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Testing multi-tier Web applications is challenging yet critical. First, because of inter-tier interactions, a fault in one tier may propagate to the others. Second, Web applications are often continuously evolving. Testing such emerging applications must efficiently generate test cases to catch up with fast-paced evolution and effectively capture cross-tier faults. We present a technique based on an inter-connection dependence model to generate sequences of Web pages that are potentially fault prone. To ensure that these sequences of Web pages will be exercised as designated, the path condition for each execution path is computed and used to determine the domain of each input parameter and database state. Input data for each Web page can then be automatically generated by using boundary value analysis. The test suite generated by our technique guarantees that inter-tier interactions will be adequately tested.