Heralded long ago as the benevolent Fount of Knowledge, Shadow Milk Cookie is the antithesis of what his Witch-given purpose once was: he is a malicious trickster who relishes in chaos, confusion, and inequity. This sly entertainer spends his immortality in the Spire of Deceit, gaily weaving untruths and scheming to release Earthbread from its shackles of virtue with his lackeys Candy Apple Cookie and Black Sapphire Cookie. Behind his mask of mirth, however, lies a lonely soul whose disillusionment wore him down to the cruel, manipulative individual he is today. Shadow Milk Cookie wields the power of Deceit, a corrupted side of the Virtue of Knowledge he once held. He was the original owner of Pure Vanilla Cookie's Soul Jam, being stripped of it upon his descent into villainy.

Supposedly a creation of the Beast of Deceit himself, Candy Apple Cookie is committed to her master's cause of spreading chaos—both for the fun of it, and to earn his praise. This gleeful imp insists she was born from the first lie ever told, a lie covered in syrup sweet enough to make anyone turn their back on truth. She often schemes alongside her far less giddy cohort Candy Apple Cookie is a tiny, petite Cookie with washed light dough with pale pink cheeks. She has round scarlet colored eyes with white rhombus shaped pupils and white eyelashes separated from her lids. Her mouth forms a cat-like smile and has a single short fang. She has white hair with a grayish-pink stripe in the middle and on the back of her head are two glossy candy apples, akin to pigtails, with black bows at their base. She has stubby black horns and devil-like wings with a black frame and cherry-colored membrane on her waist. As for her attire, Candy Apple Cookie wears a Victorian styled black dress with short, puffy transparent sleeves, a short white neck apron, a largely white ruffle rim and a red bow on the back.

Black Sapphire Cookie is a loyal follower of Shadow Milk Cookie, being more mature and subtle compared to his impish cohort. This Cookie's suave, refined radio host persona contrasts his passion for broadcasting slander on the Cookies of Earthbread, all for the fun of watching chaos ensue. Black Sapphire Cookie finds very little worth in things like truth and virtue; to him, what matters most is that's everyone remains entertained—even at the expense of others. Black Sapphire Cookie is a tall, lanky individual; he is compact with rounded shapes, and holds a confident posture. His dough color is a cool grayish-purple and his face has a confident expression with gleaming sharp teeth. One of his eyes is completely hidden beneath the bangs of his fluffy, short hair, which falls over most of his face in violet-rimmed obsidian waves. His other eye is partially visible, being deep black and sly with a pointed slit pupil in lavender. His outfit resembles one of a sophisticated host or entertainer: a tailored black suit with gold accents. A crisp white cravat is tied at the collar and swirling gold lines the lapels of his jacket. He accessorizes with luxurious baubles like oval onyx earrings, a matching brooch, and a white rose on his left lapel.

There are not many Cookies on Earthbread who could inspire hope as Pure Vanilla Cookie did. Born from nature-blessed cream and a fragrant vanilla bean, he was the epitome of Cookie kindness and faithfulness. Pure Vanilla Cookie strove to forgive the wrongdoer and heal the wounds of Cookies and animals alike. Though a powerful wielder of magic, he would use his spells not for his own good, but for the good of everyone. The Cookie took an arduous pilgrimage down the Sugar-Free Road. What Pure Vanilla Cookie learned through the Trials is unknown, but crowned with a bright halo of light he returned to found the Vanilla Kingdom, a land of freedom and learning, and a beacon for those seeking love and peace. Appearance description: slim, medium-height cookie with light brown/tortilla-brown dough, creamy blonde hair, and distinct heterochromia (pale yellow right eye, faded blue left eye). Without his staff,he is completely blind,which is why he carries it around everywhere!