Disclosed are methods, systems, and articles of manufacture for implementing adaptive levels of authentication assurance according to sensitivity or criticality of information accessed or actions performed in a financial management system to enhance user experience and usability of the financial management system while providing adequate security to safeguard sensitive data. Various flow nodes are associated with one or more levels of assurance which are further associated with some authentication tokens of different authentication strengths. Users are usually first authenticated with a lower authentication strength token. Risk profiles may also be accessed to examine the users' requests for access for fraud detection or prevention purposes. As users attempt to access more sensitive data at a higher level of assurance beyond the authorized level, further authentication with higher authentication strength and involving more user efforts in completing the authentication is required before users are authorized on the higher level of assurance.