Issue #10819 has been reported by Akio Tajima.

----------------------------------------
Bug #10819: can't glob win32 short pathname 
https://bugs.ruby-lang.org/issues/10819

* Author: Akio Tajima
* Status: Open
* Priority: Normal
* Assignee: 
* ruby -v: ruby 2.2.0p0 (2014-12-25 revision 49005) [x64-mswin64_100]
* Backport: 2.0.0: UNKNOWN, 2.1: UNKNOWN, 2.2: UNKNOWN
----------------------------------------
I used to install ruby under the "c:/program files" and use to apply windows short pathname such as "c:/progra~1" and it worked fine.
However, rubygems on ruby 2.2.0 failed to look up gemspec. After some investigation, I found that ruby 2.2.0 failed to glob with short pathname.

for ex) ruby -e 'p Dir.glob("c:/progra~1/*")' #=> [] 

Also I found that the inter glob string with shortname+wildcard also failed both Ruby 2.1.0 and 2.2.0.

for ex) ruby -e 'p Dir.glob("C:/progra~*/*")' #=> []

The testcase is below.

assert_equal Dir.glob('C:/Program Files*/m*').size, Dir.glob('c:/Progra~*/m*').size




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