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This is because the rackup file is eval'd
ruby -e 'eval("require_relative %[./mylib]")'
-e:1:in `eval': cannot infer basepath (LoadError)
from (eval):1:in `<main>'
from -e:1:in `eval'
from -e:1:in `<main>'
So, whats the solution for this?
Update your ruby version to 2.1.0. will be fixed.