More reports would be welcome, including with wireless travel routers that "hop" back to Singapore using a VPN.
To reiterate, Eight's Web site currently has zero references to VoWiFi. It's not an advertised feature within or outside Singapore. If it works, it's a bonus.
From what I can tell, eight actively blocks Wifi calling connections from overseas IP.
What constitutes overseas IP is another story, those tables are known to be not fully correct, and it is not uncommon for IP to be classified to a different country. That could be why it could sometimes work.
On top of that, it appears that eight now also blocks wifi calling connection when connected through Simba's (and possibly others) roaming data. I was able to connect through Simba's roaming data last year.
And it is not just Eight that has very poor documentation on wifi calling.
Pretty much only the traffic light MNO has any decent reference to wifi calling and all of them explicitly mentioned that it is for local use only. From experience all traffic light telcos block wifi calling when overseas, basically they want to ensure users cannot use it as a "free roaming" service.
List of wifi calling telco is actually very short :
Singtel based, only Singtel, no MVNO
M1 based, M1 & Maxx, MyRepublic 4G (not seen any reference for sometime). not Circle.life though, I would really like to see it working on CL.
Starhub based should have it enable, MyRepublic 5G & Cuniq users have reported it worked in the past.
Simba have no official support, but it does runs well on Android phones only. I have not tested on iPhone recently, in previous test it doesn't work.
Basically if you need wifi calling to work overseas using local wifi, Simba on android phone is the only option.
And you can't trust it to always work, government mandated blocking, wifi networks allowing only TCP traffic and other issues could cause it to fail, but at least the issue is not with SImba.