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During the testing of context-sensitive middleware-based software, the middleware identifies the current situation and invokes the appropriate functions of the applications. Since the middleware remains active and the situation may continue to evolve, however, the conclusion of some test cases may not be easily identified. Moreover, failures appearing in one situation may be superseded by subsequent correct outcomes and may, therefore, be hidden. We alleviate the above problems by making use of a special kind of situation, which we call checkpoints, such that the middleware will not activate the functions under test. We propose to generate test cases that start at a checkpoint and end at another. We identify functional relations that associate different execution sequences of a test case. Based on a metamorphic approach, we check the results of the test case to detect any contravention of such relations. We illustrate our technique with an example that shows how re-hidden failures may be detected.