diff --git a/main/CMakeLists.txt b/main/CMakeLists.txt
index 5dc69dcb..c9e3b879 100644
--- a/main/CMakeLists.txt
+++ b/main/CMakeLists.txt
@@ -161,6 +161,7 @@ SOURCES
     src/ui/util/helper.vala
     src/ui/util/label_hybrid.vala
     src/ui/util/sizing_bin.vala
+    src/ui/util/size_request_box.vala
     src/ui/util/scaling_image.vala
     src/ui/util/preview_file_chooser_native.vala
 CUSTOM_VAPIS
diff --git a/main/data/conversation_content_view/view.ui b/main/data/conversation_content_view/view.ui
index fc7132aa..af05d285 100644
--- a/main/data/conversation_content_view/view.ui
+++ b/main/data/conversation_content_view/view.ui
@@ -28,11 +28,12 @@
                                                         <object class="GtkEventBox" id="main_event_box">
                                                             <property name="visible">True</property>
                                                             <child>
-                                                                <object class="GtkBox" id="main">
+                                                                <object class="DinoUiSizeRequestBox" id="main">
                                                                     <property name="margin-bottom">15</property>
                                                                     <property name="expand">False</property>
                                                                     <property name="orientation">vertical</property>
                                                                     <property name="visible">True</property>
+                                                                    <property name="size-request-mode">height-for-width</property>
                                                                 </object>
                                                             </child>
                                                         </object>
diff --git a/main/src/ui/conversation_content_view/conversation_view.vala b/main/src/ui/conversation_content_view/conversation_view.vala
index c68ee5de..ac6df1fc 100644
--- a/main/src/ui/conversation_content_view/conversation_view.vala
+++ b/main/src/ui/conversation_content_view/conversation_view.vala
@@ -106,7 +106,7 @@ public class ConversationView : Box, Plugins.ConversationItemCollection, Plugins
         // Get widget under pointer
         int h = 0;
         bool @break = false;
-        Widget w = null;
+        Widget? w = null;
         main.@foreach((widget) => {
             if (break) return;
 
@@ -118,6 +118,12 @@ public class ConversationView : Box, Plugins.ConversationItemCollection, Plugins
             }
         });
 
+        if (w == null) {
+            if (currently_highlighted != null) currently_highlighted.unset_state_flags(StateFlags.PRELIGHT);
+            currently_highlighted = null;
+            return;
+        }
+
         // Get widget coordinates in main
         int widget_x, widget_y;
         w.translate_coordinates(main, 0, 0, out widget_x, out widget_y);
diff --git a/main/src/ui/util/size_request_box.vala b/main/src/ui/util/size_request_box.vala
new file mode 100644
index 00000000..c9adcb70
--- /dev/null
+++ b/main/src/ui/util/size_request_box.vala
@@ -0,0 +1,11 @@
+using Gtk;
+
+namespace Dino.Ui {
+class SizeRequestBox : Box {
+    public SizeRequestMode size_request_mode { get; set; default = SizeRequestMode.CONSTANT_SIZE; }
+
+    public override Gtk.SizeRequestMode get_request_mode() {
+        return size_request_mode;
+    }
+}
+}
\ No newline at end of file