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A computer implemented tool is described that includes an assertion generator module that can automatically generate assertions, which are usable to verify application-specific security properties, for a computer software program. An assertion checker module can automatically analyze the computer software program to ensure that it satisfies the application-specific security properties. A graphical user interface module can display feedback to diagnose security flaws detected in the computer software program based on the analysis by the assertion checker module. In support of these modules are a code preprocessor module that can translate source code of the computer software program into an intermediate abstract representation, and a database module that can store the generated assertions and associated data in a database. Each of the modules can provide functionality at any time during code construction of the computer software program.