diff --git a/packages/files/src/Domain/Service/FilesClientInterface.ts b/packages/files/src/Domain/Service/FilesClientInterface.ts
index 6f7b462c48e..3031f746170 100644
--- a/packages/files/src/Domain/Service/FilesClientInterface.ts
+++ b/packages/files/src/Domain/Service/FilesClientInterface.ts
@@ -23,6 +23,7 @@ export interface FilesClientInterface {
   finishUpload(
     operation: EncryptAndUploadFileOperation,
     fileMetadata: FileMetadata,
+    uuid: string,
   ): Promise<FileItem | ClientDisplayableError>
 
   downloadFile(
diff --git a/packages/services/src/Domain/Files/FileService.ts b/packages/services/src/Domain/Files/FileService.ts
index 67fd91e049a..10d4d04b57b 100644
--- a/packages/services/src/Domain/Files/FileService.ts
+++ b/packages/services/src/Domain/Files/FileService.ts
@@ -17,6 +17,12 @@ import {
   isEncryptedPayload,
   VaultListingInterface,
   SharedVaultListingInterface,
+  DecryptedPayload,
+  FillItemContent,
+  PayloadVaultOverrides,
+  PayloadTimestampDefaults,
+  CreateItemFromPayload,
+  DecryptedItemInterface,
 } from '@standardnotes/models'
 import { PureCryptoInterface } from '@standardnotes/sncrypto-common'
 import { LoggerInterface, spaceSeparatedStrings, UuidGenerator } from '@standardnotes/utils'
@@ -246,6 +252,7 @@ export class FileService extends AbstractService implements FilesClientInterface
   public async finishUpload(
     operation: EncryptAndUploadFileOperation,
     fileMetadata: FileMetadata,
+    uuid: string,
   ): Promise<FileItem | ClientDisplayableError> {
     const uploadSessionClosed = await this.api.closeUploadSession(
       operation.getValetToken(),
@@ -268,16 +275,22 @@ export class FileService extends AbstractService implements FilesClientInterface
       remoteIdentifier: result.remoteIdentifier,
     }
 
-    const file = await this.mutator.createItem<FileItem>(
-      ContentType.TYPES.File,
-      FillItemContentSpecialized(fileContent),
-      true,
-      operation.vault,
-    )
+    const filePayload = new DecryptedPayload<FileContent>({
+      uuid,
+      content_type: ContentType.TYPES.File,
+      content: FillItemContent<FileContent>(FillItemContentSpecialized(fileContent)),
+      dirty: true,
+      ...PayloadVaultOverrides(operation.vault),
+      ...PayloadTimestampDefaults(),
+    })
+
+    const fileItem = CreateItemFromPayload(filePayload) as DecryptedItemInterface<FileContent>
+
+    const insertedItem = await this.mutator.insertItem<FileItem>(fileItem)
 
     await this.sync.sync()
 
-    return file
+    return insertedItem
   }
 
   private async decryptCachedEntry(file: FileItem, entry: EncryptedBytes): Promise<DecryptedBytes> {
diff --git a/packages/web/src/javascripts/Components/FileDragNDropProvider.tsx b/packages/web/src/javascripts/Components/FileDragNDropProvider.tsx
index 1f57bc8201c..5b90c8b3404 100644
--- a/packages/web/src/javascripts/Components/FileDragNDropProvider.tsx
+++ b/packages/web/src/javascripts/Components/FileDragNDropProvider.tsx
@@ -8,12 +8,22 @@ import { useMemo, useState, createContext, ReactNode, useRef, useCallback, useEf
 import Portal from './Portal/Portal'
 import { ElementIds } from '@/Constants/ElementIDs'
 
-type FileDragTargetData = {
+type FileDragTargetCommonData = {
   tooltipText: string
-  callback: (files: FileItem) => void
   note?: SNNote
 }
 
