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winprint writes diagnostic logs to a logs folder alongside its settings. On Windows that’s %appdata%\Kindel\winprint\logs (or next to the executable when running in portable mode); on macOS and Linux the logs folder sits next to the wp executable (inside WinPrint.app for the GUI). Run the wp command line with --debug for more detail.

Additional printing diagnostics can be turned on via settings in the WinPrint.config.json configuration file.