diff --git a/contrib/sudoers/osx b/contrib/sudoers/osx
index 96f7f4978..ff1a28575 100644
--- a/contrib/sudoers/osx
+++ b/contrib/sudoers/osx
@@ -1,5 +1,10 @@
 Cmnd_Alias VAGRANT_EXPORTS_ADD = /usr/bin/tee -a /etc/exports
 Cmnd_Alias VAGRANT_NFSD = /sbin/nfsd restart
 Cmnd_Alias VAGRANT_EXPORTS_REMOVE = /usr/bin/sed -E -e /*/ d -ibak /etc/exports
-%admin ALL=(root) NOPASSWD: VAGRANT_EXPORTS_ADD, VAGRANT_NFSD, VAGRANT_EXPORTS_REMOVE
-
+Cmnd_Alias VAGRANT_SMB_ADD = /usr/sbin/sharing -a * -S * -s * -g * -n *
+Cmnd_Alias VAGRANT_SMB_REMOVE = /usr/sbin/sharing -r *
+Cmnd_Alias VAGRANT_SMB_LIST = /usr/sbin/sharing -l
+Cmnd_Alias VAGRANT_SMB_PLOAD = /bin/launchctl load -w /System/Library/LaunchDaemons/com.apple.smb.preferences.plist
+Cmnd_Alias VAGRANT_SMB_DLOAD = /bin/launchctl load -w /System/Library/LaunchDaemons/com.apple.smbd.plist
+Cmnd_Alias VAGRANT_SMB_DSTART = /bin/launchctl start com.apple.smbd
+%admin ALL=(root) NOPASSWD: VAGRANT_EXPORTS_ADD, VAGRANT_NFSD, VAGRANT_SMB_ADD, VAGRANT_SMB_REMOVE, VAGRANT_SMB_LIST, VAGRANT_SMB_PLOAD, VAGRANT_SMB_DLOAD VAGRANT_SMB_DSTART
\ No newline at end of file
diff --git a/lib/vagrant/config/v2/root.rb b/lib/vagrant/config/v2/root.rb
index f4a18c10b..b41e5c031 100644
--- a/lib/vagrant/config/v2/root.rb
+++ b/lib/vagrant/config/v2/root.rb
@@ -16,6 +16,7 @@ module Vagrant
           @keys              = keys || {}
           @config_map        = config_map
           @missing_key_calls = Set.new
+          @logger            = Log4r::Logger.new("vagrant::config")
         end
 
         # We use method_missing as a way to get the configuration that is
@@ -30,6 +31,7 @@ module Vagrant
             @keys[name] = config_klass.new
             return @keys[name]
           else
+            @logger.debug("missing key request name=#{name} loc=#{caller.first}")
             # Record access to a missing key as an error
             @missing_key_calls.add(name.to_s)
             return DummyConfig.new
diff --git a/lib/vagrant/errors.rb b/lib/vagrant/errors.rb
index a6928bc12..544536a39 100644
--- a/lib/vagrant/errors.rb
+++ b/lib/vagrant/errors.rb
@@ -552,6 +552,10 @@ module Vagrant
       error_key(:powershell_invalid_version)
     end
 
+    class PowerShellError < VagrantError
+      error_key(:powershell_error, "vagrant_ps.errors.powershell_error")
+    end
+
     class ProviderCantInstall < VagrantError
       error_key(:provider_cant_install)
     end
diff --git a/lib/vagrant/util/powershell.rb b/lib/vagrant/util/powershell.rb
index b5d474cec..915ae4bb5 100644
--- a/lib/vagrant/util/powershell.rb
+++ b/lib/vagrant/util/powershell.rb
@@ -1,3 +1,4 @@
+require "tmpdir"
 require_relative "subprocess"
 require_relative "which"
 
@@ -25,27 +26,33 @@ module Vagrant
       # @return [Subprocess::Result]
       def self.execute(path, *args, **opts, &block)
         validate_install!
-        command = [
-          "powershell",
-          "-NoLogo",
-          "-NoProfile",
-          "-NonInteractive",
-          "-ExecutionPolicy", "Bypass",
-          "&('#{path}')",
-          args
-        ].flatten
 
-        # Append on the options hash since Subprocess doesn't use
-        # Ruby 2.0 style options yet.
-        command << opts
+        if opts.delete(:sudo) || opts.delete(:runas)
+          powerup_command(path, args, opts)
+        else
+          command = [
+            "powershell",
+            "-NoLogo",
+            "-NoProfile",
+            "-NonInteractive",
+            "-ExecutionPolicy", "Bypass",
+            "&('#{path}')",
+            args
+          ].flatten
 
-        Subprocess.execute(*command, &block)
+          # Append on the options hash since Subprocess doesn't use
+          # Ruby 2.0 style options yet.
+          command << opts
+
+          Subprocess.execute(*command, &block)
+        end
       end
 
       # Execute a powershell command.
       #
       # @param [String] command PowerShell command to execute.
-      # @return [Subprocess::Result]
+      # @return [nil, String] Returns nil if exit code is non-zero.
+      #   Returns stdout string if exit code is zero.
       def self.execute_cmd(command)
         validate_install!
         c = [
@@ -56,7 +63,7 @@ module Vagrant
           "-ExecutionPolicy", "Bypass",
           "-Command",
           command
-        ].flatten
+        ].flatten.compact
 
         r = Subprocess.execute(*c)
         return nil if r.exit_code != 0
@@ -75,7 +82,7 @@ module Vagrant
             "-NonInteractive",
             "-ExecutionPolicy", "Bypass",
             "-Command",
-            "$PSVersionTable.PSVersion.Major"
+            "Write-Output $PSVersionTable.PSVersion.Major"
           ].flatten
 
           r = Subprocess.execute(*command)
@@ -101,6 +108,60 @@ module Vagrant
         end
         @_powershell_validation
       end
+
+      # Powerup the given command to perform privileged operations.
+      #
+      # @param [String] path
+      # @param [Array<String>] args
+      # @return [Array<String>]
+      def self.powerup_command(path, args, opts)
+        Dir.mktmpdir("vagrant") do |dpath|
+          all_args = ["-NoProfile", "-NonInteractive", "-ExecutionPolicy", "Bypass", path] + args
+          arg_list = "@('" + all_args.join("', '") + "')"
+          stdout = File.join(dpath, "stdout.txt")
+          stderr = File.join(dpath, "stderr.txt")
+          exitcode = File.join(dpath, "exitcode.txt")
+
+          script = "$sp = Start-Process -FilePath powershell -ArgumentList #{arg_list} " \
+            "-PassThru -Wait -RedirectStandardOutput '#{stdout}' -RedirectStandardError '#{stderr}' -WindowStyle Hidden; " \
+            "if($sp){ Set-Content -Path '#{exitcode}' -Value $sp.ExitCode;exit $sp.ExitCode; }else{ exit 1 }"
+
+          # escape quotes so we can nest our script within a start-process
+          script.gsub!("'", "''")
+
+          cmd = [
+            "powershell",
+            "-NoLogo",
+            "-NoProfile",
+            "-NonInteractive",
+            "-ExecutionPolicy", "Bypass",
+            "-Command", "$p = Start-Process -FilePath powershell -ArgumentList " \
+              "@('-NoLogo', '-NoProfile', '-NonInteractive', '-ExecutionPolicy', 'Bypass', '-Command', '#{script}') " \
+              "-PassThru -Wait -WindowStyle Hidden -Verb RunAs; if($p){ exit $p.ExitCode; }else{ exit 1 }"
+          ]
+
+          result = Subprocess.execute(*cmd.push(opts))
+          if File.exist?(stdout)
+            r_stdout = File.read(stdout)
+          else
+            r_stdout = result.stdout
+          end
+          if File.exist?(stderr)
+            r_stderr = File.read(stderr)
+          else
+            r_stderr = result.stderr
+          end
+
+          code = 1
+          if File.exist?(exitcode)
+            code_txt = File.read(exitcode).strip
+            if code_txt.match(/^\d+$/)
+              code = code_txt.to_i
+            end
+          end
+          Subprocess::Result.new(code, r_stdout, r_stderr)
+        end
+      end
     end
   end
 end
diff --git a/plugins/guests/darwin/cap/mount_smb_shared_folder.rb b/plugins/guests/darwin/cap/mount_smb_shared_folder.rb
index 5f1cdaec4..d2bab0806 100644
--- a/plugins/guests/darwin/cap/mount_smb_shared_folder.rb
+++ b/plugins/guests/darwin/cap/mount_smb_shared_folder.rb
@@ -20,6 +20,9 @@ module VagrantPlugins
           end
 
