diff --git a/apps/sim/app/workspace/[workspaceId]/components/folders/folder-context-menu.tsx b/apps/sim/app/workspace/[workspaceId]/components/folders/folder-context-menu.tsx
index 62d0ec5cacf..35f72a05818 100644
--- a/apps/sim/app/workspace/[workspaceId]/components/folders/folder-context-menu.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/components/folders/folder-context-menu.tsx
@@ -14,6 +14,7 @@ import {
 import { Duplicate, Eye, FolderInput, Pencil, Pin, Trash } from '@sim/emcn/icons'
 import type { MoveOptionNode } from '@/app/workspace/[workspaceId]/components/folders/move-options'
 import { renderMoveOptions } from '@/app/workspace/[workspaceId]/components/folders/move-options'
+import { selectionActionLabel } from '@/app/workspace/[workspaceId]/components/resource/selection-label'
 
 interface FolderContextMenuProps {
   isOpen: boolean
@@ -29,6 +30,7 @@ interface FolderContextMenuProps {
   pinned: boolean
   moveOptions?: MoveOptionNode[]
   canEdit: boolean
+  selectedCount: number
 }
 
 /**
@@ -56,8 +58,12 @@ export const FolderContextMenu = memo(function FolderContextMenu({
   pinned,
   moveOptions,
   canEdit,
+  selectedCount,
 }: FolderContextMenuProps) {
+  const isMultiSelect = selectedCount > 1
   const hasMove = Boolean(onMove && moveOptions && moveOptions.length > 0)
+  const hasActionsAboveDestructive = !isMultiSelect || hasMove
+  const hasAvailableActions = !isMultiSelect || canEdit
 
