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Normally with a trial key there's not really a need to de-activate them. The situation I'm more familiar with is that if a potential customer decides to purchase Tableau Server then their actual key will take priority over the trial key once it's applied and since the trial key is time based it will quickly roll off. Though this would be the case of two trial keys. I would think it would work in similar fashion that if you apply the newer trial key that it would take priority over the existing one. A restart of Tableau Server is usual necessary for a newer key to be recognized.
Thank you, it has worked fine without de-activating the older key