diff --git a/packages/web/src/javascripts/Components/ApplicationView/ApplicationView.tsx b/packages/web/src/javascripts/Components/ApplicationView/ApplicationView.tsx
index 78db68a34..7e46b3261 100644
--- a/packages/web/src/javascripts/Components/ApplicationView/ApplicationView.tsx
+++ b/packages/web/src/javascripts/Components/ApplicationView/ApplicationView.tsx
@@ -216,6 +216,8 @@ const ApplicationView: FunctionComponent<Props> = ({ application, mainApplicatio
                     <FileContextMenuWrapper
                       filesController={viewControllerManager.filesController}
                       selectionController={viewControllerManager.selectionController}
+                      navigationController={viewControllerManager.navigationController}
+                      linkingController={viewControllerManager.linkingController}
                     />
                     <PurchaseFlowWrapper application={application} viewControllerManager={viewControllerManager} />
                     <ConfirmSignoutContainer
diff --git a/packages/web/src/javascripts/Components/ContentListView/ContentListView.tsx b/packages/web/src/javascripts/Components/ContentListView/ContentListView.tsx
index 1c5c3eac9..38a47f125 100644
--- a/packages/web/src/javascripts/Components/ContentListView/ContentListView.tsx
+++ b/packages/web/src/javascripts/Components/ContentListView/ContentListView.tsx
@@ -358,6 +358,7 @@ const ContentListView = forwardRef<HTMLDivElement, Props>(
               filesController={filesController}
               featuresController={featuresController}
               linkingController={linkingController}
+              navigationController={navigationController}
             />
           ) : (
             <ContentList
diff --git a/packages/web/src/javascripts/Components/FileContextMenu/FileContextMenu.tsx b/packages/web/src/javascripts/Components/FileContextMenu/FileContextMenu.tsx
index 41bda00b8..2510b9eb2 100644
--- a/packages/web/src/javascripts/Components/FileContextMenu/FileContextMenu.tsx
+++ b/packages/web/src/javascripts/Components/FileContextMenu/FileContextMenu.tsx
@@ -1,4 +1,6 @@
 import { FilesController } from '@/Controllers/FilesController'
+import { LinkingController } from '@/Controllers/LinkingController'
+import { NavigationController } from '@/Controllers/Navigation/NavigationController'
 import { SelectedItemsController } from '@/Controllers/SelectedItemsController'
 import { observer } from 'mobx-react-lite'
 import { FunctionComponent } from 'react'
@@ -9,36 +11,47 @@ import FileMenuOptions from './FileMenuOptions'
 type Props = {
   filesController: FilesController
   selectionController: SelectedItemsController
+  linkingController: LinkingController
+  navigationController: NavigationController
 }
 
-const FileContextMenu: FunctionComponent<Props> = observer(({ filesController, selectionController }) => {
-  const { showFileContextMenu, setShowFileContextMenu, fileContextMenuLocation } = filesController
-  const { selectedFiles } = selectionController
+const FileContextMenu: FunctionComponent<Props> = observer(
+  ({ filesController, selectionController, linkingController, navigationController }) => {
+    const { showFileContextMenu, setShowFileContextMenu, fileContextMenuLocation } = filesController
+    const { selectedFiles } = selectionController
 
-  return (
-    <Popover
-      open={showFileContextMenu}
-      anchorPoint={fileContextMenuLocation}
-      togglePopover={() => setShowFileContextMenu(!showFileContextMenu)}
-      align="start"
-      className="py-2"
-    >
-      <Menu a11yLabel="File context menu" isOpen={showFileContextMenu}>
-        <FileMenuOptions
-          filesController={filesController}
-          selectedFiles={selectedFiles}
-          closeMenu={() => setShowFileContextMenu(false)}
-          shouldShowRenameOption={false}
-          shouldShowAttachOption={false}
-        />
-      </Menu>
-    </Popover>
-  )
-})
+    return (
+      <Popover
+        open={showFileContextMenu}
+        anchorPoint={fileContextMenuLocation}
+        togglePopover={() => setShowFileContextMenu(!showFileContextMenu)}
+        align="start"
+        className="py-2"
+      >
+        <Menu a11yLabel="File context menu" isOpen={showFileContextMenu}>
+          <FileMenuOptions
+            filesController={filesController}
+            linkingController={linkingController}
+            navigationController={navigationController}
+            selectedFiles={selectedFiles}
+            closeMenu={() => setShowFileContextMenu(false)}
+            shouldShowRenameOption={false}
+            shouldShowAttachOption={false}
+          />
+        </Menu>
+      </Popover>
+    )
+  },
+)
 