   return (
     <DropdownMenu open={isOpen} onOpenChange={(open) => !open && onClose()} modal={false}>
@@ -75,42 +81,54 @@ export const FolderContextMenu = memo(function FolderContextMenu({
         sideOffset={4}
         onCloseAutoFocus={(e) => e.preventDefault()}
       >
-        <DropdownMenuItem onSelect={onOpen}>
-          <Eye />
-          Open
-        </DropdownMenuItem>
-        <DropdownMenuItem onSelect={onTogglePin}>
-          <Pin />
-          {pinned ? 'Unpin' : 'Pin'}
-        </DropdownMenuItem>
-        {onCopyId && (
-          <DropdownMenuItem onSelect={onCopyId}>
-            <Duplicate />
-            Copy ID
-          </DropdownMenuItem>
-        )}
-        {canEdit && (
+        {!hasAvailableActions ? (
+          <DropdownMenuItem disabled>No actions available</DropdownMenuItem>
+        ) : (
           <>
-            <DropdownMenuItem onSelect={onRename}>
-              <Pencil />
-              Rename
-            </DropdownMenuItem>
-            {hasMove && (
-              <DropdownMenuSub>
-                <DropdownMenuSubTrigger>
-                  <FolderInput />
-                  Move to
-                </DropdownMenuSubTrigger>
-                <DropdownMenuSubContent>
-                  {renderMoveOptions(moveOptions!, onMove!)}
-                </DropdownMenuSubContent>
-              </DropdownMenuSub>
+            {!isMultiSelect && (
+              <>
+                <DropdownMenuItem onSelect={onOpen}>
+                  <Eye />
+                  Open
+                </DropdownMenuItem>
+                <DropdownMenuItem onSelect={onTogglePin}>
+                  <Pin />
+                  {pinned ? 'Unpin' : 'Pin'}
+                </DropdownMenuItem>
+                {onCopyId && (
+                  <DropdownMenuItem onSelect={onCopyId}>
+                    <Duplicate />
+                    Copy ID
+                  </DropdownMenuItem>
+                )}
+              </>
+            )}
+            {canEdit && (
+              <>
+                {!isMultiSelect && (
+                  <DropdownMenuItem onSelect={onRename}>
+                    <Pencil />
+                    Rename
+                  </DropdownMenuItem>
+                )}
+                {hasMove && (
+                  <DropdownMenuSub>
+                    <DropdownMenuSubTrigger>
+                      <FolderInput />
+                      {selectionActionLabel('Move', selectedCount, 'Move to')}
+                    </DropdownMenuSubTrigger>
+                    <DropdownMenuSubContent>
+                      {renderMoveOptions(moveOptions!, onMove!)}
+                    </DropdownMenuSubContent>
+                  </DropdownMenuSub>
+                )}
+                {hasActionsAboveDestructive && <DropdownMenuSeparator />}
+                <DropdownMenuItem onSelect={onDelete}>
+                  <Trash />
+                  {selectionActionLabel('Delete', selectedCount)}
+                </DropdownMenuItem>
+              </>
             )}
-            <DropdownMenuSeparator />
-            <DropdownMenuItem onSelect={onDelete}>
-              <Trash />
-              Delete
-            </DropdownMenuItem>
           </>
         )}
       </DropdownMenuContent>
diff --git a/apps/sim/app/workspace/[workspaceId]/components/resource/selection-aware-context-menus.test.tsx b/apps/sim/app/workspace/[workspaceId]/components/resource/selection-aware-context-menus.test.tsx
new file mode 100644
index 00000000000..5a792131fd5
--- /dev/null
+++ b/apps/sim/app/workspace/[workspaceId]/components/resource/selection-aware-context-menus.test.tsx
@@ -0,0 +1,207 @@
+import type { ReactNode } from 'react'
+import { renderToStaticMarkup } from 'react-dom/server'
+import { describe, expect, it, vi } from 'vitest'
+
+vi.mock('@sim/emcn', () => ({
+  DropdownMenu: ({ children, open }: { children: ReactNode; open: boolean }) =>
+    open ? <>{children}</> : null,
+  DropdownMenuContent: ({ children }: { children: ReactNode }) => <>{children}</>,
+  DropdownMenuItem: ({ children }: { children: ReactNode }) => <span>{children}</span>,
+  DropdownMenuSeparator: () => <hr />,
+  DropdownMenuSub: ({ children }: { children: ReactNode }) => <>{children}</>,
+  DropdownMenuSubContent: ({ children }: { children: ReactNode }) => <>{children}</>,
+  DropdownMenuSubTrigger: ({ children }: { children: ReactNode }) => <span>{children}</span>,
+  DropdownMenuTrigger: ({ children }: { children: ReactNode }) => <>{children}</>,
+  Upload: () => null,
+}))
+
+vi.mock('@sim/emcn/icons', () => ({
+  Database: () => null,
+  Download: () => null,
+  Duplicate: () => null,
+  Eye: () => null,
+  FolderInput: () => null,
+  Pencil: () => null,
+  Pin: () => null,
+  Plus: () => null,
+  SquareArrowUpRight: () => null,
+  TagIcon: () => null,
+  Trash: () => null,
+}))
+
+vi.mock('@/app/workspace/[workspaceId]/components/folders', () => ({
+  renderMoveOptions: () => <span>Destination</span>,
+}))
+
+vi.mock('@/app/workspace/[workspaceId]/components/folders/move-options', () => ({
+  renderMoveOptions: () => <span>Destination</span>,
+}))
+
+import { FolderContextMenu } from '@/app/workspace/[workspaceId]/components/folders/folder-context-menu'
+import { ChunkContextMenu } from '@/app/workspace/[workspaceId]/knowledge/[id]/[documentId]/components/chunk-context-menu/chunk-context-menu'
+import { DocumentContextMenu } from '@/app/workspace/[workspaceId]/knowledge/[id]/components/document-context-menu/document-context-menu'
+import { KnowledgeBaseContextMenu } from '@/app/workspace/[workspaceId]/knowledge/components/knowledge-base-context-menu/knowledge-base-context-menu'
+import { TableContextMenu } from '@/app/workspace/[workspaceId]/tables/components/table-context-menu/table-context-menu'
+
+const POSITION = { x: 0, y: 0 }
+const MOVE_OPTIONS = [{ value: '__root__', label: 'Root', children: [] }]
+
+describe('selection-aware resource context menus', () => {
+  it('limits a multi-table menu to actions that can target the selection', () => {
+    const menu = renderToStaticMarkup(
+      <TableContextMenu
+        isOpen
+        position={POSITION}
+        onClose={() => {}}
+        onCopyId={() => {}}
+        onTogglePin={() => {}}
+        onDelete={() => {}}
+        onViewSchema={() => {}}
+        onRename={() => {}}
+        onImportCsv={() => {}}
+        onExportCsv={() => {}}
+        onMove={() => {}}
+        moveOptions={MOVE_OPTIONS}
+        selectedCount={3}
+      />
+    )
+
+    expect(menu).toContain('Move 3 items')
+    expect(menu).toContain('Delete 3 items')
+    expect(menu).not.toContain('View Schema')
+    expect(menu).not.toContain('Rename')
+    expect(menu).not.toContain('Copy ID')
+    expect(menu).not.toContain('Pin')
+  })
+
+  it('limits a multi-base menu to actions that can target the selection', () => {
+    const menu = renderToStaticMarkup(
+      <KnowledgeBaseContextMenu
+        isOpen
+        position={POSITION}
+        onClose={() => {}}
+        onOpenInNewTab={() => {}}
+        onViewTags={() => {}}
+        onCopyId={() => {}}
+        onTogglePin={() => {}}
+        onEdit={() => {}}
+        onDelete={() => {}}
+        onMove={() => {}}
+        moveOptions={MOVE_OPTIONS}
+        selectedCount={2}
+      />
+    )
+
+    expect(menu).toContain('Move 2 items')
+    expect(menu).toContain('Delete 2 items')
+    expect(menu).not.toContain('Open in new tab')
+    expect(menu).not.toContain('View tags')
+    expect(menu).not.toContain('Copy ID')
+    expect(menu).not.toContain('Pin')
+    expect(menu).not.toContain('Edit')
+  })
+
+  it('uses the same group-action contract when a selected folder opens the menu', () => {
+    const menu = renderToStaticMarkup(
+      <FolderContextMenu
+        isOpen
+        position={POSITION}
+        onClose={() => {}}
+        onOpen={() => {}}
+        onRename={() => {}}
+        onDelete={() => {}}
+        onCopyId={() => {}}
+        onMove={() => {}}
+        onTogglePin={() => {}}
+        pinned={false}
+        moveOptions={MOVE_OPTIONS}
+        canEdit
+        selectedCount={4}
+      />
+    )
+
+    expect(menu).toContain('Move 4 items')
+    expect(menu).toContain('Delete 4 items')
+    expect(menu).not.toContain('Open')
+    expect(menu).not.toContain('Rename')
+    expect(menu).not.toContain('Copy ID')
+    expect(menu).not.toContain('Pin')
+  })
+
+  it('explains when a read-only multi-folder selection has no actions', () => {
+    const menu = renderToStaticMarkup(
+      <FolderContextMenu
+        isOpen
+        position={POSITION}
+        onClose={() => {}}
+        onOpen={() => {}}
+        onRename={() => {}}
+        onDelete={() => {}}
+        onTogglePin={() => {}}
+        pinned={false}
+        canEdit={false}
+        selectedCount={2}
+      />
+    )
+
+    expect(menu).toContain('No actions available')
+    expect(menu).not.toContain('Open')
+    expect(menu).not.toContain('Delete')
+  })
+
+  it('counts only the documents affected by a mixed-selection toggle', () => {
+    const menu = renderToStaticMarkup(
+      <DocumentContextMenu
+        isOpen
+        position={POSITION}
+        onClose={() => {}}
+        hasDocument
+        selectedCount={25}
+        enabledCount={7}
+        disabledCount={18}
+        onToggleEnabled={() => {}}
+        onDelete={() => {}}
+      />
+    )
+
+    expect(menu).toContain('Enable 18 items')
+    expect(menu).toContain('Delete 25 items')
+  })
+
+  it('does not overstate an unknown select-all toggle count', () => {
+    const menu = renderToStaticMarkup(
+      <DocumentContextMenu
+        isOpen
+        position={POSITION}
+        onClose={() => {}}
+        hasDocument
+        selectedCount={25}
+        enabledCount={25}
+        disabledCount={25}
+        hasExactToggleCount={false}
+        onToggleEnabled={() => {}}
+      />
+    )
+
+    expect(menu).toContain('Enable selected items')
+    expect(menu).not.toContain('Enable 25 items')
+  })
+
+  it('counts only the chunks affected by a multi-selection toggle', () => {
+    const menu = renderToStaticMarkup(
+      <ChunkContextMenu
+        isOpen
+        position={POSITION}
+        onClose={() => {}}
+        hasChunk
+        selectedCount={3}
+        enabledCount={3}
+        onToggleEnabled={() => {}}
+        onDelete={() => {}}
+      />
+    )
+
+    expect(menu).toContain('Disable 3 items')
+    expect(menu).toContain('Delete 3 items')
+  })
+})
diff --git a/apps/sim/app/workspace/[workspaceId]/components/resource/selection-label.test.ts b/apps/sim/app/workspace/[workspaceId]/components/resource/selection-label.test.ts
new file mode 100644
index 00000000000..55ca76109ba
--- /dev/null
+++ b/apps/sim/app/workspace/[workspaceId]/components/resource/selection-label.test.ts
@@ -0,0 +1,69 @@
+import { describe, expect, it } from 'vitest'
+import {
+  selectionActionLabel,
+  selectionLabel,
+  selectionToggleActionLabel,
+} from '@/app/workspace/[workspaceId]/components/resource/selection-label'
+
+describe('selection labels', () => {
+  it('uses the selected item name for a single-row confirmation', () => {
+    expect(selectionLabel(1, 'Quarterly data')).toBe('Quarterly data')
+  })
+
+  it('uses the selection count for a multi-row confirmation', () => {
+    expect(selectionLabel(3, 'Quarterly data')).toBe('3 selected items')
+  })
+
+  it('keeps single-row action labels terse', () => {
+    expect(selectionActionLabel('Move', 1, 'Move to')).toBe('Move to')
+  })
+
+  it('states the scope of a multi-row action', () => {
+    expect(selectionActionLabel('Delete', 3)).toBe('Delete 3 items')
+  })
+
+  it('counts only disabled items for a mixed-selection enable action', () => {
+    expect(
+      selectionToggleActionLabel({
+        selectedCount: 5,
+        enabledCount: 2,
+        disabledCount: 3,
+        isSelectedItemEnabled: true,
+      })
+    ).toBe('Enable 3 items')
+  })
+
+  it('keeps a singular affected count visible within a larger selection', () => {
+    expect(
+      selectionToggleActionLabel({
+        selectedCount: 5,
+        enabledCount: 4,
+        disabledCount: 1,
+        isSelectedItemEnabled: true,
+      })
+    ).toBe('Enable 1 item')
+  })
+
+  it('counts enabled items when a selection can only be disabled', () => {
+    expect(
+      selectionToggleActionLabel({
+        selectedCount: 4,
+        enabledCount: 4,
+        disabledCount: 0,
+        isSelectedItemEnabled: true,
+      })
+    ).toBe('Disable 4 items')
+  })
+
+  it('keeps the action selection-aware when the affected subset count is unknown', () => {
+    expect(
+      selectionToggleActionLabel({
+        selectedCount: 10,
+        enabledCount: 10,
+        disabledCount: 10,
+        isSelectedItemEnabled: true,
+        hasExactAffectedCount: false,
+      })
+    ).toBe('Enable selected items')
+  })
+})
diff --git a/apps/sim/app/workspace/[workspaceId]/components/resource/selection-label.ts b/apps/sim/app/workspace/[workspaceId]/components/resource/selection-label.ts
index fc812dbee55..b0f88be128b 100644
--- a/apps/sim/app/workspace/[workspaceId]/components/resource/selection-label.ts
+++ b/apps/sim/app/workspace/[workspaceId]/components/resource/selection-label.ts
@@ -7,3 +7,37 @@ export function selectionLabel(count: number, firstName: string | undefined): st
   if (count === 1) return firstName ?? 'selected item'
   return `${count} selected items`
 }
+
+export function selectionActionLabel(
+  action: string,
+  selectedCount: number,
+  singleItemLabel = action
+): string {
+  if (selectedCount <= 1) return singleItemLabel
+  return countedSelectionActionLabel(action, selectedCount)
+}
+
+function countedSelectionActionLabel(action: string, count: number): string {
+  return `${action} ${count} ${count === 1 ? 'item' : 'items'}`
+}
+
+interface SelectionToggleActionLabelOptions {
+  selectedCount: number
+  enabledCount: number
+  disabledCount: number
+  isSelectedItemEnabled: boolean
+  hasExactAffectedCount?: boolean
+}
+
+export function selectionToggleActionLabel({
+  selectedCount,
+  enabledCount,
+  disabledCount,
+  isSelectedItemEnabled,
+  hasExactAffectedCount = true,
+}: SelectionToggleActionLabelOptions): string {
+  if (selectedCount <= 1) return isSelectedItemEnabled ? 'Disable' : 'Enable'
+  const action = disabledCount > 0 ? 'Enable' : 'Disable'
+  if (!hasExactAffectedCount) return `${action} selected items`
+  return countedSelectionActionLabel(action, disabledCount > 0 ? disabledCount : enabledCount)
+}
diff --git a/apps/sim/app/workspace/[workspaceId]/files/components/file-row-context-menu/file-row-context-menu.tsx b/apps/sim/app/workspace/[workspaceId]/files/components/file-row-context-menu/file-row-context-menu.tsx
index fbc651748aa..79ffba59465 100644
--- a/apps/sim/app/workspace/[workspaceId]/files/components/file-row-context-menu/file-row-context-menu.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/files/components/file-row-context-menu/file-row-context-menu.tsx
@@ -18,6 +18,7 @@ import {
 import { Download, Link, Pin, Send, Trash } from '@sim/emcn/icons'
 import type { MoveOptionNode } from '@/app/workspace/[workspaceId]/components/folders'
 import { renderMoveOption } from '@/app/workspace/[workspaceId]/components/folders'
+import { selectionActionLabel } from '@/app/workspace/[workspaceId]/components/resource/selection-label'
 
