diff --git a/frontend/src/components/EditorLayout.tsx b/frontend/src/components/EditorLayout.tsx
index 1425915c..ce2fa018 100644
--- a/frontend/src/components/EditorLayout.tsx
+++ b/frontend/src/components/EditorLayout.tsx
@@ -75,6 +75,8 @@ import { usePinnedStacks } from '@/hooks/usePinnedStacks';
 import { useSidebarGroupCollapse } from '@/hooks/useSidebarGroupCollapse';
 import type { StackRowStatus } from '@/components/sidebar/stack-status-utils';
 import type { FilterChip, StackMenuCtx } from '@/components/sidebar/sidebar-types';
+import { useBulkStackActions, type BulkAction } from '@/hooks/useBulkStackActions';
+import { isInputFocused, isPaletteOpen } from '@/lib/keyboard-guards';
 import { StackFileExplorer } from '@/components/files/StackFileExplorer';
 
 interface ContainerInfo {
@@ -1964,6 +1966,62 @@ export default function EditorLayout() {
     return filteredFiles;
   }, [filteredFiles, filterChip, stackStatuses, stackUpdates]);
 
+  const [bulkMode, setBulkMode] = useState(false);
+  const [selectedFiles, setSelectedFiles] = useState<Set<string>>(new Set());
+
+  const toggleBulkMode = useCallback(() => {
+    setBulkMode(prev => {
+      if (prev) setSelectedFiles(new Set());
+      return !prev;
+    });
+  }, []);
+
+  const toggleSelect = useCallback((file: string) => {
+    setSelectedFiles(prev => {
+      const next = new Set(prev);
+      if (next.has(file)) next.delete(file);
+      else next.add(file);
+      return next;
+    });
+  }, []);
+
+  const clearSelection = useCallback(() => {
+    setSelectedFiles(new Set());
+  }, []);
+
+  const { runBulk } = useBulkStackActions();
+
+  const handleBulkAction = useCallback((action: BulkAction) => {
+    const files = Array.from(selectedFiles);
+    runBulk(action, files, {
+      onAfter: () => { refreshStacks(true); clearSelection(); },
+    });
+  }, [selectedFiles, runBulk, clearSelection]);
+
+  const chipFilteredFilesRef = useRef(chipFilteredFiles);
+  useEffect(() => { chipFilteredFilesRef.current = chipFilteredFiles; }, [chipFilteredFiles]);
+
+  useEffect(() => {
+    const handler = (e: KeyboardEvent) => {
+      if (isInputFocused()) return;
+      if (isPaletteOpen()) return;
+
+      if (e.key === 'b' && !e.metaKey && !e.ctrlKey) {
+        e.preventDefault();
+        toggleBulkMode();
+      } else if (e.key === 'Escape' && bulkMode) {
+        e.preventDefault();
+        setBulkMode(false);
+        setSelectedFiles(new Set());
+      } else if ((e.metaKey || e.ctrlKey) && e.key === 'a' && bulkMode) {
+        e.preventDefault();
+        setSelectedFiles(new Set(chipFilteredFilesRef.current));
+      }
+    };
+    window.addEventListener('keydown', handler);
+    return () => window.removeEventListener('keydown', handler);
+  }, [bulkMode, toggleBulkMode]);
+
   const { isCollapsed, toggle: toggleCollapse } = useSidebarGroupCollapse(activeNode?.id);
 
   const remoteResults = useMemo(() => {
@@ -2333,6 +2391,13 @@ export default function EditorLayout() {
         notifications={notifications}
         tickerConnected={tickerConnected}
         onOpenActivity={() => setActiveView('global-observability')}
+        bulkMode={bulkMode}
+        selectedFiles={selectedFiles}
+        isPaid={isPaid}
+        onToggleBulkMode={toggleBulkMode}
+        onToggleSelect={toggleSelect}
+        onClearSelection={clearSelection}
+        onBulkAction={handleBulkAction}
       />
 
       {/* Main Content Area */}
diff --git a/frontend/src/components/sidebar/SidebarActions.tsx b/frontend/src/components/sidebar/SidebarActions.tsx
index 753fe35c..fffb5217 100644
--- a/frontend/src/components/sidebar/SidebarActions.tsx
+++ b/frontend/src/components/sidebar/SidebarActions.tsx
@@ -1,18 +1,39 @@
 import type { ReactNode } from 'react';
 import { Button } from '@/components/ui/button';
 import { Tooltip, TooltipContent, TooltipProvider, TooltipTrigger } from '@/components/ui/tooltip';
-import { FolderSearch, Loader2 } from 'lucide-react';
+import { FolderSearch, Loader2, LayoutList } from 'lucide-react';
+import { cn } from '@/lib/utils';
 
 interface SidebarActionsProps {
   createStackSlot: ReactNode;
   onScan: () => void;
   isScanning: boolean;
+  bulkMode: boolean;
+  onToggleBulkMode: () => void;
 }
 
