It's very common for customers to think that their playlist is not updating. However, before you come to that conclusion, consider how playlist updates work.
You can change a playlist assigned to a player or update the playlist itself. In both situations, a new playlist is pulled down in the background. Any errors during the download process will cause the synchronization / download process to start over. Poor internet or WiFi connections can cause this process to start over several times. Once a download is complete, a check is performed for errors. Finally, the player waits for the current playlist to be completely played before the swap is made. If the download completed while in the middle of a playlist, the cutover will not happen until the end of the next full play. If the playlist is long, this could also extend the time it takes for the new playlist to be active.
These steps all make sure you never experience a screen in a bad state and poor customer experience. Once considering all these factors, most customers come to the conclusion that the playlist update function is working as designed. If you still feel that your player is having a problem, try using the real-time mode or remote restart feature. If these features fail, you likely have a poor connection to the player that needs to be resolved before playlist updates work properly.