diff --git a/config/software/openssl.rb b/config/software/openssl.rb
index 1ee4c6627..5f0f2c2a3 100644
--- a/config/software/openssl.rb
+++ b/config/software/openssl.rb
@@ -24,13 +24,14 @@
 # For OpenSSL versions < 3, we have to compile FIPS separately
 dependency "openssl-fips" if (fips_mode? && version.satisfies?("< 3"))
 
-default_version "1.0.2zg" # do_not_auto_update
+default_version "3.0.9" # do_not_auto_update
 
 # Openssl builds engines as libraries into a special directory. We need to include
 # that directory in lib_dirs so omnibus can sign them during macOS deep signing.
-lib_dirs lib_dirs.concat(["#{install_dir}/embedded/lib/engines"])
-lib_dirs lib_dirs.concat(["#{install_dir}/embedded/lib/engines-1.1"]) if version.start_with?("1.1")
-if version.start_with?("3.")
+if version.start_with?("1.1")
+  lib_dirs lib_dirs.concat(["#{install_dir}/embedded/lib/engines"])
+  lib_dirs lib_dirs.concat(["#{install_dir}/embedded/lib/engines-1.1"])
+elsif version.start_with?("3.")
   lib_dirs lib_dirs.concat(["#{install_dir}/embedded/lib/engines-3"])
   lib_dirs lib_dirs.concat(["#{install_dir}/embedded/lib/ossl-modules"])
 end
@@ -312,7 +313,7 @@
     
         # add OPENSSL_FIPS to the environment _if_ fips is active
         fips_env=fips_mode? ? env.merge({"OPENSSL_FIPS" => "1"}) : env
-        command "#{ENV["OMNIBUS_TOOLCHAIN_INSTALL_DIR"]}/embedded/bin/gem install openssl-#{openssl_gem_version}.gem --no-document -- --with-openssl-dir=#{install_dir}/embedded/bin", env: fips_env
+        command "#{ENV["OMNIBUS_TOOLCHAIN_INSTALL_DIR"]}/embedded/bin/gem install openssl-#{openssl_gem_version}.gem --no-document -- --with-openssl-dir=#{install_dir}/embedded", env: fips_env
     
         command "#{ENV["OMNIBUS_TOOLCHAIN_INSTALL_DIR"]}/embedded/bin/gem info openssl"
         command "#{install_dir}/embedded/bin/openssl list -provider-path providers -provider fips -providers"
diff --git a/config/software/ruby-msys2-devkit.rb b/config/software/ruby-msys2-devkit.rb
index 1b66e0c55..8812bd64e 100644
--- a/config/software/ruby-msys2-devkit.rb
+++ b/config/software/ruby-msys2-devkit.rb
@@ -15,7 +15,7 @@
 #
 
 name "ruby-msys2-devkit"
-default_version "3.0.6-1"
+default_version "3.0.7-1"
 
 license "BSD-3-Clause"
 license_file "https://raw.githubusercontent.com/oneclick/rubyinstaller2/master/LICENSE.txt"
@@ -30,6 +30,11 @@
                   authorization: "X-JFrog-Art-Api:#{ENV["ARTIFACTORY_TOKEN"]}"
 end
 
+version "3.0.7-1" do
+  source url: "https://github.com/oneclick/rubyinstaller2/releases/download/RubyInstaller-#{version}/rubyinstaller-devkit-#{version}-x64.exe",
+          sha256: "fc1750a8203abd1c96b98cb76931224233650cb8d0e4f3d3b7996af045de1eef"
+end
+
 version "3.1.2-1" do
   source url: "https://github.com/oneclick/rubyinstaller2/releases/download/RubyInstaller-#{version}/rubyinstaller-devkit-#{version}-x64.exe",
           sha256: "5f0fd4a206b164a627c46e619d2babbcafb0ed4bc3e409267b9a73b6c58bdec1"
diff --git a/config/software/ruby.rb b/config/software/ruby.rb
index 816e4ca3b..2b1114b03 100644
--- a/config/software/ruby.rb
+++ b/config/software/ruby.rb
@@ -49,6 +49,7 @@
 version("3.1.2")      { source sha256: "61843112389f02b735428b53bb64cf988ad9fb81858b8248e22e57336f24a83e" }
 version("3.1.1")      { source sha256: "fe6e4782de97443978ddba8ba4be38d222aa24dc3e3f02a6a8e7701c0eeb619d" }
 
+version("3.0.7")      { source sha256: "fc1750a8203abd1c96b98cb76931224233650cb8d0e4f3d3b7996af045de1eef" }
 version("3.0.6")      { source sha256: "6e6cbd490030d7910c0ff20edefab4294dfcd1046f0f8f47f78b597987ac683e" }
 version("3.0.5")      { source sha256: "9afc6380a027a4fe1ae1a3e2eccb6b497b9c5ac0631c12ca56f9b7beb4848776" }
 version("3.0.4")      { source sha256: "70b47c207af04bce9acea262308fb42893d3e244f39a4abc586920a1c723722b" }