-export function SidebarActions({ createStackSlot, onScan, isScanning }: SidebarActionsProps) {
+export function SidebarActions({ createStackSlot, onScan, isScanning, bulkMode, onToggleBulkMode }: SidebarActionsProps) {
   return (
     <div className="p-4 flex gap-2">
       <div className="flex-1">{createStackSlot}</div>
+      <TooltipProvider>
+        <Tooltip>
+          <TooltipTrigger asChild>
+            <Button
+              variant="outline"
+              size="icon"
+              className={cn('rounded-lg shrink-0 shadow-btn-glow', bulkMode && 'border-brand/40 text-brand bg-brand/10')}
+              onClick={onToggleBulkMode}
+              aria-pressed={bulkMode}
+            >
+              <LayoutList className="w-4 h-4" strokeWidth={1.5} />
+            </Button>
+          </TooltipTrigger>
+          <TooltipContent side="bottom">
+            <p>Bulk mode (B)</p>
+          </TooltipContent>
+        </Tooltip>
+      </TooltipProvider>
       <TooltipProvider>
         <Tooltip>
           <TooltipTrigger asChild>
diff --git a/frontend/src/components/sidebar/SidebarBulkBar.tsx b/frontend/src/components/sidebar/SidebarBulkBar.tsx
new file mode 100644
index 00000000..afed486c
--- /dev/null
+++ b/frontend/src/components/sidebar/SidebarBulkBar.tsx
@@ -0,0 +1,54 @@
+import { X } from 'lucide-react';
+import { Button } from '@/components/ui/button';
+import { Tooltip, TooltipContent, TooltipProvider, TooltipTrigger } from '@/components/ui/tooltip';
+import { TierBadge } from '@/components/TierBadge';
+import type { BulkAction } from '@/hooks/useBulkStackActions';
+
+interface SidebarBulkBarProps {
+  selectedCount: number;
+  isPaid: boolean;
+  onAction: (action: BulkAction) => void;
+  onClear: () => void;
+}
+
+export function SidebarBulkBar({ selectedCount, isPaid, onAction, onClear }: SidebarBulkBarProps) {
+  return (
+    <div className="px-3 py-2 border-b border-glass-border bg-glass-highlight/20">
+      <div className="flex items-center justify-between mb-1.5">
+        <span className="font-mono text-[10px] text-brand tracking-[0.08em]">{selectedCount} selected</span>
+        <button
+          type="button"
+          onClick={onClear}
+          className="text-stat-icon hover:text-foreground transition-colors"
+          aria-label="Clear selection"
+        >
+          <X className="w-3.5 h-3.5" />
+        </button>
+      </div>
+      <div className="flex gap-1 flex-wrap">
+        <Button variant="outline" size="sm" className="h-6 px-2 text-[10px] font-mono" onClick={() => onAction('start')}>Start</Button>
+        <Button variant="outline" size="sm" className="h-6 px-2 text-[10px] font-mono" onClick={() => onAction('stop')}>Stop</Button>
+        <Button variant="outline" size="sm" className="h-6 px-2 text-[10px] font-mono" onClick={() => onAction('restart')}>Restart</Button>
+        {isPaid ? (
+          <Button variant="outline" size="sm" className="h-6 px-2 text-[10px] font-mono" onClick={() => onAction('update')}>Update</Button>
+        ) : (
+          <TooltipProvider>
+            <Tooltip>
+              <TooltipTrigger asChild>
+                <span>
+                  <Button variant="outline" size="sm" className="h-6 px-2 text-[10px] font-mono gap-1 pointer-events-none opacity-60" disabled>
+                    Update
+                    <TierBadge tier="paid" />
+                  </Button>
+                </span>
+              </TooltipTrigger>
+              <TooltipContent side="bottom">
+                <p>Bulk update requires a Skipper license</p>
+              </TooltipContent>
+            </Tooltip>
+          </TooltipProvider>
+        )}
+      </div>
+    </div>
+  );
+}
diff --git a/frontend/src/components/sidebar/StackList.tsx b/frontend/src/components/sidebar/StackList.tsx
index 5b36118c..315a7d33 100644
--- a/frontend/src/components/sidebar/StackList.tsx
+++ b/frontend/src/components/sidebar/StackList.tsx
@@ -95,11 +95,19 @@ function buildGroups(
   return result;
 }
 