 interface FileRowContextMenuProps {
   isOpen: boolean
@@ -98,7 +99,7 @@ export const FileRowContextMenu = memo(function FileRowContextMenu({
         {onDownload && (
           <DropdownMenuItem onSelect={onDownload}>
             <Download />
-            {isMultiSelect ? `Download ${selectedCount} items` : 'Download'}
+            {selectionActionLabel('Download', selectedCount)}
           </DropdownMenuItem>
         )}
         {!isMultiSelect && (
@@ -125,7 +126,7 @@ export const FileRowContextMenu = memo(function FileRowContextMenu({
               <DropdownMenuSub>
                 <DropdownMenuSubTrigger>
                   <FolderInput />
-                  {isMultiSelect ? `Move ${selectedCount} items` : 'Move to'}
+                  {selectionActionLabel('Move', selectedCount, 'Move to')}
                 </DropdownMenuSubTrigger>
                 <DropdownMenuSubContent>
                   <DropdownMenuItem onSelect={() => onMove(moveOptions[0].value)}>
@@ -140,7 +141,7 @@ export const FileRowContextMenu = memo(function FileRowContextMenu({
             {hasActionsAboveDestructive && <DropdownMenuSeparator />}
             <DropdownMenuItem onSelect={onDelete}>
               <Trash />
-              {isMultiSelect ? `Delete ${selectedCount} items` : 'Delete'}
+              {selectionActionLabel('Delete', selectedCount)}
             </DropdownMenuItem>
           </>
         )}
diff --git a/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/[documentId]/components/chunk-context-menu/chunk-context-menu.tsx b/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/[documentId]/components/chunk-context-menu/chunk-context-menu.tsx
index 8a73d105395..e7488424da5 100644
--- a/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/[documentId]/components/chunk-context-menu/chunk-context-menu.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/[documentId]/components/chunk-context-menu/chunk-context-menu.tsx
@@ -8,6 +8,10 @@ import {
   DropdownMenuTrigger,
 } from '@sim/emcn'
 import { Duplicate, Eye, Pencil, Plus, SquareArrowUpRight, Trash } from '@sim/emcn/icons'
+import {
+  selectionActionLabel,
+  selectionToggleActionLabel,
+} from '@/app/workspace/[workspaceId]/components/resource/selection-label'
 
