@smoysauce Try USB cable connection from iPhone to PC. If it still won't work, it could be iOS version issue.

  @Somnus thanks for the suggestion. USB works and all that. If I use my old TPLink archer wifi router it works just fine too. But for some reason when using the Omada network it doesn't. Sometimes it will pop-up for a minute in iTunes but then when I try to sync, it goes away. So it makes me think something is being blocked. Maybe I'll try to systematically go through the settings and try disabling/enabling different things to see if something makes it work consistently.

  @smoysauce What's the model number of your EAP? I guess it may also related to Guest Network or so on settings.

  @Somnus Thanks again. EAP610 v2. I don't utilize guest networks. iPhone and laptop are on the same SSID, VLAN and all that and are pingable. Like I said, I am thinking something is blocking the bonjour or discovery service as it will occasionally pop-up for a bit but then disappear, so still trying to investigate that a bit.