           smb_password = Shellwords.shellescape(options[:smb_password])
+          # Ensure password is scrubbed
+          Vagrant::Util::CredentialScrubber.sensitive(smb_password)
+
           mount_options = options[:mount_options];
           mount_command = "mount -t smbfs " +
             (mount_options ? "-o '#{mount_options.join(",")}' " : "") +
diff --git a/plugins/guests/linux/cap/mount_smb_shared_folder.rb b/plugins/guests/linux/cap/mount_smb_shared_folder.rb
index c0d1bf3f3..dfc592639 100644
--- a/plugins/guests/linux/cap/mount_smb_shared_folder.rb
+++ b/plugins/guests/linux/cap/mount_smb_shared_folder.rb
@@ -22,9 +22,15 @@ module VagrantPlugins
           # If a domain is provided in the username, separate it
           username, domain = (options[:smb_username] || '').split('@', 2)
           smb_password = options[:smb_password]
+          # Ensure password is scrubbed
+          Vagrant::Util::CredentialScrubber.sensitive(smb_password)
 
           options[:mount_options] ||= []
-          options[:mount_options] << "sec=ntlm"
+          if machine.env.host.capability?(:smb_mount_options)
+            options[:mount_options] += machine.env.host.capability(:smb_mount_options)
+          else
+            options[:mount_options] << "sec=ntlm"
+          end
           options[:mount_options] << "credentials=/etc/smb_creds_#{name}"
 
           mount_options = "-o uid=#{mount_uid},gid=#{mount_gid}"
@@ -46,22 +52,26 @@ SCRIPT
 
           # Attempt to mount the folder. We retry here a few times because
           # it can fail early on.
-
-          retryable(on: Vagrant::Errors::LinuxMountFailed, tries: 10, sleep: 2) do
-            no_such_device = false
-            stderr = ""
-            status = machine.communicate.sudo(mount_command, error_check: false) do |type, data|
-              if type == :stderr
-                no_such_device = true if data =~ /No such device/i
-                stderr += data.to_s
+          begin
+            retryable(on: Vagrant::Errors::LinuxMountFailed, tries: 10, sleep: 2) do
+              no_such_device = false
+              stderr = ""
+              status = machine.communicate.sudo(mount_command, error_check: false) do |type, data|
+                if type == :stderr
+                  no_such_device = true if data =~ /No such device/i
+                  stderr += data.to_s
+                end
+              end
+              if status != 0 || no_such_device
+                raise Vagrant::Errors::LinuxMountFailed,
+                  command: mount_command,
+                  output: stderr
               end
             end
-            if status != 0 || no_such_device
-              clean_command = mount_command.gsub(smb_password, "PASSWORDHIDDEN")
-              raise Vagrant::Errors::LinuxMountFailed,
-                command: clean_command,
-                output: stderr
-            end
+          ensure
+            # Always remove credentials file after mounting attempts
+            # have been completed
+            machine.communicate.sudo("rm /etc/smb_creds_#{name}")
           end
 
           emit_upstart_notification(machine, expanded_guest_path)
diff --git a/plugins/guests/windows/cap/mount_shared_folder.rb b/plugins/guests/windows/cap/mount_shared_folder.rb
index 4a313849b..f1088f6b8 100644
--- a/plugins/guests/windows/cap/mount_shared_folder.rb
+++ b/plugins/guests/windows/cap/mount_shared_folder.rb
@@ -18,6 +18,10 @@ module VagrantPlugins
         end
 