+type FileDragTargetCallbacks =
+  | {
+      callback: (files: FileItem) => void
+      handleFileUpload?: never
+    }
+  | {
+      handleFileUpload: (fileOrHandle: File | FileSystemFileHandle) => void
+      callback?: never
+    }
+type FileDragTargetData = FileDragTargetCommonData & FileDragTargetCallbacks
+
 type FileDnDContextData = {
   isDraggingFiles: boolean
   addDragTarget: (target: HTMLElement, data: FileDragTargetData) => void
@@ -203,6 +213,11 @@ const FileDragNDropProvider = ({ application, children }: Props) => {
 
           const dragTarget = closestDragTarget ? dragTargets.current.get(closestDragTarget) : undefined
 
+          if (dragTarget?.handleFileUpload) {
+            dragTarget.handleFileUpload(fileOrHandle)
+            return
+          }
+
           const uploadedFile = await application.filesController.uploadNewFile(fileOrHandle, {
             note: dragTarget?.note,
           })
@@ -211,7 +226,9 @@ const FileDragNDropProvider = ({ application, children }: Props) => {
             return
           }
 
-          dragTarget?.callback(uploadedFile)
+          if (dragTarget?.callback) {
+            dragTarget.callback(uploadedFile)
+          }
         })
 
         dragCounter.current = 0
diff --git a/packages/web/src/javascripts/Components/NoteView/NoteViewFileDropTarget.tsx b/packages/web/src/javascripts/Components/NoteView/NoteViewFileDropTarget.tsx
index de418a2e3f5..4c9655ad150 100644
--- a/packages/web/src/javascripts/Components/NoteView/NoteViewFileDropTarget.tsx
+++ b/packages/web/src/javascripts/Components/NoteView/NoteViewFileDropTarget.tsx
@@ -1,6 +1,6 @@
 import { FilesController } from '@/Controllers/FilesController'
 import { LinkingController } from '@/Controllers/LinkingController'
-import { SNNote } from '@standardnotes/snjs'
+import { NoteType, SNNote } from '@standardnotes/snjs'
 import { useEffect } from 'react'
 import { useApplication } from '../ApplicationProvider'
 import { useFileDragNDrop } from '../FileDragNDropProvider'
@@ -20,17 +20,28 @@ const NoteViewFileDropTarget = ({ note, linkingController, noteViewElement, file
     const target = noteViewElement
 
     if (target) {
-      addDragTarget(target, {
-        tooltipText: 'Drop your files to upload and link them to the current note',
-        callback: async (uploadedFile) => {
-          await linkingController.linkItems(note, uploadedFile)
-          void application.changeAndSaveItem.execute(uploadedFile, (mutator) => {
-            mutator.protected = note.protected
-          })
-          filesController.notifyObserversOfUploadedFileLinkingToCurrentNote(uploadedFile.uuid)
-        },
-        note,
-      })
+      const tooltipText = 'Drop your files to upload and link them to the current note'
+      if (note.noteType === NoteType.Super) {
+        addDragTarget(target, {
+          tooltipText,
+          handleFileUpload: (fileOrHandle) => {
+            filesController.uploadAndInsertFileToCurrentNote(fileOrHandle)
+          },
+          note,
+        })
+      } else {
+        addDragTarget(target, {
+          tooltipText,
+          callback: async (uploadedFile) => {
+            await linkingController.linkItems(note, uploadedFile)
+            void application.changeAndSaveItem.execute(uploadedFile, (mutator) => {
+              mutator.protected = note.protected
+            })
+            filesController.notifyObserversOfUploadedFileLinkingToCurrentNote(uploadedFile.uuid)
+          },
+          note,
+        })
+      }
     }
 
     return () => {
diff --git a/packages/web/src/javascripts/Components/SuperEditor/Plugins/Commands.ts b/packages/web/src/javascripts/Components/SuperEditor/Plugins/Commands.ts
index 33bfb5e54dd..a6f60180b27 100644
--- a/packages/web/src/javascripts/Components/SuperEditor/Plugins/Commands.ts
+++ b/packages/web/src/javascripts/Components/SuperEditor/Plugins/Commands.ts
@@ -1,6 +1,7 @@
 import { createCommand, LexicalCommand } from 'lexical'
 
