diff --git a/packages/web/src/javascripts/Components/ApplicationView/ApplicationView.tsx b/packages/web/src/javascripts/Components/ApplicationView/ApplicationView.tsx
index a28f6625166..ccad56b07c1 100644
--- a/packages/web/src/javascripts/Components/ApplicationView/ApplicationView.tsx
+++ b/packages/web/src/javascripts/Components/ApplicationView/ApplicationView.tsx
@@ -29,6 +29,7 @@ import AndroidBackHandlerProvider from '@/NativeMobileWeb/useAndroidBackHandler'
 import ConfirmDeleteAccountContainer from '@/Components/ConfirmDeleteAccountModal/ConfirmDeleteAccountModal'
 import DarkModeHandler from '../DarkModeHandler/DarkModeHandler'
 import ApplicationProvider from './ApplicationProvider'
+import { ErrorBoundary } from '@/Utils/ErrorBoundary'
 
 type Props = {
   application: WebApplication
@@ -219,7 +220,9 @@ const ApplicationView: FunctionComponent<Props> = ({ application, mainApplicatio
                     searchOptionsController={viewControllerManager.searchOptionsController}
                     linkingController={viewControllerManager.linkingController}
                   />
-                  <NoteGroupView application={application} />
+                  <ErrorBoundary>
+                    <NoteGroupView application={application} />
+                  </ErrorBoundary>
                 </FileDragNDropProvider>
               </div>
 
diff --git a/packages/web/src/javascripts/Components/BlockEditor/BlockEditorComponent.tsx b/packages/web/src/javascripts/Components/BlockEditor/BlockEditorComponent.tsx
index 367f6d03766..1aa2a1af648 100644
--- a/packages/web/src/javascripts/Components/BlockEditor/BlockEditorComponent.tsx
+++ b/packages/web/src/javascripts/Components/BlockEditor/BlockEditorComponent.tsx
@@ -9,10 +9,12 @@ import FilePlugin from './Plugins/EncryptedFilePlugin/FilePlugin'
 import BlockPickerMenuPlugin from './Plugins/BlockPickerPlugin/BlockPickerPlugin'
 import { ErrorBoundary } from '@/Utils/ErrorBoundary'
 import { LinkingController } from '@/Controllers/LinkingController'
-import LinkingControllerProvider from './Contexts/LinkingControllerProvider'
+import LinkingControllerProvider from '../../Controllers/LinkingControllerProvider'
 import { BubbleNode } from './Plugins/ItemBubblePlugin/Nodes/BubbleNode'
 import ItemBubblePlugin from './Plugins/ItemBubblePlugin/ItemBubblePlugin'
 import { NodeObserverPlugin } from './Plugins/NodeObserverPlugin/NodeObserverPlugin'
+import { FilesController } from '@/Controllers/FilesController'
+import FilesControllerProvider from '@/Controllers/FilesControllerProvider'
 
 const StringEllipses = '...'
 const NotePreviewCharLimit = 160
@@ -21,9 +23,10 @@ type Props = {
   application: WebApplication
   note: SNNote
   linkingController: LinkingController
+  filesController: FilesController
 }
 
-export const BlockEditor: FunctionComponent<Props> = ({ note, application, linkingController }) => {
+export const BlockEditor: FunctionComponent<Props> = ({ note, application, linkingController, filesController }) => {
   const controller = useRef(new BlockEditorController(note, application))
 
