch of its own",
+      task: task(),
+      expected: "code",
+    },
+    {
+      name: "repository and linked branch",
+      task: task({ linkedBranch: "posthog-code/fix-login" }),
+      expected: "code · posthog-code/fix-login",
+    },
+    {
+      name: "the worktree's checked-out branch when no branch is linked yet",
+      task: task({ workspaceMode: "worktree", branchName: "wt/parser" }),
+      expected: "code · wt/parser",
+    },
+    {
+      name: "the linked branch in preference to the checked-out branch",
+      task: task({
+        workspaceMode: "worktree",
+        branchName: "wt/parser",
+        linkedBranch: "posthog-code/parser",
+      }),
+      expected: "code · posthog-code/parser",
+    },
+    {
+      name: "no branch for a local task sitting on the default branch",
+      // A local workspace reports whatever branch the checkout is on, which is
+      // shared by every local task in the repo. Only `linkedBranch` is the
+      // task's own, so `main` must not leak into the line.
+      task: task({ workspaceMode: "local", branchName: "main" }),
+      expected: "code",
+    },
+    {
+      name: "repository only for a cloud task with no linked branch",
+      task: task({ workspaceMode: "cloud" }),
+      expected: "code",
+    },
+    {
+      name: "the custom-images group name for image-builder tasks",
+      task: task({ repository: null, originProduct: "image_builder" }),
+      expected: "Custom images",
+    },
+    {
+      name: "the branch alone when the task has no repository",
+      task: task({ repository: null, linkedBranch: "posthog-code/orphan" }),
+      expected: "posthog-code/orphan",
+    },
+    {
+      name: "null when there is neither a repository nor a branch",
+      task: task({ repository: null }),
+      expected: null,
+    },
+  ])("renders $name", ({ task: subject, expected }) => {
+    expect(formatTaskContext(subject)).toBe(expected);
+  });
+
+  it("labels the repository with the registered folder's name", () => {
+    expect(formatTaskContext(task(), [mainClone])).toBe("PostHog Desktop");
+  });
+
+  it("labels a worktree task with its main checkout's folder name", () => {
+    const worktree: TaskContextFolder = {
+      name: "code-wt",
+      path: "/repos/code-wt",
+      remoteUrl: "posthog/code",
+      mainRepoPath: "/repos/code",
+    };
+
+    expect(
+      formatTaskContext(
+        task({ workspaceMode: "worktree", branchName: "wt/parser" }),
+        [worktree, mainClone],
+      ),
+    ).toBe("PostHog Desktop · wt/parser");
+  });
+
+  it("falls back to the repository name when no folder is registered", () => {
+    const unrelated: TaskContextFolder = {
+      name: "posthog",
+      path: "/repos/posthog",
+      remoteUrl: "posthog/posthog",
+      mainRepoPath: null,
+    };
+
+    expect(formatTaskContext(task(), [unrelated])).toBe("code");
+  });
+});
diff --git a/packages/core/src/sidebar/taskContext.ts b/packages/core/src/sidebar/taskContext.ts
new file mode 100644
index 0000000000..6ac82f47c8
--- /dev/null
+++ b/packages/core/src/sidebar/taskContext.ts
@@ -0,0 +1,64 @@
+import {
+  CUSTOM_IMAGES_GROUP_NAME,
+  findGroupFolder,
+  type GroupableFolder,
+} from "./groupTasks";
+import type { TaskData } from "./sidebarData.types";
+
+/** The `TaskData` fields a context line reads. */
+export type TaskContextTask = Pick<
+  TaskData,
+  | "repository"
+  | "originProduct"
+  | "workspaceMode"
+  | "branchName"
+  | "linkedBranch"
+>;
+
+/** A registered folder, plus the display name the group header would use. */
+export interface TaskContextFolder extends GroupableFolder {
+  name: string;
+}
+
+function repositoryLabel(
+  task: TaskContextTask,
+  folders: TaskContextFolder[],
+): string | null {
+  if (task.originProduct === "image_builder") return CUSTOM_IMAGES_GROUP_NAME;
+  const repository = task.repository;
+  if (!repository) return null;
+  // Prefer the registered folder's name, which is what the group header for
+  // this repo reads when a folder is registered. Without one we take the bare
+  // repo name and skip the organization prefix `groupByRepository` adds when
+  // two groups collide on a name: that is a decision across the whole group
+  // set, and pinned tasks are partitioned out before the groups are built, so
+  // a pinned task's repo may have no group to borrow a name from at all.
