diff --git a/packages/web/src/javascripts/Components/ContentListView/ContentListView.tsx b/packages/web/src/javascripts/Components/ContentListView/ContentListView.tsx
index 541e94d65..75aa4018c 100644
--- a/packages/web/src/javascripts/Components/ContentListView/ContentListView.tsx
+++ b/packages/web/src/javascripts/Components/ContentListView/ContentListView.tsx
@@ -382,7 +382,7 @@ const ContentListView = forwardRef<HTMLDivElement, Props>(
           )
         ) : null}
         {isMobileScreen && itemListController.isMultipleSelectionMode && (
-          <MobileMultiSelectionToolbar notesController={notesController} />
+          <MobileMultiSelectionToolbar notesController={notesController} navigationController={navigationController} />
         )}
         <div className="absolute bottom-0 h-safe-bottom w-full" />
         {children}
diff --git a/packages/web/src/javascripts/Components/ContentListView/MobileMultiSelectionToolbar.tsx b/packages/web/src/javascripts/Components/ContentListView/MobileMultiSelectionToolbar.tsx
index 04d2f5ea9..a7f17570f 100644
--- a/packages/web/src/javascripts/Components/ContentListView/MobileMultiSelectionToolbar.tsx
+++ b/packages/web/src/javascripts/Components/ContentListView/MobileMultiSelectionToolbar.tsx
@@ -1,12 +1,17 @@
 import { NotesController } from '@/Controllers/NotesController/NotesController'
 import Icon from '../Icon/Icon'
+import { NavigationController } from '@/Controllers/Navigation/NavigationController'
+import { observer } from 'mobx-react-lite'
+import { SystemViewId, isSmartView } from '@standardnotes/snjs'
 
 type Props = {
   notesController: NotesController
+  navigationController: NavigationController
 }
 
-const MobileMultiSelectionToolbar = ({ notesController }: Props) => {
+const MobileMultiSelectionToolbar = ({ notesController, navigationController }: Props) => {
   const { selectedNotes } = notesController
+  const { selected } = navigationController
 
   const archived = selectedNotes.some((note) => note.archived)
 
@@ -26,7 +31,16 @@ const MobileMultiSelectionToolbar = ({ notesController }: Props) => {
       </button>
       <button
         className="flex-grow px-2 py-3 active:bg-passive-3"
-        onClick={() => notesController.setTrashSelectedNotes(true).catch(console.error)}
+        onClick={() => {
+          const isInTrashView = selected && isSmartView(selected) && selected.uuid === SystemViewId.TrashedNotes
+          const allSelectedNotesAreTrashed = selectedNotes.every((note) => note.trashed)
+          const shouldDeletePermanently = isInTrashView || allSelectedNotesAreTrashed
+          if (shouldDeletePermanently) {
+            notesController.deleteNotesPermanently().catch(console.error)
+          } else {
+            notesController.setTrashSelectedNotes(true).catch(console.error)
+          }
+        }}
       >
         <Icon type="trash" className="mx-auto text-info" size="large" />
       </button>
@@ -40,4 +54,4 @@ const MobileMultiSelectionToolbar = ({ notesController }: Props) => {
   )
 }
 
-export default MobileMultiSelectionToolbar
+export default observer(MobileMultiSelectionToolbar)
diff --git a/packages/web/src/javascripts/Constants/Strings.ts b/packages/web/src/javascripts/Constants/Strings.ts
index c2620f85c..3ec6d5c99 100644
--- a/packages/web/src/javascripts/Constants/Strings.ts
+++ b/packages/web/src/javascripts/Constants/Strings.ts
@@ -109,6 +109,7 @@ export const Strings = {
   protectingNoteWithoutProtectionSources:
     'Access to this note will not be restricted until you set up a passcode or account.',
   trashItemsTitle: 'Move to Trash',
+  deleteItemsPermanentlyTitle: 'Delete Permanently',
   trashNotesText: 'Are you sure you want to move these notes to the trash?',
   trashFilesText: 'Are you sure you want to move these files to the trash?',
   enterPasscode: 'Please enter a passcode.',
diff --git a/packages/web/src/javascripts/Controllers/NotesController/NotesController.ts b/packages/web/src/javascripts/Controllers/NotesController/NotesController.ts
index 55a2f17a7..df952652f 100644
--- a/packages/web/src/javascripts/Controllers/NotesController/NotesController.ts
+++ b/packages/web/src/javascripts/Controllers/NotesController/NotesController.ts
@@ -213,7 +213,7 @@ export class NotesController
       return false
     }
 
-    const title = Strings.trashItemsTitle
+    const title = permanently ? Strings.deleteItemsPermanentlyTitle : Strings.trashItemsTitle
     let noteTitle = undefined
     if (this.selectedNotesCount === 1) {
       const selectedNote = this.getSelectedNotesList()[0]