-export function StackList(props: StackListProps) {
+interface StackListBulkProps {
+  bulkMode: boolean;
+  selectedFiles: Set<string>;
+  onToggleSelect: (file: string) => void;
+}
+
+export function StackList(props: StackListProps & StackListBulkProps) {
   const {
     files, isLoading, isPaid, selectedFile, searchQuery, stackLabelMap, stackStatuses,
     stackUpdates, gitSourcePendingMap, pinnedFiles, isCollapsed, toggleCollapse,
-    isBusy, getDisplayName, onSelectFile, buildMenuCtx, remoteResults, remoteLoading, onSelectRemoteFile,
+    isBusy, getDisplayName, onSelectFile, buildMenuCtx,
+    bulkMode, selectedFiles, onToggleSelect,
+    remoteResults, remoteLoading, onSelectRemoteFile,
   } = props;
 
   const groups = useMemo(
@@ -152,6 +160,9 @@ export function StackList(props: StackListProps) {
                     hasGitPending={!!gitSourcePendingMap[file]}
                     onSelect={onSelectFile}
                     kebabSlot={<StackKebabMenu file={file} ctx={ctx} />}
+                    bulkMode={bulkMode}
+                    isSelected={selectedFiles.has(file)}
+                    onToggleSelect={onToggleSelect}
                   />
                 </CommandItem>
               </StackContextMenu>
diff --git a/frontend/src/components/sidebar/StackRow.tsx b/frontend/src/components/sidebar/StackRow.tsx
index ace91f50..e6899e67 100644
--- a/frontend/src/components/sidebar/StackRow.tsx
+++ b/frontend/src/components/sidebar/StackRow.tsx
@@ -1,6 +1,7 @@
 import type { ReactNode } from 'react';
 import { GitBranch, Loader2 } from 'lucide-react';
 import { Cursor, CursorContainer, CursorFollow, CursorProvider } from '@/components/animate-ui/primitives/animate/cursor';
+import { Checkbox } from '@/components/ui/checkbox';
 import { LabelDot } from '@/components/LabelPill';
 import type { Label } from '@/components/label-types';
 import { cn } from '@/lib/utils';
@@ -20,6 +21,9 @@ interface StackRowProps {
   hasGitPending: boolean;
   onSelect: (file: string) => void;
   kebabSlot: ReactNode;
+  bulkMode?: boolean;
+  isSelected?: boolean;
+  onToggleSelect?: (file: string) => void;
 }
 
 function RowTooltip({ trigger, label }: { trigger: ReactNode; label: string }) {
@@ -39,22 +43,51 @@ function RowTooltip({ trigger, label }: { trigger: ReactNode; label: string }) {
 const MAX_VISIBLE_LABELS = 3;
 
 export function StackRow(props: StackRowProps) {
-  const { file, displayName, status, isBusy, isActive, isPaid, labels, hasUpdate, hasGitPending, onSelect, kebabSlot } = props;
+  const {
+    file, displayName, status, isBusy, isActive, isPaid, labels,
+    hasUpdate, hasGitPending, onSelect, kebabSlot,
+    bulkMode = false, isSelected = false, onToggleSelect,
+  } = props;
 
   const visibleLabels = isPaid ? labels.slice(0, MAX_VISIBLE_LABELS) : [];
   const overflowCount = isPaid ? Math.max(0, labels.length - MAX_VISIBLE_LABELS) : 0;
 
