diff --git a/packages/web/src/javascripts/Application/Dependencies/WebDependencies.ts b/packages/web/src/javascripts/Application/Dependencies/WebDependencies.ts
index da93e90f7..15d19a767 100644
--- a/packages/web/src/javascripts/Application/Dependencies/WebDependencies.ts
+++ b/packages/web/src/javascripts/Application/Dependencies/WebDependencies.ts
@@ -350,6 +350,7 @@ export class WebDependencies extends DependencyContainer {
         this.get<FilePreviewModalController>(Web_TYPES.FilePreviewModalController),
         this.get<ArchiveManager>(Web_TYPES.ArchiveManager),
         this.get<VaultDisplayService>(Web_TYPES.VaultDisplayService),
+        application.vaults,
         application.items,
         application.files,
         application.mutator,
diff --git a/packages/web/src/javascripts/Components/FileDragNDropProvider.tsx b/packages/web/src/javascripts/Components/FileDragNDropProvider.tsx
index de2f63fe3..1f57bc820 100644
--- a/packages/web/src/javascripts/Components/FileDragNDropProvider.tsx
+++ b/packages/web/src/javascripts/Components/FileDragNDropProvider.tsx
@@ -3,7 +3,7 @@ import { usePremiumModal } from '@/Hooks/usePremiumModal'
 import { classNames } from '@standardnotes/utils'
 import { isHandlingFileDrag } from '@/Utils/DragTypeCheck'
 import { StreamingFileReader } from '@standardnotes/filepicker'
-import { FileItem } from '@standardnotes/snjs'
+import { FileItem, SNNote } from '@standardnotes/snjs'
 import { useMemo, useState, createContext, ReactNode, useRef, useCallback, useEffect, useContext, memo } from 'react'
 import Portal from './Portal/Portal'
 import { ElementIds } from '@/Constants/ElementIDs'
@@ -11,6 +11,7 @@ import { ElementIds } from '@/Constants/ElementIDs'
 type FileDragTargetData = {
   tooltipText: string
   callback: (files: FileItem) => void
+  note?: SNNote
 }
 
 type FileDnDContextData = {
@@ -200,15 +201,17 @@ const FileDragNDropProvider = ({ application, children }: Props) => {
             return
           }
 
-          const uploadedFile = await application.filesController.uploadNewFile(fileOrHandle)
+          const dragTarget = closestDragTarget ? dragTargets.current.get(closestDragTarget) : undefined
+
+          const uploadedFile = await application.filesController.uploadNewFile(fileOrHandle, {
+            note: dragTarget?.note,
+          })
 
           if (!uploadedFile) {
             return
           }
 
-          if (closestDragTarget && dragTargets.current.has(closestDragTarget)) {
-            dragTargets.current.get(closestDragTarget)?.callback(uploadedFile)
-          }
+          dragTarget?.callback(uploadedFile)
         })
 
         dragCounter.current = 0
diff --git a/packages/web/src/javascripts/Components/LinkedItems/LinkedItemsPanel.tsx b/packages/web/src/javascripts/Components/LinkedItems/LinkedItemsPanel.tsx
index e766bf8cf..7b4fda5f8 100644
--- a/packages/web/src/javascripts/Components/LinkedItems/LinkedItemsPanel.tsx
+++ b/packages/web/src/javascripts/Components/LinkedItems/LinkedItemsPanel.tsx
@@ -9,7 +9,7 @@ import Icon from '../Icon/Icon'
 import DecoratedInput from '../Input/DecoratedInput'
 import LinkedItemSearchResults from './LinkedItemSearchResults'
 import { LinkedItemsSectionItem } from './LinkedItemsSectionItem'
-import { DecryptedItem } from '@standardnotes/snjs'
+import { DecryptedItem, SNNote } from '@standardnotes/snjs'
 import { useItemLinks } from '@/Hooks/useItemLinks'
 import { mergeRefs } from '@/Hooks/mergeRefs'
 
@@ -41,7 +41,7 @@ const LinkedItemsPanel = ({ item }: { item: DecryptedItem }) => {
       return
     }
 
-    void application.filesController.selectAndUploadNewFiles((file) => {
+    void application.filesController.selectAndUploadNewFiles(item instanceof SNNote ? item : undefined, (file) => {
       void linkItems(item, file)
     })
   }
diff --git a/packages/web/src/javascripts/Components/NoteView/NoteViewFileDropTarget.tsx b/packages/web/src/javascripts/Components/NoteView/NoteViewFileDropTarget.tsx
index bf70ec7c9..de418a2e3 100644
--- a/packages/web/src/javascripts/Components/NoteView/NoteViewFileDropTarget.tsx
+++ b/packages/web/src/javascripts/Components/NoteView/NoteViewFileDropTarget.tsx
@@ -29,6 +29,7 @@ const NoteViewFileDropTarget = ({ note, linkingController, noteViewElement, file
           })
           filesController.notifyObserversOfUploadedFileLinkingToCurrentNote(uploadedFile.uuid)
         },
+        note,
       })
     }
 
diff --git a/packages/web/src/javascripts/Controllers/FilesController.ts b/packages/web/src/javascripts/Controllers/FilesController.ts
index 24ecec228..82eee7262 100644
--- a/packages/web/src/javascripts/Controllers/FilesController.ts
+++ b/packages/web/src/javascripts/Controllers/FilesController.ts
@@ -35,7 +35,9 @@ import {
   MutatorClientInterface,
   Platform,
   ProtectionsClientInterface,
+  SNNote,
   SyncServiceInterface,
+  VaultServiceInterface,
 } from '@standardnotes/snjs'
 import { addToast, dismissToast, ToastType, updateToast } from '@standardnotes/toast'
 import { action, makeObservable, observable, reaction } from 'mobx'
@@ -80,6 +82,7 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
     private filePreviewModalController: FilePreviewModalController,
     private archiveService: ArchiveManager,
     private vaultDisplayService: VaultDisplayServiceInterface,
+    private vaults: VaultServiceInterface,
     private items: ItemManagerInterface,
     private files: FilesClientInterface,
     private mutator: MutatorClientInterface,
@@ -369,14 +372,16 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
     return false
   }
 
-  public async selectAndUploadNewFiles(callback?: (file: FileItem) => void) {
+  public async selectAndUploadNewFiles(note?: SNNote, callback?: (file: FileItem) => void) {
     const selectedFiles = await this.reader.selectFiles()
 
     selectedFiles.forEach(async (file) => {
       if (this.alertIfFileExceedsSizeLimit(file)) {
         return
       }
-      const uploadedFile = await this.uploadNewFile(file)
+      const uploadedFile = await this.uploadNewFile(file, {
+        note,
+      })
       if (uploadedFile && callback) {
         callback(uploadedFile)
       }
@@ -385,7 +390,15 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
 
   public async uploadNewFile(
     fileOrHandle: File | FileSystemFileHandle,
-    showToast = true,
+    {
+      showToast,
+      note,
+    }: {
+      showToast?: boolean
+      note?: SNNote
+    } = {
+      showToast: true,
+    },
   ): Promise<FileItem | undefined> {
     let toastId: string | undefined
 
@@ -407,9 +420,11 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
         return
       }
 
+      const vaultForNote = note ? this.vaults.getItemVault(note) : undefined
+
       const operation = await this.files.beginNewFileUpload(
         fileToUpload.size,
-        this.vaultDisplayService.exclusivelyShownVault,
+        vaultForNote || this.vaultDisplayService.exclusivelyShownVault,
       )
 
       if (operation instanceof ClientDisplayableError) {