         def self.mount_smb_shared_folder(machine, name, guestpath, options)
+          if !options[:smb_password].to_s.empty?
+            # Ensure password is scrubbed
+            Vagrant::Util::CredentialScrubber.sensitive(options[:smb_password])
+          end
           machine.communicate.execute("cmdkey /add:#{options[:smb_host]} /user:#{options[:smb_username]} /pass:#{options[:smb_password]}", {shell: :powershell, elevated: true})
           mount_shared_folder(machine, name, guestpath, "\\\\#{options[:smb_host]}\\")
         end
diff --git a/plugins/hosts/darwin/cap/configured_ip_addresses.rb b/plugins/hosts/darwin/cap/configured_ip_addresses.rb
new file mode 100644
index 000000000..063295ea1
--- /dev/null
+++ b/plugins/hosts/darwin/cap/configured_ip_addresses.rb
@@ -0,0 +1,18 @@
+require "socket"
+
+module VagrantPlugins
+  module HostDarwin
+    module Cap
+      class ConfiguredIPAddresses
+
+        def self.configured_ip_addresses(env)
+          Socket.getifaddrs.map do |interface|
+            if interface.addr.ipv4? && !interface.addr.ipv4_loopback?
+              interface.addr.ip_address
+            end
+          end.compact
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/hosts/darwin/cap/smb.rb b/plugins/hosts/darwin/cap/smb.rb
new file mode 100644
index 000000000..2547ca74e
--- /dev/null
+++ b/plugins/hosts/darwin/cap/smb.rb
@@ -0,0 +1,125 @@
+module VagrantPlugins
+  module HostDarwin
+    module Cap
+      class SMB
+
+        @@logger = Log4r::Logger.new("vagrant::host::darwin::smb")
+
+        # If we have the sharing binary available, smb is installed
+        def self.smb_installed(env)
+          File.exist?("/usr/sbin/sharing")
+        end
+
+        # Check if the required SMB services are loaded and enabled. If they are
+        # not, then start them up
+        def self.smb_start(env)
+          result = Vagrant::Util::Subprocess.execute("pwpolicy", "gethashtypes")
+          if result.exit_code == 0 && !result.stdout.include?("SMB-NT")
+            @@logger.error("SMB compatible password has not been stored")
+            raise SyncedFolderSMB::Errors::SMBCredentialsMissing
+          end
+          result = Vagrant::Util::Subprocess.execute("launchctl", "list", "com.apple.smb.preferences")
+          if result.exit_code != 0
+            @@logger.warn("smb preferences service not enabled. enabling and starting...")
+            cmd = ["/bin/launchctl", "load", "-w", "/System/Library/LaunchDaemons/com.apple.smb.preferences.plist"]
+            result = Vagrant::Util::Subprocess.execute("/usr/bin/sudo", *cmd)
+            if result.exit_code != 0
+              raise SyncedFolderSMB::Errors::SMBStartFailed,
+                command: cmd.join(" "),
+                stderr: result.stderr,
+                stdout: result.stdout
+            end
+          end
+          result = Vagrant::Util::Subprocess.execute("launchctl", "list", "com.apple.smbd")
+          if result.exit_code != 0
+            @@logger.warn("smbd service not enabled. enabling and starting...")
+            cmd = ["/bin/launchctl", "load", "-w", "/System/Library/LaunchDaemons/com.apple.smbd.plist"]
+            result = Vagrant::Util::Subprocess.execute("/usr/bin/sudo", *cmd)
+            if result.exit_code != 0
+              raise SyncedFolderSMB::Errors::SMBStartFailed,
+                command: cmd.join(" "),
+                stderr: result.stderr,
+                stdout: result.stdout
+            end
+            Vagrant::Util::Subprocess.execute("/usr/bin/sudo", "/bin/launchctl", "start", "com.apple.smbd")
+          end
+        end
+
+        # Required options for mounting a share hosted
+        # on macos.
+        def self.smb_mount_options(env)
+          ["sec=ntlmssp", "nounix", "noperm"]
+        end
+
+        def self.smb_cleanup(env, machine, opts)
+          m_id = machine_id(machine)
+          result = Vagrant::Util::Subprocess.execute("/usr/bin/sudo", "/usr/sbin/sharing", "-l")
+          if result.exit_code != 0
+            @@logger.warn("failed to locate any shares for cleanup")
+          end
+          shares = result.stdout.split("\n").map do |line|
+            if line.start_with?("name:")
+              share_name = line.sub("name:", "").strip
+              share_name if share_name.start_with?("vgt-#{m_id}")
+            end
+          end.compact
+          @@logger.debug("shares to be removed: #{shares}")
+          shares.each do |share_name|
+            @@logger.info("removing share name=#{share_name}")
+            share_name.strip!
+            result = Vagrant::Util::Subprocess.execute("/usr/bin/sudo",
+              "/usr/sbin/sharing", "-r", share_name)
+            if result.exit_code != 0
+              # Removing always returns 0 even if there are currently
+              # guests attached so if we get a non-zero value just
+              # log it as unexpected
+              @@logger.warn("removing share `#{share_name}` returned non-zero")
+            end
+          end
+        end
+
+        def self.smb_prepare(env, machine, folders, opts)
+          folders.each do |id, data|
+            hostpath = data[:hostpath]
+
+            chksum_id = Digest::MD5.hexdigest(id)
+            name = "vgt-#{machine_id(machine)}-#{chksum_id}"
+            data[:smb_id] ||= name
+
+            @@logger.info("creating new share name=#{name} id=#{data[:smb_id]}")
+
+            cmd = [
+              "/usr/bin/sudo",
+              "/usr/sbin/sharing",
+              "-a", hostpath,
+              "-S", data[:smb_id],
+              "-s", "001",
+              "-g", "000",
+              "-n", name
+            ]
+
+            r = Vagrant::Util::Subprocess.execute(*cmd)
+
+            if r.exit_code != 0
+              raise VagrantPlugins::SyncedFolderSMB::Errors::DefineShareFailed,
+                host: hostpath.to_s,
+                stderr: r.stderr,
+                stdout: r.stdout
+            end
+          end
+        end
+
+        # Generates a unique identifier for the given machine
+        # based on the name, provider name, and working directory
+        # of the environment.
+        #
+        # @param [Vagrant::Machine] machine
+        # @return [String]
+        def self.machine_id(machine)
+          @@logger.debug("generating machine ID name=#{machine.name} cwd=#{machine.env.cwd}")
+          Digest::MD5.hexdigest("#{machine.name}-#{machine.provider_name}-#{machine.env.cwd}")
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/hosts/darwin/plugin.rb b/plugins/hosts/darwin/plugin.rb
index f37bcd9dd..7b08af3f1 100644
--- a/plugins/hosts/darwin/plugin.rb
+++ b/plugins/hosts/darwin/plugin.rb
@@ -20,6 +20,36 @@ module VagrantPlugins
         require_relative "cap/rdp"
         Cap::RDP
       end
+
+      host_capability("darwin", "smb_installed") do
+        require_relative "cap/smb"
+        Cap::SMB
+      end
+
+      host_capability("darwin", "smb_prepare") do
+        require_relative "cap/smb"
+        Cap::SMB
+      end
+
+      host_capability("darwin", "smb_mount_options") do
+        require_relative "cap/smb"
+        Cap::SMB
+      end
+
+      host_capability("darwin", "smb_cleanup") do
+        require_relative "cap/smb"
+        Cap::SMB
+      end
+
+      host_capability("darwin", "smb_start") do
+        require_relative "cap/smb"
+        Cap::SMB
+      end
+
+      host_capability("darwin", "configured_ip_addresses") do
+        require_relative "cap/configured_ip_addresses"
+        Cap::ConfiguredIPAddresses
+      end
     end
   end
 end
diff --git a/plugins/hosts/windows/cap/configured_ip_addresses.rb b/plugins/hosts/windows/cap/configured_ip_addresses.rb
new file mode 100644
index 000000000..cc95775b5
--- /dev/null
+++ b/plugins/hosts/windows/cap/configured_ip_addresses.rb
@@ -0,0 +1,29 @@
+require "pathname"
+require "tempfile"
+
+require "vagrant/util/downloader"
+require "vagrant/util/file_checksum"
+require "vagrant/util/powershell"
+require "vagrant/util/subprocess"
+
+module VagrantPlugins
+  module HostWindows
+    module Cap
+      class ConfiguredIPAddresses
+
+        def self.configured_ip_addresses(env)
+          script_path = File.expand_path("../../scripts/host_info.ps1", __FILE__)
+          r = Vagrant::Util::PowerShell.execute(script_path)
+          if r.exit_code != 0
+            raise Vagrant::Errors::PowerShellError,
+              script: script_path,
+              stderr: r.stderr
+          end
+
+          res = JSON.parse(r.stdout)["ip_addresses"]
+          Array(res)
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/hosts/windows/cap/smb.rb b/plugins/hosts/windows/cap/smb.rb
new file mode 100644
index 000000000..457807f9c
--- /dev/null
+++ b/plugins/hosts/windows/cap/smb.rb
@@ -0,0 +1,136 @@
+module VagrantPlugins
+  module HostWindows
+    module Cap
+      class SMB
+
+        # Number of seconds to display UAC warning to user
+        UAC_PROMPT_WAIT = 4
+
+        @@logger = Log4r::Logger.new("vagrant::host::windows::smb")
+
+        def self.smb_installed(env)
+          psv = Vagrant::Util::PowerShell.version.to_i
+          if psv < 3
+            return false
+          end
+
+          true