 interface ChunkContextMenuProps {
   isOpen: boolean
@@ -26,7 +30,7 @@ interface ChunkContextMenuProps {
   disableAddChunk?: boolean
   disableEdit?: boolean
   isConnectorDocument?: boolean
-  selectedCount?: number
+  selectedCount: number
   enabledCount?: number
   disabledCount?: number
 }
@@ -53,19 +57,17 @@ export function ChunkContextMenu({
   disableAddChunk = false,
   disableEdit = false,
   isConnectorDocument = false,
-  selectedCount = 1,
+  selectedCount,
   enabledCount = 0,
   disabledCount = 0,
 }: ChunkContextMenuProps) {
   const isMultiSelect = selectedCount > 1
-
-  const getToggleLabel = () => {
-    if (isMultiSelect) {
-      if (disabledCount > 0) return 'Enable'
-      return 'Disable'
-    }
-    return isChunkEnabled ? 'Disable' : 'Enable'
-  }
+  const toggleLabel = selectionToggleActionLabel({
+    selectedCount,
+    enabledCount,
+    disabledCount,
+    isSelectedItemEnabled: isChunkEnabled,
+  })
 
   const hasNavigationSection = !isMultiSelect && !!onOpenInNewTab
   const hasEditSection = !isMultiSelect && (!!onEdit || !!onCopyContent)
@@ -118,7 +120,7 @@ export function ChunkContextMenu({
             {onToggleEnabled && (
               <DropdownMenuItem disabled={disableToggleEnabled} onSelect={onToggleEnabled}>
                 <Eye />
-                {getToggleLabel()}
+                {toggleLabel}
               </DropdownMenuItem>
             )}
 
@@ -126,7 +128,7 @@ export function ChunkContextMenu({
             {onDelete && (
               <DropdownMenuItem disabled={disableDelete} onSelect={onDelete}>
                 <Trash />
-                Delete
+                {selectionActionLabel('Delete', selectedCount)}
               </DropdownMenuItem>
             )}
           </>
diff --git a/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/base.tsx b/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/base.tsx
index 76a061a032d..32a08870988 100644
--- a/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/base.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/base.tsx
@@ -687,6 +687,7 @@ export function KnowledgeBase({
    * Handles selecting/deselecting a document
    */
   const handleSelectDocument = (docId: string, checked: boolean) => {
+    setIsSelectAllMode(false)
     setSelectedDocuments((prev) => {
       const newSet = new Set(prev)
       if (checked) {
@@ -908,6 +909,7 @@ export function KnowledgeBase({
       ? 0
       : pagination.total
     : selectedDocumentsList.filter((doc) => !doc.enabled).length
+  const selectedDocumentCount = isSelectAllMode ? pagination.total : selectedDocuments.size
 
   const handleDocumentContextMenu = useCallback(
     (e: React.MouseEvent, docId: string) => {
@@ -917,6 +919,7 @@ export function KnowledgeBase({
       const isCurrentlySelected = selectedDocuments.has(doc.id)
 
       if (!isCurrentlySelected) {
+        setIsSelectAllMode(false)
         setSelectedDocuments(new Set([doc.id]))
       }
 
