VIM highlighting example: Emacs:
Similar issue:
That final end should be red, the color of the rest of the case keywords. The syntax stack on the end is: ['rubyCaseExpression', 'rubyArrayLiteral']. So vim somehow thinks the Array hasn't closed.
Ruby's heredoc highlighting pushes Vim's regexp based syntax highlighting to its limits. I would say it's unlikely issues of this nature are fixable.
VIM highlighting example:


Emacs: