Thanks for your feedback and patience while we looked into this for you.
First, be sure you are finishing the round properly in standalone mode. This is how the sync happens between the watch and phone. You'll turn off airplane mode, wait until the watch connects and only then "finish the round" on phone.
We can help better with additional information from your watch and the phone. When you are noticing this issue, please open the watch app, scroll down until there's an information screen, tap 'Bug report'. Then send a bug report from the phone using the regular steps. This is for Samsung watches only. Next, from the phone, tap the action menu (three bars in the upper left), scroll down to "report a problem" and follow the prompts to send a report. Both of these actions will give us additional insight by sending the logs from the round. Those emails will send to our support team, not on the forum here. - Cindy