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As it stands several key gems cannot be upgraded because of version conflicts. Specifically, v4 of sinatra depends on rack (>= 3, < 4) and that conflicts with sprockets-sass. This is because DevDocs depends on sprockets-sass, but the latest version of that is only compatible with sprockets < 4 and finally sprockets 3.75 (the highest version compatible with sprockets-sass) requires rack <3.
In short, we can't upgrade sinatra or rack because there's no compatible version of sprockets-sass and that's unmaintained at this point.
Fork sprockets-sass and make it compatible with sprockets 4 (and Ruby 3)
Inline the imports and convert application.css.scss to application.css.scss.erb, which should work since the issue sprockets-sass solved was specifically @importing files, not compiling .erb files.
I'm not sure how long 1. would take. I looked into it, but I didn't make much headway.
Option 2. would be ugly, but not awful. Reason being, the imported files are not used more than once, so the code wouldn't get any less DRY. We would end up with one massive file, though.
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