Combination of Regexp encoding options and forced encodings (I suppose) should lead to the SyntaxError:
# encoding: us-ascii
p /\xFF/u.encoding
ruby script.rb
script.rb: --> script.rb
invalid multibyte escape: /\xFF/
> 3 p /\xFF/u.encoding
script.rb:3: invalid multibyte escape: /\xFF/ (SyntaxError)