I use the X10 wifi as the controller. Interesting to note if I send commands through the app nothing happens. The module is a 2477s on/off insteon wall switch.
So you're using the Insteon 2477s in the X10 mode correct? I'ld first try to reprogram the X10 address in the 2477s as I've found that they do "forget" from time to time and the two way function for X10 can be flaky. You might also want to remove any secondary X10 Scene Address that may be present as well. See:
https://www.smarthome.com/pages/insteon-x10-programmingThe most reliable way to control that switch is to use it in its native Insteon mode.
To do that I'd recommend that you replace the X10 WM100 with a Smartenit P2 bundled with an Insteon 2412U PLM for $59.95 from:
https://smartenit.com/shop/zigbee-insteon-x10-multi-protocol-gateway-hub/ Be sure to select X10/Insteon PLM in the options box.
The P2 Hub will do everything that the WM100 does and more. In addition to controlling both X10 and Insteon simultaneously, it offers control with Alexa or Google Home, a well designed app and even built in ZigBee control should you ever need it. While you can control it from any smartphone or PC from anywhere, the unit itself needs to be plugged into a router or switch as it does not have internal WiFi. The G2 model does but it's much more expensive. The unit also has its own real time clock so it doesn't rely on the app to get the current time. It calculates daily sunrise/sunset based on your home address entered at initial setup.
The P2 will find the Insteon switch when you set it up so it's very easy. The Automation Rules will let you set up whatever type of conditional scheduling you like. I've been using one for almost 2 years now and it's rock solid.