"Nightly/daily building and smoke testing" have become widespread since they often reveal bugs early in the software development process. During these builds, software is compiled, linked, and (re)tested with the goal of validating its basic functionality. Although successful for conventional software, smoke tests are difficult to develop and automatically rerun for software that has a graphical user interface (GUI). In this paper, we describe a framework called DART (Daily Automated Regression Tester) that addresses the needs of frequent and automated re-testing of GUI software. The key to our success is automation: DART automates everything from structural GUI analysis, test case generation, test oracle creation, to code instrumentation, test execution, coverage evaluation, regeneration of test cases, and their re-execution. Together with the operating system?s task scheduler, DART can execute frequently with little input from the developer/tester to retest the GUI software. We provide results of experiments showing the time taken and memory required for GUI analysis, test case and test oracle generation, and test execution. We also empirically compare the relative costs of employing different levels of detail in the GUI test cases.