+        end
+
+        def self.smb_cleanup(env, machine, opts)
+          script_path = File.expand_path("../../scripts/unset_share.ps1", __FILE__)
+
+          m_id = machine_id(machine)
+          prune_shares = existing_shares.map do |share_name, share_info|
+            if share_info["Description"].start_with?("vgt-#{m_id}-")
+              @@logger.info("removing smb share name=#{share_name} id=#{m_id}")
+              share_name
+            else
+              @@logger.info("skipping smb share removal, not owned name=#{share_name}")
+              @@logger.debug("smb share ID not present name=#{share_name} id=#{m_id} description=#{share_info["Description"]}")
+              nil
+            end
+          end.compact
+
+          @@logger.debug("shares to be removed: #{prune_shares}")
+
+          if prune_shares.size > 0
+            machine.env.ui.warn("\n" + I18n.t("vagrant_sf_smb.uac.prune_warning") + "\n")
+            sleep UAC_PROMPT_WAIT
+            @@logger.info("remove shares: #{prune_shares}")
+            result = Vagrant::Util::PowerShell.execute(script_path, *prune_shares, sudo: true)
+            if result.exit_code != 0
+              failed_name = result.stdout.to_s.sub("share name: ", "")
+              raise SyncedFolderSMB::Errors::PruneShareFailed,
+                name: failed_name,
+                stderr: result.stderr,
+                stdout: result.stdout
+            end
+          end
+        end
+
+        def self.smb_prepare(env, machine, folders, opts)
+          script_path = File.expand_path("../../scripts/set_share.ps1", __FILE__)
+
+          shares = []
+          current_shares = existing_shares
+          folders.each do |id, data|
+            hostpath = data[:hostpath].to_s
+
+            chksum_id = Digest::MD5.hexdigest(id)
+            name = "vgt-#{machine_id(machine)}-#{chksum_id}"
+            data[:smb_id] ||= name
+
+            # Check if this name is already in use
+            if share_info = current_shares[data[:smb_id]]
+              exist_path = File.expand_path(share_info["Path"]).downcase
+              request_path = File.expand_path(hostpath).downcase
+              if !hostpath.empty? && exist_path != request_path
+                raise SyncedFolderSMB::Errors::SMBNameError,
+                  path: hostpath,
+                  existing_path: share_info["Path"],
+                  name: data[:smb_id]
+              end
+              @@logger.info("skip creation of existing share name=#{name} id=#{data[:smb_id]}")
+              next
+            end
+
+            @@logger.info("creating new share name=#{name} id=#{data[:smb_id]}")
+
+            shares << [
+              "\"#{hostpath.gsub("/", "\\")}\"",
+              name,
+              data[:smb_id]
+            ]
+          end
+          if !shares.empty?
+            machine.env.ui.warn("\n" + I18n.t("vagrant_sf_smb.uac.create_warning") + "\n")
+            sleep(UAC_PROMPT_WAIT)
+            result = Vagrant::Util::PowerShell.execute(script_path, *shares, sudo: true)
+            if result.exit_code != 0
+              share_path = result.stdout.to_s.sub("share path: ", "")
+              raise SyncedFolderSMB::Errors::DefineShareFailed,
+                host: share_path,
+                stderr: result.stderr,
+                stdout: result.stdout
+            end
+          end
+        end
+
+        # Generate a list of existing local smb shares
+        #
+        # @return [Hash]
+        def self.existing_shares
+          result = Vagrant::Util::PowerShell.execute_cmd("Get-SmbShare|Format-List")
+          if result.nil?
+            raise SyncedFolderSMB::Errors::SMBListFailed
+          end
+          shares = {}
+          name = nil
+          result.lines.each do |line|
+            key, value = line.split(":", 2).map(&:strip)
+            if key == "Name"
+              name = value
+              shares[name] = {}
+            end
+            next if name.nil? || key.to_s.empty?
+            shares[name][key] = value
+          end
+          @@logger.debug("local share listing: #{shares}")
+          shares
+        end
+
+        # Generates a unique identifier for the given machine
+        # based on the name, provider name, and working directory
+        # of the environment.
+        #
+        # @param [Vagrant::Machine] machine
+        # @return [String]
+        def self.machine_id(machine)
+          @@logger.debug("generating machine ID name=#{machine.name} cwd=#{machine.env.cwd}")
+          Digest::MD5.hexdigest("#{machine.name}-#{machine.provider_name}-#{machine.env.cwd}")
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/hosts/windows/plugin.rb b/plugins/hosts/windows/plugin.rb
index 84a38836b..38691d0a8 100644
--- a/plugins/hosts/windows/plugin.rb
+++ b/plugins/hosts/windows/plugin.rb
@@ -30,6 +30,26 @@ module VagrantPlugins
         require_relative "cap/ps"
         Cap::PS
       end
+
+      host_capability("windows", "smb_installed") do
+        require_relative "cap/smb"
+        Cap::SMB
+      end
+
+      host_capability("windows", "smb_prepare") do
+        require_relative "cap/smb"
+        Cap::SMB
+      end
+
+      host_capability("windows", "smb_cleanup") do
+        require_relative "cap/smb"
+        Cap::SMB
+      end
+
+      host_capability("windows", "configured_ip_addresses") do
+        require_relative "cap/configured_ip_addresses"
+        Cap::ConfiguredIPAddresses
+      end
     end
   end
 end
diff --git a/plugins/synced_folders/smb/scripts/host_info.ps1 b/plugins/hosts/windows/scripts/host_info.ps1
similarity index 100%
rename from plugins/synced_folders/smb/scripts/host_info.ps1
rename to plugins/hosts/windows/scripts/host_info.ps1
diff --git a/plugins/hosts/windows/scripts/set_share.ps1 b/plugins/hosts/windows/scripts/set_share.ps1
new file mode 100644
index 000000000..b483088af
--- /dev/null
+++ b/plugins/hosts/windows/scripts/set_share.ps1
@@ -0,0 +1,37 @@
+# The names of the user are language dependent!
+$objSID = New-Object System.Security.Principal.SecurityIdentifier("S-1-1-0")
+$objUser = $objSID.Translate([System.Security.Principal.NTAccount])
+
+$grant = "$objUser,Full"
+
+for ($i=0; $i -le $args.length; $i = $i + 3) {
+    $path = $args[$i]
+    $share_name = $args[$i+1]
+    $share_id = $args[$i+2]
+
+
+    if ($path -eq $null) {
+        Write-Warning "empty path argument encountered - complete"
+        exit 0
+    }
+
+    if ($share_name -eq $null) {
+        Write-Output "share path: ${path}"
+        Write-Error "error - no share name provided"
+        exit 1
+    }
+
+    if ($share_id -eq $null) {
+        Write-Output "share path: ${path}"
+        Write-Error "error - no share ID provided"
+        exit 1
+    }
+
+    $result = net share $share_id=$path /unlimited /GRANT:$grant /REMARK:"${share_name}"
+    if ($LastExitCode -ne 0) {
+        $host.ui.WriteLine("share path: ${path}")
+        $host.ui.WriteErrorLine("error ${result}")
+        exit 1
+    }
+}
+exit 0
diff --git a/plugins/hosts/windows/scripts/unset_share.ps1 b/plugins/hosts/windows/scripts/unset_share.ps1
new file mode 100644
index 000000000..4fec74d30
--- /dev/null
+++ b/plugins/hosts/windows/scripts/unset_share.ps1
@@ -0,0 +1,10 @@
+ForEach ($share_name in $args) {
+    $result = net share $share_name /DELETE
+    if ($LastExitCode -ne 0) {
+        Write-Output "share name: ${share_name}"
+        Write-Error "error - ${result}"
+        exit 1
+    }
+}
+Write-Output "share removal completed"
+exit 0
diff --git a/plugins/providers/hyperv/action.rb b/plugins/providers/hyperv/action.rb
index 867191396..f5e9b25c6 100644
--- a/plugins/providers/hyperv/action.rb
+++ b/plugins/providers/hyperv/action.rb
@@ -41,6 +41,7 @@ module VagrantPlugins
               b2.use ProvisionerCleanup, :before
               b2.use StopInstance
               b2.use DeleteVM
+              b2.use SyncedFolderCleanup
             end
           end
         end
@@ -144,6 +145,7 @@ module VagrantPlugins
               b2.use StartInstance
               b2.use WaitForIPAddress
               b2.use WaitForCommunicator, [:running]
+              b2.use SyncedFolderCleanup
               b2.use SyncedFolders
               b2.use SetHostname
             end
diff --git a/plugins/synced_folders/smb/config.rb b/plugins/synced_folders/smb/config.rb
new file mode 100644
index 000000000..d853092ac
--- /dev/null
+++ b/plugins/synced_folders/smb/config.rb
@@ -0,0 +1,23 @@
+require "vagrant"
+
+module VagrantPlugins
+  module SyncedFolderSMB
+    class Config < Vagrant.plugin("2", :config)
+      attr_accessor :functional
+
+      def initialize
+        super
+
+        @functional = UNSET_VALUE
+      end
+
+      def finalize!
+        @functional = true if @functional == UNSET_VALUE
+      end
+
+      def to_s
+        "SMB"
+      end
+    end
+  end
+end
diff --git a/plugins/synced_folders/smb/errors.rb b/plugins/synced_folders/smb/errors.rb
index 4a5d2503e..761924207 100644
--- a/plugins/synced_folders/smb/errors.rb
+++ b/plugins/synced_folders/smb/errors.rb
@@ -6,10 +6,34 @@ module VagrantPlugins
         error_namespace("vagrant_sf_smb.errors")
       end
 
