I've just successfully setup Ruby, Gems and RubySSPI under Cygwin and I am delighted to say that it seems to work flawlessly. There is one caveat though: the apply_sspi_patch applies a slightly dodgy path in the new http.rb. It generated this on line 2:
require 'net/net\http.orig.1'
whereas it should read like this:
require 'net/http.orig.1'
After making this change, I was able to run gems through ISA perfectly.
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RE: apply_sspi_patch and Cygwin [ reply ]