diff --git a/.github/workflows/delivery.yml b/.github/workflows/delivery.yml
index dd0d3cfcc..63d6d678b 100644
--- a/.github/workflows/delivery.yml
+++ b/.github/workflows/delivery.yml
@@ -6,7 +6,7 @@ jobs:
   commit-compile:
     name: Commit - Compile
     if: ${{ github.ref_type == 'branch' }}
-    runs-on: ubuntu-latest
+    runs-on: ${{ matrix.operating-system }}-latest
     steps:
       - name: Checkout Repository
         uses: actions/checkout@v3
@@ -16,43 +16,50 @@ jobs:
           ruby-version: '${{ matrix.ruby-version }}'
           bundler: '2.4'
           bundler-cache: true
+          cache-version: '1-os-${{ matrix.operating-system }}-rv-${{ matrix.ruby-version }}'
       - name: Upload Bundler Lockfile
         uses: actions/upload-artifact@v3
         with:
-          name: bundler-lockfile-ruby-${{ matrix.ruby-version }}
+          name: bundler-lockfile-os-${{ matrix.operating-system }}-rv-${{ matrix.ruby-version }}
           path: gems.locked
           if-no-files-found: error
     strategy:
       fail-fast: false
       matrix:
-        ruby-version:
-          - '2.7'
-          - '3.0'
-          - '3.1'
+        include:
+          - operating-system: ubuntu
+            ruby-version: '2.7'
+          - operating-system: ubuntu
+            ruby-version: '3.0'
+          - operating-system: ubuntu
+            ruby-version: '3.1'
+          - operating-system: windows
+            ruby-version: '3.1'
   commit-unit-test:
     name: Commit - Unit Test
     needs:
       - commit-compile
     if: ${{ github.ref_type == 'branch' }}
-    runs-on: ubuntu-latest
+    runs-on: ${{ matrix.operating-system }}-latest
     steps:
       - name: Checkout Repository
         uses: actions/checkout@v3
       - name: Download Bundler Lockfile
         uses: actions/download-artifact@v3
         with:
-          name: bundler-lockfile-ruby-${{ matrix.ruby-version }}
+          name: bundler-lockfile-os-${{ matrix.operating-system }}-rv-${{ matrix.ruby-version }}
       - name: Setup Ruby
         uses: ruby/setup-ruby@v1
         with:
           ruby-version: '${{ matrix.ruby-version }}'
           bundler: '2.4'
           bundler-cache: true
+          cache-version: '1-os-${{ matrix.operating-system }}-rv-${{ matrix.ruby-version }}'
       - name: Run RSpec Tests
-        if: ${{ matrix.ruby-version != '3.1' }}
+        if: ${{ !matrix.code-coverage }}
         run: bundle exec rake test:rspec
       - name: Run RSpec Tests with Code Coverage
-        if: ${{ matrix.ruby-version == '3.1' }}
+        if: ${{ matrix.code-coverage }}
         uses: paambaati/codeclimate-action@v3.2.0
         env:
           CC_TEST_REPORTER_ID: 7574433e1beed630cb9a171c688bb9e010d5028f00f7218d6e845fe138c65168
@@ -61,10 +68,19 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        ruby-version:
-          - '2.7'
-          - '3.0'
-          - '3.1'
+        include:
+          - code-coverage: false
+            operating-system: ubuntu
+            ruby-version: '2.7'
+          - code-coverage: false
+            operating-system: ubuntu
+            ruby-version: '3.0'
+          - code-coverage: true
+            operating-system: ubuntu
+            ruby-version: '3.1'
+          - code-coverage: false
+            operating-system: windows
+            ruby-version: '3.1'
   commit-assemble:
     name: Commit - Assemble
     needs:
@@ -77,13 +93,14 @@ jobs:
       - name: Download Bundler Lockfile
         uses: actions/download-artifact@v3
         with:
-          name: bundler-lockfile-ruby-3.1
+          name: bundler-lockfile-os-ubuntu-rv-3.1
       - name: Setup Ruby
         uses: ruby/setup-ruby@v1
         with:
           ruby-version: '3.1'
           bundler: '2.4'
           bundler-cache: true
+          cache-version: '1-os-ubuntu-rv-3.1'
       - name: Build Ruby Gem
         env:
           GEM_PRIVATE_KEY: ${{ secrets.GEM_PRIVATE_KEY }}
diff --git a/spec/lib/kitchen/driver/terraform_spec.rb b/spec/lib/kitchen/driver/terraform_spec.rb
index 3fdc60cd0..4f9f69e87 100644
--- a/spec/lib/kitchen/driver/terraform_spec.rb
+++ b/spec/lib/kitchen/driver/terraform_spec.rb
@@ -50,7 +50,6 @@
     ::Kitchen::Instance.new(
       driver: subject,
       lifecycle_hooks: ::Kitchen::LifecycleHooks.new(config, state_file),
-      logger: ::Kitchen::Logger.new,
       platform: ::Kitchen::Platform.new(name: "test-platform"),
       provisioner: ::Kitchen::Provisioner::Base.new,
       state_file: state_file,
diff --git a/spec/lib/kitchen/provisioner/terraform_spec.rb b/spec/lib/kitchen/provisioner/terraform_spec.rb
index 6b5a35009..36df0f726 100644
--- a/spec/lib/kitchen/provisioner/terraform_spec.rb
+++ b/spec/lib/kitchen/provisioner/terraform_spec.rb
@@ -50,7 +50,6 @@
     ::Kitchen::Instance.new(
       driver: driver,
       lifecycle_hooks: ::Kitchen::LifecycleHooks.new(config, state_file),
-      logger: logger,
       platform: ::Kitchen::Platform.new(name: "test-platform"),
       provisioner: subject,
       state_file: state_file,
@@ -70,7 +69,7 @@
         config: driver_config,
         connection: kind_of(::Kitchen::Terraform::Transport::Connection),
         debug_connection: kind_of(::Kitchen::Terraform::Transport::Connection),
-        logger: logger,
+        logger: ::Kitchen.logger,
         version_requirement: kind_of(::Gem::Requirement),
         workspace_name: kind_of(::String),
       ).and_return(converge)
diff --git a/spec/lib/kitchen/terraform/driver/create_spec.rb b/spec/lib/kitchen/terraform/driver/create_spec.rb
index 09b251734..47edbf1c1 100644
--- a/spec/lib/kitchen/terraform/driver/create_spec.rb
+++ b/spec/lib/kitchen/terraform/driver/create_spec.rb
@@ -29,7 +29,7 @@
     described_class.new(
       config: config,
       connection: connection,
-      logger: logger,
+      logger: ::Kitchen.logger,
       workspace_name: double(::String),
       version_requirement: ::Gem::Requirement.new(">= 0.1.0"),
     )
diff --git a/spec/lib/kitchen/terraform/driver/destroy_spec.rb b/spec/lib/kitchen/terraform/driver/destroy_spec.rb
index 398af18eb..036bc6b7b 100644
--- a/spec/lib/kitchen/terraform/driver/destroy_spec.rb
+++ b/spec/lib/kitchen/terraform/driver/destroy_spec.rb
@@ -31,7 +31,7 @@
     described_class.new(
       config: config,
       connection: connection,
-      logger: logger,
+      logger: ::Kitchen.logger,
       workspace_name: "test-workspace",
       version_requirement: ::Gem::Requirement.new(">= 0.1.0"),
     )
diff --git a/spec/lib/kitchen/terraform/inspec_runner_spec.rb b/spec/lib/kitchen/terraform/inspec_runner_spec.rb
index e295a1106..2b03e5845 100644
--- a/spec/lib/kitchen/terraform/inspec_runner_spec.rb
+++ b/spec/lib/kitchen/terraform/inspec_runner_spec.rb
@@ -24,15 +24,15 @@
 
