Cookie has worked for V.I.L.E. for years as the accountant for their illegal activities, managing the organization's finances and collecting data. She comes to the Isle of V.I.L.E. annually to upload an encrypted hard drive containing their sensitive data concerning operation reports and projected earnings, as well as classified information supplied by V.I.L.E. operatives from all over the world, to the isolated central servers, due to V.I.L.E.'s mistrust of wireless uploading.
Since she was a child, Black Sheep, being the prankster she was, would always throw a water balloon at Cookie and her escort when they landed at V.I.L.E. During one of these pranks, Cookie's escort dropped his cell phone after being punched by Coach Brunt, which Black Sheep pick-pocketed.
The day she left V.I.L.E., Black Sheep apologized to Cookie for the pranks she pulled. As she left for the server room, Cookie recommended Black Sheep should leave pick-pocketing and such behind, and go into white-collar crime. She later went after Black Sheep when she realized she stole the hard-drive, but was tied-up by Black Sheep and thrown into a closet. Black Sheep stole Cookie's red fedora and matching jacket, which she wore into tricking the guards in order to escape.
Cookie is an educated and proper woman of experienced years. Over the years, she came to expect young Black Sheep's surprise water balloon pranks every December 1 she arrived. On the night Black Sheep escaped, she gave advice to the young girl and forgave her for the previous years of pranks after a heartfelt apology, but still saw her as a child.
- Cookie appears to be an homage to the previous incarnation of Carmen Sandiego, as she shares several traits with the character:
- Her voice actress, Rita Moreno, was the original voice of Carmen Sandiego in the 1994 animated series.
- During her talk with the 2019 character, the elevator music played the theme song of the aforementioned series.
- Booker slightly resembles an older version of 1994's Carmen. Even Booker's coat is evocative of the 1994 version, right down to the orange stripe on the fedora.
- This resemblance has led fans to theorize that Cookie may be the "original" Carmen, given her connections to VILE are parallel to the 1994 version's role and how "Black Sheep"'s Carmen persona originated from her theft of Booker's coat which contained "Carmen Brand Outerwear, San Diego" on its brand name tag.
- Her name is a reference to the expression "cook the books", which refers to altering accounting records illegally.