+      class SMBNotSupported < SMBError
+        error_key(:not_supported)
+      end
+
+      class SMBStartFailed < SMBError
+        error_key(:start_failed)
+      end
+
+      class SMBCredentialsMissing < SMBError
+        error_key(:credentials_missing)
+      end
+
+      class SMBListFailed < SMBError
+        error_key(:list_failed)
+      end
+
+      class SMBNameError < SMBError
+        error_key(:name_error)
+      end
+
       class DefineShareFailed < SMBError
         error_key(:define_share_failed)
       end
 
+      class PruneShareFailed < SMBError
+        error_key(:prune_share_failed)
+      end
+
       class NoHostIPAddr < SMBError
         error_key(:no_routable_host_addr)
       end
diff --git a/plugins/synced_folders/smb/plugin.rb b/plugins/synced_folders/smb/plugin.rb
index 02aca938b..bfb58a5b2 100644
--- a/plugins/synced_folders/smb/plugin.rb
+++ b/plugins/synced_folders/smb/plugin.rb
@@ -9,9 +9,14 @@ module VagrantPlugins
       name "SMB synced folders"
       description <<-EOF
       The SMB synced folders plugin enables you to use SMB folders on
-      Windows and share them to guest machines.
+      Windows or macOS and share them to guest machines.
       EOF
 
+      config("smb") do
+        require_relative "config"
+        Config
+      end
+
       synced_folder("smb", 7) do
         require_relative "synced_folder"
         init!
diff --git a/plugins/synced_folders/smb/scripts/set_share.ps1 b/plugins/synced_folders/smb/scripts/set_share.ps1
deleted file mode 100644
index 469483f38..000000000
--- a/plugins/synced_folders/smb/scripts/set_share.ps1
+++ /dev/null
@@ -1,44 +0,0 @@
-Param(
-    [Parameter(Mandatory=$true)]
-    [string]$path,
-    [Parameter(Mandatory=$true)]
-    [string]$share_name,
-    [string]$host_share_username = $null
-)
-
-$ErrorAction = "Stop"
-
-if (net share | Select-String $share_name) {
-  net share $share_name /delete /y
-}
-
-# The names of the user are language dependent!
-$objSID = New-Object System.Security.Principal.SecurityIdentifier("S-1-1-0")
-$objUser = $objSID.Translate([System.Security.Principal.NTAccount])
-
-$grant = "$objUser,Full"
-
-if (![string]::IsNullOrEmpty($host_share_username)) {
-    $computer_name = $(Get-WmiObject Win32_Computersystem).name
-    $grant         = "$computer_name\$host_share_username,Full"
-
-    # Here we need to set the proper ACL for this folder. This lets full
-    # recursive access to this folder.
-    <#
-    Get-ChildItem $path -recurse -Force |% {
-        $current_acl = Get-ACL $_.fullname
-        $permission = "$computer_name\$host_share_username","FullControl","ContainerInherit,ObjectInherit","None","Allow"
-        $acl_access_rule = New-Object System.Security.AccessControl.FileSystemAccessRule $permission
-        $current_acl.SetAccessRule($acl_access_rule)
-        $current_acl | Set-Acl $_.fullname
-    }
-    #>
-}
-
-$result = net share $share_name=$path /unlimited /GRANT:$grant
-if ($LastExitCode -eq 0) {
-    exit 0
-}
-
-$host.ui.WriteErrorLine("Error: $result")
-exit 1
diff --git a/plugins/synced_folders/smb/synced_folder.rb b/plugins/synced_folders/smb/synced_folder.rb
index acdcc802e..426def425 100644
--- a/plugins/synced_folders/smb/synced_folder.rb
+++ b/plugins/synced_folders/smb/synced_folder.rb
@@ -6,6 +6,8 @@ require "log4r"
 require "vagrant/util/platform"
 require "vagrant/util/powershell"
 
+require_relative "errors"
+
 module VagrantPlugins
   module SyncedFolderSMB
     class SyncedFolder < Vagrant.plugin("2", :synced_folder)
@@ -13,76 +15,57 @@ module VagrantPlugins
         super
 
         @logger = Log4r::Logger.new("vagrant::synced_folders::smb")
-        @creds  = {}
       end
 
       def usable?(machine, raise_error=false)
-        if !Vagrant::Util::Platform.windows?
-          raise Errors::WindowsHostRequired if raise_error
-          return false
-        end
-
-        if !Vagrant::Util::Platform.windows_admin?
-          raise Errors::WindowsAdminRequired if raise_error
-          return false
-        end
-
-        psv = Vagrant::Util::PowerShell.version.to_i
-        if psv < 3
-          if raise_error
-            raise Errors::PowershellVersion,
-              version: psv.to_s
-          end
-          return false
-        end
-
-        true
+        # If the machine explicitly states SMB is not supported, then
+        # believe it
+        return false if !machine.config.smb.functional
+        return true if machine.env.host.capability?(:smb_installed) &&
+          machine.env.host.capability(:smb_installed)
+        return false if !raise_error
+        raise Errors::SMBNotSupported
       end
 
       def prepare(machine, folders, opts)
         machine.ui.output(I18n.t("vagrant_sf_smb.preparing"))
 
-        script_path = File.expand_path("../scripts/set_share.ps1", __FILE__)
+        # Check if this host can start and SMB service
+        if machine.env.host.capability?(:smb_start)
+          machine.env.host.capability(:smb_start)
+        end
+
+        smb_username = smb_password = nil
 
         # If we need auth information, then ask the user.
         have_auth = false
         folders.each do |id, data|
           if data[:smb_username] && data[:smb_password]
-            @creds[:username] = data[:smb_username]
-            @creds[:password] = data[:smb_password]
+            smb_username = data[:smb_username]
+            smb_password = data[:smb_password]
             have_auth = true
             break
           end
         end
 
         if !have_auth
-          machine.ui.detail(I18n.t("vagrant_sf_smb.warning_password") + "\n ")
-          @creds[:username] = machine.ui.ask("Username: ")
-          @creds[:password] = machine.ui.ask("Password (will be hidden): ", echo: false)
+          machine.env.ui.detail(I18n.t("vagrant_sf_smb.warning_password") + "\n ")
+          smb_username = machine.env.ui.ask("Username: ")
+          smb_password = machine.env.ui.ask("Password (will be hidden): ", echo: false)
         end
 
         folders.each do |id, data|
-          hostpath = data[:hostpath]
+          data[:smb_username] ||= smb_username
+          data[:smb_password] ||= smb_password
 
-          data[:smb_id] ||= Digest::MD5.hexdigest(
-            "#{machine.id}-#{id.gsub("/", "-")}")
-
-          args = []
-          args << "-path" << "\"#{hostpath.gsub("/", "\\")}\""
-          args << "-share_name" << data[:smb_id]
-          #args << "-host_share_username" << @creds[:username]
-
-          r = Vagrant::Util::PowerShell.execute(script_path, *args)
-          if r.exit_code != 0
-            raise Errors::DefineShareFailed,
-              host: hostpath.to_s,
-              stderr: r.stderr,
-              stdout: r.stdout
-          end
+          # Register password as sensitive
+          Vagrant::Util::CredentialScrubber.sensitive(data[:smb_password])
         end
+
+        machine.env.host.capability(:smb_prepare, machine, folders, opts)
       end
 
-      def enable(machine, folders, nfsopts)
+      def enable(machine, folders, opts)
         machine.ui.output(I18n.t("vagrant_sf_smb.mounting"))
 
         # Make sure that this machine knows this dance
@@ -109,7 +92,7 @@ module VagrantPlugins
         end
 
         if need_host_ip
-          candidate_ips = load_host_ips
+          candidate_ips = machine.env.host.capability(:configured_ip_addresses)
           @logger.debug("Potential host IPs: #{candidate_ips.inspect}")
           host_ip = machine.guest.capability(
             :choose_addressable_ip_addr, candidate_ips)
@@ -122,10 +105,7 @@ module VagrantPlugins
         ssh_info = machine.ssh_info
 
         folders.each do |id, data|
-          data = data.dup
           data[:smb_host] ||= host_ip
-          data[:smb_username] ||= @creds[:username]
-          data[:smb_password] ||= @creds[:password]
 
