Hello. My name is Michael. I can help you with your question.
Typically, syncing issues between a Mac and the SkyCaddie are due to the computer's firewall. The firewall is blocking CaddieSync from communicating with the device. In order to allow CaddieSync to communicate freely with your SkyCaddie (without compromising the security of your computer), please add CaddieSync as an exception in your firewall settings.To add CaddieSync as an exception:
Please let me know if that works, or if you need additional assistance.