diff --git a/plugins/provisioners/chef/cap/windows/chef_installed.rb b/plugins/provisioners/chef/cap/windows/chef_installed.rb
new file mode 100644
index 000000000..c95ea8498
--- /dev/null
+++ b/plugins/provisioners/chef/cap/windows/chef_installed.rb
@@ -0,0 +1,20 @@
+module VagrantPlugins
+  module Chef
+    module Cap
+      module Windows
+        module ChefInstalled
+          # Check if Chef is installed at the given version.
+          # @return [true, false]
+          def self.chef_installed(machine, version)
+            if version != :latest
+              command = 'if ((&knife --version) -Match "Chef: "' + version + '"){ exit 0 } else { exit 1 }'
+            else
+              command = 'if ((&knife --version) -Match "Chef: *"){ exit 0 } else { exit 1 }'
+            end
+            machine.communicate.test(command, sudo: true)
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/provisioners/chef/plugin.rb b/plugins/provisioners/chef/plugin.rb
index 5a1b2876f..540429fad 100644
--- a/plugins/provisioners/chef/plugin.rb
+++ b/plugins/provisioners/chef/plugin.rb
@@ -58,6 +58,11 @@ module VagrantPlugins
         Cap::Linux::ChefInstalled
       end
 
+      guest_capability(:windows, :chef_installed) do
+        require_relative "cap/windows/chef_installed"
+        Cap::Windows::ChefInstalled
+      end
+
       guest_capability(:debian, :chef_install) do
         require_relative "cap/debian/chef_install"
         Cap::Debian::ChefInstall
diff --git a/plugins/provisioners/chef/provisioner/base.rb b/plugins/provisioners/chef/provisioner/base.rb
index a5efb5be4..aed44eaf0 100644
--- a/plugins/provisioners/chef/provisioner/base.rb
+++ b/plugins/provisioners/chef/provisioner/base.rb
@@ -37,8 +37,14 @@ module VagrantPlugins
         def verify_binary(binary)
           # Checks for the existence of chef binary and error if it
           # doesn't exist.
+          if windows?
+            command = "if ((&'#{binary}' -v) -Match 'Chef: *'){ exit 0 } else { exit 1 }"
+          else
+            command = "sh -c 'command -v #{binary}'"
+          end
+
           @machine.communicate.sudo(
-            "sh -c 'command -v #{binary}'",
+            command,
             error_class: ChefError,
             error_key: :chef_not_detected,
             binary: binary,
@@ -66,8 +72,12 @@ module VagrantPlugins
 
           @machine.communicate.tap do |comm|
             paths.each do |path|
-              comm.sudo("mkdir -p #{path}")
-              comm.sudo("chown -h #{@machine.ssh_info[:username]} #{path}")
+              if windows?
+                comm.sudo("mkdir ""#{path}"" -f")
+              else
+                comm.sudo("mkdir -p #{path}")
+                comm.sudo("chown -h #{@machine.ssh_info[:username]} #{path}")
+              end
             end
           end
         end
@@ -133,7 +143,13 @@ module VagrantPlugins
 
           remote_file = File.join(@config.provisioning_path, "dna.json")
           @machine.communicate.tap do |comm|
-            comm.sudo("rm -f #{remote_file}", error_check: false)
+            if windows?
+              command = "if (test-path '#{remote_file}') {rm '#{remote_file}' -force -recurse}"
+            else
+              command = "rm -f #{remote_file}"
+            end
+
+            comm.sudo(command, error_check: false)
             comm.upload(temp.path, remote_file)
           end
         end
@@ -146,7 +162,13 @@ module VagrantPlugins
             "vagrant.provisioners.chef.upload_encrypted_data_bag_secret_key")
 
           @machine.communicate.tap do |comm|
-            comm.sudo("rm -f #{remote_file}", error_check: false)
+            if windows?
+              command = "if (test-path ""#{remote_file}"") {rm ""#{remote_file}"" -force -recurse}"
+            else
+              command = "rm -f #{remote_file}"
+            end
+
+            comm.sudo(command, error_check: false)
             comm.upload(encrypted_data_bag_secret_key_path, remote_file)
           end
         end
@@ -154,7 +176,13 @@ module VagrantPlugins
         def delete_encrypted_data_bag_secret
           remote_file = guest_encrypted_data_bag_secret_key_path
           if remote_file
-            @machine.communicate.sudo("rm -f #{remote_file}", error_check: false)
+            if windows?
+              command = "if (test-path ""#{remote_file}"") {rm ""#{remote_file}"" -force -recurse}"
+            else
+              command = "rm -f #{remote_file}"
+            end
+
+            @machine.communicate.sudo(command, error_check: false)
           end
         end
 
diff --git a/plugins/provisioners/chef/provisioner/chef_apply.rb b/plugins/provisioners/chef/provisioner/chef_apply.rb
index 1ff4790b6..602c81f3d 100644
--- a/plugins/provisioners/chef/provisioner/chef_apply.rb
+++ b/plugins/provisioners/chef/provisioner/chef_apply.rb
@@ -18,8 +18,12 @@ module VagrantPlugins
           user = @machine.ssh_info[:username]
 
           # Reset upload path permissions for the current ssh user
-          @machine.communicate.sudo("mkdir -p #{config.upload_path}")
-          @machine.communicate.sudo("chown -R #{user} #{config.upload_path}")
+          if windows?
+            @machine.communicate.sudo("mkdir ""#{config.upload_path}"" -f")
+          else
+            @machine.communicate.sudo("mkdir -p #{config.upload_path}")
+            @machine.communicate.sudo("chown -R #{user} #{config.upload_path}")
+          end
 
           # Upload the recipe
           upload_recipe
diff --git a/plugins/provisioners/chef/provisioner/chef_client.rb b/plugins/provisioners/chef/provisioner/chef_client.rb
index c9b0ab6c0..f0209d2a0 100644
--- a/plugins/provisioners/chef/provisioner/chef_client.rb
+++ b/plugins/provisioners/chef/provisioner/chef_client.rb
@@ -39,7 +39,11 @@ module VagrantPlugins
           @machine.ui.info I18n.t("vagrant.provisioners.chef.client_key_folder")
           path = Pathname.new(@config.client_key_path)
 
-          @machine.communicate.sudo("mkdir -p #{path.dirname}")
+          if windows?
+            @machine.communicate.sudo("mkdir ""#{path.dirname}"" -f")
+          else
+            @machine.communicate.sudo("mkdir -p #{path.dirname}")
+          end
         end
 
         def upload_validation_key