1. A system to aid in the prevention of file enumeration attacks, the system comprising: a web server associated with a website; a data repository; and a developer device configured for automatically: determining, in response to an indication from a developer, a list of files comprising each file stored in the data repository that is associated with the website; determining a list of user roles comprising each user role stored in the data repository that is associated with the website; creating a user to be stored in the data repository associated with a first user role in the list of user roles; modifying the user stored in the data repository, via a repository application programming interface (“API”), to be associated with a second user role from the list of user roles; for each combination of (i) user role in the list of user roles and (ii) file in the list of files, logging into the website as the user role and attempting to open the file via the API, wherein logging into the website as the user role comprises logging into the website via a Hypertext Transfer Protocol (“HTTP”) request to the web server as the user associated with the first user role in the list of user roles and logging in as the modified user associated with the second user role in the list of user roles; and sending a report indicating a success or a failure of each combination.