Update 10/13 5:59PM PDT: At about 4PM I received another call from a senior advisor, they wanted yet more screenshots of some settings. Im not sure if the previous advisor I spoke to earlier today made a mistake or what happened. Anyway, this particular advisor told me that she personally knew the engineer and she spent a good 30-40 minutes testing out various scenarios with me. These involved turning the phone off and making sure watch was on WIFI while she attempted to call me. Not to my surprise I never did receive a call on the watch, but the advisor told me that on her end the phone never rang and it never went to voice mail, it was just dead silent.
She then had me turn the phone off and attempt to make an outbound wifi call from the watch, and as we all know, all calls failed. I appreciated her willingness to try some things our. I think now she had a better understanding of whats going on.
She then proceeded to get screen shots of WiFi calling enabled setting on phone, calling on other devices, iCloud account, faceTim settings, and 2 wifi network settings. She also go a screen shot of the Watch.app phone settings, where the Wifi Calling toggle is. She was surprised it was not showing up and I explained that it will only show up if I remove the cell plan from the watch. She thought that was very peculiar and wrote that down too. I also mentioned that I knew at least 2 people on ATT that are also having the issue, but im not sure if she made a note of it.
She also tried to contact the engineer working on the case so she could get live feedback from them, but was unable to make contact. So she wrote a report and sent it back to engineering. I have a callback scheduled for Monday 2PM PDT.
Update 10:26pm PDT: I removed the cellular plan from my watch again, and as we already knew, in the watch.app phone setting WiFi calling toggle now appeared. So I decided to put my phone in airplane mode and made sure watch was connected to WiFi. I then placed 2 successful WiFi calls that correctly showed up on caller ID as my normal phone number. Things are very strange here.
Update 11:45PM PDT: I re-activated the cellular plan on the phone, and of course now lost the ability to make wifi calls. Tests where done by putting iPhone into airplane modre and turning off cellular on the watch. Watch switched to wifi, all calls failed, nothing new here.
After re-enabling the Cellular toggle on the watch I went into the settings->General->About on the watch. Then I noticed that there was a field titled "Network" at this time it read T-Mobile WiFi. I thought that was interesting, watch was connected to WiFi and the cellular toggle was on. So the watch was correctly recognizing the network as T-Mobile Wifi. So I placed some calls and they went through no problem and I have to wait to see what T-mobile logs them as.
What is peculiar is that i've done this before, i've made calls that seem to be WiFi Calls but are logged as regular cell calls. So i'm interested to see what t-mobile logs these calls as. I have a attached a screenshot below. Another interesting thing is if I turn off the cellular toggle off but still connected to Wifi, the network field reads "Not Available" which reinforces the idea that the eSIM has to be powered on for the watch to connect to T-Mobile for Wifi calling. It will also read "Not Available" when watch is connected to phone by bluetooth. The part that doesn't make sense is why calls are logged as cellular calls. Will update when T-Mobile shows my calls and how they are logged.
