diff --git a/src/frontend/src/components/core/playgroundComponent/chat-view/chat-header/components/__tests__/chat-sidebar.test.tsx b/src/frontend/src/components/core/playgroundComponent/chat-view/chat-header/components/__tests__/chat-sidebar.test.tsx
new file mode 100644
index 0000000000..97938766e9
--- /dev/null
+++ b/src/frontend/src/components/core/playgroundComponent/chat-view/chat-header/components/__tests__/chat-sidebar.test.tsx
@@ -0,0 +1,106 @@
+import { fireEvent, render, screen } from "@testing-library/react";
+import { ChatSidebar } from "../chat-sidebar";
+
+jest.mock(
+  "@/components/core/playgroundComponent/hooks/use-get-flow-id",
+  () => ({
+    useGetFlowId: () => "flow-1",
+  }),
+);
+
+type FlowState = { playgroundPage: boolean };
+jest.mock("@/stores/flowStore", () => ({
+  __esModule: true,
+  default: <TResult,>(selector: (state: FlowState) => TResult) =>
+    selector({ playgroundPage: false }),
+}));
+
+type AlertState = { setSuccessData: jest.Mock };
+jest.mock("@/stores/alertStore", () => ({
+  __esModule: true,
+  default: <TResult,>(selector: (state: AlertState) => TResult) =>
+    selector({ setSuccessData: jest.fn() }),
+}));
+
+jest.mock("../session-selector", () => ({
+  SessionSelector: ({
+    session,
+    onToggleSelect,
+  }: {
+    session: string;
+    onToggleSelect?: () => void;
+  }) => (
+    <button
+      type="button"
+      data-testid={`session-row-${session}`}
+      onClick={onToggleSelect}
+    >
+      {session}
+    </button>
+  ),
+}));
+
+const baseProps = {
+  sessions: ["flow-1", "New Session 0", "New Session 1"],
+  onSessionSelect: jest.fn(),
+  currentSessionId: "flow-1",
+  onDeleteSession: jest.fn(),
+  onRenameSession: jest.fn().mockResolvedValue(undefined),
+  onBulkDeleteSessions: jest.fn(),
+};
+
+const checkAll = () =>
+  fireEvent.click(screen.getByTestId("select-all-checkbox"));
+
+describe("ChatSidebar — Select All row alignment", () => {
+  it("does not render the bulk-delete button while nothing is selected", () => {
+    render(<ChatSidebar {...baseProps} />);
+    expect(screen.queryByTestId("bulk-delete-button")).not.toBeInTheDocument();
+  });
+
+  it("renders the bulk-delete button with the same h-8 w-8 p-2 shape as a SessionMoreMenu trigger", () => {
+    render(<ChatSidebar {...baseProps} />);
+    checkAll();
+    const trash = screen.getByTestId("bulk-delete-button");
+    expect(trash).toBeInTheDocument();
+    expect(trash.className).toContain("h-8");
+    expect(trash.className).toContain("w-8");
+    expect(trash.className).toContain("p-2");
+    // No leftover sm-button padding that would skew horizontal centering.
+    expect(trash.className).not.toContain("p-0");
+  });
+
+  it("hosts the bulk-delete button in an h-8 row with no extra vertical padding", () => {
+    render(<ChatSidebar {...baseProps} />);
+    checkAll();
+    const trash = screen.getByTestId("bulk-delete-button");
+    // Walk up to the Select All row wrapper. Its className must include
+    // `h-8` and must not add `py-1` / `py-*` padding that would push the
+    // trash button's center down relative to the SessionSelector rows.
+    const row = trash.closest("div.flex.items-center.justify-between");
+    expect(row).not.toBeNull();
+    expect(row!.className).toContain("h-8");
+    expect(row!.className).not.toMatch(/\bpy-\d/);
+    expect(row!.className).not.toMatch(/\bmb-\d/);
+  });
+
+  it("calls onBulkDeleteSessions with the checked sessions when clicked", () => {
+    const onBulkDeleteSessions = jest.fn();
+    render(
+      <ChatSidebar
+        {...baseProps}
+        onBulkDeleteSessions={onBulkDeleteSessions}
+      />,
+    );
+    checkAll();
+    fireEvent.click(screen.getByTestId("bulk-delete-button"));
+    expect(onBulkDeleteSessions).toHaveBeenCalledTimes(1);
+    const [ids] = onBulkDeleteSessions.mock.calls[0];
+    expect(ids).toEqual(
+      expect.arrayContaining(["New Session 0", "New Session 1"]),
+    );
+    // Default session (currentFlowId) is non-selectable and must not be
+    // included in the bulk delete payload.