 export const INSERT_FILE_COMMAND: LexicalCommand<string> = createCommand('INSERT_FILE_COMMAND')
+export const UPLOAD_AND_INSERT_FILE_COMMAND: LexicalCommand<File> = createCommand('UPLOAD_AND_INSERT_FILE_COMMAND')
 export const INSERT_BUBBLE_COMMAND: LexicalCommand<string> = createCommand('INSERT_BUBBLE_COMMAND')
 export const INSERT_DATETIME_COMMAND: LexicalCommand<'date' | 'time' | 'datetime'> =
   createCommand('INSERT_DATETIME_COMMAND')
diff --git a/packages/web/src/javascripts/Components/SuperEditor/Plugins/EncryptedFilePlugin/FilePlugin.tsx b/packages/web/src/javascripts/Components/SuperEditor/Plugins/EncryptedFilePlugin/FilePlugin.tsx
index 9648eff9a18..8c55db05676 100644
--- a/packages/web/src/javascripts/Components/SuperEditor/Plugins/EncryptedFilePlugin/FilePlugin.tsx
+++ b/packages/web/src/javascripts/Components/SuperEditor/Plugins/EncryptedFilePlugin/FilePlugin.tsx
@@ -1,4 +1,4 @@
-import { INSERT_FILE_COMMAND } from '../Commands'
+import { INSERT_FILE_COMMAND, UPLOAD_AND_INSERT_FILE_COMMAND } from '../Commands'
 import { useLexicalComposerContext } from '@lexical/react/LexicalComposerContext'
 
 import { useEffect, useState } from 'react'
@@ -19,45 +19,24 @@ import { FilesControllerEvent } from '@/Controllers/FilesController'
 import { useLinkingController } from '@/Controllers/LinkingControllerProvider'
 import { useApplication } from '@/Components/ApplicationProvider'
 import { SNNote } from '@standardnotes/snjs'
-import Spinner from '../../../Spinner/Spinner'
 import Modal from '../../Lexical/UI/Modal'
 import Button from '@/Components/Button/Button'
 import { isMobileScreen } from '../../../../Utils'
 
 export const OPEN_FILE_UPLOAD_MODAL_COMMAND = createCommand('OPEN_FILE_UPLOAD_MODAL_COMMAND')
 
-function UploadFileDialog({ currentNote, onClose }: { currentNote: SNNote; onClose: () => void }) {
-  const application = useApplication()
+function UploadFileDialog({ onClose }: { onClose: () => void }) {
   const [editor] = useLexicalComposerContext()
-  const filesController = useFilesController()
-  const linkingController = useLinkingController()
 
   const [file, setFile] = useState<File>()
-  const [isUploadingFile, setIsUploadingFile] = useState(false)
 
   const onClick = () => {
     if (!file) {
       return
     }
 
-    setIsUploadingFile(true)
-    filesController
-      .uploadNewFile(file)
-      .then((uploadedFile) => {
-        if (!uploadedFile) {
-          return
-        }
-        editor.dispatchCommand(INSERT_FILE_COMMAND, uploadedFile.uuid)
-        void linkingController.linkItemToSelectedItem(uploadedFile)
-        void application.changeAndSaveItem.execute(uploadedFile, (mutator) => {
-          mutator.protected = currentNote.protected
-        })
-      })
-      .catch(console.error)
-      .finally(() => {
-        setIsUploadingFile(false)
-        onClose()
-      })
+    editor.dispatchCommand(UPLOAD_AND_INSERT_FILE_COMMAND, file)
+    onClose()
   }
 
   return (
@@ -72,13 +51,9 @@ function UploadFileDialog({ currentNote, onClose }: { currentNote: SNNote; onClo
         }}
       />
       <div className="mt-1.5 flex justify-end">
-        {isUploadingFile ? (
-          <Spinner className="h-4 w-4" />
-        ) : (
-          <Button onClick={onClick} disabled={!file} small={isMobileScreen()}>
-            Upload
-          </Button>
-        )}
+        <Button onClick={onClick} disabled={!file} small={isMobileScreen()}>
+          Upload
+        </Button>
       </div>
     </>
   )
@@ -99,17 +74,23 @@ export default function FilePlugin({ currentNote }: { currentNote: SNNote }): JS
 
