A system and method for bypassing secondary user authentication based at least in part on the detection of a whitelisting deviation from a user pattern are disclosed. In one implementation, the system includes a pattern determination module, a fraudulent login identifier module, a whitelisting deviation detection module and a user authentication generation module. The pattern determination module determines a user pattern. The fraudulent login identifier module identifies a potentially fraudulent login and triggers a secondary authentication challenge. The whitelisting deviation detection module compares user information to the user pattern and determines based on the comparison whether a whitelisting deviation from the user pattern has occurred. The user authentication generation module generates and sends a secondary user authentication challenge responsive to the identification of a potentially fraudulent login by the fraudulent login identification module unless bypassed responsive to the determination that a whitelisting deviation has occurred.