A system for proactively extracting data from complex documents is disclosed. The system may include one or more processors, an NLP device, a trained machine learning device, and a memory in communication with the one or more processors and storing instructions that, when executed by the one or more processors, are configured to cause the system to, receive one or more documents from a client device, extract one or more extractable data entries from the one or more data entries, generate, one or more normalized data entries, and proactively generate and add one or more completed data entries in place of one or more placeholders in a first document template. The system may receive a natural language prompt from a user device and determine a machine-readable semantic representation. The system may identify sensitive data entries and generate a graphical user interface identifying completed data entries and associated confidence intervals.