@@ -1422,15 +1425,15 @@ export function KnowledgeBase({
         srTitle='Delete Documents'
         title='Delete Documents'
         text={[
-          `Are you sure you want to delete ${selectedDocuments.size} document${selectedDocuments.size === 1 ? '' : 's'}? `,
+          `Are you sure you want to delete ${selectedDocumentCount} document${selectedDocumentCount === 1 ? '' : 's'}? `,
           {
-            text: `This will permanently delete the selected document${selectedDocuments.size === 1 ? '' : 's'}.`,
+            text: `This will permanently delete the selected document${selectedDocumentCount === 1 ? '' : 's'}.`,
             error: true,
           },
           ' This action cannot be undone.',
         ]}
         confirm={{
-          label: `Delete ${selectedDocuments.size} Document${selectedDocuments.size === 1 ? '' : 's'}`,
+          label: `Delete ${selectedDocumentCount} Document${selectedDocumentCount === 1 ? '' : 's'}`,
           onClick: confirmBulkDelete,
           pending: isBulkOperating,
           pendingLabel: 'Deleting...',
@@ -1501,11 +1504,12 @@ export function KnowledgeBase({
         onClose={handleContextMenuClose}
         hasDocument={contextMenuDocument !== null}
         isDocumentEnabled={contextMenuDocument?.enabled ?? true}
-        selectedCount={selectedDocuments.size}
+        selectedCount={selectedDocumentCount}
         enabledCount={enabledCount}
         disabledCount={disabledCount}
+        hasExactToggleCount={!isSelectAllMode || enabledFilter !== 'all'}
         onOpenInNewTab={
-          contextMenuDocument && selectedDocuments.size === 1
+          contextMenuDocument && selectedDocumentCount === 1
             ? () => {
                 const urlParams = new URLSearchParams({
                   kbName: knowledgeBaseName,
@@ -1519,14 +1523,14 @@ export function KnowledgeBase({
             : undefined
         }
         onOpenSource={
-          contextMenuDocument?.sourceUrl && selectedDocuments.size === 1
+          contextMenuDocument?.sourceUrl && selectedDocumentCount === 1
             ? () => window.open(contextMenuDocument.sourceUrl!, '_blank', 'noopener,noreferrer')
             : undefined
         }
         onRename={contextMenuDocument ? () => handleRenameDocument(contextMenuDocument) : undefined}
         onToggleEnabled={
           contextMenuDocument
-            ? selectedDocuments.size > 1
+            ? selectedDocumentCount > 1
               ? () => {
                   if (disabledCount > 0) {
                     handleBulkEnable()
@@ -1538,13 +1542,13 @@ export function KnowledgeBase({
             : undefined
         }
         onViewTags={
-          contextMenuDocument && selectedDocuments.size === 1 && userPermissions.canEdit
+          contextMenuDocument && selectedDocumentCount === 1 && userPermissions.canEdit
             ? () => handleViewDocumentTags(contextMenuDocument)
             : undefined
         }
         onDelete={
           contextMenuDocument
-            ? selectedDocuments.size > 1
+            ? selectedDocumentCount > 1
               ? handleBulkDelete
               : () => handleDeleteDocument(contextMenuDocument.id)
             : undefined
diff --git a/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/components/document-context-menu/document-context-menu.tsx b/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/components/document-context-menu/document-context-menu.tsx
index 3f3cb03f63c..c6d9075d0b1 100644
--- a/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/components/document-context-menu/document-context-menu.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/knowledge/[id]/components/document-context-menu/document-context-menu.tsx
@@ -8,6 +8,10 @@ import {
   DropdownMenuTrigger,
 } from '@sim/emcn'
 import { Eye, Pencil, Plus, SquareArrowUpRight, TagIcon, Trash } from '@sim/emcn/icons'
+import {
+  selectionActionLabel,
+  selectionToggleActionLabel,
+} from '@/app/workspace/[workspaceId]/components/resource/selection-label'
 
 interface DocumentContextMenuProps {
   isOpen: boolean
@@ -26,9 +30,10 @@ interface DocumentContextMenuProps {
   disableToggleEnabled?: boolean
   disableDelete?: boolean
   disableAddDocument?: boolean
-  selectedCount?: number
+  selectedCount: number
   enabledCount?: number
   disabledCount?: number
+  hasExactToggleCount?: boolean
 }
 
 /**
@@ -53,19 +58,19 @@ export function DocumentContextMenu({
   disableToggleEnabled = false,
   disableDelete = false,
   disableAddDocument = false,
-  selectedCount = 1,
+  selectedCount,
   enabledCount = 0,
   disabledCount = 0,
+  hasExactToggleCount = true,
 }: DocumentContextMenuProps) {
   const isMultiSelect = selectedCount > 1
-
-  const getToggleLabel = () => {
-    if (isMultiSelect) {
-      if (disabledCount > 0) return 'Enable'
-      return 'Disable'
-    }
-    return isDocumentEnabled ? 'Disable' : 'Enable'
-  }
+  const toggleLabel = selectionToggleActionLabel({
+    selectedCount,
+    enabledCount,
+    disabledCount,
+    isSelectedItemEnabled: isDocumentEnabled,
+    hasExactAffectedCount: hasExactToggleCount,
+  })
 
   const hasNavigationSection = !isMultiSelect && (!!onOpenInNewTab || !!onOpenSource)
   const hasEditSection = !isMultiSelect && (!!onRename || !!onViewTags)
@@ -124,7 +129,7 @@ export function DocumentContextMenu({
             {onToggleEnabled && (
               <DropdownMenuItem disabled={disableToggleEnabled} onSelect={onToggleEnabled}>
                 <Eye />
-                {getToggleLabel()}
+                {toggleLabel}
               </DropdownMenuItem>
             )}
 