   describe ".logger=" do
     before do
-      described_class.logger = logger
+      described_class.logger = ::Kitchen.logger
     end
 
     specify "should extend the logger interface to be compatible with InSpec" do
-      expect(logger.logdev.filename).to be false
+      expect(::Kitchen.logger.logdev.filename).to be false
     end
 
     specify "should set the Inspec logger" do
-      expect(::Inspec::Log.logger).to be logger
+      expect(::Inspec::Log.logger).to be ::Kitchen.logger
     end
   end
 
@@ -42,7 +42,7 @@
     end
 
     let :full_options do
-      { key: "value", logger: logger }
+      { key: "value", logger: ::Kitchen.logger }
     end
 
     let :loader do
@@ -67,7 +67,7 @@
       allow(loader).to receive :exit_on_load_error
       allow(::Inspec::Runner).to receive(:new).with(full_options).and_return runner
       allow(runner).to receive(:add_target).with profile_location
-      described_class.logger = logger
+      described_class.logger = ::Kitchen.logger
     end
 
     context "when the InSpec runner raises an error and a host is not targeted" do
@@ -84,7 +84,7 @@
 
     context "when the InSpec runner raises an error and a host is targeted" do
       let :full_options do
-        { host: "test", key: "value", logger: logger }
+        { host: "test", key: "value", logger: ::Kitchen.logger }
       end
 
