Overview
Troubled Windows (とらぶるうぃんどうず or とらぶる・うぃんどうず) presents itself as intro to an anime. Due to it being a flash animation it features interactivity, where the viewer can click to cause different visuals in the animation.
The video also contains references to other media such as Nadia: The Secret of Blue Water, The Powerpuff Girls, My Life as a Teenage Robot and more.
Flash has been disable sense 2o21, to view it in this form go to here
Music
The song for the flash is Sakuranbo Kiss ~Bakuhatsu da mo~n~ (さくらんぼキッス ~爆発だも〜ん~, Cherry Kiss ~it's an explosion mo~n~) by KOTOKO. The origin of the song comes from the Colorful Kiss visual novel series.
A fansub was made for the video leading it to spread as well as the spread of OS-tan onto english imageboards.
Fan Book
A commercial fanbook was made by Ohzora Publishing titled Trouble Windows OS-tan FanBook (とらぶる・うぃんどうず OSたんファンブック) with illustrations by over 25 contributors. It also came with figures manufacture by the Pink Company. These figures are 95-tan, ME-tan, XP-tan with a molded space for 2k-tan.
Video
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XP-tan 2k-tan 95-tan ME-tan Ohzora Publishing Pink Company Windows OS Personification OS Girl