     const uploadFilesList = (files: FileList) => {
       Array.from(files).forEach(async (file) => {
-        try {
-          const uploadedFile = await filesController.uploadNewFile(file)
-          if (uploadedFile) {
-            editor.dispatchCommand(INSERT_FILE_COMMAND, uploadedFile.uuid)
-            void linkingController.linkItemToSelectedItem(uploadedFile)
-            void application.changeAndSaveItem.execute(uploadedFile, (mutator) => {
-              mutator.protected = currentNote.protected
-            })
-          }
-        } catch (error) {
-          console.error(error)
+        editor.dispatchCommand(UPLOAD_AND_INSERT_FILE_COMMAND, file)
+      })
+    }
+
+    const insertFileNode = (uuid: string, onInsert?: (node: FileNode) => void) => {
+      editor.update(() => {
+        const fileNode = $createFileNode(uuid)
+        $insertNodes([fileNode])
+        if ($isRootOrShadowRoot(fileNode.getParentOrThrow())) {
+          $wrapNodeInElement(fileNode, $createParagraphNode).selectEnd()
+        }
+        const newLineNode = $createParagraphNode()
+        fileNode.getParentOrThrow().insertAfter(newLineNode)
+        newLineNode.selectEnd()
+        editor.focus()
+        if (onInsert) {
+          onInsert(fileNode)
         }
       })
     }
@@ -118,14 +99,34 @@ export default function FilePlugin({ currentNote }: { currentNote: SNNote }): JS
       editor.registerCommand<string>(
         INSERT_FILE_COMMAND,
         (payload) => {
-          const fileNode = $createFileNode(payload)
-          $insertNodes([fileNode])
-          if ($isRootOrShadowRoot(fileNode.getParentOrThrow())) {
-            $wrapNodeInElement(fileNode, $createParagraphNode).selectEnd()
-          }
-          const newLineNode = $createParagraphNode()
-          fileNode.getParentOrThrow().insertAfter(newLineNode)
-
+          insertFileNode(payload)
+          return true
+        },
+        COMMAND_PRIORITY_EDITOR,
+      ),
+      editor.registerCommand(
+        UPLOAD_AND_INSERT_FILE_COMMAND,
+        (file) => {
+          const note = currentNote
+          let fileNode: FileNode | undefined
+          filesController
+            .uploadNewFile(file, {
+              showToast: false,
+              onUploadStart(fileUuid) {
+                insertFileNode(fileUuid, (node) => (fileNode = node))
+              },
+            })
+            .then((uploadedFile) => {
+              if (uploadedFile) {
+                void linkingController.linkItems(note, uploadedFile)
+                void application.changeAndSaveItem.execute(uploadedFile, (mutator) => {
+                  mutator.protected = note.protected
+                })
+              } else {
+                editor.update(() => fileNode?.remove())
+              }
+            })
+            .catch(console.error)
           return true
         },
         COMMAND_PRIORITY_EDITOR,
@@ -150,28 +151,26 @@ export default function FilePlugin({ currentNote }: { currentNote: SNNote }): JS
         },
         COMMAND_PRIORITY_NORMAL,
       ),
-      editor.registerNodeTransform(FileNode, (node) => {
-        /**
-         * When adding the node we wrap it with a paragraph to avoid insertion errors,
-         * however that causes issues with selection. We unwrap the node to fix that.
-         */
-        const parent = node.getParent()
-        if (!parent) {
-          return
-        }
-        if (parent.getChildrenSize() === 1) {
-          parent.insertBefore(node)
-          parent.remove()
-        }
-      }),
     )
-  }, [application, currentNote.protected, editor, filesController, linkingController])
+  }, [application, currentNote, editor, filesController, linkingController])
 