   const handleChange = useCallback(
@@ -51,19 +54,21 @@ export const BlockEditor: FunctionComponent<Props> = ({ note, application, linki
     <div className="relative h-full w-full p-5">
       <ErrorBoundary>
         <LinkingControllerProvider controller={linkingController}>
-          <BlocksEditorComposer initialValue={note.text} nodes={[FileNode, BubbleNode]}>
-            <BlocksEditor
-              onChange={handleChange}
-              className="relative relative resize-none text-base focus:shadow-none focus:outline-none"
-            >
-              <ItemSelectionPlugin currentNote={note} />
-              <FilePlugin />
-              <ItemBubblePlugin />
-              <BlockPickerMenuPlugin />
-              <NodeObserverPlugin nodeType={BubbleNode} onRemove={handleBubbleRemove} />
-              <NodeObserverPlugin nodeType={FileNode} onRemove={handleBubbleRemove} />
-            </BlocksEditor>
-          </BlocksEditorComposer>
+          <FilesControllerProvider controller={filesController}>
+            <BlocksEditorComposer initialValue={note.text} nodes={[FileNode, BubbleNode]}>
+              <BlocksEditor
+                onChange={handleChange}
+                className="relative relative resize-none text-base focus:shadow-none focus:outline-none"
+              >
+                <ItemSelectionPlugin currentNote={note} />
+                <FilePlugin />
+                <ItemBubblePlugin />
+                <BlockPickerMenuPlugin />
+                <NodeObserverPlugin nodeType={BubbleNode} onRemove={handleBubbleRemove} />
+                <NodeObserverPlugin nodeType={FileNode} onRemove={handleBubbleRemove} />
+              </BlocksEditor>
+            </BlocksEditorComposer>
+          </FilesControllerProvider>
         </LinkingControllerProvider>
       </ErrorBoundary>
     </div>
diff --git a/packages/web/src/javascripts/Components/BlockEditor/Plugins/EncryptedFilePlugin/FilePlugin.ts b/packages/web/src/javascripts/Components/BlockEditor/Plugins/EncryptedFilePlugin/FilePlugin.ts
index 60ce6e77d71..01073b4edf8 100644
--- a/packages/web/src/javascripts/Components/BlockEditor/Plugins/EncryptedFilePlugin/FilePlugin.ts
+++ b/packages/web/src/javascripts/Components/BlockEditor/Plugins/EncryptedFilePlugin/FilePlugin.ts
@@ -6,9 +6,12 @@ import { FileNode } from './Nodes/FileNode'
 import { $createParagraphNode, $insertNodes, $isRootOrShadowRoot, COMMAND_PRIORITY_EDITOR } from 'lexical'
 import { $createFileNode } from './Nodes/FileUtils'
 import { $wrapNodeInElement } from '@lexical/utils'
+import { useFilesController } from '@/Controllers/FilesControllerProvider'
+import { FilesControllerEvent } from '@/Controllers/FilesController'
 
 export default function FilePlugin(): JSX.Element | null {
   const [editor] = useLexicalComposerContext()
+  const filesController = useFilesController()
 
   useEffect(() => {
     if (!editor.hasNodes([FileNode])) {
@@ -19,7 +22,6 @@ export default function FilePlugin(): JSX.Element | null {
       INSERT_FILE_COMMAND,
       (payload) => {
         const fileNode = $createFileNode(payload)
-        // $insertNodeToNearestRoot(fileNode)
         $insertNodes([fileNode])
         if ($isRootOrShadowRoot(fileNode.getParentOrThrow())) {
           $wrapNodeInElement(fileNode, $createParagraphNode).selectEnd()
@@ -31,5 +33,16 @@ export default function FilePlugin(): JSX.Element | null {
     )
   }, [editor])
 
+  useEffect(() => {
+    const disposer = filesController.addEventObserver((event, data) => {
+      if (event === FilesControllerEvent.FileUploadedToNote) {
+        const fileUuid = data[FilesControllerEvent.FileUploadedToNote].uuid
+        editor.dispatchCommand(INSERT_FILE_COMMAND, fileUuid)
+      }
+    })
+
+    return disposer
+  }, [filesController, editor])
+
   return null
 }
diff --git a/packages/web/src/javascripts/Components/BlockEditor/Plugins/ItemBubblePlugin/Nodes/BubbleComponent.tsx b/packages/web/src/javascripts/Components/BlockEditor/Plugins/ItemBubblePlugin/Nodes/BubbleComponent.tsx
index e820044c6bf..66b43957a43 100644
--- a/packages/web/src/javascripts/Components/BlockEditor/Plugins/ItemBubblePlugin/Nodes/BubbleComponent.tsx
+++ b/packages/web/src/javascripts/Components/BlockEditor/Plugins/ItemBubblePlugin/Nodes/BubbleComponent.tsx
@@ -2,7 +2,7 @@ import { useCallback, useMemo } from 'react'
 import { useApplication } from '@/Components/ApplicationView/ApplicationProvider'
 import LinkedItemBubble from '@/Components/LinkedItems/LinkedItemBubble'
 import { createLinkFromItem } from '@/Utils/Items/Search/createLinkFromItem'
-import { useLinkingController } from '@/Components/BlockEditor/Contexts/LinkingControllerProvider'
+import { useLinkingController } from '@/Controllers/LinkingControllerProvider'
 import { LinkableItem } from '@/Utils/Items/Search/LinkableItem'
 import { useResponsiveAppPane } from '@/Components/ResponsivePane/ResponsivePaneProvider'
 import { LexicalNode } from 'lexical'
diff --git a/packages/web/src/javascripts/Components/BlockEditor/Plugins/ItemSelectionPlugin/ItemSelectionPlugin.tsx b/packages/web/src/javascripts/Components/BlockEditor/Plugins/ItemSelectionPlugin/ItemSelectionPlugin.tsx
index d40974a5671..ba20b06f0c0 100644
--- a/packages/web/src/javascripts/Components/BlockEditor/Plugins/ItemSelectionPlugin/ItemSelectionPlugin.tsx
+++ b/packages/web/src/javascripts/Components/BlockEditor/Plugins/ItemSelectionPlugin/ItemSelectionPlugin.tsx
@@ -9,7 +9,7 @@ import { ContentType, SNNote } from '@standardnotes/snjs'
 import { getLinkingSearchResults } from '@/Utils/Items/Search/getSearchResults'
 import Popover from '@/Components/Popover/Popover'
 import { INSERT_BUBBLE_COMMAND, INSERT_FILE_COMMAND } from '../Commands'
-import { useLinkingController } from '../../Contexts/LinkingControllerProvider'
+import { useLinkingController } from '../../../../Controllers/LinkingControllerProvider'
 import { PopoverClassNames } from '../ClassNames'
 
