Miss Moneypenny, later assigned the first names of Eve or Jane, is a fictional character in the James Bond novels and films.

In Ian Fleming's first draft of Casino Royale (1953), Moneypenny's name was originally "Miss 'Petty' Pettaval", which was taken from Kathleen Pettigrew, the personal assistant to MI6 director Stewart Menzies.

[1] Other candidates for Moneypenny's inspiration include Vera Atkins of Special Operations Executive;[2] Paddy Ridsdale, a Naval Intelligence secretary;[1] Joan Bright Astley, whom Fleming dated during World War II, and who was noted for giving a warm and friendly reception to senior officers who visited her office to view confidential papers;[3] and Joan Howe, Fleming's red-haired secretary at The Times who had typed the manuscript of Casino Royale.

Moneypenny, now played by Naomie Harris and given the first name Eve, is originally a field officer assigned to work with Bond on an operation in Istanbul.

She is temporarily suspended for this and reassigned to desk duty, assisting Gareth Mallory (Ralph Fiennes), the Chairman of the Intelligence and Security Committee, who has been assigned to watch over MI6.

By the end of the film, she decides to retire from fieldwork and becomes Mallory's secretary once he takes over the role of M. "Of course she's in love with Bond, but she's too much a lady to go chasing after him.

In the novels, Bond also has his own secretary, Loelia Ponsonby and later Mary Goodnight, both of whose lines and relationships were often transferred to Miss Moneypenny for the films.

In Die Another Day (2002), she puts on Q's (John Cleese) virtual reality glasses and runs a simulation in which she and Bond finally consummate their relationship.

The last three actresses to play Moneypenny (Caroline Bliss, Samantha Bond and Naomie Harris) are all alumni of Bristol Old Vic Theatre School.

In The Last Resort: A Memoir of Zimbabwe (2009), Douglas Rogers dedicated chapter 11 (titled "Miss Moneypenny") to his father Ian's black market currency dealer in Mutare.

[14] In the 2011 British TV drama series The Hour, set in the mid-1950s when Fleming's James Bond books first became popular, the characters Freddie and Bel address each other as 'Moneypenny' and 'James.