Abstract: Disclosed herein are systems and methods for automated conversion and management of web server configuration files using a conversion application. In one aspect, an exemplary method comprises receiving an input configuration file for conversion from an Apache configuration file to an NGINX configuration file, parsing the input configuration file into tokens for processing to construct an Apache configuration tree in memory, building a structured Apache configuration tree from the tokens and storing in memory, traversing the Apache configuration tree examining each element of the Apache configuration tree, and for each Apache directive or block that is encountered during the examination, invoking a directive conversion plugin for handling requirements of the respective Apache directive or block, building an NGINX configuration tree corresponding to the Apache configuration tree, and writing the NGINX configuration depicted in the NGINX configuration tree to an NGINX configuration file.