diff --git a/configs/components/_base-ruby.rb b/configs/components/_base-ruby.rb
index a5d05f97d..1f9cd82dd 100644
--- a/configs/components/_base-ruby.rb
+++ b/configs/components/_base-ruby.rb
@@ -114,15 +114,32 @@
   [ "#{platform[:make]} -j$(shell expr $(shell #{platform[:num_cores]}) + 1) install" ]
 end
 
+# For the pdk runtime, the ruby bin directory is different then the main bin
+# directory. In order to run ruby *outside* of the normal pdk.bat then we need
+# to copy all dlls that ruby depends on from the main bin directory to ruby's
+# bin directory. This is because the main bin directory is not in our system
+# PATH and Windows doesn't support RPATH. However, as mentioned in
+# https://learn.microsoft.com/en-us/windows/win32/dlls/dynamic-link-library-search-order,
+# Windows searches for DLLs in "The folder the calling process was loaded from
+# (the executable's folder)."
+#
+# The agent runtime used to have the same issue prior to puppet 6, for example
+# RE-7593. However, Windows paths were changed to match *nix in puppet 6, see
+# commit 4b9d126dd5b. So only the pdk has this issue.
 if platform.is_windows? && settings[:bindir] != ruby_bindir
-  # As things stand right now, ssl should build under [INSTALLDIR]\Puppet\puppet on
-  # windows. However, if things need to run *outside* of the normal batch file runs
-  # (puppet.bat ,mco.bat etcc) the location of openssl away from where ruby is
-  # installed will cause a failure. Specifically this is meant to help services like
-  # mco that require openssl but don't have access to environment.bat. Refer to
-  # https://tickets.puppetlabs.com/browse/RE-7593 for details on why this causes
-  # failures and why these copies fix that.
-  #                   -Sean P. McDonald 07/01/2016
+  bindir = settings[:bindir]
+
+  # Ruby 3+
+  if Gem::Version.new(pkg.get_version) >= Gem::Version.new('3.0')
+    pkg.install do
+      [
+        "cp #{settings[:gcc_bindir]}/libssp-0.dll #{ruby_bindir}",
+        "cp #{bindir}/libffi-8.dll #{ruby_bindir}",
+        "cp #{bindir}/libyaml-0-2.dll #{ruby_bindir}"
+      ]
+    end
+  end
+
   if platform.architecture == "x64"
     gcc_postfix = 'seh'
     ssl_postfix = '-x64'
@@ -131,6 +148,7 @@
     ssl_postfix = ''
   end
 
+  # OpenSSL
   if Gem::Version.new(settings[:openssl_version]) >= Gem::Version.new('3.0')
     ssl_lib = "libssl-3#{ssl_postfix}.dll"
     crypto_lib = "libcrypto-3#{ssl_postfix}.dll"
@@ -144,9 +162,9 @@
 
   pkg.install do
     [
-      "cp #{settings[:bindir]}/libgcc_s_#{gcc_postfix}-1.dll #{ruby_bindir}",
-      "cp #{settings[:bindir]}/#{ssl_lib} #{ruby_bindir}",
-      "cp #{settings[:bindir]}/#{crypto_lib} #{ruby_bindir}",
+      "cp #{bindir}/libgcc_s_#{gcc_postfix}-1.dll #{ruby_bindir}",
+      "cp #{bindir}/#{ssl_lib} #{ruby_bindir}",
+      "cp #{bindir}/#{crypto_lib} #{ruby_bindir}"
     ]
   end
 
diff --git a/configs/components/runtime-pdk.rb b/configs/components/runtime-pdk.rb
index 92645efaf..d3e60783a 100644
--- a/configs/components/runtime-pdk.rb
+++ b/configs/components/runtime-pdk.rb
@@ -7,26 +7,30 @@
       pkg.install_file File.join(settings[:gcc_bindir], dll), File.join(settings[:bindir], dll)
     end
 
-    # Ruby needs zlib
+    tools_bindir = File.join(settings[:tools_root], 'bin')
+
+    # curl, openssl, etc need zlib, so install in *main* bin dir
     pkg.build_requires "pl-zlib-#{platform.architecture}"
-    pkg.install_file "#{settings[:tools_root]}/bin/zlib1.dll", "#{settings[:bindir]}/zlib1.dll"
+    pkg.install_file "#{tools_bindir}/zlib1.dll", "#{settings[:bindir]}/zlib1.dll"
 
