Hi all, First of all. IOS 14.1 and WatchOS 6 (6.2.8) are compatible (I'm using Apple Watch Series 2). If you are having problem you can try the following steps. Issue : You are getting an error message saying "Unable to Check for Update" after you pair your Apple Watch. You have "Start Over" the process and keeps getting the same error. Try to pair your watch use different iPhone (Doesn't matter if its running IOS 14.1 or 13.x). In my situation I'm using IOS 14.1 You should get an update message saying that you can update your WatchOS to ver 6.2.8. Do the update and let the Watch complete the update process. After the reboot, you can perform another reset on your Watch by keep pressing the watch screen for a few seconds. Pair the watch with your original phone. Note: I'm using a combine 2.4 and 5 Ghz and still able to update. However feel free to try using 2.4 Ghz Wi-Fi only. If you have a combine 2.4 and 5Ghz Wi-Fi like me and can't disable the 5Ghz, you can use Windows 10 Wi-Fi hotspot options where you can lock the signal to 2.4Ghz only. Hope this helps.