diff --git a/app/assets/javascripts/app/controllers/widget/text_tools.coffee b/app/assets/javascripts/app/controllers/widget/text_tools.coffee
index 8333ce8936..11b4941a22 100644
--- a/app/assets/javascripts/app/controllers/widget/text_tools.coffee
+++ b/app/assets/javascripts/app/controllers/widget/text_tools.coffee
@@ -78,7 +78,7 @@ class App.WidgetTextTools extends App.Controller
   @contextData: (ce) ->
     $(ce.element).data().plugin_texttools?.searchCondition or {}
 
-  @showModal: (e, ce, selection, el) ->
+  @showModal: (e, ce, selection, el, callback) ->
     textToolId = $(e.target).data('id')
 
     new App.TextToolsModal(
@@ -86,10 +86,12 @@ class App.WidgetTextTools extends App.Controller
       contextData: @contextData(ce)
       textTool: App.AITextTool.find(textToolId)
       selectedText: selection.content
-      approve: (result) -> ce.replaceSelection(selection.ranges, result)
+      approve: (result) ->
+        ce.replaceSelection(selection.ranges, result)
+        callback() if callback
     )
 
-  @renderDropdown: (e, ce, selection, el) ->
+  @renderDropdown: (e, ce, selection, el, callback) ->
     bubbleMenuElement = $(e.target).closest('.js-bubbleMenu')
     popupContainerElement = bubbleMenuElement.find('.dropup-container')
 
@@ -107,7 +109,7 @@ class App.WidgetTextTools extends App.Controller
 
     textToolsDropdown.off('mousedown.text-tools-dropdown').on 'mousedown.text-tools-dropdown', '.js-action', (e) ->
       e.preventDefault()
-      App.WidgetTextTools.showModal(e, ce, selection, el)
+      App.WidgetTextTools.showModal(e, ce, selection, el, callback)
       textToolsDropdown.removeClass('open')
       popupContainerElement.parent().removeClass('show-dropdown')
 
diff --git a/app/assets/javascripts/app/lib/mixins/richtext_bubble_menu.coffee b/app/assets/javascripts/app/lib/mixins/richtext_bubble_menu.coffee
index 4f8dc1e88c..a0f34b5eed 100644
--- a/app/assets/javascripts/app/lib/mixins/richtext_bubble_menu.coffee
+++ b/app/assets/javascripts/app/lib/mixins/richtext_bubble_menu.coffee
@@ -43,7 +43,7 @@ App.RichtextBubbleMenu =
         actionKey = actionNode.dataset.key
         activeAction = _.find(@allActions(), (item) -> item.key is actionKey)
 
-        activeAction.action(e, ce, selection, el) if activeAction
+        activeAction.action(e, ce, selection, el, closeDropdown) if activeAction
 
         return false
       )
@@ -61,8 +61,8 @@ App.RichtextBubbleMenu =
 
       setTimeout ->
         $(window).off('click.bubble-menu, keyup.bubble-menu').on 'click.bubble-menu, keyup.bubble-menu', (e) ->
-          return if e.type is 'keyup' and e.key.startsWith('Shift')
-          return if e.target.closest('.bubble-menu') # keep the bubble menu open if click is on the menu itself
+          return if not window.getSelection().isCollapsed # keep the bubble menu open if there is still a selection
+          return if e.target.closest('.bubble-menu') # keep the bubble menu open if the click is on the menu itself
 
           closeDropdown()
           $(window).off('click.bubble-menu, keyup.bubble-menu')