diff --git a/.github/workflows/tests.yml b/.github/workflows/tests.yml
index c31c1915..d3a86cd7 100644
--- a/.github/workflows/tests.yml
+++ b/.github/workflows/tests.yml
@@ -4,38 +4,49 @@ on: [push, pull_request]
 
 jobs:
   Tests:
-    runs-on: ubuntu-18.04
+    runs-on: ubuntu-20.04
     strategy:
+      fail-fast: false
       matrix:
         os:
         - centos
         - debian
-        - ubuntu-16
-        - ubuntu-18
+        - ubuntu
     steps:
     - uses: actions/checkout@v2
+
+    - name: Set Python Cache Key
+      run: echo "PY=$(python --version --version | sha256sum | cut -d' ' -f1)" >> $GITHUB_ENV
+
     - uses: actions/cache@v2
       with:
         path: |
           bundle
           virtualenv
-        key: Tests-${{ matrix.os }}-${{ hashFiles('Gemfile', 'test-requirements.txt') }}
+        key: Tests-${{ matrix.os }}-${{ env.PY }}-${{ hashFiles('Gemfile', 'test-requirements.txt') }}
+
     - name: Install System Deps
       run: |
         sudo apt-get update
         sudo apt-get install -y curl git python3-pip ruby-dev ruby-bundler shellcheck virtualenv
+
     - name: Install Python Deps
       run: |
         if [ ! -e virtualenv/bin/activate ]; then /usr/bin/virtualenv -p /usr/bin/python3 virtualenv; fi
         . virtualenv/bin/activate
         pip3 install -U -r test-requirements.txt
+
     - name: Install Ruby Deps
       run: |
-        /usr/bin/bundle install --without vagrant windows --path bundle
+        /usr/bin/bundle config set --local path 'bundle'
+        /usr/bin/bundle config set --local without 'vagrant windows'
+        /usr/bin/bundle install
+
     - name: Install GPG Key
       run: |
         install -d -m 700 gpgkeys
         gpg --no-default-keyring --homedir gpgkeys --import < tests/gpgkeys/test.txt
+
     - name: Test
       run: |
         . virtualenv/bin/activate
@@ -43,6 +54,7 @@ jobs:
         shellcheck assets/*.sh*
         LANG=en_US.UTF-8 /usr/bin/bundle exec rake "integration:verify[${{ matrix.os }}]"
         /usr/bin/bundle exec kitchen list ${{ matrix.os }}
+
     - name: Cleanup
       run: |
         /usr/bin/bundle exec rake "integration:destroy[${{ matrix.os }}]"
diff --git a/.kitchen.yml b/.kitchen.yml
index 1ea777a1..98673648 100644
--- a/.kitchen.yml
+++ b/.kitchen.yml
@@ -86,20 +86,11 @@ platforms:
         sudo apt-get update
         DEBIAN_FRONTEND=noninteractive sudo apt-get install -y software-properties-common
       salt_bootstrap_options: -X -x python3 -p git -p curl -p sudo -p software-properties-common stable 3000.6
-  - name: ubuntu-16.04
+  - name: debian-10
     provisioner:
-      salt_apt_repo: 'https://repo.saltproject.io/py3/ubuntu/16.04/amd64/archive'
-      salt_apt_repo_key: 'https://repo.saltproject.io/py3/ubuntu/16.04/amd64/latest/SALTSTACK-GPG-KEY.pub'
-      init_environment: |
-        sudo mkdir -p /tmp/kitchen/var/cache/salt/master
-        sudo apt-get update
-        DEBIAN_FRONTEND=noninteractive sudo apt-get install -y software-properties-common
-      salt_bootstrap_options: -X -x python3 -p git -p curl -p sudo -p software-properties-common stable 3000.6
-  - name: debian-9
-    provisioner:
-      salt_apt_repo: 'https://repo.saltproject.io/py3/debian/9/amd64/archive'
-      salt_apt_repo_key: 'https://repo.saltproject.io/py3/debian/9/amd64/latest/SALTSTACK-GPG-KEY.pub'
-  - name: centos-7
+      salt_apt_repo: 'https://repo.saltproject.io/py3/debian/10/amd64/archive'
+      salt_apt_repo_key: 'https://repo.saltproject.io/py3/debian/10/amd64/latest/SALTSTACK-GPG-KEY.pub'
+  - name: centos-8
     driver_config:
       provision_command:
         - echo . /etc/profile >> ~kitchen/.bashrc
@@ -108,8 +99,8 @@ platforms:
         - yum install -y epel-release
         - yum install -y python3-pip python3-devel gcc git gcc-c++
     provisioner:
-      salt_yum_repo: 'https://repo.saltproject.io/py3/redhat/7/x86_64/archive/%s'
-      salt_yum_rpm_key: 'https://repo.saltproject.io/py3/redhat/7/x86_64/latest/SALTSTACK-GPG-KEY.pub'
+      salt_yum_repo: 'https://repo.saltproject.io/py3/redhat/8/x86_64/archive/%s'
+      salt_yum_rpm_key: 'https://repo.saltproject.io/py3/redhat/8/x86_64/latest/SALTSTACK-GPG-KEY.pub'
 <% if @vagrant != false %>
   - name: windows-2012r2
     driver:
diff --git a/lib/kitchen/provisioner/install.erb b/lib/kitchen/provisioner/install.erb
index 14a3c0ff..30df68ec 100644
--- a/lib/kitchen/provisioner/install.erb
+++ b/lib/kitchen/provisioner/install.erb
@@ -40,7 +40,12 @@ then
 elif [ -z "${SALT_VERSION}" -a "#{salt_install}" = "pip" ]
 then
   echo "Make sure setuptools and pip are new enough"
-  #{sudo(salt_pip_bin)} install "setuptools>=30" "pip>=9"
+  export REQUIREMENTS_FILE=$(mktemp)
+  echo "setuptools >=30,<54.* ; python_version < '3.6'" > $REQUIREMENTS_FILE
+  echo "setuptools >=30,!=50.*,!=51.*,!=52.*; python_version >= '3.6'" > $REQUIREMENTS_FILE
+  echo "pip >=9,<21.0.0 ; python_version < '3.6'" >> $REQUIREMENTS_FILE
+  echo "pip >=9 ; python_version >= '3.6'" >> $REQUIREMENTS_FILE
+  #{sudo(salt_pip_bin)} install -r $REQUIREMENTS_FILE
   echo #{sudo(salt_pip_bin)} #{salt_pip_install_command} #{salt_pip_pkg}
   #{sudo(salt_pip_bin)} #{salt_pip_install_command} #{salt_pip_pkg}
 elif [ -z "${SALT_VERSION}" -a "#{salt_install}" = "apt" ]
diff --git a/lib/kitchen/verifier/nox.rb b/lib/kitchen/verifier/nox.rb
index 2c560ca8..3216dcdc 100644
--- a/lib/kitchen/verifier/nox.rb
+++ b/lib/kitchen/verifier/nox.rb
@@ -15,12 +15,17 @@ class Nox < Kitchen::Verifier::Base
       default_config :tests, []
       default_config :save, {}
       default_config :windows, nil
+      default_config :windows do |verifier|
+        verifier.windows_os? ? true : false
+      end
       default_config :verbose, false
       default_config :run_destructive, false
       default_config :runtests, false
       default_config :coverage, false
       default_config :junitxml, false
       default_config :from_filenames, []
+      default_config :from_filenames_basename, "changed-files-list.txt"
+      default_config :from_filenames_path, false
       default_config :enable_filenames, false
       default_config :passthrough_opts, []
       default_config :output_columns, 120
@@ -29,15 +34,33 @@ class Nox < Kitchen::Verifier::Base
       default_config :environment_vars, {}
       default_config :zip_windows_artifacts, false
 
