We talk about our tDiary's policy and strategies to support Ruby 1.9. tDiary is very popular web application among Rubyist. Our tDiary has been evolving with Ruby. In January, 2009, Ruby 1.9.1 was released which we had looked forward to. We of course began to support Ruby 1.9. But we faced various type of difficulties on our way of support. To overcome these difficulties, we ploted some strategies. In this talk, we show our policy and strategies. We also show the future roadmap which we plan to do after dealing with Ruby 1.9.