@@ -132,7 +137,7 @@ export function DocumentContextMenu({
             {onDelete && (
               <DropdownMenuItem disabled={disableDelete} onSelect={onDelete}>
                 <Trash />
-                Delete
+                {selectionActionLabel('Delete', selectedCount)}
               </DropdownMenuItem>
             )}
           </>
diff --git a/apps/sim/app/workspace/[workspaceId]/knowledge/components/knowledge-base-context-menu/knowledge-base-context-menu.tsx b/apps/sim/app/workspace/[workspaceId]/knowledge/components/knowledge-base-context-menu/knowledge-base-context-menu.tsx
index 2f5fdad09e7..83ce9100c4d 100644
--- a/apps/sim/app/workspace/[workspaceId]/knowledge/components/knowledge-base-context-menu/knowledge-base-context-menu.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/knowledge/components/knowledge-base-context-menu/knowledge-base-context-menu.tsx
@@ -22,6 +22,7 @@ import {
 } from '@sim/emcn/icons'
 import type { MoveOptionNode } from '@/app/workspace/[workspaceId]/components/folders'
 import { renderMoveOptions } from '@/app/workspace/[workspaceId]/components/folders'
+import { selectionActionLabel } from '@/app/workspace/[workspaceId]/components/resource/selection-label'
 
 interface KnowledgeBaseContextMenuProps {
   isOpen: boolean
@@ -44,6 +45,7 @@ interface KnowledgeBaseContextMenuProps {
   showDelete?: boolean
   disableEdit?: boolean
   disableDelete?: boolean
+  selectedCount: number
 }
 
 /**
@@ -69,11 +71,14 @@ export const KnowledgeBaseContextMenu = memo(function KnowledgeBaseContextMenu({
   showDelete = true,
   disableEdit = false,
   disableDelete = false,
+  selectedCount,
 }: KnowledgeBaseContextMenuProps) {
-  const hasNavigationSection = showOpenInNewTab && !!onOpenInNewTab
-  const hasInfoSection = (showViewTags && !!onViewTags) || !!onCopyId || !!onTogglePin
+  const isMultiSelect = selectedCount > 1
+  const hasNavigationSection = !isMultiSelect && showOpenInNewTab && !!onOpenInNewTab
+  const hasInfoSection =
+    !isMultiSelect && ((showViewTags && !!onViewTags) || !!onCopyId || !!onTogglePin)
   const hasMoveSection = !disableEdit && !!onMove && !!moveOptions && moveOptions.length > 0
-  const hasEditSection = (showEdit && !!onEdit) || hasMoveSection
+  const hasEditSection = (!isMultiSelect && showEdit && !!onEdit) || hasMoveSection
   const hasDestructiveSection = showDelete && !!onDelete
   const hasActionsAboveDestructive = hasNavigationSection || hasInfoSection || hasEditSection
 
@@ -105,25 +110,25 @@ export const KnowledgeBaseContextMenu = memo(function KnowledgeBaseContextMenu({
             Open in new tab
           </DropdownMenuItem>
         )}
-        {showViewTags && onViewTags && (
+        {!isMultiSelect && showViewTags && onViewTags && (
           <DropdownMenuItem onSelect={onViewTags}>
             <TagIcon />
             View tags
           </DropdownMenuItem>
         )}
-        {onCopyId && (
+        {!isMultiSelect && onCopyId && (
           <DropdownMenuItem onSelect={onCopyId}>
             <Duplicate />
             Copy ID
           </DropdownMenuItem>
         )}
-        {onTogglePin && (
+        {!isMultiSelect && onTogglePin && (
           <DropdownMenuItem onSelect={onTogglePin}>
             <Pin />
             {pinned ? 'Unpin' : 'Pin'}
           </DropdownMenuItem>
         )}
-        {showEdit && onEdit && (
+        {!isMultiSelect && showEdit && onEdit && (
           <DropdownMenuItem disabled={disableEdit} onSelect={onEdit}>
             <Pencil />
             Edit
@@ -134,7 +139,7 @@ export const KnowledgeBaseContextMenu = memo(function KnowledgeBaseContextMenu({
           <DropdownMenuSub>
             <DropdownMenuSubTrigger>
               <FolderInput />
-              Move to
+              {selectionActionLabel('Move', selectedCount, 'Move to')}
             </DropdownMenuSubTrigger>
             <DropdownMenuSubContent>
               {renderMoveOptions(moveOptions!, onMove!)}
@@ -146,7 +151,7 @@ export const KnowledgeBaseContextMenu = memo(function KnowledgeBaseContextMenu({
         {showDelete && onDelete && (
           <DropdownMenuItem disabled={disableDelete} onSelect={onDelete}>
             <Trash />
-            Delete
+            {selectionActionLabel('Delete', selectedCount)}
           </DropdownMenuItem>
         )}
       </DropdownMenuContent>
diff --git a/apps/sim/app/workspace/[workspaceId]/knowledge/knowledge.tsx b/apps/sim/app/workspace/[workspaceId]/knowledge/knowledge.tsx
index 8ed1934a1a2..2c8258ad4f9 100644
--- a/apps/sim/app/workspace/[workspaceId]/knowledge/knowledge.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/knowledge/knowledge.tsx
@@ -1462,6 +1462,7 @@ export function Knowledge() {
           showDelete
           disableEdit={!canEdit}
           disableDelete={!canEdit}
+          selectedCount={selectedRowIds.size}
         />
       )}
 
@@ -1479,6 +1480,7 @@ export function Knowledge() {
           onMove={handleMoveFolderFromMenu}
           moveOptions={activeFolderMoveOptions}
           canEdit={canEdit}
+          selectedCount={selectedRowIds.size}
         />
       )}
 
diff --git a/apps/sim/app/workspace/[workspaceId]/tables/components/table-context-menu/table-context-menu.tsx b/apps/sim/app/workspace/[workspaceId]/tables/components/table-context-menu/table-context-menu.tsx
index 9bb7fbef27d..b7897ce9b03 100644
--- a/apps/sim/app/workspace/[workspaceId]/tables/components/table-context-menu/table-context-menu.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/tables/components/table-context-menu/table-context-menu.tsx
@@ -14,6 +14,7 @@ import {
 import { Database, Download, Duplicate, FolderInput, Pencil, Pin, Trash } from '@sim/emcn/icons'
 import type { MoveOptionNode } from '@/app/workspace/[workspaceId]/components/folders'
 import { renderMoveOptions } from '@/app/workspace/[workspaceId]/components/folders'
+import { selectionActionLabel } from '@/app/workspace/[workspaceId]/components/resource/selection-label'
 
 interface TableContextMenuProps {
   isOpen: boolean
@@ -35,6 +36,7 @@ interface TableContextMenuProps {
   disableRename?: boolean
   disableImport?: boolean
   disableExport?: boolean
+  selectedCount: number
   menuRef?: React.RefObject<HTMLDivElement | null>
 }
 
