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Well, the no_proxy implementation is not really full featured. Here is a list of upstream RFE tickets which might be relevant:

https://bugs.ruby-lang.org/issues/10251
https://bugs.ruby-lang.org/issues/8317 (this included patch, you probably want to test it if it helps)
https://bugs.ruby-lang.org/issues/12062

So it seems upstream applied the patches from

https://bugs.ruby-lang.org/issues/8317
https://bugs.ruby-lang.org/issues/12062

as well. I requested backport to older versions as well:

https://bugs.ruby-lang.org/issues/12421

Would you mind to test which of the patches resolves the issues you describe above?

Since the problem described in this bug report should be
resolved in a recent advisory, it has been closed with a
resolution of ERRATA.

For information on the advisory, and where to find the updated
files, follow the link below.

If the solution does not work for you, open a new bug report.

https://rhn.redhat.com/errata/RHEA-2016-2422.html