+    expect(ids).not.toContain("flow-1");
+  });
+});
diff --git a/src/frontend/src/components/core/playgroundComponent/chat-view/chat-header/components/chat-sidebar.tsx b/src/frontend/src/components/core/playgroundComponent/chat-view/chat-header/components/chat-sidebar.tsx
index 7d2ef4a8ce..49c8692973 100644
--- a/src/frontend/src/components/core/playgroundComponent/chat-view/chat-header/components/chat-sidebar.tsx
+++ b/src/frontend/src/components/core/playgroundComponent/chat-view/chat-header/components/chat-sidebar.tsx
@@ -3,8 +3,8 @@ import { useTranslation } from "react-i18next";
 import ForwardedIconComponent from "@/components/common/genericIconComponent";
 import ShadTooltip from "@/components/common/shadTooltipComponent";
 import { Button } from "@/components/ui/button";
-import useFlowStore from "@/stores/flowStore";
 import useAlertStore from "@/stores/alertStore";
+import useFlowStore from "@/stores/flowStore";
 import { cn } from "@/utils/utils";
 import { useGetFlowId } from "../../../hooks/use-get-flow-id";
 import { SessionSelector } from "./session-selector";
@@ -142,18 +142,23 @@ export function ChatSidebar({
       ) : (
         <div className="flex flex-col gap-1">
           {sessions.map((session, index) => {
-            const isDefaultSession = session === currentFlowId;
             const isFirstNonDefaultSession =
               index > 0 && sessions[index - 1] === currentFlowId;
 
             return (
               <div key={session}>
-                {/* Show Select All controls after the default session */}
+                {/* Show Select All controls after the default session.
+                    Wrapper is sized + padded to mirror a SessionSelector
+                    row (h-8, no extra vertical padding) so the trash
+                    button lines up vertically and horizontally with the
+                    `⋮` MoreMenu triggers in the session rows below. */}
                 {isFirstNonDefaultSession && selectableSessions.length > 0 && (
-                  <div className="flex items-center justify-between px-2 py-1 mb-1">
-                    <div
-                      className="flex items-center gap-2 cursor-pointer"
+                  <div className="flex h-8 items-center justify-between">
+                    <button
+                      type="button"
+                      className="flex items-center gap-2 cursor-pointer px-2 bg-transparent border-0 p-0"
                       onClick={handleSelectAll}
+                      aria-pressed={allSelected}
                       data-testid="select-all-checkbox"
                     >
                       <div className="flex items-center justify-center w-4 h-4 flex-shrink-0">
@@ -170,31 +175,29 @@ export function ChatSidebar({
                       <span className="text-sm text-muted-foreground select-none">
                         {t("chat.selectAll")}
                       </span>
-                    </div>
-                    <div className="w-8 h-8 flex items-center justify-center">
-                      {selectedSessions.size > 0 && (
-                        <ShadTooltip
-                          styleClasses="z-50"
-                          content={t("chat.deleteSessionsCount", {
-                            count: selectedSessions.size,
-                          })}
-                          side="top"
+                    </button>
+                    {selectedSessions.size > 0 && (
+                      <ShadTooltip
+                        styleClasses="z-50"
+                        content={t("chat.deleteSessionsCount", {
+                          count: selectedSessions.size,
+                        })}
+                        side="top"
+                      >
+                        <Button
+                          data-testid="bulk-delete-button"
+                          variant="ghost"
+                          size="icon"
+                          className="h-8 w-8 p-2 rounded text-status-red hover:text-status-red hover:bg-error-background"
+                          onClick={handleBulkDelete}
                         >
-                          <Button
-                            data-testid="bulk-delete-button"
-                            variant="ghost"
-                            size="sm"
-                            className="h-8 w-8 p-0 text-status-red hover:text-status-red hover:bg-error-background"
-                            onClick={handleBulkDelete}
-                          >
-                            <ForwardedIconComponent
-                              name="Trash2"
-                              className="h-4 w-4"
-                            />
-                          </Button>
-                        </ShadTooltip>
-                      )}
-                    </div>
+                          <ForwardedIconComponent
+                            name="Trash2"
+                            className="h-4 w-4"
+                          />
+                        </Button>
+                      </ShadTooltip>
+                    )}
                   </div>
                 )}
                 <SessionSelector