 FileContextMenu.displayName = 'FileContextMenu'
 
-const FileContextMenuWrapper: FunctionComponent<Props> = ({ filesController, selectionController }) => {
+const FileContextMenuWrapper: FunctionComponent<Props> = ({
+  filesController,
+  linkingController,
+  navigationController,
+  selectionController,
+}) => {
   const { showFileContextMenu } = filesController
   const { selectedFiles } = selectionController
 
@@ -48,7 +61,14 @@ const FileContextMenuWrapper: FunctionComponent<Props> = ({ filesController, sel
     return null
   }
 
-  return <FileContextMenu filesController={filesController} selectionController={selectionController} />
+  return (
+    <FileContextMenu
+      filesController={filesController}
+      linkingController={linkingController}
+      navigationController={navigationController}
+      selectionController={selectionController}
+    />
+  )
 }
 
 export default observer(FileContextMenuWrapper)
diff --git a/packages/web/src/javascripts/Components/FileContextMenu/FileMenuOptions.tsx b/packages/web/src/javascripts/Components/FileContextMenu/FileMenuOptions.tsx
index 0b0e9e959..10ae996fa 100644
--- a/packages/web/src/javascripts/Components/FileContextMenu/FileMenuOptions.tsx
+++ b/packages/web/src/javascripts/Components/FileContextMenu/FileMenuOptions.tsx
@@ -11,10 +11,16 @@ import MenuItem from '../Menu/MenuItem'
 import { FileContextMenuBackupOption } from './FileContextMenuBackupOption'
 import MenuSwitchButtonItem from '../Menu/MenuSwitchButtonItem'
 import { FileItem } from '@standardnotes/snjs'
+import AddTagOption from '../NotesOptions/AddTagOption'
+import { MenuItemIconSize } from '@/Constants/TailwindClassNames'
+import { LinkingController } from '@/Controllers/LinkingController'
+import { NavigationController } from '@/Controllers/Navigation/NavigationController'
 
 type Props = {
   closeMenu: () => void
   filesController: FilesController
+  linkingController: LinkingController
+  navigationController: NavigationController
   isFileAttachedToNote?: boolean
   renameToggleCallback?: (isRenamingFile: boolean) => void
   shouldShowRenameOption: boolean
@@ -25,6 +31,8 @@ type Props = {
 const FileMenuOptions: FunctionComponent<Props> = ({
   closeMenu,
   filesController,
+  linkingController,
+  navigationController,
   isFileAttachedToNote,
   renameToggleCallback,
   shouldShowRenameOption,
@@ -82,6 +90,12 @@ const FileMenuOptions: FunctionComponent<Props> = ({
           ) : null}
         </>
       )}
+      <AddTagOption
+        navigationController={navigationController}
+        linkingController={linkingController}
+        selectedItems={selectedFiles}
+        iconClassName={`text-neutral mr-2 ${MenuItemIconSize}`}
+      />
       <MenuSwitchButtonItem
         checked={hasProtectedFiles}
         onChange={(hasProtectedFiles) => {
diff --git a/packages/web/src/javascripts/Components/FileContextMenu/FileOptionsPanel.tsx b/packages/web/src/javascripts/Components/FileContextMenu/FileOptionsPanel.tsx
index dec830ca1..7148a7c3c 100644
--- a/packages/web/src/javascripts/Components/FileContextMenu/FileOptionsPanel.tsx
+++ b/packages/web/src/javascripts/Components/FileContextMenu/FileOptionsPanel.tsx
@@ -6,13 +6,22 @@ import { SelectedItemsController } from '@/Controllers/SelectedItemsController'
 import Popover from '../Popover/Popover'
 import RoundIconButton from '../Button/RoundIconButton'
 import Menu from '../Menu/Menu'
+import { LinkingController } from '@/Controllers/LinkingController'
+import { NavigationController } from '@/Controllers/Navigation/NavigationController'
 
 type Props = {
   filesController: FilesController
   selectionController: SelectedItemsController
+  linkingController: LinkingController
+  navigationController: NavigationController
 }
 
