diff --git a/app/assets/javascripts/components/AttachedFilesPopover/AttachedFilesButton.tsx b/app/assets/javascripts/components/AttachedFilesPopover/AttachedFilesButton.tsx
index 4ec4a7b36..acaa042b8 100644
--- a/app/assets/javascripts/components/AttachedFilesPopover/AttachedFilesButton.tsx
+++ b/app/assets/javascripts/components/AttachedFilesPopover/AttachedFilesButton.tsx
@@ -12,7 +12,13 @@ import { FunctionComponent } from 'preact';
 import { useCallback, useEffect, useRef, useState } from 'preact/hooks';
 import { Icon } from '../Icon';
 import { useCloseOnClickOutside } from '../utils';
-import { ChallengeReason, ContentType, SNFile } from '@standardnotes/snjs';
+import {
+  ChallengeReason,
+  ContentType,
+  FeatureIdentifier,
+  FeatureStatus,
+  SNFile,
+} from '@standardnotes/snjs';
 import { confirmDialog } from '@/services/alertService';
 import { addToast, dismissToast, ToastType } from '@standardnotes/stylekit';
 import { StreamingFileReader } from '@standardnotes/filepicker';
@@ -21,6 +27,7 @@ import {
   PopoverFileItemActionType,
 } from './PopoverFileItemAction';
 import { AttachedFilesPopover, PopoverTabs } from './AttachedFilesPopover';
+import { usePremiumModal } from '../Premium/usePremiumModal';
 
 type Props = {
   application: WebApplication;
@@ -28,8 +35,26 @@ type Props = {
   onClickPreprocessing?: () => Promise<void>;
 };
 
+const createDragOverlay = () => {
+  if (document.getElementById('drag-overlay')) {
+    return;
+  }
+
+  const overlayElementTemplate =
+    '<div class="sn-component" id="drag-overlay"><div class="absolute top-0 left-0 w-full h-full z-index-1001"></div></div>';
+  const overlayFragment = document
+    .createRange()
+    .createContextualFragment(overlayElementTemplate);
+  document.body.appendChild(overlayFragment);
+};
+
+const removeDragOverlay = () => {
+  document.getElementById('drag-overlay')?.remove();
+};
+
 export const AttachedFilesButton: FunctionComponent<Props> = observer(
   ({ application, appState, onClickPreprocessing }) => {
+    const premiumModal = usePremiumModal();
     const note = Object.values(appState.notes.selectedNotes)[0];
 
     const [open, setOpen] = useState(false);
@@ -69,6 +94,14 @@ export const AttachedFilesButton: FunctionComponent<Props> = observer(
     }, [application, reloadAttachedFilesCount]);
 
     const toggleAttachedFilesMenu = useCallback(async () => {
+      if (
+        application.features.getFeatureStatus(FeatureIdentifier.Files) !==
+        FeatureStatus.Entitled
+      ) {
+        premiumModal.activate('Files');
+        return;
+      }
+
       const rect = buttonRef.current?.getBoundingClientRect();
       if (rect) {
         const { clientHeight } = document.documentElement;
@@ -98,7 +131,7 @@ export const AttachedFilesButton: FunctionComponent<Props> = observer(
 
         setOpen(newOpenState);
       }
-    }, [onClickPreprocessing, open]);
+    }, [application.features, onClickPreprocessing, open, premiumModal]);
 
     const deleteFile = async (file: SNFile) => {
       const shouldDelete = await confirmDialog({
@@ -230,6 +263,7 @@ export const AttachedFilesButton: FunctionComponent<Props> = observer(
 
         if (event.dataTransfer?.items.length) {
           setIsDraggingFiles(true);
+          createDragOverlay();
           if (!open) {
             toggleAttachedFilesMenu();
           }
@@ -248,6 +282,8 @@ export const AttachedFilesButton: FunctionComponent<Props> = observer(
         return;
       }
 
+      removeDragOverlay();
+
       setIsDraggingFiles(false);
     };
 