   useEffect(() => {
     const disposer = filesController.addEventObserver((event, data) => {
-      if (event === FilesControllerEvent.FileUploadedToNote) {
+      if (event === FilesControllerEvent.FileUploadedToNote && data[FilesControllerEvent.FileUploadedToNote]) {
         const fileUuid = data[FilesControllerEvent.FileUploadedToNote].uuid
         editor.dispatchCommand(INSERT_FILE_COMMAND, fileUuid)
+      } else if (event === FilesControllerEvent.UploadAndInsertFile && data[FilesControllerEvent.UploadAndInsertFile]) {
+        const { fileOrHandle } = data[FilesControllerEvent.UploadAndInsertFile]
+        if (fileOrHandle instanceof FileSystemFileHandle) {
+          fileOrHandle
+            .getFile()
+            .then((file) => {
+              editor.dispatchCommand(UPLOAD_AND_INSERT_FILE_COMMAND, file)
+            })
+            .catch(console.error)
+        } else {
+          editor.dispatchCommand(UPLOAD_AND_INSERT_FILE_COMMAND, fileOrHandle)
+        }
       }
     })
 
@@ -181,7 +180,7 @@ export default function FilePlugin({ currentNote }: { currentNote: SNNote }): JS
   if (showFileUploadModal) {
     return (
       <Modal onClose={() => setShowFileUploadModal(false)} title="Upload File">
-        <UploadFileDialog currentNote={currentNote} onClose={() => setShowFileUploadModal(false)} />
+        <UploadFileDialog onClose={() => setShowFileUploadModal(false)} />
       </Modal>
     )
   }
diff --git a/packages/web/src/javascripts/Components/SuperEditor/Plugins/EncryptedFilePlugin/Nodes/FileComponent.tsx b/packages/web/src/javascripts/Components/SuperEditor/Plugins/EncryptedFilePlugin/Nodes/FileComponent.tsx
index f212724893c..98428f892bb 100644
--- a/packages/web/src/javascripts/Components/SuperEditor/Plugins/EncryptedFilePlugin/Nodes/FileComponent.tsx
+++ b/packages/web/src/javascripts/Components/SuperEditor/Plugins/EncryptedFilePlugin/Nodes/FileComponent.tsx
@@ -6,6 +6,9 @@ import FilePreview from '@/Components/FilePreview/FilePreview'
 import { FileItem } from '@standardnotes/snjs'
 import { useLexicalComposerContext } from '@lexical/react/LexicalComposerContext'
 import { useLexicalNodeSelection } from '@lexical/react/useLexicalNodeSelection'
+import { observer } from 'mobx-react-lite'
+import Spinner from '@/Components/Spinner/Spinner'
+import { FilesControllerEvent } from '@/Controllers/FilesController'
 
 export type FileComponentProps = Readonly<{
   className: Readonly<{
@@ -19,10 +22,11 @@ export type FileComponentProps = Readonly<{
   setZoomLevel: (zoomLevel: number) => void
 }>
 
-export function FileComponent({ className, format, nodeKey, fileUuid, zoomLevel, setZoomLevel }: FileComponentProps) {
+function FileComponent({ className, format, nodeKey, fileUuid, zoomLevel, setZoomLevel }: FileComponentProps) {
   const application = useApplication()
   const [editor] = useLexicalComposerContext()
-  const file = useMemo(() => application.items.findItem<FileItem>(fileUuid), [application, fileUuid])
+  const [file, setFile] = useState(() => application.items.findItem<FileItem>(fileUuid))
+  const uploadProgress = application.filesController.uploadProgressMap.get(fileUuid)
 
   const [canLoad, setCanLoad] = useState(false)
 
@@ -90,6 +94,41 @@ export function FileComponent({ className, format, nodeKey, fileUuid, zoomLevel,
     )
   }, [editor, isSelected, nodeKey, setSelected])
 
