diff --git a/.github/workflows/runtime_tests.yml b/.github/workflows/runtime_tests.yml
index 8830ab10..f3163047 100644
--- a/.github/workflows/runtime_tests.yml
+++ b/.github/workflows/runtime_tests.yml
@@ -32,7 +32,7 @@ jobs:
         run: |
           stat=0
           for projfile in configs/projects/[a-z]*.rb; do
-            for plat in el-8-x86_64 ubuntu-22.04-amd64 windows-2019-x64; do
+            for plat in el-8-x86_64 ubuntu-22.04-amd64 windows-all-x64; do
               proj=$(basename -s .rb "$projfile")
               if [[ "$proj" =~ ^pe- && "$plat" =~ ^(windows|osx) ]]; then
                 echo Skipping ${proj} on ${plat}, PE projects don\'t support Windows or macOS
diff --git a/configs/components/ruby-3.2.rb b/configs/components/ruby-3.2.rb
index 9d88d7d6..16dec74e 100644
--- a/configs/components/ruby-3.2.rb
+++ b/configs/components/ruby-3.2.rb
@@ -158,10 +158,7 @@
     'sles-12-ppc64le',
     'solaris-11-sparc',
     'solaris-113-sparc',
-    'windows-2012r2-x64',
-    'windows-2012r2-x86',
-    'windows-2019-x64',
-    'windowsfips-2012r2-x64',
+    'windows-all-x64',
     'windowsfips-2016-x64'
   ]
 
diff --git a/configs/platforms/windows-2019-x64.rb b/configs/platforms/windows-all-x64.rb
similarity index 97%
rename from configs/platforms/windows-2019-x64.rb
rename to configs/platforms/windows-all-x64.rb
index e02a8bff..e6e9d664 100644
--- a/configs/platforms/windows-2019-x64.rb
+++ b/configs/platforms/windows-all-x64.rb
@@ -1,4 +1,4 @@
-platform "windows-2019-x64" do |plat|
+platform "windows-all-x64" do |plat|
   plat.vmpooler_template "win-2019-x86_64"
   
   # Not currently used
diff --git a/resources/patches/.DS_Store b/resources/patches/.DS_Store
new file mode 100644
index 00000000..bac731c9
Binary files /dev/null and b/resources/patches/.DS_Store differ
diff --git a/setup.bat b/setup.bat
deleted file mode 100644
index 7ccdd4d3..00000000
--- a/setup.bat
+++ /dev/null
@@ -1 +0,0 @@
-C:\setup-x86_64.exe -q -P ruby,ruby-devel,gcc-core,make,git,libyaml-devel
diff --git a/setup.ps1 b/setup.ps1
new file mode 100644
index 00000000..9ef2e0d7
--- /dev/null
+++ b/setup.ps1
@@ -0,0 +1,4 @@
+$url="https://cygwin.com/setup-x86_64.exe"
+$dest="C:\setup-x86_64.exe"
+Invoke-WebRequest -Uri $url -OutFile $dest
+cmd /c "C:\setup-x86_64.exe -s https://cygwin.osuosl.org -q -P ruby,ruby-devel,gcc-core,make,git,libyaml-devel"
diff --git a/tasks/upload.rake b/tasks/upload.rake
index c564eb3f..4a28925e 100644
--- a/tasks/upload.rake
+++ b/tasks/upload.rake
@@ -16,12 +16,12 @@ namespace :vox do
     # Ensure the AWS CLI isn't going to fail with the given parameters
     run_command("#{s3} ls s3://#{bucket}/")
 
-    prepend = File.directory?('/cygdrive/') ? 'C:/cygwin64/' : ''
-    files = Dir.glob("#{prepend}#{__dir__}/../output/*#{munged_tag}*#{platform}*")
-    puts 'No files for the given tag found in the output directory.' if files.empty?
+    files = Dir.glob("#{__dir__}/../output/*#{munged_tag}*#{platform}*")
+    abort 'No files for the given tag found in the output directory.' if files.empty?
 
     path = "s3://#{bucket}/#{repo}/#{args[:tag]}"
     files.each do |f|
+      f = `cygpath -m #{f}`.chomp if platform =~ /windows-/
       run_command("#{s3} cp #{f} #{path}/#{File.basename(f)}", silent: false)
     end
   end