This paper presents a software system called WebMonitoring. The system is designed for solving certain problems in the process of information search on the web. The first problem is improving entering of queries at search engines and enabling more complex searches than keyword-based ones. The second problem is providing access to web page content that is inaccessible by common search engines due to search engine’s crawling limitations or time difference between the moment a web page is set up on the Internet and the moment the crawler finds it. The architecture of the WebMonitoring system relies upon finite state machines and the concept of monitoring the web. We present the system’s architecture and usage. Some modules were originally developed for the purpose of the WebMonitoring system, and some rely on UNITEX, linguistically oriented software system. We hereby evaluate the WebMonitoring system and give directions for further development.