A computerized process of detecting content blocking software may include forwarding, to a client device, instructions to enable scanning of a web browser and a file with features resembling advertisement content, and receiving a report from the forwarded instructions indicative of a response of a webpage generated by a web browser of the client device in response to the loaded file. The computerized process may also include analyzing the report based on an expected response of the web browser, and indicating the presence of the content blocking software based on the analysis.