I wonder what I can do to fix the Ruby Regex syntax highlighting when there are quotes in the Regex?
Here is where the problem is:

And compare it to the similar where there are no quotes:

(I’m already using the latest vim-ruby plugin).
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Actually it seems you have some problems with vim setup (or maybe outdated version of vim) — everything works fine for me. I have vim 7.3.346 packaged for Debian.
Standard ruby syntax files and syntax files from vim-ruby both do the job.
If updating is not an option or doesn’t help please attach output of :syntax and :script commands. Here is a hint how to simplify the proccess.