 type Props = {
diff --git a/packages/web/src/javascripts/Components/NoteView/NoteView.tsx b/packages/web/src/javascripts/Components/NoteView/NoteView.tsx
index d86c4c9cf6c..edbcf09ae2d 100644
--- a/packages/web/src/javascripts/Components/NoteView/NoteView.tsx
+++ b/packages/web/src/javascripts/Components/NoteView/NoteView.tsx
@@ -8,7 +8,6 @@ import ProtectedItemOverlay from '@/Components/ProtectedItemOverlay/ProtectedIte
 import { ElementIds } from '@/Constants/ElementIDs'
 import { PrefDefaults } from '@/Constants/PrefDefaults'
 import { StringDeleteNote, STRING_DELETE_LOCKED_ATTEMPT, STRING_DELETE_PLACEHOLDER_ATTEMPT } from '@/Constants/Strings'
-import { featureTrunkEnabled, FeatureTrunkName } from '@/FeatureTrunk'
 import { log, LoggingDomain } from '@/Logging'
 import { debounce, isDesktopApplication, isMobileScreen } from '@/Utils'
 import { classNames } from '@/Utils/ConcatenateClassNames'
@@ -996,7 +995,7 @@ class NoteView extends AbstractComponent<NoteViewProps, State> {
     const renderHeaderOptions = isMobileScreen() ? !this.state.plaintextEditorFocused : true
 
     const editorMode =
-      featureTrunkEnabled(FeatureTrunkName.Blocks) && this.note.noteType === NoteType.Blocks
+      this.note.noteType === NoteType.Blocks
         ? 'blocks'
         : this.state.editorStateDidLoad && !this.state.editorComponentViewer && !this.state.textareaUnloading
         ? 'plain'
@@ -1155,6 +1154,7 @@ class NoteView extends AbstractComponent<NoteViewProps, State> {
                 application={this.application}
                 note={this.note}
                 linkingController={this.viewControllerManager.linkingController}
+                filesController={this.viewControllerManager.filesController}
               />
             </div>
           )}
diff --git a/packages/web/src/javascripts/Controllers/Abstract/AbstractViewController.ts b/packages/web/src/javascripts/Controllers/Abstract/AbstractViewController.ts
index 9dcc477a54b..c9c37c19965 100644
--- a/packages/web/src/javascripts/Controllers/Abstract/AbstractViewController.ts
+++ b/packages/web/src/javascripts/Controllers/Abstract/AbstractViewController.ts
@@ -1,11 +1,14 @@
 import { CrossControllerEvent } from '../CrossControllerEvent'
-import { InternalEventBus, InternalEventPublishStrategy } from '@standardnotes/snjs'
+import { InternalEventBus, InternalEventPublishStrategy, removeFromArray } from '@standardnotes/snjs'
 import { WebApplication } from '../../Application/Application'
 import { Disposer } from '@/Types/Disposer'
 
-export abstract class AbstractViewController {
+type ControllerEventObserver<Event = void, EventData = void> = (event: Event, data: EventData) => void
+
+export abstract class AbstractViewController<Event = void, EventData = void> {
   dealloced = false
   protected disposers: Disposer[] = []
+  private eventObservers: ControllerEventObserver<Event, EventData>[] = []
 
   constructor(public application: WebApplication, protected eventBus: InternalEventBus) {}
 
