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Misfile is a webcomic by Chris Hazelton. It chronicles the story of Ash Upton and Emily McArthur who, after a universal filing error in the Celestial Filing Depository, find that their lives are very different than they were the day prior. Emily has become two years younger and Ash has swapped sexes completely, and is now a girl. In order to make things the way they were, they must play along to ensure that Rumisiel (the Angel who caused this mess in the first place!) gets back into heaven before the bosses find out and make the changes permanent.
The sequel, Misfile: Hell High, is available here: https://www.comic-rocket.com/explore/misfile-universe-hell-high/