@dave45056 Well I figured this out on my own. I'll post this answer in case anyone is considering this combination. The Lutron MACL-153M is not a true 3-way switch. They call it a "Single pole/...

Does anyone know if the other switch in a 3 way config can be a smart-ish switch like the Lutron MACL-153M-WH. I'm having trouble making this work, but it would be ideal if it did as the other box...