       let :options do
diff --git a/spec/lib/kitchen/terraform/provisioner/converge_spec.rb b/spec/lib/kitchen/terraform/provisioner/converge_spec.rb
index 80a9ea587..052a09437 100644
--- a/spec/lib/kitchen/terraform/provisioner/converge_spec.rb
+++ b/spec/lib/kitchen/terraform/provisioner/converge_spec.rb
@@ -35,7 +35,7 @@
       config: config,
       connection: connection,
       debug_connection: debug_connection,
-      logger: logger,
+      logger: ::Kitchen.logger,
       workspace_name: "test-workspace",
       version_requirement: ::Gem::Requirement.new(">= 0.1.0"),
     )
diff --git a/spec/lib/kitchen/terraform/system_spec.rb b/spec/lib/kitchen/terraform/system_spec.rb
index fd48c5941..ef2b2269f 100644
--- a/spec/lib/kitchen/terraform/system_spec.rb
+++ b/spec/lib/kitchen/terraform/system_spec.rb
@@ -23,7 +23,7 @@
 
 ::RSpec.describe ::Kitchen::Terraform::System do
   subject do
-    described_class.new configuration_attributes: configuration_attributes, logger: logger
+    described_class.new configuration_attributes: configuration_attributes, logger: ::Kitchen.logger
   end
 
   include_context "Kitchen::Logger"
diff --git a/spec/lib/kitchen/terraform/transport/connection_spec.rb b/spec/lib/kitchen/terraform/transport/connection_spec.rb
index a06917753..f834ceb2b 100644
--- a/spec/lib/kitchen/terraform/transport/connection_spec.rb
+++ b/spec/lib/kitchen/terraform/transport/connection_spec.rb
@@ -40,11 +40,22 @@
     instance_double ::String
   end
 
+  let :instance_name do
+    instance_double ::String
+  end
+
+  let :kitchen_root do
+    # kitchen_root must support implicit string conversion
+    "test-kitchen-root"
+  end
+
   let :options do
     {
       client: client,
       command_timeout: command_timeout,
       environment: { environment_variable_key => environment_variable_value },
+      instance_name: instance_name,
+      kitchen_root: kitchen_root,
       root_module_directory: root_module_directory,
     }
   end
@@ -63,10 +74,8 @@
     end
 
     specify "should invoke the ShellOut superclass implementation with the client and options configured" do
-      allow(shell_out).to receive :run_command
-      allow(shell_out).to receive :execution_time
-      allow(shell_out).to receive :error!
-      allow(shell_out).to receive(:stdout).and_return :superclass
+      allow(subject).to receive(:run_from_file_command).with("#{client} #{command}").and_return "#{client} #{command}"
+      allow(subject).to receive :close
       allow(::Mixlib::ShellOut).to receive(:new).with(
         "#{client} #{command}",
         including({
@@ -80,7 +89,12 @@
         })
       ).and_return shell_out
 
-      expect(subject.execute(command)).to eq :superclass
+      expect(shell_out).to receive :run_command
+      expect(shell_out).to receive :execution_time
+      expect(shell_out).to receive :error!
+      expect(shell_out).to receive :stdout
+
+      subject.execute command
     end
   end
 end
diff --git a/spec/lib/kitchen/terraform/verify_version_rescue_strategy/permissive_spec.rb b/spec/lib/kitchen/terraform/verify_version_rescue_strategy/permissive_spec.rb
index 22f3e45a6..3e44d273a 100644
--- a/spec/lib/kitchen/terraform/verify_version_rescue_strategy/permissive_spec.rb
+++ b/spec/lib/kitchen/terraform/verify_version_rescue_strategy/permissive_spec.rb
@@ -20,14 +20,14 @@
 
 ::RSpec.describe ::Kitchen::Terraform::VerifyVersionRescueStrategy::Permissive do
   subject do
-    described_class.new logger: logger
+    described_class.new logger: ::Kitchen.logger
   end
 
   include_context "Kitchen::Logger"
 
   describe "#call" do
     specify "should warn the user that the Terraform client version is unsupported" do
-      expect(logger).to receive :warn
+      expect(::Kitchen.logger).to receive :warn
     end
 
