diff --git a/lib/redmine/menu_manager.rb b/lib/redmine/menu_manager.rb
index af7d67b77..34cea79fa 100644
--- a/lib/redmine/menu_manager.rb
+++ b/lib/redmine/menu_manager.rb
@@ -84,6 +84,14 @@ module TreeNodePatch
 
     end
 
+    # Wrapp remove! making sure to decrement the last_items counter if
+    # the removed child was a last item
+    def remove!(child)
+      @last_items_count -= +1 if child && child.last
+      super
+    end
+
+
     # Will return the position (zero-based) of the current child in
     # it's parent
     def position
@@ -352,7 +360,7 @@ module Redmine
             target_root.add(MenuItem.new(name, url, options))
           end
           
-        elsif options.delete(:last)
+        elsif options[:last] # don't delete, needs to be stored
           target_root.add_last(MenuItem.new(name, url, options))
         else
           target_root.add(MenuItem.new(name, url, options))
@@ -386,7 +394,7 @@ module Redmine
     
     class MenuItem < Tree::TreeNode
       include Redmine::I18n
-      attr_reader :name, :url, :param, :condition, :parent, :child_menus
+      attr_reader :name, :url, :param, :condition, :parent, :child_menus, :last
       
       def initialize(name, url, options)
         raise ArgumentError, "Invalid option :if for menu item '#{name}'" if options[:if] && !options[:if].respond_to?(:call)
@@ -403,6 +411,7 @@ module Redmine
         @html_options[:class] = [@html_options[:class], @name.to_s.dasherize].compact.join(' ')
         @parent = options[:parent]
         @child_menus = options[:children]
+        @last = options[:last] || false
         super @name.to_sym
       end
       
diff --git a/test/unit/lib/redmine/menu_manager/mapper_test.rb b/test/unit/lib/redmine/menu_manager/mapper_test.rb
index 699c0cf2c..a23b624f7 100644
--- a/test/unit/lib/redmine/menu_manager/mapper_test.rb
+++ b/test/unit/lib/redmine/menu_manager/mapper_test.rb
@@ -17,7 +17,7 @@
 
 require File.dirname(__FILE__) + '/../../../../test_helper'
 
-class Redmine::MenuManager::MapperTest < Test::Unit::TestCase
+class Redmine::MenuManager::MapperTest < ActiveSupport::TestCase
   context "Mapper#initialize" do
     should "be tested"
   end
@@ -163,4 +163,21 @@ class Redmine::MenuManager::MapperTest < Test::Unit::TestCase
     menu_mapper = Redmine::MenuManager::Mapper.new(:test_menu, {})
     assert_nil menu_mapper.delete(:test_missing)
   end
+
+  test 'deleting all items' do
+    # Exposed by deleting :last items
+    Redmine::MenuManager.map :test_menu do |menu|
+      menu.push :not_last, Redmine::Info.help_url
+      menu.push :administration, { :controller => 'projects', :action => 'show'}, {:last => true}
+      menu.push :help, Redmine::Info.help_url, :last => true
+    end
+
+    assert_nothing_raised do
+      Redmine::MenuManager.map :test_menu do |menu|
+        menu.delete(:administration)
+        menu.delete(:help)
+        menu.push :test_overview, { :controller => 'projects', :action => 'show'}, {}
+     end
+    end
+  end
 end