           # Default the owner/group of the folder to the SSH user
           data[:owner] ||= ssh_info[:username]
@@ -141,25 +121,8 @@ module VagrantPlugins
       end
 
       def cleanup(machine, opts)
-
-      end
-
-      protected
-
-      def load_host_ips
-        script_path = File.expand_path("../scripts/host_info.ps1", __FILE__)
-        r = Vagrant::Util::PowerShell.execute(script_path)
-        if r.exit_code != 0
-          raise Errors::PowershellError,
-            script: script_path,
-            stderr: r.stderr
-        end
-
-        res = JSON.parse(r.stdout)["ip_addresses"]
-        if res.instance_of? String
-          [ res ]
-        else
-          res
+        if machine.env.host.capability?(:smb_cleanup)
+          machine.env.host.capability(:smb_cleanup, machine, opts)
         end
       end
     end
diff --git a/templates/locales/synced_folder_smb.yml b/templates/locales/synced_folder_smb.yml
index 442c99405..3521ff4ff 100644
--- a/templates/locales/synced_folder_smb.yml
+++ b/templates/locales/synced_folder_smb.yml
@@ -1,5 +1,10 @@
 en:
   vagrant_sf_smb:
+    not_supported: |-
+      It appears your machine doesn't support SMB, has not been
+      properly configured for SMB, or there is not an adapter to
+      enable SMB on this machine for Vagrant. Ensure SMB host
+      functionality is available on this machine and try again.
     mounting: |-
       Mounting SMB shared folders...
     mounting_single: |-
@@ -9,9 +14,29 @@ en:
     warning_password: |-
       You will be asked for the username and password to use for the SMB
       folders shortly. Please use the proper username/password of your
-      Windows account.
+      account.
 
+    uac:
+      prune_warning: |-
+        Vagrant requires administator access for pruning SMB shares and
+        may request access to complete removal of stale shares.
+      create_warning: |-
+        Vagrant requires administator access to create SMB shares and
+        may request access to complete setup of configured shares.
     errors:
+      start_failed: |-
+        Vagrant failed to automatically start the SMB service. Ensure the
+        required services can be started and try again.
+
+        Command: %{command}
+
+        Stderr: %{stderr}
+
+        Stdout: %{stdout}
+      credentials_missing: |-
+        Vagrant SMB synced folders require the account password to be stored
+        in an NT compatible format. Please update your sharing settings to
+        enable a Windows compatible password and try again.
       define_share_failed: |-
         Exporting an SMB share failed! Details about the failure are shown
         below. Please inspect the error message and correct any problems.
@@ -21,6 +46,27 @@ en:
         Stderr: %{stderr}
 
         Stdout: %{stdout}
+      prune_share_failed: |-
+        Pruning an SMB share failed! Details about the failure are shown
+        below. Please inspect the error message and correct any problems.
+
+        Share name: %{name}
+
+        Stderr: %{stderr}
+
+        Stdout: %{stdout}
+      name_error: |-
+        Vagrant is unable to setup a requested SMB share. An SMB share already
+        exists with the given name.
+
+        Share name: %{name}
+
+        Current path: %{existing_path}
+
+        Requested path: %{path}
+      list_failed: |-
+        Vagrant failed to generate a list of local SMB shares. Please try
+        running the command again.
       no_routable_host_addr: |-
         We couldn't detect an IP address that was routable to this
         machine from the guest machine! Please verify networking is properly
@@ -29,16 +75,6 @@ en:
 
         As another option, you can manually specify an IP for the machine
         to mount from using the `smb_host` option to the synced folder.
-      powershell_error: |-
-        An error occurred while executing a PowerShell script. This error
-        is shown below. Please read the error message and see if this is
-        a configuration error with your system. If it is not, then please
-        report a bug.
-
-        Script: %{script}
-        Error:
-
-        %{stderr}
       powershell_version: |-
         PowerShell version 3 or later is required for SMB synced folders
         to work on Windows. You have version: '%{version}'. Please update
diff --git a/test/unit/plugins/guests/linux/cap/mount_smb_shared_folder.rb b/test/unit/plugins/guests/linux/cap/mount_smb_shared_folder.rb
index cde67e6a6..62d4745f2 100644
--- a/test/unit/plugins/guests/linux/cap/mount_smb_shared_folder.rb
+++ b/test/unit/plugins/guests/linux/cap/mount_smb_shared_folder.rb
@@ -63,6 +63,11 @@ describe "VagrantPlugins::GuestLinux::Cap::MountSMBSharedFolder" do
       cap.mount_smb_shared_folder(machine, mount_name, mount_guest_path, folder_options)
     end
 