     after do
diff --git a/spec/lib/kitchen/terraform/verify_version_spec.rb b/spec/lib/kitchen/terraform/verify_version_spec.rb
index bab5fe3b3..2475caee3 100644
--- a/spec/lib/kitchen/terraform/verify_version_spec.rb
+++ b/spec/lib/kitchen/terraform/verify_version_spec.rb
@@ -24,7 +24,7 @@
   subject do
     described_class.new(
       config: config,
-      logger: logger,
+      logger: ::Kitchen.logger,
       version_requirement: version_requirement,
     )
   end
diff --git a/spec/lib/kitchen/transport/terraform_spec.rb b/spec/lib/kitchen/transport/terraform_spec.rb
index 29b71e407..f62adbf24 100644
--- a/spec/lib/kitchen/transport/terraform_spec.rb
+++ b/spec/lib/kitchen/transport/terraform_spec.rb
@@ -37,7 +37,6 @@
     ::Kitchen::Instance.new(
       driver: ::Kitchen::Driver::Base.new,
       lifecycle_hooks: ::Kitchen::LifecycleHooks.new(config, state_file),
-      logger: logger,
       platform: ::Kitchen::Platform.new(name: "test-platform"),
       provisioner: ::Kitchen::Provisioner::Base.new,
       state_file: state_file,
diff --git a/spec/lib/kitchen/verifier/terraform_spec.rb b/spec/lib/kitchen/verifier/terraform_spec.rb
index 6cfc09402..2a264e08b 100644
--- a/spec/lib/kitchen/verifier/terraform_spec.rb
+++ b/spec/lib/kitchen/verifier/terraform_spec.rb
@@ -89,7 +89,6 @@
     ::Kitchen::Instance.new(
       driver: ::Kitchen::Driver::Base.new,
       lifecycle_hooks: ::Kitchen::LifecycleHooks.new(config, state_file),
-      logger: logger,
       platform: ::Kitchen::Platform.new(name: "test-platform"),
       provisioner: ::Kitchen::Provisioner::Base.new,
       state_file: state_file,
diff --git a/spec/spec_helper.rb b/spec/spec_helper.rb
index 0427ea6e3..df8f3dd17 100644
--- a/spec/spec_helper.rb
+++ b/spec/spec_helper.rb
@@ -26,7 +26,7 @@
     expect_configuration.max_formatted_output_length = nil
   end
 
-  configuration.fail_fast = true
+  configuration.fail_fast = false
 
   configuration.mock_with :rspec do |mocks|
     mocks.verify_doubled_constant_names = true
diff --git a/spec/support/kitchen/logger_context.rb b/spec/support/kitchen/logger_context.rb
index ba46dbf92..df7ac26bc 100644
--- a/spec/support/kitchen/logger_context.rb
+++ b/spec/support/kitchen/logger_context.rb
@@ -17,7 +17,7 @@
 require "kitchen/logger"
 
 ::RSpec.shared_context "Kitchen::Logger" do
-  let :logger do
-    ::Kitchen::Logger.new stdout: ::File.open(::File::NULL, "w")
+  before do
+    ::Kitchen.logger = ::Kitchen::Logger.new stdout: ::File.open(::File::NULL, "w")
   end
 end
diff --git a/spec/support/kitchen/terraform/config_attribute/client_examples.rb b/spec/support/kitchen/terraform/config_attribute/client_examples.rb
index 010f26a35..613aef814 100644
--- a/spec/support/kitchen/terraform/config_attribute/client_examples.rb
+++ b/spec/support/kitchen/terraform/config_attribute/client_examples.rb
@@ -88,7 +88,10 @@
 
     context "when the configured client does exist and is executable" do
       let :value do
-        $0
+        file = ::Tempfile.new ["client", ".exe"]
+        file.chmod 0777
+
+        file
       end
 
       specify "should return false" do
diff --git a/spec/support/kitchen/terraform/config_attribute/systems_examples.rb b/spec/support/kitchen/terraform/config_attribute/systems_examples.rb
index f6656e1f3..d5c69601c 100644
--- a/spec/support/kitchen/terraform/config_attribute/systems_examples.rb
+++ b/spec/support/kitchen/terraform/config_attribute/systems_examples.rb
@@ -14,11 +14,15 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
+require "support/kitchen/logger_context"
+
 ::RSpec.shared_examples "Kitchen::Terraform::ConfigAttribute::Systems" do
   subject do
     described_class.new config
   end
 
+  include_context "Kitchen::Logger"
+
   let :config do
     {
       kitchen_root: "kitchen_root",
@@ -50,7 +54,10 @@
 
     context "when the configured systems are not empty" do
       before do
-        config.store :systems, [::Kitchen::Terraform::System.new(configuration_attributes: {}, logger: logger)]
+        config.store(
+          :systems,
+          [::Kitchen::Terraform::System.new(configuration_attributes: {}, logger: ::Kitchen.logger)]
+        )
       end
 
       specify "should return false" do