@@ -23,5 +26,19 @@ export abstract class AbstractViewController {
     }
 
     ;(this.disposers as unknown) = undefined
+
+    this.eventObservers.length = 0
+  }
+
+  addEventObserver(observer: ControllerEventObserver<Event, EventData>): () => void {
+    this.eventObservers.push(observer)
+
+    return () => {
+      removeFromArray(this.eventObservers, observer)
+    }
+  }
+
+  notifyEvent(event: Event, data: EventData): void {
+    this.eventObservers.forEach((observer) => observer(event, data))
   }
 }
diff --git a/packages/web/src/javascripts/Controllers/FilesController.ts b/packages/web/src/javascripts/Controllers/FilesController.ts
index 3643c06b428..53bf88f1614 100644
--- a/packages/web/src/javascripts/Controllers/FilesController.ts
+++ b/packages/web/src/javascripts/Controllers/FilesController.ts
@@ -34,7 +34,17 @@ const NonMutatingFileActions = [PopoverFileItemActionType.DownloadFile, PopoverF
 
 type FileContextMenuLocation = { x: number; y: number }
 
-export class FilesController extends AbstractViewController {
+export type FilesControllerEventData = {
+  [FilesControllerEvent.FileUploadedToNote]: {
+    uuid: string
+  }
+}
+
+export enum FilesControllerEvent {
+  FileUploadedToNote,
+}
+
+export class FilesController extends AbstractViewController<FilesControllerEvent, FilesControllerEventData> {
   allFiles: FileItem[] = []
   attachedFiles: FileItem[] = []
   showFileContextMenu = false
@@ -388,6 +398,10 @@ export class FilesController extends AbstractViewController {
           type: ToastType.Success,
           message: `Uploaded file "${uploadedFile.name}"`,
         })
+
+        this.notifyEvent(FilesControllerEvent.FileUploadedToNote, {
+          [FilesControllerEvent.FileUploadedToNote]: { uuid: uploadedFile.uuid },
+        })
       }
 
       return uploadedFiles
diff --git a/packages/web/src/javascripts/Controllers/FilesControllerProvider.tsx b/packages/web/src/javascripts/Controllers/FilesControllerProvider.tsx
new file mode 100644
index 00000000000..dcd77760f2c
--- /dev/null
+++ b/packages/web/src/javascripts/Controllers/FilesControllerProvider.tsx
@@ -0,0 +1,35 @@
+import { ReactNode, createContext, useContext, memo } from 'react'
+import { observer } from 'mobx-react-lite'
+import { FilesController } from '@/Controllers/FilesController'
+
+const FilesControllerContext = createContext<FilesController | undefined>(undefined)
+
+export const useFilesController = () => {
+  const value = useContext(FilesControllerContext)
+
+  if (!value) {
+    throw new Error('Component must be a child of <FilesControllerProvider />')
+  }
+
+  return value
+}
+
+type ChildrenProps = {
+  children: ReactNode
+}
+
+type ProviderProps = {
+  controller: FilesController
+} & ChildrenProps
+
+const MemoizedChildren = memo(({ children }: ChildrenProps) => <>{children}</>)
+
+const FilesControllerProvider = ({ controller, children }: ProviderProps) => {
+  return (
+    <FilesControllerContext.Provider value={controller}>
+      <MemoizedChildren children={children} />
+    </FilesControllerContext.Provider>
+  )
+}
+
+export default observer(FilesControllerProvider)
diff --git a/packages/web/src/javascripts/Components/BlockEditor/Contexts/LinkingControllerProvider.tsx b/packages/web/src/javascripts/Controllers/LinkingControllerProvider.tsx
similarity index 99%
rename from packages/web/src/javascripts/Components/BlockEditor/Contexts/LinkingControllerProvider.tsx
rename to packages/web/src/javascripts/Controllers/LinkingControllerProvider.tsx
index 8ee1f42229c..f27a5247841 100644
--- a/packages/web/src/javascripts/Components/BlockEditor/Contexts/LinkingControllerProvider.tsx
+++ b/packages/web/src/javascripts/Controllers/LinkingControllerProvider.tsx
@@ -1,5 +1,4 @@
 import { ReactNode, createContext, useContext, memo } from 'react'
-
 import { observer } from 'mobx-react-lite'
 import { LinkingController } from '@/Controllers/LinkingController'