The pragmatic answer to this question is to understand the risks of a failure. What would be the cost of a failure in that part of the program? If the cost is high, it may be wise to invest more in testing, explore more corner cases, and try different techniques to ensure quality. But if the cost is low, being less thorough may be good enough. Personally, I stop testing when I have been through all the steps a couple of times and cannot see a case I am not testing.
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