@@ -257,6 +293,7 @@ export const AttachedFilesButton: FunctionComponent<Props> = observer(
         event.stopPropagation();
 
         setIsDraggingFiles(false);
+        removeDragOverlay();
 
         if (event.dataTransfer?.items.length) {
           Array.from(event.dataTransfer.items).forEach(async (item) => {
diff --git a/app/assets/javascripts/components/NoteView/NoteView.tsx b/app/assets/javascripts/components/NoteView/NoteView.tsx
index 33d8f21bb..01a8df836 100644
--- a/app/assets/javascripts/components/NoteView/NoteView.tsx
+++ b/app/assets/javascripts/components/NoteView/NoteView.tsx
@@ -12,13 +12,10 @@ import {
   ComponentMutator,
   PayloadSource,
   ComponentViewer,
-  ComponentManagerEvent,
   TransactionalMutation,
   ItemMutator,
   ProposedSecondsToDeferUILevelSessionExpirationDuringActiveInteraction,
   NoteViewController,
-  FeatureIdentifier,
-  FeatureStatus,
 } from '@standardnotes/snjs';
 import { debounce, isDesktopApplication } from '@/utils';
 import { KeyboardModifier, KeyboardKey } from '@/services/ioService';
@@ -103,7 +100,6 @@ type State = {
   editorTitle: string;
   editorText: string;
   isDesktop?: boolean;
-  isEntitledToFiles: boolean;
   lockText: string;
   marginResizersEnabled?: boolean;
   monospaceFont?: boolean;
@@ -172,9 +168,6 @@ export class NoteView extends PureComponent<Props, State> {
       editorText: '',
       editorTitle: '',
       isDesktop: isDesktopApplication(),
-      isEntitledToFiles:
-        this.application.features.getFeatureStatus(FeatureIdentifier.Files) ===
-        FeatureStatus.Entitled,
       lockText: 'Note Editing Disabled',
       noteStatus: undefined,
       noteLocked: this.controller.note.locked,
@@ -328,15 +321,6 @@ export class NoteView extends PureComponent<Props, State> {
   /** @override */
   async onAppEvent(eventName: ApplicationEvent) {
     switch (eventName) {
-      case ApplicationEvent.FeaturesUpdated:
-      case ApplicationEvent.UserRolesChanged:
-        this.setState({
-          isEntitledToFiles:
-            this.application.features.getFeatureStatus(
-              FeatureIdentifier.Files
-            ) === FeatureStatus.Entitled,
-        });
-        break;
       case ApplicationEvent.PreferencesChanged:
         this.reloadPreferences();
         break;
@@ -1043,18 +1027,17 @@ export class NoteView extends PureComponent<Props, State> {
                       )}
                     </div>
                   </div>
-                  {this.state.isEntitledToFiles &&
-                    window.enabledUnfinishedFeatures && (
-                      <div className="mr-3">
-                        <AttachedFilesButton
-                          application={this.application}
-                          appState={this.appState}
-                          onClickPreprocessing={
-                            this.ensureNoteIsInsertedBeforeUIAction
-                          }
-                        />
-                      </div>
-                    )}
+                  {window.enabledUnfinishedFeatures && (
+                    <div className="mr-3">
+                      <AttachedFilesButton
+                        application={this.application}
+                        appState={this.appState}
+                        onClickPreprocessing={
+                          this.ensureNoteIsInsertedBeforeUIAction
+                        }
+                      />
+                    </div>
+                  )}
                   <div className="mr-3">
                     <ChangeEditorButton
                       application={this.application}
diff --git a/app/assets/stylesheets/_sn.scss b/app/assets/stylesheets/_sn.scss
index 7ec1f9d25..eafd24cd5 100644
--- a/app/assets/stylesheets/_sn.scss
+++ b/app/assets/stylesheets/_sn.scss
@@ -1013,3 +1013,7 @@
     transform: translateY(0%);
   }
 }
+
+.z-index-1001 {
+  z-index: 1001;
+}