I noticed if I removed my stylesheet import from my application.js webpack would compile correctly. Line 22 in my screenshot below.
What I realized was with Tailwindcss 1.0 I had an application.scss file but paying close attention to the docs and other examples online people were using the plain .css file extension for their application stylesheet.
After changing my file extension to .css everything fell into place and started to work.
I’m sure with if you need scss you can configure it to use scss, but for my use case I don’t need it.
I hope this helps!
Here are some links that helped me get to the bottom of this: