It has been less than a year since Princesses Celestia and Luna took their places on the thrones of Equestria and Luna has a lack of confidence in her abilities. When mistakes are made after birthing their blessings, the sun and the moon, the kingdom slowly loses confidence in their young princess'. Struggling against time, the princesses must find a way to correct the disastrous mistakes that they have made while convincing themselves that they have the power to be true alicorn monarchy.

While conducting some late-night research for an assignment from the princess Twilight Sparkle is sidetracked by a book entitled 'Dear Princess Luna'. Upon analysis the young mare finds herself reading the story of her life...if Princess Luna took Princess Celestia's place as her tutor. As Twilight reads on and on she begins to realise how conflicted as to how lucky...or unlucky she had been to be taught by Celestia.