+  return findGroupFolder(folders, repository.fullPath)?.name ?? repository.name;
+}
+
+function branchLabel(task: TaskContextTask): string | null {
+  // `linkedBranch` is the branch the task produced, and is deliberately left
+  // unset while a task sits on the repo's default branch — so this never
+  // degrades into a "· main" that repeats on every row. A worktree falls back
+  // to its checked-out branch, which is the whole reason the worktree exists.
+  if (task.linkedBranch) return task.linkedBranch;
+  return task.workspaceMode === "worktree" ? task.branchName : null;
+}
+
+/**
+ * "Where does this task live" line for a task row rendered outside its
+ * repository group — today the pinned section, which floats above the per-repo
+ * groups and so loses the context its group header would have given it.
+ *
+ * Reads as `<repository> · <branch>`, dropping either half when unknown, and
+ * returns null when the task has no repository or branch to report at all.
+ */
+export function formatTaskContext(
+  task: TaskContextTask,
+  folders: TaskContextFolder[] = [],
+): string | null {
+  const repository = repositoryLabel(task, folders);
+  const branch = branchLabel(task);
+  if (repository && branch) return `${repository} · ${branch}`;
+  return repository ?? branch;
+}
diff --git a/packages/ui/src/features/sidebar/components/SidebarItem.tsx b/packages/ui/src/features/sidebar/components/SidebarItem.tsx
index 6a7506cb48..f167f5cde9 100644
--- a/packages/ui/src/features/sidebar/components/SidebarItem.tsx
+++ b/packages/ui/src/features/sidebar/components/SidebarItem.tsx
@@ -38,9 +38,11 @@ interface SidebarItemProps {
 function SidebarItemLabel({
   label,
   grow,
+  className,
 }: {
   label: React.ReactNode;
   grow: boolean;
+  className?: string;
 }) {
   const canTooltip = typeof label === "string" || typeof label === "number";
 
@@ -56,7 +58,10 @@ function SidebarItemLabel({
   }, []);
 
   const span = (
-    <span ref={measureRef} className={cn("min-w-0 truncate", grow && "flex-1")}>
+    <span
+      ref={measureRef}
+      className={cn("min-w-0 truncate", grow && "flex-1", className)}
+    >
       {label}
     </span>
   );
@@ -99,6 +104,9 @@ export function SidebarItem({
         "group flex w-full cursor-default text-left text-[13px] leading-snug transition-colors",
         "focus-visible:-outline-offset-2 focus-visible:outline-2 focus-visible:outline-accent-8",
         "disabled:opacity-100 data-active:bg-fill-selected data-selected:bg-(--gray-3)",
+        // Quill's Button pins a fixed single-line height, which would clip the
+        // second line — opt out and grow with the content instead.
+        subtitle && "h-auto! min-h-7 py-1",
         isDimmed && "opacity-50",
       )}
       data-active={isActive || undefined}
@@ -130,9 +138,13 @@ export function SidebarItem({
           {endContent}
         </span>
         {subtitle ? (
-          <span className="truncate text-gray-10 group-data-active:text-gray-11">
-            {subtitle}
-          </span>
+          // Shares the label's truncate-plus-tooltip treatment, so a long
+          // `repository · branch` stays readable when it doesn't fit.
+          <SidebarItemLabel
+            label={subtitle}
+            grow={false}
+            className="text-[11px] text-gray-10 leading-tight group-data-active:text-gray-11"
+          />
         ) : null}
       </span>
     </Button>
diff --git a/packages/ui/src/features/sidebar/components/TaskListView.tsx b/packages/ui/src/features/sidebar/components/TaskListView.tsx
index f21d0b11fc..0a507149d4 100644
--- a/packages/ui/src/features/sidebar/components/TaskListView.tsx
+++ b/packages/ui/src/features/sidebar/components/TaskListView.tsx
@@ -11,6 +11,7 @@ import type {
   TaskData,
   TaskGroup,
 } from "@posthog/core/sidebar/sidebarData.types";
+import { formatTaskContext } from "@posthog/core/sidebar/taskContext";
 import { MenuLabel } from "@posthog/quill";
 import { builderHog } from "@posthog/ui/assets/hedgehogs";
 import { useFolders } from "@posthog/ui/features/folders/useFolders";
@@ -61,6 +62,7 @@ function SectionLabel({ label }: { label: string }) {
 
 function TaskRow({
   task,
+  subtitle,
   isActive,
   isSelected,
   hideHoverActions,
@@ -76,6 +78,7 @@ function TaskRow({
   depth = 0,
 }: {
   task: TaskData;
+  subtitle?: string;
   isActive: boolean;
   isSelected: boolean;
   hideHoverActions: boolean;
@@ -105,6 +108,7 @@ function TaskRow({
       depth={depth}
       taskId={task.id}
       label={task.title}
+      subtitle={subtitle}
       isActive={isActive}
       isSelected={isSelected}
       isArchiving={isArchiving}
@@ -208,6 +212,10 @@ export function TaskListView({
             <TaskRow
               key={task.id}
               task={task}
+              // Pinned rows float above the per-project groups, so each one
+              // restates its own context. Without it a long pinned list gives no
+              // clue which repository — let alone which branch — a task is in.