@@ -56,7 +58,11 @@ export function TableContextMenu({
   disableRename = false,
   disableImport = false,
   disableExport = false,
+  selectedCount,
 }: TableContextMenuProps) {
+  const isMultiSelect = selectedCount > 1
+  const hasMoveAction = !!(onMove && moveOptions && moveOptions.length > 0)
+
   /**
    * `Move to` needs a NON-EMPTY `moveOptions`, not just the handler — the looser
    * `onMove` alone draws the rule with nothing above it for a table whose other
@@ -66,13 +72,9 @@ export function TableContextMenu({
    * group, with both sides built from the items' exact render conditions.
    */
   const hasActionsAboveDestructive =
-    onViewSchema ||
-    onRename ||
-    onImportCsv ||
-    onExportCsv ||
-    (onMove && moveOptions && moveOptions.length > 0) ||
-    onCopyId ||
-    onTogglePin
+    hasMoveAction ||
+    (!isMultiSelect &&
+      !!(onViewSchema || onRename || onImportCsv || onExportCsv || onCopyId || onTogglePin))
 
   return (
     <DropdownMenu open={isOpen} onOpenChange={(open) => !open && onClose()} modal={false}>
@@ -96,25 +98,25 @@ export function TableContextMenu({
         sideOffset={4}
         onCloseAutoFocus={(e) => e.preventDefault()}
       >
-        {onViewSchema && (
+        {!isMultiSelect && onViewSchema && (
           <DropdownMenuItem onSelect={onViewSchema}>
             <Database />
             View Schema
           </DropdownMenuItem>
         )}
-        {onRename && (
+        {!isMultiSelect && onRename && (
           <DropdownMenuItem disabled={disableRename} onSelect={onRename}>
             <Pencil />
             Rename
           </DropdownMenuItem>
         )}
-        {onImportCsv && (
+        {!isMultiSelect && onImportCsv && (
           <DropdownMenuItem disabled={disableImport} onSelect={onImportCsv}>
             <Upload />
             Import CSV
           </DropdownMenuItem>
         )}
-        {onExportCsv && (
+        {!isMultiSelect && onExportCsv && (
           <DropdownMenuItem disabled={disableExport} onSelect={onExportCsv}>
             <Download />
             Export CSV
@@ -124,20 +126,20 @@ export function TableContextMenu({
           <DropdownMenuSub>
             <DropdownMenuSubTrigger>
               <FolderInput />
-              Move to
+              {selectionActionLabel('Move', selectedCount, 'Move to')}
             </DropdownMenuSubTrigger>
             <DropdownMenuSubContent>
               {renderMoveOptions(moveOptions, onMove)}
             </DropdownMenuSubContent>
           </DropdownMenuSub>
         )}
-        {onTogglePin && (
+        {!isMultiSelect && onTogglePin && (
           <DropdownMenuItem onSelect={onTogglePin}>
             <Pin />
             {pinned ? 'Unpin' : 'Pin'}
           </DropdownMenuItem>
         )}
-        {onCopyId && (
+        {!isMultiSelect && onCopyId && (
           <DropdownMenuItem onSelect={onCopyId}>
             <Duplicate />
             Copy ID
@@ -147,7 +149,7 @@ export function TableContextMenu({
         {onDelete && (
           <DropdownMenuItem disabled={disableDelete} onSelect={onDelete}>
             <Trash />
-            Delete
+            {selectionActionLabel('Delete', selectedCount)}
           </DropdownMenuItem>
         )}
       </DropdownMenuContent>
diff --git a/apps/sim/app/workspace/[workspaceId]/tables/tables.tsx b/apps/sim/app/workspace/[workspaceId]/tables/tables.tsx
index c6d3c51f10f..4410f1bd017 100644
--- a/apps/sim/app/workspace/[workspaceId]/tables/tables.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/tables/tables.tsx
@@ -1395,6 +1395,7 @@ export function Tables() {
         disableDelete={!canEdit}
         disableRename={!canEdit}
         disableImport={!canEdit}
+        selectedCount={selectedRowIds.size}
       />
 
       <FolderContextMenu
@@ -1417,6 +1418,7 @@ export function Tables() {
         onMove={canEdit ? handleMoveFolderFromMenu : undefined}
         moveOptions={canEdit ? activeFolderMoveOptions : undefined}
         canEdit={canEdit}
+        selectedCount={selectedRowIds.size}
       />
 
       {activeTable && (
diff --git a/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/components/workflow-list/components/context-menu/context-menu.test.tsx b/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/components/workflow-list/components/context-menu/context-menu.test.tsx
index 12b7d7c8902..2b73e2dc4a7 100644
--- a/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/components/workflow-list/components/context-menu/context-menu.test.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/components/workflow-list/components/context-menu/context-menu.test.tsx
@@ -35,7 +35,7 @@ function mountSurroundingMenu() {
   surroundingMenuItem = item
 }
 
-function renderMenu(onClose: () => void, onDelete: () => void = () => {}) {
+function renderMenu(onClose: () => void, onDelete: () => void = () => {}, selectedCount = 1) {
   ;(globalThis as { IS_REACT_ACT_ENVIRONMENT?: boolean }).IS_REACT_ACT_ENVIRONMENT = true
   mountSurroundingMenu()
   plainButton = document.createElement('button')
@@ -53,6 +53,7 @@ function renderMenu(onClose: () => void, onDelete: () => void = () => {}) {
         onDelete={onDelete}
         showRename={false}
         showDuplicate={false}
+        selectedCount={selectedCount}
       />
     )
   )
@@ -136,6 +137,16 @@ describe('sidebar context menu dismissal', () => {
 
     expect(onClose).toHaveBeenCalled()
   })
+
+  it('states when delete applies to a multi-item selection', () => {
+    renderMenu(vi.fn(), vi.fn(), 3)
+
+    expect(
+      Array.from(document.querySelectorAll('[role="menuitem"]')).some(
+        (item) => item.textContent === 'Delete 3 items'
+      )
+    ).toBe(true)
+  })
 })
 
 describe('separators', () => {
diff --git a/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/components/workflow-list/components/context-menu/context-menu.tsx b/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/components/workflow-list/components/context-menu/context-menu.tsx
index 3d4cfef1a2e..447b69008e2 100644
--- a/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/components/workflow-list/components/context-menu/context-menu.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/components/workflow-list/components/context-menu/context-menu.tsx
@@ -26,6 +26,7 @@ import {
   Unlock,
   X,
 } from '@sim/emcn/icons'
+import { selectionActionLabel } from '@/app/workspace/[workspaceId]/components/resource/selection-label'
 
 interface ContextMenuProps {
   isOpen: boolean
@@ -96,6 +97,7 @@ interface ContextMenuProps {
   onUploadLogo?: () => void
   showUploadLogo?: boolean
   disableUploadLogo?: boolean
+  selectedCount?: number
 }
 
 /**
@@ -164,6 +166,7 @@ export function ContextMenu({
   onUploadLogo,
   showUploadLogo = false,
   disableUploadLogo = false,
+  selectedCount = 1,
 }: ContextMenuProps) {
   const hasActionsAboveDestructive =
     (showOpenInNewTab && onOpenInNewTab) ||
@@ -345,7 +348,7 @@ export function ContextMenu({
             }}
           >
             <Duplicate />
-            Duplicate
+            {selectionActionLabel('Duplicate', selectedCount)}
           </DropdownMenuItem>
         )}
         {showExport && onExport && (
@@ -357,7 +360,7 @@ export function ContextMenu({
             }}
           >
             <Download />
-            Export
+            {selectionActionLabel('Export', selectedCount)}
           </DropdownMenuItem>
         )}
         {openInNewTabPosition === 'last' && showOpenInNewTab && onOpenInNewTab && (
@@ -394,7 +397,7 @@ export function ContextMenu({
             }}
           >
             <Trash />
-            Delete
+            {selectionActionLabel('Delete', selectedCount)}
           </DropdownMenuItem>
         )}
         {showCloseTab && onCloseTab && (
diff --git a/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/components/workflow-list/components/folder-item/folder-item.tsx b/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/components/workflow-list/components/folder-item/folder-item.tsx
index 0cc55efc27c..4877ba28400 100644
--- a/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/components/workflow-list/components/folder-item/folder-item.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/components/workflow-list/components/folder-item/folder-item.tsx
@@ -475,6 +475,10 @@ export const FolderItem = memo(function FolderItem({ workspaceId, folder }: Fold
   const isMixedSelection = useMemo(() => {
     return capturedSelectionRef.current?.isMixed ?? false
   }, [isContextMenuOpen])
+  const contextMenuSelectedCount = capturedSelectionRef.current
+    ? capturedSelectionRef.current.workflowIds.length +
+      capturedSelectionRef.current.folderIds.length
+    : 1
 
   const hasExportableContent = useMemo(() => {
     if (!capturedSelectionRef.current) return hasWorkflows
@@ -583,8 +587,8 @@ export const FolderItem = memo(function FolderItem({ workspaceId, folder }: Fold
         onDuplicate={handleDuplicate}
         onExport={handleExport}
         onDelete={handleOpenDeleteModal}
-        showCreate={!isMixedSelection}
-        showCreateFolder={!isMixedSelection}
+        showCreate={!isMixedSelection && selectedFolders.size <= 1}
+        showCreateFolder={!isMixedSelection && selectedFolders.size <= 1}
         showRename={!isMixedSelection && selectedFolders.size <= 1}
         showDuplicate={true}
         showExport={true}
@@ -605,6 +609,7 @@ export const FolderItem = memo(function FolderItem({ workspaceId, folder }: Fold
         showLock={!isMixedSelection && selectedFolders.size <= 1}
         disableLock={!userPermissions.canAdmin || inheritedFolderLocked}
         isLocked={effectiveLocked}
+        selectedCount={contextMenuSelectedCount}
       />
 
       <DeleteModal
diff --git a/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/components/workflow-list/components/workflow-item/workflow-item.tsx b/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/components/workflow-list/components/workflow-item/workflow-item.tsx
index 472e967cc9d..009052d2d44 100644
--- a/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/components/workflow-list/components/workflow-item/workflow-item.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/components/workflow-list/components/workflow-item/workflow-item.tsx
@@ -200,6 +200,10 @@ export const WorkflowItem = memo(function WorkflowItem({
   const isMixedSelection = useMemo(() => {
     return capturedSelectionRef.current?.isMixed ?? false
   }, [isContextMenuOpen])
+  const contextMenuSelectedCount = capturedSelectionRef.current
+    ? capturedSelectionRef.current.workflowIds.length +
+      capturedSelectionRef.current.folderIds.length
+    : 1
 
   const captureSelectionState = useCallback(() => {
     const store = useFolderStore.getState()
@@ -503,6 +507,7 @@ export const WorkflowItem = memo(function WorkflowItem({
         showLock={!isMixedSelection && selectedWorkflows.size <= 1}
         disableLock={!userPermissions.canAdmin || inheritedFolderLocked}
         isLocked={effectiveLocked}
+        selectedCount={contextMenuSelectedCount}
       />
 
       <DeleteModal
diff --git a/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/sidebar.tsx b/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/sidebar.tsx
index cbec949a489..5e41c897fbc 100644
--- a/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/sidebar.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/sidebar.tsx
@@ -1857,6 +1857,7 @@ export const Sidebar = memo(function Sidebar({
                   showDuplicate={false}
                   disableRename={!canEdit}
                   disableDelete={!canEdit}
+                  selectedCount={contextMenuSelectionRef.current.chatIds.length}
                 />
 
                 <DeleteModal