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If I use "Executions" as a method of protection, can I manually increase the counter by my program?
Yes, you can use the function WLTrialExtendExpiration, where you can extend the expiration of your application. Also, you can use create a trial extension key in case that you have enabled the "Trial Extension" option (in the Trial Settings panel) when your application was protected.
Please, notice that you can only extend the trial expirations that you have selected in your application. That is, if you have protected your application with expiration by executions, you can only extend the executions number from WLTrialExtendExpiration or using trial extension keys.