-const FilesOptionsPanel = ({ filesController, selectionController }: Props) => {
+const FilesOptionsPanel = ({
+  filesController,
+  linkingController,
+  navigationController,
+  selectionController,
+}: Props) => {
   const [isOpen, setIsOpen] = useState(false)
   const buttonRef = useRef<HTMLButtonElement>(null)
 
@@ -25,6 +34,8 @@ const FilesOptionsPanel = ({ filesController, selectionController }: Props) => {
         <Menu a11yLabel="File options panel" isOpen={isOpen}>
           <FileMenuOptions
             filesController={filesController}
+            linkingController={linkingController}
+            navigationController={navigationController}
             selectedFiles={selectionController.selectedFiles}
             closeMenu={() => {
               setIsOpen(false)
diff --git a/packages/web/src/javascripts/Components/FileView/FileViewWithoutProtection.tsx b/packages/web/src/javascripts/Components/FileView/FileViewWithoutProtection.tsx
index 523d5278c..8a468a1ed 100644
--- a/packages/web/src/javascripts/Components/FileView/FileViewWithoutProtection.tsx
+++ b/packages/web/src/javascripts/Components/FileView/FileViewWithoutProtection.tsx
@@ -112,6 +112,8 @@ const FileViewWithoutProtection = ({ application, viewControllerManager, file }:
               <FileOptionsPanel
                 filesController={viewControllerManager.filesController}
                 selectionController={viewControllerManager.selectionController}
+                linkingController={viewControllerManager.linkingController}
+                navigationController={viewControllerManager.navigationController}
               />
             </div>
           </div>
diff --git a/packages/web/src/javascripts/Components/FilesTableView/FilesTableView.tsx b/packages/web/src/javascripts/Components/FilesTableView/FilesTableView.tsx
index 0a01e65f8..e167be5bf 100644
--- a/packages/web/src/javascripts/Components/FilesTableView/FilesTableView.tsx
+++ b/packages/web/src/javascripts/Components/FilesTableView/FilesTableView.tsx
@@ -31,8 +31,19 @@ import { LinkingController } from '@/Controllers/LinkingController'
 import { FeaturesController } from '@/Controllers/FeaturesController'
 import { MutuallyExclusiveMediaQueryBreakpoints, useMediaQuery } from '@/Hooks/useMediaQuery'
 import { useApplication } from '../ApplicationProvider'
+import { NavigationController } from '@/Controllers/Navigation/NavigationController'
 
-const ContextMenuCell = ({ files, filesController }: { files: FileItem[]; filesController: FilesController }) => {
+const ContextMenuCell = ({
+  files,
+  filesController,
+  navigationController,
+  linkingController,
+}: {
+  files: FileItem[]
+  filesController: FilesController
+  navigationController: NavigationController
+  linkingController: LinkingController
+}) => {
   const [contextMenuVisible, setContextMenuVisible] = useState(false)
   const anchorElementRef = useRef<HTMLButtonElement>(null)
 
@@ -61,6 +72,8 @@ const ContextMenuCell = ({ files, filesController }: { files: FileItem[]; filesC
       >
         <Menu a11yLabel="File context menu" isOpen={contextMenuVisible}>
           <FileMenuOptions
+            linkingController={linkingController}
+            navigationController={navigationController}
             closeMenu={() => {
               setContextMenuVisible(false)
             }}
@@ -160,9 +173,16 @@ type Props = {
   filesController: FilesController
   featuresController: FeaturesController
   linkingController: LinkingController
+  navigationController: NavigationController
 }
 