+              subtitle={formatTaskContext(task, folders) ?? undefined}
               isActive={activeTaskId === task.id}
               isSelected={selectedIdSet.has(task.id)}
               hideHoverActions={hasMultiSelection}
diff --git a/packages/ui/src/features/sidebar/components/items/TaskItem.stories.tsx b/packages/ui/src/features/sidebar/components/items/TaskItem.stories.tsx
new file mode 100644
index 0000000000..5f7be085b0
--- /dev/null
+++ b/packages/ui/src/features/sidebar/components/items/TaskItem.stories.tsx
@@ -0,0 +1,174 @@
+import {
+  formatTaskContext,
+  type TaskContextTask,
+} from "@posthog/core/sidebar/taskContext";
+import { MenuLabel } from "@posthog/quill";
+import type { Meta, StoryObj } from "@storybook/react-vite";
+import { TaskItem } from "./TaskItem";
+
+const HOUR = 3_600_000;
+
+const CODE_REPO = {
+  fullPath: "posthog/code",
+  name: "code",
+  organization: "PostHog",
+};
+const POSTHOG_REPO = {
+  fullPath: "posthog/posthog",
+  name: "posthog",
+  organization: "PostHog",
+};
+
+/** The context line exactly as the sidebar builds it for a pinned row. */
+function context(task: Partial<TaskContextTask>): string | undefined {
+  return (
+    formatTaskContext({
+      repository: null,
+      branchName: null,
+      linkedBranch: null,
+      ...task,
+    }) ?? undefined
+  );
+}
+
+interface Row {
+  taskId: string;
+  label: string;
+  subtitle?: string;
+  /** Age of the task's last activity, resolved to a timestamp at render. */
+  ageHours: number;
+  isPinned?: boolean;
+  workspaceMode?: "local" | "worktree" | "cloud";
+  taskRunStatus?: "completed";
+  prState?: "open";
+}
+
+const noop = () => {};
+
+function TaskRows({
+  rows,
+  sectionLabel,
+}: {
+  rows: Row[];
+  sectionLabel?: string;
+}) {
+  // Ages become timestamps here rather than in `args`, so the relative labels
+  // are read off the same clock that renders them. The visual-regression runner
+  // freezes the clock in a decorator (apps/code/.storybook/preview.tsx) while
+  // story args are evaluated at import time against the real one — anchoring
+  // args to `Date.now()` collapses every label to "now" in CI.
+  const now = Date.now();
+  return (
+    <div className="flex w-[280px] flex-col bg-gray-2 py-1">
+      {sectionLabel ? (
+        <MenuLabel className="flex items-center py-0">{sectionLabel}</MenuLabel>
+      ) : null}
+      {rows.map(({ ageHours, ...row }) => (
+        <TaskItem
+          key={row.taskId}
+          {...row}
+          timestamp={now - ageHours * HOUR}
+          isActive={false}
+          onClick={noop}
+          onContextMenu={noop}
+          onArchive={noop}
+          onTogglePin={noop}
+        />
+      ))}
+    </div>
+  );
+}
+
+const meta: Meta<typeof TaskRows> = {
+  title: "Sidebar/TaskItem",
+  component: TaskRows,
+  decorators: [
+    (Story) => (
+      <div style={{ margin: "2rem" }}>
+        <Story />
+      </div>
+    ),
+  ],
+};
+
+export default meta;
+type Story = StoryObj<typeof TaskRows>;
+
+/**
+ * A row inside a repository group: one line, because the group header above it
+ * already says which repository the task belongs to.
+ */
+export const InRepositoryGroup: Story = {
+  args: {
+    sectionLabel: "code",
+    rows: [
+      {
+        taskId: "t1",
+        label: "Add keyboard shortcuts to the command palette",
+        ageHours: 1,
+        workspaceMode: "cloud",
+        taskRunStatus: "completed",
+      },
+      {
+        taskId: "t2",
+        label: "Support drag and drop between projects",
+        ageHours: 26,
+        workspaceMode: "worktree",
+        prState: "open",
+      },
+    ],
+  },
+};
+
+/**
+ * The pinned section floats above every repository group, so each row carries
+ * its own `repository · branch` context line.
