I am not sure if this is a driver issue, using the T3 to T2 adapter, or something else. However, Monitor 1 is being detected because my Ethernet will USB peripherals show up and work. If I connect Monitor 2 to the MacBook and Monitor 1 to Monitor 2, I will get a display on Monitor 2 but not Monitor 1. Monitor 1 also has Ethernet and USB peripherals connected. My current setup is Monitor 1 connects to the MacBook and Monitor 2 connects to Monitor 1. Switching which monitor plugs into the laptop vs the other monitor (see below).
Plugged each monitor in individually (each one works fine). However, if I reboot into Windows 10 then my second Thunderbolt display does not show up and Windows cannot see it. Under macOS, both Thunderbolt displays and the internal laptop display are detected and show up normal. I recently upgraded to a 2018 MacBook Pro 15' with Touch Bar and purchased the Apple Thunderbolt 3 to Thunderbolt 2 adapter to be able to connect the monitors. My Boot Camp install runs just fine with both displays detected and working within Windows. My old setup was a 2015 MacBook Pro 15' with two Apple Thunderbolt Displays daisy chained together. So I have an odd problem and cannot seem to find anyone else that has the same issue.