-const FilesTableView = ({ application, filesController, featuresController, linkingController }: Props) => {
+const FilesTableView = ({
+  application,
+  filesController,
+  featuresController,
+  linkingController,
+  navigationController,
+}: Props) => {
   const files = application.items
     .getDisplayableNotesAndFiles()
     .filter((item) => item.content_type === ContentType.File) as FileItem[]
@@ -312,12 +332,22 @@ const FilesTableView = ({ application, filesController, featuresController, link
             featuresController={featuresController}
             linkingController={linkingController}
           />
-          <ContextMenuCell files={[file]} filesController={filesController} />
+          <ContextMenuCell
+            files={[file]}
+            filesController={filesController}
+            linkingController={linkingController}
+            navigationController={navigationController}
+          />
         </div>
       )
     },
     selectionActions: (fileIds) => (
-      <ContextMenuCell files={files.filter((file) => fileIds.includes(file.uuid))} filesController={filesController} />
+      <ContextMenuCell
+        files={files.filter((file) => fileIds.includes(file.uuid))}
+        filesController={filesController}
+        linkingController={linkingController}
+        navigationController={navigationController}
+      />
     ),
     showSelectionActions: true,
   })
@@ -347,6 +377,8 @@ const FilesTableView = ({ application, filesController, featuresController, link
               shouldShowRenameOption={false}
               shouldShowAttachOption={false}
               selectedFiles={[contextMenuFile]}
+              linkingController={linkingController}
+              navigationController={navigationController}
             />
           </Menu>
         </Popover>
diff --git a/packages/web/src/javascripts/Components/MultipleSelectedFiles/MultipleSelectedFiles.tsx b/packages/web/src/javascripts/Components/MultipleSelectedFiles/MultipleSelectedFiles.tsx
index 4394a141f..2e8ccc393 100644
--- a/packages/web/src/javascripts/Components/MultipleSelectedFiles/MultipleSelectedFiles.tsx
+++ b/packages/web/src/javascripts/Components/MultipleSelectedFiles/MultipleSelectedFiles.tsx
@@ -5,13 +5,22 @@ import { useCallback } from 'react'
 import FileOptionsPanel from '../FileContextMenu/FileOptionsPanel'
 import { FilesController } from '@/Controllers/FilesController'
 import { SelectedItemsController } from '@/Controllers/SelectedItemsController'
+import { NavigationController } from '@/Controllers/Navigation/NavigationController'
+import { LinkingController } from '@/Controllers/LinkingController'
 
 type Props = {
   filesController: FilesController
   selectionController: SelectedItemsController
+  linkingController: LinkingController
+  navigationController: NavigationController
 }
 
-const MultipleSelectedFiles = ({ filesController, selectionController }: Props) => {
+const MultipleSelectedFiles = ({
+  filesController,
+  selectionController,
+  linkingController,
+  navigationController,
+}: Props) => {
   const count = selectionController.selectedFilesCount
 
   const cancelMultipleSelection = useCallback(() => {
@@ -23,7 +32,12 @@ const MultipleSelectedFiles = ({ filesController, selectionController }: Props)
       <div className="flex w-full items-center justify-between p-4">
         <h1 className="m-0 text-lg font-bold">{count} selected files</h1>
         <div>
-          <FileOptionsPanel filesController={filesController} selectionController={selectionController} />
+          <FileOptionsPanel
+            filesController={filesController}
+            selectionController={selectionController}
+            linkingController={linkingController}
+            navigationController={navigationController}
+          />
         </div>
       </div>
       <div className="flex min-h-full w-full max-w-md flex-grow flex-col items-center justify-center">
diff --git a/packages/web/src/javascripts/Components/NoteGroupView/NoteGroupView.tsx b/packages/web/src/javascripts/Components/NoteGroupView/NoteGroupView.tsx
index 983b3cb8c..3a5ead97c 100644
--- a/packages/web/src/javascripts/Components/NoteGroupView/NoteGroupView.tsx
+++ b/packages/web/src/javascripts/Components/NoteGroupView/NoteGroupView.tsx
@@ -118,6 +118,8 @@ class NoteGroupView extends AbstractComponent<Props, State> {
           <MultipleSelectedFiles
             filesController={this.viewControllerManager.filesController}
             selectionController={this.viewControllerManager.selectionController}
+            navigationController={this.viewControllerManager.navigationController}
+            linkingController={this.viewControllerManager.linkingController}
           />
         )}
         {shouldNotShowMultipleSelectedItems && hasControllers && (
diff --git a/packages/web/src/javascripts/Components/NotesOptions/AddTagOption.tsx b/packages/web/src/javascripts/Components/NotesOptions/AddTagOption.tsx
index ac395c268..1996131fa 100644
--- a/packages/web/src/javascripts/Components/NotesOptions/AddTagOption.tsx
+++ b/packages/web/src/javascripts/Components/NotesOptions/AddTagOption.tsx
@@ -2,22 +2,28 @@ import { observer } from 'mobx-react-lite'
 import { FunctionComponent, useCallback, useRef, useState } from 'react'
 import Icon from '@/Components/Icon/Icon'
 import { NavigationController } from '@/Controllers/Navigation/NavigationController'
-import { NotesController } from '@/Controllers/NotesController/NotesController'
 import { KeyboardKey } from '@standardnotes/ui-services'
 import Popover from '../Popover/Popover'
-import { IconType } from '@standardnotes/snjs'
+import { classNames, DecryptedItemInterface, IconType, SNTag } from '@standardnotes/snjs'
 import { getTitleForLinkedTag } from '@/Utils/Items/Display/getTitleForLinkedTag'
 import { useApplication } from '../ApplicationProvider'
 import MenuItem from '../Menu/MenuItem'
 import Menu from '../Menu/Menu'
+import { LinkingController } from '@/Controllers/LinkingController'
 
