Kami Nomi zo Shiru Sekai: Megami-Hen 1x4

Keima attempts to finish and get the heroine, Sora Asuka from the PFP Bishōjo game "Crayon". But the game has many bugs including one that loops a previous scene over and over again. No making things any better is the fact saving the game only crashes it and game company that made it is now bankrupt thus there are no patches to fix the game. In order to avoid the bug loop and finish the game, Keima forcefully enlists a reluctant Elsie to help record the choices that he made in the game. Elsie is at first confused on why Keima takes the game seriously but soon respect his dedication to help the girls in his games just like the girls he helps in real life. After many attempts, Keima finally manages to avoid the loop bug and goes to the next scene but unexpectedly gets into another bug, resolving him to try again much to Elsie's horror. A wikipedia article about "Crayon" reveals a rumor that someone managed to get the ending, hinting Keima was able to finish the game.