@khurtlwilliams,

For Devices Setup via Wi-Fi, I always recommend to navigate to the network settings on your phone and disable private addressing on both your home network, and for the SSID created by the plug. If the device disconnects from your phone to test the wireless connection, the device may not communicate with your phone, as it will have a different address from when it was first connected.

I would recommend configuring these devices from the Kasa App, which will automatically trigger the Homekit setup process for iPhones. The screen that the Kasa App presents may also provide additional information about what may be the problem.

If you have a guest network or an IoT network option on your router, I would recommend attempting to configure these devices to use this network, as there are far fewer features that can interfere with IoT communication on this SSID.

We do have a troubleshooting FAQ for Homekit, so take a look and see if any of these solutions will help: Troubleshooting Homekit Setup