+ */
+export const Pinned: Story = {
+  args: {
+    sectionLabel: "Pinned",
+    rows: [
+      {
+        taskId: "p1",
+        label: "Fix flaky timeout in the worktree cleanup test",
+        subtitle: context({
+          repository: POSTHOG_REPO,
+          workspaceMode: "worktree",
+          branchName: "fix/worktree-cleanup-flake",
+        }),
+        ageHours: 0,
+        isPinned: true,
+        workspaceMode: "worktree",
+      },
+      {
+        taskId: "p2",
+        label: "Add a retry banner to the diff viewer",
+        subtitle: context({
+          repository: CODE_REPO,
+          workspaceMode: "local",
+          branchName: "main",
+          linkedBranch: "posthog-code/diff-retry-banner",
+        }),
+        ageHours: 3,
+        isPinned: true,
+        prState: "open",
+      },
+      {
+        taskId: "p3",
+        label: "Document the release checklist for the desktop app",
+        subtitle: context({ repository: CODE_REPO, workspaceMode: "cloud" }),
+        ageHours: 27,
+        isPinned: true,
+        workspaceMode: "cloud",
+        taskRunStatus: "completed",
+      },
+      {
+        taskId: "p4",
+        label: "Try out the new onboarding copy",
+        subtitle: context({}),
+        ageHours: 30,
+        isPinned: true,
+      },
+    ],
+  },
+};
diff --git a/packages/ui/src/features/sidebar/components/items/TaskItem.test.tsx b/packages/ui/src/features/sidebar/components/items/TaskItem.test.tsx
new file mode 100644
index 0000000000..0044d10fde
--- /dev/null
+++ b/packages/ui/src/features/sidebar/components/items/TaskItem.test.tsx
@@ -0,0 +1,43 @@
+import { render, screen } from "@testing-library/react";
+import { describe, expect, it, vi } from "vitest";
+import { TaskItem } from "./TaskItem";
+
+vi.mock("@posthog/ui/router/navigationBridge", () => ({
+  navigateToPullRequestView: vi.fn(),
+}));
+
+function renderTaskItem(props: { subtitle?: string } = {}) {
+  return render(
+    <TaskItem
+      taskId="task-1"
+      label="Write runbook for 5xx errors"
+      isActive={false}
+      onClick={() => {}}
+      onContextMenu={() => {}}
+      {...props}
+    />,
+  );
+}
+
+describe("TaskItem", () => {
+  it("renders the context line under the title when given one", () => {
+    renderTaskItem({ subtitle: "code · posthog-code/fix-login" });
+
+    expect(
+      screen.getByText("code · posthog-code/fix-login"),
+    ).toBeInTheDocument();
+  });
+
+  it("stays a single line when there is no context to show", () => {
+    renderTaskItem();
+
+    // Only the title renders — rows inside a repository group already get their
+    // repository from the group header, so they must not grow a second line.
+    expect(
+      screen.getByText("Write runbook for 5xx errors"),
+    ).toBeInTheDocument();
+    expect(screen.getByRole("button").textContent).toBe(
+      "Write runbook for 5xx errors",
+    );
+  });
+});
diff --git a/packages/ui/src/features/sidebar/components/items/TaskItem.tsx b/packages/ui/src/features/sidebar/components/items/TaskItem.tsx
index 3d68b86474..3f3a146a49 100644
--- a/packages/ui/src/features/sidebar/components/items/TaskItem.tsx
+++ b/packages/ui/src/features/sidebar/components/items/TaskItem.tsx
@@ -33,6 +33,8 @@ interface TaskItemProps {
   depth?: number;
   taskId: string;
   label: string;
+  /** Second line under the title, e.g. the task's `repository · branch`. */
+  subtitle?: string;
   isActive: boolean;
   isSelected?: boolean;
   /** Archive request in flight: show a spinner and suppress hover actions. */
@@ -106,6 +108,7 @@ export function TaskItem({
   depth = 0,
   taskId,
   label,
+  subtitle,
   isActive,
   isSelected = false,
   isArchiving = false,
@@ -208,6 +211,7 @@ export function TaskItem({
       depth={depth}
       icon={icon}
       label={label}
+      subtitle={subtitle}
       isActive={isActive}
       isSelected={isSelected}
       isDimmed={isArchiving}