2019 and NG: Once I purchase WebDrive, will I need to uninstall the trial version?
No. You can simply activate with your valid purchase license within the WebDrive application.
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How can I move WebDrive to a new machine? Use the Export feature in WebDrive to export your Site Database and User Settings out to a .reg file. Run WebDrive, then from the main menu, select FILE -> EXPORT and export your data out to a file. Copy that ...