 type Props = {
   navigationController: NavigationController
-  notesController: NotesController
+  linkingController: LinkingController
+  selectedItems: DecryptedItemInterface[]
   iconClassName: string
 }
 
-const AddTagOption: FunctionComponent<Props> = ({ navigationController, notesController, iconClassName }) => {
+const AddTagOption: FunctionComponent<Props> = ({
+  navigationController,
+  linkingController,
+  selectedItems,
+  iconClassName,
+}) => {
   const application = useApplication()
   const menuContainerRef = useRef<HTMLDivElement>(null)
   const buttonRef = useRef<HTMLButtonElement>(null)
@@ -28,6 +34,18 @@ const AddTagOption: FunctionComponent<Props> = ({ navigationController, notesCon
     setIsOpen((isOpen) => !isOpen)
   }, [])
 
+  const isTagLinkedToSelectedItems = (tag: SNTag) => {
+    return selectedItems.every((item) => application.getItemTags(item).find((itemTag) => itemTag.uuid === tag.uuid))
+  }
+
+  const linkTagToSelectedItems = (tag: SNTag) => {
+    selectedItems.forEach((item) => linkingController.linkItems(item, tag))
+  }
+
+  const unlinkTagFromSelectedItems = (tag: SNTag) => {
+    selectedItems.forEach((item) => linkingController.unlinkItems(item, tag))
+  }
+
   return (
     <div ref={menuContainerRef}>
       <MenuItem
@@ -59,9 +77,7 @@ const AddTagOption: FunctionComponent<Props> = ({ navigationController, notesCon
             <MenuItem
               key={tag.uuid}
               onClick={() => {
-                notesController.isTagInSelectedNotes(tag)
-                  ? notesController.removeTagFromSelectedNotes(tag).catch(console.error)
-                  : notesController.addTagToSelectedNotes(tag).catch(console.error)
+                isTagLinkedToSelectedItems(tag) ? unlinkTagFromSelectedItems(tag) : linkTagToSelectedItems(tag)
               }}
             >
               {tag.iconString && (
@@ -72,8 +88,10 @@ const AddTagOption: FunctionComponent<Props> = ({ navigationController, notesCon
                 />
               )}
               <span
-                className={`overflow-hidden overflow-ellipsis whitespace-nowrap
-                        ${notesController.isTagInSelectedNotes(tag) ? 'font-bold' : ''}`}
+                className={classNames(
+                  'overflow-hidden overflow-ellipsis whitespace-nowrap',
+                  isTagLinkedToSelectedItems(tag) ? 'font-bold' : '',
+                )}
               >
                 {getTitleForLinkedTag(tag, application)?.longTitle}
               </span>
diff --git a/packages/web/src/javascripts/Components/NotesOptions/NotesOptions.tsx b/packages/web/src/javascripts/Components/NotesOptions/NotesOptions.tsx
index 83f92e465..1ced1c5bb 100644
--- a/packages/web/src/javascripts/Components/NotesOptions/NotesOptions.tsx
+++ b/packages/web/src/javascripts/Components/NotesOptions/NotesOptions.tsx
@@ -42,6 +42,7 @@ const NotesOptions = ({
   application,
   navigationController,
   notesController,
+  linkingController,
   historyModalController,
   closeMenu,
 }: NotesOptionsProps) => {
@@ -214,7 +215,8 @@ const NotesOptions = ({
         <AddTagOption
           iconClassName={iconClass}
           navigationController={navigationController}
-          notesController={notesController}
+          selectedItems={notes}
+          linkingController={linkingController}
         />
       )}
       <MenuItem