diff --git a/plugins/provisioners/chef/provisioner/base.rb b/plugins/provisioners/chef/provisioner/base.rb
index 4be66f346..f0e34a2ee 100644
--- a/plugins/provisioners/chef/provisioner/base.rb
+++ b/plugins/provisioners/chef/provisioner/base.rb
@@ -138,6 +138,10 @@ module VagrantPlugins
             File.join(@config.provisioning_path, "encrypted_data_bag_secret_key")
           end
         end
+
+        def windows?
+          @machine.config.vm.communicator == :winrm
+        end
       end
     end
   end
diff --git a/plugins/provisioners/chef/provisioner/chef_client.rb b/plugins/provisioners/chef/provisioner/chef_client.rb
index 2e5f07b64..50c8e82eb 100644
--- a/plugins/provisioners/chef/provisioner/chef_client.rb
+++ b/plugins/provisioners/chef/provisioner/chef_client.rb
@@ -58,6 +58,14 @@ module VagrantPlugins
             @machine.ui.warn(I18n.t("vagrant.chef_run_list_empty"))
           end
 
+          if windows?
+            # This re-establishes our symbolic links if they were
+            # created between now and a reboot
+            @machine.communicate.execute(
+              "& net use a-non-existant-share",
+              error_check: false)
+          end
+
           command_env = @config.binary_env ? "#{@config.binary_env} " : ""
           command_args = @config.arguments ? " #{@config.arguments}" : ""
           command = "#{command_env}#{chef_binary_path("chef-client")} " +
diff --git a/plugins/provisioners/chef/provisioner/chef_solo.rb b/plugins/provisioners/chef/provisioner/chef_solo.rb
index 7f9e304ac..394111c02 100644
--- a/plugins/provisioners/chef/provisioner/chef_solo.rb
+++ b/plugins/provisioners/chef/provisioner/chef_solo.rb
@@ -134,6 +134,14 @@ module VagrantPlugins
             @machine.ui.warn(I18n.t("vagrant.chef_run_list_empty"))
           end
 
+          if windows?
+            # This re-establishes our symbolic links if they were
+            # created between now and a reboot
+            @machine.communicate.execute(
+              "& net use a-non-existant-share",
+              error_check: false)
+          end
+
           options = [
             "-c #{@config.provisioning_path}/solo.rb",
             "-j #{@config.provisioning_path}/dna.json"