+  useEffect(() => {
+    return application.filesController.addEventObserver((event, data) => {
+      if (event === FilesControllerEvent.FileUploadFinished && data[FilesControllerEvent.FileUploadFinished]) {
+        const { uploadedFile } = data[FilesControllerEvent.FileUploadFinished]
+        if (uploadedFile.uuid === fileUuid) {
+          setFile(uploadedFile)
+        }
+      }
+    })
+  }, [application.filesController, fileUuid])
+
+  if (uploadProgress && (uploadProgress.progress < 100 || !file)) {
+    const progress = uploadProgress.progress
+    return (
+      <BlockWithAlignableContents className={className} format={format} nodeKey={nodeKey}>
+        <div className="flex flex-col items-center justify-center gap-2 p-4 text-center" ref={blockWrapperRef}>
+          <div className="flex items-center gap-2">
+            <Spinner className="h-4 w-4" />
+            Uploading file "{uploadProgress.file.name}"... ({progress}%)
+          </div>
+          <div className="w-full max-w-[50%] overflow-hidden rounded bg-contrast">
+            <div
+              className="h-2 rounded rounded-tl-none bg-info transition-[width] duration-100"
+              role="progressbar"
+              style={{
+                width: `${progress}%`,
+              }}
+              aria-valuenow={progress}
+            />
+          </div>
+        </div>
+      </BlockWithAlignableContents>
+    )
+  }
+
   if (!file) {
     return (
       <BlockWithAlignableContents className={className} format={format} nodeKey={nodeKey}>
@@ -114,3 +153,5 @@ export function FileComponent({ className, format, nodeKey, fileUuid, zoomLevel,
     </BlockWithAlignableContents>
   )
 }
+
+export default observer(FileComponent)
diff --git a/packages/web/src/javascripts/Components/SuperEditor/Plugins/EncryptedFilePlugin/Nodes/FileNode.tsx b/packages/web/src/javascripts/Components/SuperEditor/Plugins/EncryptedFilePlugin/Nodes/FileNode.tsx
index 0f86d135b42..b02b1e95e87 100644
--- a/packages/web/src/javascripts/Components/SuperEditor/Plugins/EncryptedFilePlugin/Nodes/FileNode.tsx
+++ b/packages/web/src/javascripts/Components/SuperEditor/Plugins/EncryptedFilePlugin/Nodes/FileNode.tsx
@@ -1,7 +1,7 @@
 import { DOMConversionMap, DOMExportOutput, EditorConfig, ElementFormatType, LexicalEditor, NodeKey } from 'lexical'
 import { DecoratorBlockNode } from '@lexical/react/LexicalDecoratorBlockNode'
 import { $createFileNode, convertToFileElement } from './FileUtils'
-import { FileComponent } from './FileComponent'
+import FileComponent from './FileComponent'
 import { SerializedFileNode } from './SerializedFileNode'
 import { ItemNodeInterface } from '../../ItemNodeInterface'
 
diff --git a/packages/web/src/javascripts/Controllers/FilesController.ts b/packages/web/src/javascripts/Controllers/FilesController.ts
index dd2a116273c..35998571ddc 100644
--- a/packages/web/src/javascripts/Controllers/FilesController.ts
+++ b/packages/web/src/javascripts/Controllers/FilesController.ts
@@ -38,6 +38,7 @@ import {
   ProtectionsClientInterface,
   SNNote,
   SyncServiceInterface,
+  UuidGenerator,
   VaultServiceInterface,
 } from '@standardnotes/snjs'
 import { addToast, dismissToast, ToastType, updateToast } from '@standardnotes/toast'
@@ -52,14 +53,22 @@ const NonMutatingFileActions = [FileItemActionType.DownloadFile, FileItemActionT
 
 type FileContextMenuLocation = { x: number; y: number }
 
+export enum FilesControllerEvent {
+  FileUploadedToNote = 'FileUploadedToNote',
+  FileUploadFinished = 'FileUploadFinished',
+  UploadAndInsertFile = 'UploadAndInsertFile',
+}
+
 export type FilesControllerEventData = {
-  [FilesControllerEvent.FileUploadedToNote]: {
+  [FilesControllerEvent.FileUploadedToNote]?: {
     uuid: string
   }
-}
-
-export enum FilesControllerEvent {
-  FileUploadedToNote,
+  [FilesControllerEvent.FileUploadFinished]?: {
+    uploadedFile: FileItem
+  }
+  [FilesControllerEvent.UploadAndInsertFile]?: {
+    fileOrHandle: File | FileSystemFileHandle
+  }
 }
 
 export class FilesController extends AbstractViewController<FilesControllerEvent, FilesControllerEventData> {
@@ -73,6 +82,14 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
   reader = this.shouldUseStreamingAPI ? StreamingFileReader : ClassicFileReader
   maxFileSize = this.reader.maximumFileSize()
 