+  const handleClick = () => {
+    if (bulkMode) onToggleSelect?.(file);
+    else onSelect(file);
+  };
+
+  const handleKeyDown = (e: React.KeyboardEvent) => {
+    if (e.key === 'Enter' || e.key === ' ') {
+      e.preventDefault();
+      handleClick();
+    }
+  };
+
   return (
     <div
       data-testid="stack-row"
+      data-bulk={bulkMode ? 'true' : undefined}
       role="button"
       tabIndex={0}
       className={cn(sidebarRowBase, isActive && sidebarRowActive)}
-      onClick={() => onSelect(file)}
-      onKeyDown={(e) => { if (e.key === 'Enter' || e.key === ' ') { e.preventDefault(); onSelect(file); } }}
+      onClick={handleClick}
+      onKeyDown={handleKeyDown}
     >
-      {/* Reserved checkbox slot — revealed in bulk mode (PR2) */}
-      <span className={sidebarRowCheckboxSlot} aria-hidden="true" />
+      <span
+        className={cn(sidebarRowCheckboxSlot, bulkMode && 'opacity-100 pointer-events-auto')}
+        onClick={e => { e.stopPropagation(); onToggleSelect?.(file); }}
+        aria-hidden={!bulkMode}
+      >
+        {bulkMode && (
+          <Checkbox
+            checked={isSelected}
+            className="w-3.5 h-3.5 border-muted-foreground/40 data-[state=checked]:border-brand data-[state=checked]:bg-brand"
+            tabIndex={-1}
+            aria-label={`Select ${displayName}`}
+          />
+        )}
+      </span>
 
       {/* Status pill */}
       <span className={cn('font-mono text-[10px] shrink-0 w-[22px] flex items-center', statusColor(status, isBusy))}>
diff --git a/frontend/src/components/sidebar/StackSidebar.tsx b/frontend/src/components/sidebar/StackSidebar.tsx
index 21475e48..c1a60f4a 100644
--- a/frontend/src/components/sidebar/StackSidebar.tsx
+++ b/frontend/src/components/sidebar/StackSidebar.tsx
@@ -5,10 +5,12 @@ import type { NotificationItem } from '@/components/dashboard/types';
 import { SidebarActions } from './SidebarActions';
 import { SidebarActivityTicker } from './SidebarActivityTicker';
 import { SidebarBrand } from './SidebarBrand';
+import { SidebarBulkBar } from './SidebarBulkBar';
 import { SidebarFilterChips, type FilterCounts } from './SidebarFilterChips';
 import { SidebarSearch } from './SidebarSearch';
 import { StackList, type StackListProps } from './StackList';
 import type { FilterChip } from './sidebar-types';
+import type { BulkAction } from '@/hooks/useBulkStackActions';
 
 export interface StackSidebarProps {
   isDarkMode: boolean;
@@ -26,6 +28,13 @@ export interface StackSidebarProps {
   notifications: NotificationItem[];
   tickerConnected: boolean;
   onOpenActivity: () => void;
+  bulkMode: boolean;
+  selectedFiles: Set<string>;
+  isPaid: boolean;
+  onToggleBulkMode: () => void;
+  onToggleSelect: (file: string) => void;
+  onClearSelection: () => void;
+  onBulkAction: (action: BulkAction) => void;
 }
 
 export function StackSidebar(props: StackSidebarProps) {
@@ -33,6 +42,7 @@ export function StackSidebar(props: StackSidebarProps) {
     isDarkMode, nodeSwitcherSlot, createStackSlot, onScan, isScanning, canCreate,
     searchQuery, onSearchChange, filterChip, filterCounts, onFilterChipChange,
     list, notifications, tickerConnected, onOpenActivity,
+    bulkMode, selectedFiles, isPaid, onToggleBulkMode, onToggleSelect, onClearSelection, onBulkAction,
   } = props;
 