-      def call(state)
-        if config[:windows].nil?
-          # Since windows is not set, lets try and guess since kitchen actually knows this infomation
-          if instance.platform.os_type == 'windows'
-            config[:windows] = true
-          else
-            config[:windows] = false
-          end
+      def initialize(config = {})
+        super(config)
+        debug("Running kitchen-salt nox verifier initialize method")
+
+        if ENV['NOX_ENABLE_FROM_FILENAMES']
+          config[:enable_filenames] = true
         end
+
+        if config[:enable_filenames] and ENV['CHANGE_TARGET'] and ENV['BRANCH_NAME'] and ENV['FORCE_FULL'] != 'true'
+          require 'git'
+          repo = Git.open(Dir.pwd)
+          config[:from_filenames] = repo.diff("origin/#{ENV['CHANGE_TARGET']}",
+                                              "origin/#{ENV['BRANCH_NAME']}").name_status.keys.select{|file| file.end_with?('.py')}
+          debug("Populating `from_filenames` with: #{config[:from_filenames]}")
+        end
+        if config[:windows] && config[:from_filenames].any?
+          # On windows, if the changed files list is too big, it will error.
+          # Let's then pass an absolute path to a text file which contains the list of changed
+          # files, one per line.
+          config[:from_filenames_path] = "#{Dir.pwd}\\#{config[:from_filenames_basename]}"
+          from_filenames_contents = "#{config[:from_filenames].join('\n')}"
+          File.open(config[:from_filenames_path], "w") { |f| f.write from_filenames_contents }
+          debug("Created #{config[:from_filenames_path]} with contents:\n#{from_filenames_contents}")
+        end
+      end
+
+      def call(state)
         debug("Detected platform for instance #{instance.name}: #{instance.platform.os_type}. Config's windows setting value: #{config[:windows]}")
         if (ENV['ONLY_DOWNLOAD_ARTEFACTS'] || '') == '1'
           only_download_artefacts = true
@@ -64,10 +87,6 @@ def call(state)
           ENV['KITCHEN_TESTS'].split(' ').each{|test| config[:tests].push(test)}
         end
 