+  uploadProgressMap: Map<
+    string,
+    {
+      file: File
+      progress: number
+    }
+  > = new Map()
+
   override deinit(): void {
     super.deinit()
     ;(this.notesController as unknown) = undefined
@@ -111,6 +128,8 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
       setShowFileContextMenu: action,
       setShowProtectedOverlay: action,
       setFileContextMenuLocation: action,
+
+      uploadProgressMap: observable,
     })
 
     this.disposers.push(
@@ -453,9 +472,11 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
     options: {
       showToast?: boolean
       note?: SNNote
+      onUploadStart?: (fileUuid: string) => void
+      onUploadFinish?: () => void
     } = {},
   ): Promise<FileItem | undefined> {
-    const { showToast = true, note } = options
+    const { showToast = true, note, onUploadStart, onUploadFinish } = options
 
     let toastId: string | undefined
     let canShowProgressNotification = false
@@ -482,6 +503,17 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
         return
       }
 
+      const uuid = UuidGenerator.GenerateUuid()
+
+      this.uploadProgressMap.set(uuid, {
+        file: fileToUpload,
+        progress: 0,
+      })
+
+      if (onUploadStart) {
+        onUploadStart(uuid)
+      }
+
       const vaultForNote = note ? this.vaults.getItemVault(note) : undefined
 
       const operation = await this.files.beginNewFileUpload(
@@ -499,6 +531,11 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
 
       const initialProgress = operation.getProgress().percentComplete
 
+      this.uploadProgressMap.set(uuid, {
+        file: fileToUpload,
+        progress: initialProgress,
+      })
+
       if (showToast) {
         if (this.mobileDevice && canShowProgressNotification) {
           toastId = await this.mobileDevice.displayNotification({
@@ -521,6 +558,10 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
         await this.files.pushBytesForUpload(operation, data, index, isLast)
 
         const percentComplete = Math.round(operation.getProgress().percentComplete)
+        this.uploadProgressMap.set(uuid, {
+          file: fileToUpload,
+          progress: percentComplete,
+        })
         if (toastId) {
           if (this.mobileDevice && canShowProgressNotification) {
             await this.mobileDevice.displayNotification({
@@ -547,7 +588,7 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
         fileResult.mimeType = await this.archiveService.getMimeType(ext)
       }
 
-      const uploadedFile = await this.files.finishUpload(operation, fileResult)
+      const uploadedFile = await this.files.finishUpload(operation, fileResult, uuid)
 
       if (uploadedFile instanceof ClientDisplayableError) {
         addToast({
@@ -557,6 +598,14 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
         throw new Error(uploadedFile.text)
       }
 
+      if (onUploadFinish) {
+        onUploadFinish()
+      }
+
+      this.notifyEvent(FilesControllerEvent.FileUploadFinished, {
+        [FilesControllerEvent.FileUploadFinished]: { uploadedFile },
+      })
+
       if (toastId) {
         if (this.mobileDevice && canShowProgressNotification) {
           this.mobileDevice.cancelNotification(toastId).catch(console.error)
@@ -635,6 +684,12 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
     })
   }
 
+  uploadAndInsertFileToCurrentNote(fileOrHandle: File | FileSystemFileHandle) {
+    this.notifyEvent(FilesControllerEvent.UploadAndInsertFile, {
+      [FilesControllerEvent.UploadAndInsertFile]: { fileOrHandle },
+    })
+  }
+
   deleteFilesPermanently = async (files: FileItem[]) => {
     const title = Strings.trashItemsTitle
     const text = files.length === 1 ? StringUtils.deleteFile(files[0].name) : Strings.deleteMultipleFiles