diff --git a/packages/web/src/javascripts/Components/NoteView/NoteViewFileDropTarget.tsx b/packages/web/src/javascripts/Components/NoteView/NoteViewFileDropTarget.tsx
index 9a538e08f..ed822f429 100644
--- a/packages/web/src/javascripts/Components/NoteView/NoteViewFileDropTarget.tsx
+++ b/packages/web/src/javascripts/Components/NoteView/NoteViewFileDropTarget.tsx
@@ -2,6 +2,7 @@ import { FilesController } from '@/Controllers/FilesController'
 import { LinkingController } from '@/Controllers/LinkingController'
 import { SNNote } from '@standardnotes/snjs'
 import { useEffect } from 'react'
+import { useApplication } from '../ApplicationProvider'
 import { useFileDragNDrop } from '../FileDragNDropProvider'
 
 type Props = {
@@ -12,6 +13,7 @@ type Props = {
 }
 
 const NoteViewFileDropTarget = ({ note, linkingController, noteViewElement, filesController }: Props) => {
+  const application = useApplication()
   const { isDraggingFiles, addDragTarget, removeDragTarget } = useFileDragNDrop()
 
   useEffect(() => {
@@ -22,6 +24,9 @@ const NoteViewFileDropTarget = ({ note, linkingController, noteViewElement, file
         tooltipText: 'Drop your files to upload and link them to the current note',
         callback: async (uploadedFile) => {
           await linkingController.linkItems(note, uploadedFile)
+          void application.mutator.changeAndSaveItem(uploadedFile, (mutator) => {
+            mutator.protected = note.protected
+          })
           filesController.notifyObserversOfUploadedFileLinkingToCurrentNote(uploadedFile.uuid)
         },
       })
@@ -32,7 +37,7 @@ const NoteViewFileDropTarget = ({ note, linkingController, noteViewElement, file
         removeDragTarget(target)
       }
     }
-  }, [addDragTarget, linkingController, note, noteViewElement, removeDragTarget, filesController])
+  }, [addDragTarget, linkingController, note, noteViewElement, removeDragTarget, filesController, application.mutator])
 
   return isDraggingFiles ? (
     // Required to block drag events to editor iframe
diff --git a/packages/web/src/javascripts/Components/SuperEditor/Plugins/EncryptedFilePlugin/FilePlugin.ts b/packages/web/src/javascripts/Components/SuperEditor/Plugins/EncryptedFilePlugin/FilePlugin.ts
index b544e3f46..6cac9925e 100644
--- a/packages/web/src/javascripts/Components/SuperEditor/Plugins/EncryptedFilePlugin/FilePlugin.ts
+++ b/packages/web/src/javascripts/Components/SuperEditor/Plugins/EncryptedFilePlugin/FilePlugin.ts
@@ -16,8 +16,11 @@ import { $wrapNodeInElement, mergeRegister } from '@lexical/utils'
 import { useFilesController } from '@/Controllers/FilesControllerProvider'
 import { FilesControllerEvent } from '@/Controllers/FilesController'
 import { useLinkingController } from '@/Controllers/LinkingControllerProvider'
+import { useApplication } from '@/Components/ApplicationProvider'
+import { SNNote } from '@standardnotes/snjs'
 
-export default function FilePlugin(): JSX.Element | null {
+export default function FilePlugin({ currentNote }: { currentNote: SNNote }): JSX.Element | null {
+  const application = useApplication()
   const [editor] = useLexicalComposerContext()
   const filesController = useFilesController()
   const linkingController = useLinkingController()
@@ -34,6 +37,9 @@ export default function FilePlugin(): JSX.Element | null {
           if (uploadedFile) {
             editor.dispatchCommand(INSERT_FILE_COMMAND, uploadedFile.uuid)
             void linkingController.linkItemToSelectedItem(uploadedFile)
+            void application.mutator.changeAndSaveItem(uploadedFile, (mutator) => {
+              mutator.protected = currentNote.protected
+            })
           }
         } catch (error) {
           console.error(error)
@@ -70,7 +76,7 @@ export default function FilePlugin(): JSX.Element | null {
         COMMAND_PRIORITY_NORMAL,
       ),
     )
-  }, [editor, filesController, linkingController])
+  }, [application.mutator, currentNote.protected, editor, filesController, linkingController])
 
   useEffect(() => {
     const disposer = filesController.addEventObserver((event, data) => {
diff --git a/packages/web/src/javascripts/Components/SuperEditor/SuperEditor.tsx b/packages/web/src/javascripts/Components/SuperEditor/SuperEditor.tsx
index 8b2e97a77..463269a4c 100644
--- a/packages/web/src/javascripts/Components/SuperEditor/SuperEditor.tsx
+++ b/packages/web/src/javascripts/Components/SuperEditor/SuperEditor.tsx
@@ -183,7 +183,7 @@ export const SuperEditor: FunctionComponent<Props> = ({
                 spellcheck={spellcheck}
               >
                 <ItemSelectionPlugin currentNote={note.current} />
-                <FilePlugin />
+                <FilePlugin currentNote={note.current} />
                 <ItemBubblePlugin />
                 <BlockPickerMenuPlugin />
                 <GetMarkdownPlugin ref={getMarkdownPlugin} />