You mentioned ping. If you’re using Termux you may need to manually update its DNS settings (different from the system DNS). The file is /data/data/com.termux/files/usr/etc/resolv.conf
To make it roam you probably want your home dns first then some internet resolvers after that.
Not sure if this is new in 14, but you used to have to select an app first, then select the contact in that app. Now apps can present the contacts to the share menu directly so no double tap. Funnily enough, Google Chat was the last app on my phone to support this feature.