diff --git a/data/gui/roster_window.ui b/data/gui/roster_window.ui
index f47bbb26c..7c8eb9007 100644
--- a/data/gui/roster_window.ui
+++ b/data/gui/roster_window.ui
@@ -319,6 +319,7 @@
                     <child>
                       <object class="GtkCheckMenuItem" id="show_roster_menuitem">
                         <property name="visible">True</property>
+                        <property name="sensitive">False</property>
                         <property name="can_focus">False</property>
                         <property name="events">GDK_POINTER_MOTION_MASK | GDK_POINTER_MOTION_HINT_MASK | GDK_BUTTON_PRESS_MASK | GDK_BUTTON_RELEASE_MASK</property>
                         <property name="label" translatable="yes">Show _Roster</property>
diff --git a/src/message_window.py b/src/message_window.py
index 4b8b94be1..8f1ee7a41 100644
--- a/src/message_window.py
+++ b/src/message_window.py
@@ -86,6 +86,8 @@ class MessageWindow(object):
             self.parent_paned = parent_paned
             self.notebook.reparent(self.parent_paned)
             self.parent_paned.pack2(self.notebook, resize=True, shrink=True)
+            gajim.interface.roster.xml.get_object('show_roster_menuitem').\
+                set_sensitive(True)
             orig_window.destroy()
             del orig_window
 
@@ -615,6 +617,8 @@ class MessageWindow(object):
                 # Don't close parent window, just remove the child
                 child = self.parent_paned.get_child2()
                 self.parent_paned.remove(child)
+                gajim.interface.roster.xml.get_object('show_roster_menuitem').\
+                    set_sensitive(False)
             else:
                 self.window.destroy()
             return # don't show_title, we are dead
@@ -1261,6 +1265,8 @@ class MessageWindowMgr(GObject.GObject):
                 # Don't close parent window, just remove the child
                 child = w.parent_paned.get_child2()
                 w.parent_paned.remove(child)
+                gajim.interface.roster.xml.get_object('show_roster_menuitem').\
+                    set_sensitive(False)
                 gtkgui_helpers.resize_window(w.window,
                         gajim.config.get('roster_width'),
                         gajim.config.get('roster_height'))