diff --git a/app/assets/javascripts/Components/AttachedFilesPopover/AttachedFilesButton.tsx b/app/assets/javascripts/Components/AttachedFilesPopover/AttachedFilesButton.tsx
index d555d94f9..1ca005cdf 100644
--- a/app/assets/javascripts/Components/AttachedFilesPopover/AttachedFilesButton.tsx
+++ b/app/assets/javascripts/Components/AttachedFilesPopover/AttachedFilesButton.tsx
@@ -41,7 +41,7 @@ export const AttachedFilesButton: FunctionComponent<Props> = observer(
     const buttonRef = useRef<HTMLButtonElement>(null)
     const panelRef = useRef<HTMLDivElement>(null)
     const containerRef = useRef<HTMLDivElement>(null)
-    const [closeOnBlur, keepMenuOpen] = useCloseOnBlur(containerRef, setOpen)
+    const [closeOnBlur, keepMenuOpen] = useCloseOnBlur(containerRef, setOpen, true)
 
     useEffect(() => {
       if (appState.filePreviewModal.isOpen) {
diff --git a/app/assets/javascripts/Hooks/useCloseOnBlur.ts b/app/assets/javascripts/Hooks/useCloseOnBlur.ts
index 0396859c5..9655a930c 100644
--- a/app/assets/javascripts/Hooks/useCloseOnBlur.ts
+++ b/app/assets/javascripts/Hooks/useCloseOnBlur.ts
@@ -8,16 +8,20 @@ import { StateUpdater, useCallback, useState } from 'preact/hooks'
 export function useCloseOnBlur(
   container: { current?: HTMLDivElement | null },
   setOpen: (open: boolean) => void,
+  keepOpenOnDialogs = false,
 ): [(event: { relatedTarget: EventTarget | null }) => void, StateUpdater<boolean>] {
   const [locked, setLocked] = useState(false)
   return [
     useCallback(
       function onBlur(event: { relatedTarget: EventTarget | null }) {
-        if (!locked && !container.current?.contains(event.relatedTarget as Node)) {
-          setOpen(false)
-        }
+        setTimeout(() => {
+          const keepOpen = keepOpenOnDialogs && document.activeElement?.closest('[role="dialog"], .sk-modal')
+          if (!keepOpen && !locked && !container.current?.contains(event.relatedTarget as Node)) {
+            setOpen(false)
+          }
+        })
       },
-      [container, setOpen, locked],
+      [keepOpenOnDialogs, locked, container, setOpen],
     ),
     setLocked,
   ]