It may be unrelated to the original server issue but sending faces from iPhone to Gear watches (and WearOS) is a recurring problem. Once you find the right combination of connections the faces will send beautifully... until the connection breaks again.
Here's what I've found to be more successful than other methods (using an iPhone Xs and Galaxy Watch and also with Gear S3):
1) Make sure watch WiFi is ON and connected to same network as phone
2) Start BOTH Samsung Galaxy Watch App and Facer for IOS on the phone
3) Leave them running for 30 minutes or more
4) Stop the Samsung Galaxy Watch app on the phone (kill the app by swiping up or "x" depending on your IOS)
5) Try sending the watch face from the phone or web
6) NOTE: The Web will send faces if you're using Facer Premium on the phone which I recommend
This may not always work but it's the best method that I've found.
If it doesn't work the first time, "rinse and repeat" until it does.
Hopefully, @Facer_Official will find the bug (or perhaps it's Apple or Samsung?) and make this a more reliable process for IOS users.