The method of quantifying risk, implemented as a computerized program, quantifies the risk of releasing security sensitive words, data objects, characters or icons which may be part of data subject to analysis (target data). Security words, etc. are categorized, pre-existing data for each category is obtained and the categories (and subsumed pre-existing data) are ranked by risk. The target data is compared to the compiled pre-existing data and a risk output is generated. For unknown or undefined words, an indeterminable category is created and is ranked. The method may include inference engines, and contextual routines to add semantic equivalents and opposites to the critical list. Search engines may be employed to add to the list. A differential rank quantifier is assigned to the security words, etc. which has a different rank than the associated category. Frequency analysis, source analysis and stochastic analysis is also used. The risk output is altered.