Since this is outside, I don't have a comp hooked up in order to check the serial monitor. And the disconnect is so sporadic that I can't catch it at the right time. I suspect reading a few other connection issue threads that the Watchdog may be maxing the memory after trying to connect repeatedly. So, I may look at turning the Watchdog off for this application and create my own functions to reconnect periodically. I have another project that I'm working on that I'm attempting to create as a low power, deep sleep device, but have found that IoT Cloud doesn't work well with this method and I believe these two issues (repeated connection attempts and Watchdog memory as well as Watchdog and IoT Cloud compatibility) are related. Hopefully I can create a workaround until this is fixed on the IoT side.
Reference to a WTD thread: