As a possible option, you may try to use .WaitProperty() method and provide a regular expression so the method will wait until either successful or failure message appears.
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Would it be possible to see the code you are executing? WaitProperty should not "fail" necessarily... If you're getting an error, it would be good to know what the error is, what code was executing it, etc.
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Why automate? I do automated testing because there's only so much a human being can do and remain healthy. Sleep is a requirement. So, while people sleep, automation that I create does what I've described above in order to make sure that nothing gets past the final defense of the testing group. I love good food, good books, good friends, and good fun.