+    it "removes the credentials file before completion" do
+      expect(comm).to receive(:sudo).with(/rm.+smb_creds_.+/)
+      cap.mount_smb_shared_folder(machine, mount_name, mount_guest_path, folder_options)
+    end
+
     it "sends upstart notification after mount" do
       expect(comm).to receive(:sudo).with(/emit/)
       cap.mount_smb_shared_folder(machine, mount_name, mount_guest_path, folder_options)
diff --git a/test/unit/plugins/hosts/darwin/cap/configured_ip_addresses_test.rb b/test/unit/plugins/hosts/darwin/cap/configured_ip_addresses_test.rb
new file mode 100644
index 000000000..71d79ed24
--- /dev/null
+++ b/test/unit/plugins/hosts/darwin/cap/configured_ip_addresses_test.rb
@@ -0,0 +1,31 @@
+require_relative "../../../../base"
+
+require_relative "../../../../../../plugins/hosts/darwin/cap/configured_ip_addresses"
+
+describe VagrantPlugins::HostDarwin::Cap::ConfiguredIPAddresses do
+
+  let(:subject){ VagrantPlugins::HostDarwin::Cap::ConfiguredIPAddresses }
+  let(:interfaces){ ["192.168.1.2"] }
+  before{ allow(Socket).to receive(:getifaddrs).and_return(
+    interfaces.map{|i| double(:socket, addr: Addrinfo.ip(i))}) }
+
+  it "should get list of available addresses" do
+    expect(subject.configured_ip_addresses(nil)).to eq(["192.168.1.2"])
+  end
+
+  context "with loopback address" do
+    let(:interfaces){ ["192.168.1.2", "127.0.0.1"] }
+
+    it "should not include loopback address" do
+      expect(subject.configured_ip_addresses(nil)).not_to include(["127.0.0.1"])
+    end
+  end
+
+  context "with IPv6 address" do
+    let(:interfaces){ ["192.168.1.2", "2001:200:dff:fff1:216:3eff:feb1:44d7"] }
+
+    it "should not include IPv6 address" do
+      expect(subject.configured_ip_addresses(nil)).not_to include(["2001:200:dff:fff1:216:3eff:feb1:44d7"])
+    end
+  end
+end
diff --git a/test/unit/plugins/hosts/darwin/cap/smb_test.rb b/test/unit/plugins/hosts/darwin/cap/smb_test.rb
new file mode 100644
index 000000000..5d5884bc9
--- /dev/null
+++ b/test/unit/plugins/hosts/darwin/cap/smb_test.rb
@@ -0,0 +1,129 @@
+require_relative "../../../../base"
+
+require_relative "../../../../../../plugins/hosts/darwin/cap/smb"
+
+describe VagrantPlugins::HostDarwin::Cap::SMB do
+  include_context "unit"
+
+  let(:subject){ VagrantPlugins::HostDarwin::Cap::SMB }
+  let(:machine){ double(:machine) }
+  let(:env){ double(:env) }
+  let(:options){ {} }
+  let(:result){ Vagrant::Util::Subprocess::Result }
+
+  before{ allow(subject).to receive(:machine_id).and_return("CUSTOM_ID") }
+
+  describe ".smb_installed" do
+    it "is installed if sharing binary exists" do
+      expect(File).to receive(:exist?).with("/usr/sbin/sharing").and_return(true)
+      expect(subject.smb_installed(nil)).to be(true)
+    end
+
+    it "is not installed if sharing binary does not exist" do
+      expect(File).to receive(:exist?).with("/usr/sbin/sharing").and_return(false)
+      expect(subject.smb_installed(nil)).to be(false)
+    end
+  end
+
+  describe ".smb_start" do
+    before{ allow(Vagrant::Util::Subprocess).to receive(:execute)
+        .and_return(result.new(0, "SMB-NT", "")) }
+
+    it "should check for NT compatible password" do
+      expect(Vagrant::Util::Subprocess).to receive(:execute).with("pwpolicy", "gethashtypes").
+        and_return(result.new(0, "SMB-NT", ""))
+      subject.smb_start(env)
+    end
+
+    it "should raise error if NT compatible password is not set" do
+      expect(Vagrant::Util::Subprocess).to receive(:execute).with("pwpolicy", "gethashtypes").
+        and_return(result.new(0, "", ""))
+      expect{ subject.smb_start(env) }.to raise_error(VagrantPlugins::SyncedFolderSMB::Errors::SMBCredentialsMissing)
+    end
+
+    it "should ignore if the command returns non-zero" do
+      expect(Vagrant::Util::Subprocess).to receive(:execute).with("pwpolicy", "gethashtypes").
+        and_return(result.new(1, "", ""))
+      subject.smb_start(env)
+    end
+
+    it "should not load smb preferences if it is already loaded" do
+      expect(Vagrant::Util::Subprocess).to receive(:execute).with("launchctl", "list", /preferences/).and_return(result.new(0, "", ""))
+      expect(Vagrant::Util::Subprocess).not_to receive(:execute).with(/sudo/, /launchctl/, "load", "-w", /preferences/)
+      subject.smb_start(env)
+    end
+
+    it "should load smb preferences if it is not already loaded" do
+      expect(Vagrant::Util::Subprocess).to receive(:execute).with("launchctl", "list", /preferences/).and_return(result.new(1, "", ""))
+      expect(Vagrant::Util::Subprocess).to receive(:execute).with(/sudo/, /launchctl/, "load", "-w", /preferences/).and_return(result.new(0, "", ""))
+      subject.smb_start(env)
+    end
+
+    it "should raise error if load smb preferences fails" do
+      expect(Vagrant::Util::Subprocess).to receive(:execute).with("launchctl", "list", /preferences/).and_return(result.new(1, "", ""))
+      expect(Vagrant::Util::Subprocess).to receive(:execute).with(/sudo/, /launchctl/, "load", "-w", /preferences/).and_return(result.new(1, "", ""))
+      expect{ subject.smb_start(env) }.to raise_error(VagrantPlugins::SyncedFolderSMB::Errors::SMBStartFailed)
+    end
+
+    it "should not load smbd if it is already loaded" do
+      expect(Vagrant::Util::Subprocess).to receive(:execute).with("launchctl", "list", /smbd/).and_return(result.new(0, "", ""))
+      expect(Vagrant::Util::Subprocess).not_to receive(:execute).with(/sudo/, /launchctl/, "load", "-w", /smbd/)
+      subject.smb_start(env)
+    end
+
+    it "should load smbd if it is not already loaded" do
+      expect(Vagrant::Util::Subprocess).to receive(:execute).with("launchctl", "list", /smbd/).and_return(result.new(1, "", ""))
+      expect(Vagrant::Util::Subprocess).to receive(:execute).with(/sudo/, /launchctl/, "load", "-w", /smbd/).and_return(result.new(0, "", ""))
+      subject.smb_start(env)
+    end
+
+    it "should raise error if load smbd fails" do
+      expect(Vagrant::Util::Subprocess).to receive(:execute).with("launchctl", "list", /smbd/).and_return(result.new(1, "", ""))
+      expect(Vagrant::Util::Subprocess).to receive(:execute).with(/sudo/, /launchctl/, "load", "-w", /smbd/).and_return(result.new(1, "", ""))
+      expect{ subject.smb_start(env) }.to raise_error(VagrantPlugins::SyncedFolderSMB::Errors::SMBStartFailed)
+    end
+  end
+
+  describe ".smb_cleanup" do
+    after{ subject.smb_cleanup(env, machine, options) }
+
+    it "should search for shares with generated machine ID" do
+      expect(Vagrant::Util::Subprocess).to receive(:execute).with(
+        "/usr/bin/sudo", /sharing/, "-l").and_return(result.new(0, "", ""))
+    end
+
+    it "should remove shares individually" do
+      expect(Vagrant::Util::Subprocess).to receive(:execute).
+        with("/usr/bin/sudo", /sharing/, "-l").
+        and_return(result.new(0, "name: vgt-CUSTOM_ID-1\nname: vgt-CUSTOM_ID-2\n", ""))
+      expect(Vagrant::Util::Subprocess).to receive(:execute).with(/sudo/, /sharing/, anything, /CUSTOM_ID/).
+        twice.and_return(result.new(0, "", ""))
+    end
+  end
+
+  describe ".smb_prepare" do
+    let(:folders){ {"/first/path" => {hostpath: "/first/host", smb_id: "ID1"},
+      "/second/path" => {hostpath: "/second/host"}} }
+    before{ allow(Vagrant::Util::Subprocess).to receive(:execute).and_return(result.new(0, "", "")) }
+    it "should provide ID value if not set" do
+      subject.smb_prepare(env, machine, folders, options)
+      expect(folders["/second/path"][:smb_id]).to start_with("vgt-")
+    end
+
+    it "should not modify ID if already set" do
+      subject.smb_prepare(env, machine, folders, options)
+      expect(folders["/first/path"][:smb_id]).to eq("ID1")
+    end
+
+    it "should raise error when sharing command fails" do
+      expect(Vagrant::Util::Subprocess).to receive(:execute).and_return(result.new(1, "", ""))
+      expect{ subject.smb_prepare(env, machine, folders, options) }.to raise_error(
+        VagrantPlugins::SyncedFolderSMB::Errors::DefineShareFailed)
+    end
+
+    it "should add shares individually" do
+      expect(Vagrant::Util::Subprocess).to receive(:execute).with(/sudo/, any_args).twice.and_return(result.new(0, "", ""))
+      subject.smb_prepare(env, machine, folders, options)
+    end
+  end
+end
diff --git a/test/unit/plugins/hosts/windows/cap/configure_ip_addresses_test.rb b/test/unit/plugins/hosts/windows/cap/configure_ip_addresses_test.rb
new file mode 100644
index 000000000..b9f298c1e
--- /dev/null
+++ b/test/unit/plugins/hosts/windows/cap/configure_ip_addresses_test.rb
@@ -0,0 +1,43 @@
+require_relative "../../../../base"
+
+require_relative "../../../../../../plugins/hosts/windows/cap/configured_ip_addresses"
+
+describe VagrantPlugins::HostWindows::Cap::ConfiguredIPAddresses do
+
+  let(:subject){ VagrantPlugins::HostWindows::Cap::ConfiguredIPAddresses }
+  let(:result){ Vagrant::Util::Subprocess::Result }
+  let(:addresses){ [] }
+  let(:execute_result){ result.new(0, {ip_addresses: addresses}.to_json, "") }
+
+  before{ allow(Vagrant::Util::PowerShell).to receive(:execute).
+      and_return(execute_result) }
+
+  it "should return an array" do
+    expect(subject.configured_ip_addresses(nil)).to be_kind_of(Array)
+  end
+
+  context "with single address returned" do
+    let(:addresses){ "ADDRESS" }
+
+    it "should return an array" do
+      expect(subject.configured_ip_addresses(nil)).to eq([addresses])
+    end
+  end
+
+  context "with multiple addresses returned" do
+    let(:addresses){ ["ADDRESS1", "ADDRESS2"] }
+
+    it "should return an array" do
+      expect(subject.configured_ip_addresses(nil)).to eq(addresses)
+    end
+  end
+
+  context "with failed script execution" do
+    let(:execute_result){ result.new(1, "", "") }
+
+    it "should raise error" do
+      expect{ subject.configured_ip_addresses(nil) }.to raise_error(
+        Vagrant::Errors::PowerShellError)
+    end
+  end
+end
diff --git a/test/unit/plugins/hosts/windows/cap/smb_test.rb b/test/unit/plugins/hosts/windows/cap/smb_test.rb
new file mode 100644
index 000000000..c904bc205
--- /dev/null
+++ b/test/unit/plugins/hosts/windows/cap/smb_test.rb
@@ -0,0 +1,148 @@
+require_relative "../../../../base"
+
+require_relative "../../../../../../plugins/hosts/windows/cap/smb"
+
+describe VagrantPlugins::HostWindows::Cap::SMB do
+  let(:subject){ VagrantPlugins::HostWindows::Cap::SMB }
+  let(:machine){ double(:machine, env: double(:machine_env, ui: double(:ui))) }
+  let(:env){ double(:env) }
+  let(:options){ {} }
+  let(:result){ Vagrant::Util::Subprocess::Result }
+  let(:powershell_version){ "3" }
+  let(:smblist){ <<-EOF
+Name        : vgt-CUSTOM_ID-1
+Path        : /a/path
+Description : vgt-CUSTOM_ID-1
+
+Name        : vgt-CUSTOM_ID-2
+Path        : /other/path
+Description : vgt-CUSTOM_ID-2
+
+Name        : my-share
+Path        : /my/path
+Description : Not Vagrant Owned
+
+    EOF
+  }
+
+
+  before do
+    allow(subject).to receive(:machine_id).and_return("CUSTOM_ID")
+    allow(Vagrant::Util::PowerShell).to receive(:version).and_return(powershell_version)
+    allow(Vagrant::Util::PowerShell).to receive(:execute_cmd).and_return("")
+    allow(machine.env.ui).to receive(:warn)
+    allow(subject).to receive(:sleep)
+  end
+
+  describe ".smb_installed" do
+    context "when powershell version is greater than 2" do
+      it "is valid installation" do
+        expect(subject.smb_installed(nil)).to eq(true)
+      end
+    end
+
+    context "when powershell version is less than 3" do
+      let(:powershell_version){ "2" }
+
+      it "is not a valid installation" do
+        expect(subject.smb_installed(nil)).to eq(false)
+      end
+    end
+  end
+
+  describe ".smb_cleanup" do
+    before do
+      allow(Vagrant::Util::PowerShell).to receive(:execute_cmd).with(/Get-SmbShare/).
+        and_return(smblist)
+      allow(Vagrant::Util::PowerShell).to receive(:execute).and_return(result.new(0, "", ""))
+    end
+    after{ subject.smb_cleanup(env, machine, options) }
+
+    it "should pause after warning user" do
+      expect(machine.env.ui).to receive(:warn)
+      expect(subject).to receive(:sleep)
+    end
+
+    it "should remove all shares in single call" do
+      expect(Vagrant::Util::PowerShell).to receive(:execute).with(any_args, sudo: true).once
+    end
+
+    context "when no shares are defined" do
+      before do
+        expect(Vagrant::Util::PowerShell).to receive(:execute_cmd).with(/Get-SmbShare/).
+          and_return("")
+      end
+
+      it "should not attempt to remove shares" do
+        expect(Vagrant::Util::PowerShell).not_to receive(:execute).with(any_args, sudo: true)
+      end
+
+      it "should not warn user" do
+        expect(machine.env.ui).not_to receive(:warn)
+      end
+    end
+  end
+
+  describe ".smb_prepare" do
+    let(:folders){ {"/first/path" => {hostpath: "/host/1"}, "/second/path" => {hostpath: "/host/2", smb_id: "ID1"}} }
+    let(:options){ {} }
+
+    before{ allow(Vagrant::Util::PowerShell).to receive(:execute).and_return(result.new(0, "", "")) }
+
+    it "should add ID when not defined" do
+      subject.smb_prepare(env, machine, folders, options)
+      expect(folders["/first/path"][:smb_id]).to start_with("vgt-")
+    end
+
+    it "should not modify ID when defined" do
+      subject.smb_prepare(env, machine, folders, options)
+      expect(folders["/second/path"][:smb_id]).to eq("ID1")
+    end
+
+    it "should pause after warning user" do
+      expect(machine.env.ui).to receive(:warn)
+      expect(subject).to receive(:sleep)
+      subject.smb_prepare(env, machine, folders, options)
+    end
+
+    it "should add all shares in single call" do
+      expect(Vagrant::Util::PowerShell).to receive(:execute).with(any_args, sudo: true).once
+      subject.smb_prepare(env, machine, folders, options)
+    end
+
+    context "when share already exists" do
+      let(:shares){ {"ID1" => {"Path" => "/host/2"}} }
+      before do
+        allow(File).to receive(:expand_path).and_call_original
+        expect(subject).to receive(:existing_shares).and_return(shares)
+      end
+
+      it "should expand paths when comparing existing to requested" do
+        expect(File).to receive(:expand_path).at_least(2).with("/host/2").and_return("expanded_path")
+        subject.smb_prepare(env, machine, folders, options)
+      end
+
+      context "with different path" do
+        let(:shares){ {"ID1" => {"Path" => "/host/3"}} }
+
+        it "should raise an error" do
+          expect{
+            subject.smb_prepare(env, machine, folders, options)
+          }.to raise_error(VagrantPlugins::SyncedFolderSMB::Errors::SMBNameError)
+        end
+      end
+    end
+
+    context "when no shared are defined" do
+      after{ subject.smb_prepare(env, machine, {}, options) }
+
+      it "should not attempt to add shares" do
+        expect(Vagrant::Util::PowerShell).not_to receive(:execute).with(any_args, sudo: true)
+      end
+
+      it "should not warn user" do
+        expect(machine.env.ui).not_to receive(:warn)
+      end
+    end
+  end
+end
diff --git a/test/unit/plugins/providers/virtualbox/action/prepare_nfs_settings_test.rb b/test/unit/plugins/providers/virtualbox/action/prepare_nfs_settings_test.rb
index 9345b4011..2a854671b 100644
--- a/test/unit/plugins/providers/virtualbox/action/prepare_nfs_settings_test.rb
+++ b/test/unit/plugins/providers/virtualbox/action/prepare_nfs_settings_test.rb
@@ -30,6 +30,8 @@ describe VagrantPlugins::ProviderVirtualBox::Action::PrepareNFSSettings do
     env[:test] = true
     allow(machine.env).to receive(:host) { host }
     allow(host).to receive(:capability).with(:nfs_installed) { true }
+    # We don't care about smb support so return not installed
+    allow(host).to receive(:capability?).with(:smb_installed).and_return(false)
   end
 