-        if ENV['NOX_ENABLE_FROM_FILENAMES']
-          config[:enable_filenames] = true
-        end
-
         if ENV['NOX_PASSTHROUGH_OPTS']
           ENV['NOX_PASSTHROUGH_OPTS'].split(' ').each{|opt| config[:passthrough_opts].push(opt)}
         end
@@ -108,13 +127,6 @@ def call(state)
           sys_stats = ''
         end
 
-        if config[:enable_filenames] and ENV['CHANGE_TARGET'] and ENV['BRANCH_NAME'] and ENV['FORCE_FULL'] != 'true'
-          require 'git'
-          repo = Git.open(Dir.pwd)
-          config[:from_filenames] = repo.diff("origin/#{ENV['CHANGE_TARGET']}",
-                                              "origin/#{ENV['BRANCH_NAME']}").name_status.keys.select{|file| file.end_with?('.py')}
-        end
-
         if config[:junitxml]
           junitxml = File.join(root_path, config[:testingdir], 'artifacts', 'xml-unittests-output')
           if noxenv.include? "pytest"
@@ -150,11 +162,18 @@ def call(state)
 
         if tests.nil? || tests.empty?
           # If we're not targetting specific tests...
-          extra_command = [
-            (config[:from_filenames].any? ? "--from-filenames=#{config[:from_filenames].join(',')}" : ''),
-            (config[:windows] ? "--names-file=#{root_path}\\testing\\tests\\whitelist.txt" : ''),
-          ].join(' ')
-          command = "#{command} #{extra_command}"
+          extra_command = []
+          if config[:windows]
+            extra_command.push("--names-file=#{root_path}\\testing\\tests\\whitelist.txt")
+            if config[:from_filenames_path]
+                extra_command.push("--from-filenames=#{root_path}\\testing\\#{config[:from_filenames_basename]}")
+            end
+          else
+            if config[:from_filenames].any?
+              extra_command.push("--from-filenames=#{config[:from_filenames].join(',')}")
+            end
+          end
+          command = "#{command} #{extra_command.join(' ')}"
         else
           command = "#{command} #{tests}"
         end
@@ -167,6 +186,9 @@ def call(state)
         # the one from config
         environment_vars.merge!(config[:environment_vars])
 
+        # Strip trailing whitespace
+        command = command.rstrip
+
         if config[:windows]
           command = "cmd.exe /c --% \"#{command}\" 2>&1"
         end
@@ -209,7 +231,7 @@ def call(state)
                         info("7z.exe failed, attempting zip with powershell Compress-Archive")
                         conn.execute("powershell Compress-Archive #{remote} #{remote}artifacts.zip -Force")
                       rescue => e2
-                        error("Failed to create zip")
+                        error("Failed to create zip: #{e2}")
                       end
                     end
                   end