Workaround:
$ sudo gem install rubyzip -v "~> 2.0"

Package: evil-winrm

Version: evil-winrm/kali-rolling,now 3.9-0kali2 (installed via APT)

Symptom:
$ evil-winrm -i ..... -u .... -p ...
/usr/lib/ruby/vendor_ruby/rubygems/specification.rb:1421:in block in activate_dependencies': Could not find 'rubyzip' (~> 2.0) among 150 total gem(s) (Gem::MissingSpecError) Checked in 'GEM_PATH=/home/kali/.local/share/gem/ruby/3.3.0:/var/lib/gems/3.3.0:/usr/local/lib/ruby/gems/3.3.0:/usr/lib/ruby/gems/3.3.0:/usr/lib/x86_64-linux-gnu/ruby/gems/3.3.0:/usr/share/rubygems-integration/3.3.0:/usr/share/rubygems-integration/all:/usr/lib/x86_64-linux-gnu/rubygems-integration/3.3.0' at: /usr/share/rubygems-integration/all/specifications/winrm-fs-1.3.5.gemspec, executegem envfor more information from /usr/lib/ruby/vendor_ruby/rubygems/specification.rb:1407:ineach'
from /usr/lib/ruby/vendor_ruby/rubygems/specification.rb:1407:in activate_dependencies' from /usr/lib/ruby/vendor_ruby/rubygems/specification.rb:1389:inactivate'
from /usr/lib/ruby/vendor_ruby/rubygems/specification.rb:1423:in block in activate_dependencies' from /usr/lib/ruby/vendor_ruby/rubygems/specification.rb:1407:ineach'
from /usr/lib/ruby/vendor_ruby/rubygems/specification.rb:1407:in activate_dependencies' from /usr/lib/ruby/vendor_ruby/rubygems/specification.rb:1389:inactivate'
from /usr/lib/ruby/vendor_ruby/rubygems.rb:290:in block in activate_bin_path' from /usr/lib/ruby/vendor_ruby/rubygems.rb:289:insynchronize'
from /usr/lib/ruby/vendor_ruby/rubygems.rb:289:in activate_bin_path' from /usr/bin/evil-winrm:25:in<main>'

Dependencies before workaround: rubyzip 3.2.2 (too new)
Dependencies after workaround:
$ gem list rubyzip

LOCAL GEMS

rubyzip (3.2.2, 2.4.1)

uname -a output: Linux kali 6.18.9+kali-amd64 0000001 SMP PREEMPT_DYNAMIC Kali 6.18.9-1kali1 (2026-02-10) x86_64 GNU/Linux

C Library Version: 2.42-5