An automated testing tool is described for assessing the test coverage of Pascal programs. The coverage criterion measured by this tool is that of multiple condition testing. The criterion consists of generating test cases to execute all combinations of conditions in conditional expressions. The testing tool analyzes a PASCAL source program and automatically inserts software data collection probes to measure multiple condition test coverage. When the instrumented program is executed, these software probes record execution information in a database. The database can then be queried interactively to produce a series of test coverage reports. The extent of test coverage achieved in terms of conditions and multiple conditions executed is documented. Cumulative information over a series of tests can also be maintained.