   return (
@@ -40,7 +50,13 @@ export function StackSidebar(props: StackSidebarProps) {
       <SidebarBrand isDarkMode={isDarkMode} />
       <div className="px-4 pt-2 pb-0">{nodeSwitcherSlot}</div>
       {canCreate && createStackSlot !== null && (
-        <SidebarActions createStackSlot={createStackSlot} onScan={onScan} isScanning={isScanning} />
+        <SidebarActions
+          createStackSlot={createStackSlot}
+          onScan={onScan}
+          isScanning={isScanning}
+          bulkMode={bulkMode}
+          onToggleBulkMode={onToggleBulkMode}
+        />
       )}
       <Command shouldFilter={false} className="bg-transparent flex-1 flex flex-col overflow-hidden">
         <SidebarSearch value={searchQuery} onValueChange={onSearchChange} />
@@ -49,9 +65,17 @@ export function StackSidebar(props: StackSidebarProps) {
           counts={filterCounts}
           onChange={onFilterChipChange}
         />
+        {selectedFiles.size > 0 && (
+          <SidebarBulkBar
+            selectedCount={selectedFiles.size}
+            isPaid={isPaid}
+            onAction={onBulkAction}
+            onClear={onClearSelection}
+          />
+        )}
         <ScrollArea className="flex-1 px-2 pb-2">
           <div data-stacks-loaded={list.isLoading ? 'false' : 'true'}>
-            <StackList {...list} />
+            <StackList {...list} bulkMode={bulkMode} selectedFiles={selectedFiles} onToggleSelect={onToggleSelect} />
           </div>
         </ScrollArea>
       </Command>
diff --git a/frontend/src/hooks/useBulkStackActions.ts b/frontend/src/hooks/useBulkStackActions.ts
new file mode 100644
index 00000000..e2b0845f
--- /dev/null
+++ b/frontend/src/hooks/useBulkStackActions.ts
@@ -0,0 +1,66 @@
+import { useCallback } from 'react';
+import { toast } from '@/components/ui/toast-store';
+import { apiFetch } from '@/lib/api';
+import { useLicense } from '@/context/LicenseContext';
+
+export type BulkAction = 'start' | 'stop' | 'restart' | 'update';
+
+const pastTense: Record<BulkAction, string> = {
+  start: 'started',
+  stop: 'stopped',
+  restart: 'restarted',
+  update: 'updated',
+};
+
+interface BulkCallbacks {
+  onBefore?: (files: string[]) => void;
+  onAfter?: (files: string[]) => void;
+}
+
+export function useBulkStackActions() {
+  const { isPaid } = useLicense();
+
+  const runBulk = useCallback(async (
+    action: BulkAction,
+    files: string[],
+    cbs?: BulkCallbacks,
+  ) => {
+    if (files.length === 0) return;
+    if (action === 'update' && !isPaid) {
+      toast.error('Bulk update requires a Skipper license.');
+      return;
+    }
+
+    cbs?.onBefore?.(files);
+
+    const results = await Promise.allSettled(
+      files.map(file => {
+        const stackName = file.replace(/\.(yml|yaml)$/, '');
+        const headers: Record<string, string> = action === 'update' ? { 'x-bulk-mode': '1' } : {};
+        return apiFetch(`/stacks/${encodeURIComponent(stackName)}/${action}`, {
+          method: 'POST',
+          headers,
+        }).then(res => {
+          if (!res.ok) return Promise.reject(new Error(file));
+          return file;
+        });
+      })
+    );
+
+    cbs?.onAfter?.(files);
+
+    const failed = results
+      .filter((r): r is PromiseRejectedResult => r.status === 'rejected')
+      .map(r => (r.reason as Error).message);
+    const okCount = results.length - failed.length;
+
+    if (failed.length === 0) {
+      const noun = okCount === 1 ? 'stack' : 'stacks';
+      toast.success(`${okCount} ${noun} ${pastTense[action]}`);
+    } else {
+      toast.error(`${okCount} of ${files.length} ${pastTense[action]}; ${failed.length} failed: ${failed.join(', ')}`);
+    }
+  }, [isPaid]);
+
+  return { runBulk, isPaid };
+}
diff --git a/frontend/src/hooks/useStackKeyboardShortcuts.ts b/frontend/src/hooks/useStackKeyboardShortcuts.ts
index f100bb02..21c95109 100644
--- a/frontend/src/hooks/useStackKeyboardShortcuts.ts
+++ b/frontend/src/hooks/useStackKeyboardShortcuts.ts
@@ -1,16 +1,6 @@
 import { useEffect, useRef } from 'react';
 import type { StackMenuCtx } from '@/components/sidebar/sidebar-types';
-
-function isInputFocused(): boolean {
-  const el = document.activeElement as HTMLElement | null;
-  if (!el) return false;
-  const tag = el.tagName;
-  return tag === 'INPUT' || tag === 'TEXTAREA' || el.isContentEditable;
-}
-
-function isPaletteOpen(): boolean {
-  return !!document.querySelector('[role="dialog"] [cmdk-root]');
-}
+import { isInputFocused, isPaletteOpen } from '@/lib/keyboard-guards';
 
 export function useStackKeyboardShortcuts(
   selectedFile: string | null,
diff --git a/frontend/src/lib/keyboard-guards.ts b/frontend/src/lib/keyboard-guards.ts
new file mode 100644
index 00000000..0174f37f
--- /dev/null
+++ b/frontend/src/lib/keyboard-guards.ts
@@ -0,0 +1,10 @@
+export function isInputFocused(): boolean {
+  const el = document.activeElement as HTMLElement | null;
+  if (!el) return false;
+  const tag = el.tagName;
+  return tag === 'INPUT' || tag === 'TEXTAREA' || el.isContentEditable;
+}
+
+export function isPaletteOpen(): boolean {
+  return !!document.querySelector('[role="dialog"] [cmdk-root]');
+}