     # zlib, gdbm, yaml-cpp and iconv are all runtime dependancies of ruby, and their libraries need
-    # To exist inside our vendored ruby
-    pkg.install_file "#{settings[:tools_root]}/bin/zlib1.dll", "#{settings[:ruby_bindir]}/zlib1.dll"
-    pkg.install_file "#{settings[:tools_root]}/bin/libgdbm-4.dll", "#{settings[:ruby_bindir]}/libgdbm-4.dll"
-    pkg.install_file "#{settings[:tools_root]}/bin/libgdbm_compat-4.dll", "#{settings[:ruby_bindir]}/libgdbm_compat-4.dll"
-    pkg.install_file "#{settings[:tools_root]}/bin/libiconv-2.dll", "#{settings[:ruby_bindir]}/libiconv-2.dll"
-    pkg.install_file "#{settings[:tools_root]}/bin/libffi-6.dll", "#{settings[:ruby_bindir]}/libffi-6.dll"
+    # to exist inside our primary ruby's bin dir
+    ruby_bindir = settings[:ruby_bindir]
+    pkg.install_file "#{tools_bindir}/zlib1.dll",            "#{ruby_bindir}/zlib1.dll"
+    pkg.install_file "#{tools_bindir}/libgdbm-4.dll",        "#{ruby_bindir}/libgdbm-4.dll"
+    pkg.install_file "#{tools_bindir}/libgdbm_compat-4.dll", "#{ruby_bindir}/libgdbm_compat-4.dll"
+    pkg.install_file "#{tools_bindir}/libiconv-2.dll",       "#{ruby_bindir}/libiconv-2.dll"
+    pkg.install_file "#{tools_bindir}/libffi-6.dll",         "#{ruby_bindir}/libffi-6.dll" if settings[:ruby_version].start_with?('2')
 
     # Copy the DLLs into additional ruby install bindirs as well.
     if settings.has_key?(:additional_rubies)
       settings[:additional_rubies].each do |rubyver, local_settings|
-        pkg.install_file "#{settings[:tools_root]}/bin/zlib1.dll", "#{local_settings[:ruby_bindir]}/zlib1.dll"
-        pkg.install_file "#{settings[:tools_root]}/bin/libgdbm-4.dll", "#{local_settings[:ruby_bindir]}/libgdbm-4.dll"
-        pkg.install_file "#{settings[:tools_root]}/bin/libgdbm_compat-4.dll", "#{local_settings[:ruby_bindir]}/libgdbm_compat-4.dll"
-        pkg.install_file "#{settings[:tools_root]}/bin/libiconv-2.dll", "#{local_settings[:ruby_bindir]}/libiconv-2.dll"
-        pkg.install_file "#{settings[:tools_root]}/bin/libffi-6.dll", "#{local_settings[:ruby_bindir]}/libffi-6.dll"
+        local_bindir = local_settings[:ruby_bindir]
+        pkg.install_file "#{tools_bindir}/zlib1.dll",            "#{local_bindir}/zlib1.dll"
+        pkg.install_file "#{tools_bindir}/libgdbm-4.dll",        "#{local_bindir}/libgdbm-4.dll"
+        pkg.install_file "#{tools_bindir}/libgdbm_compat-4.dll", "#{local_bindir}/libgdbm_compat-4.dll"
+        pkg.install_file "#{tools_bindir}/libiconv-2.dll",       "#{local_bindir}/libiconv-2.dll"
+        pkg.install_file "#{tools_bindir}/libffi-6.dll",         "#{local_bindir}/libffi-6.dll" if rubyver.start_with?('2')
       end
     end
 
diff --git a/configs/projects/_pdk-components.rb b/configs/projects/_pdk-components.rb
index fed6339f0..8d347e202 100644
--- a/configs/projects/_pdk-components.rb
+++ b/configs/projects/_pdk-components.rb
@@ -25,12 +25,6 @@
 proj.component 'libxslt' unless platform.is_windows?
 proj.component "ruby-#{proj.ruby_version}"
 
-# After installing ruby, we need to copy libssp to the ruby bindir on windows
-if platform.is_windows?
-  ruby_component = @project.get_component "ruby-#{proj.ruby_version}"
-  ruby_component.install.push "cp '#{settings[:bindir]}/libssp-0.dll' '#{settings[:ruby_bindir]}/libssp-0.dll'"
-end
-
 proj.component 'ruby-augeas' unless platform.is_windows?
 proj.component 'ruby-selinux' if platform.is_el? || platform.is_fedora?
 proj.component 'ruby-stomp'