Examples of the present disclosure describe systems and methods for providing advanced file modification heuristics. In aspects, software content is selected for monitoring. The monitoring comprises determining when the software content performs file accesses that are followed by read and/or write operations. The read/write operations are analyzed in real-time to determine whether the software content is modifying file content. If the monitoring indicates the software content is modifying accessed files, mathematical calculations are applied to the read-write operations to determine the nature of the modifications. Based on the determined nature of the file modifications, the actions of the software content may be categorized and halted prior to completion; thereby, mitigating malicious cyberattacks and/or unauthorized accesses.