   it "calls the next action in the chain" do
diff --git a/test/unit/plugins/synced_folders/smb/synced_folder_test.rb b/test/unit/plugins/synced_folders/smb/synced_folder_test.rb
new file mode 100644
index 000000000..a80d45a3a
--- /dev/null
+++ b/test/unit/plugins/synced_folders/smb/synced_folder_test.rb
@@ -0,0 +1,222 @@
+require_relative "../../../base"
+
+require Vagrant.source_root.join("plugins/synced_folders/smb/synced_folder")
+
+describe VagrantPlugins::SyncedFolderSMB::SyncedFolder do
+  include_context "unit"
+
+  let(:iso_env) do
+    env = isolated_environment
+    env.vagrantfile("")
+    env.create_vagrant_env
+  end
+
+  let(:guest){ double("guest") }
+  let(:host){ double("host") }
+  let(:machine) { iso_env.machine(iso_env.machine_names[0], :dummy) }
+  let(:host_caps){ [] }
+  let(:guest_caps){ [] }
+  let(:folders){ {"/first/path" => {}, "/second/path" => {}} }
+  let(:options){ {} }
+
+  before do
+    allow(machine.env).to receive(:host).and_return(host)
+    allow(machine).to receive(:guest).and_return(guest)
+    allow(machine).to receive(:ssh_info).and_return(username: 'sshuser')
+    allow(guest).to receive(:name).and_return("guest_name")
+    allow(host).to receive(:capability?).and_return(false)
+    host_caps.each do |cap|
+      allow(host).to receive(:capability?).with(cap).and_return(true)
+      allow(host).to receive(:capability).with(cap, any_args).and_return(true)
+    end
+    allow(guest).to receive(:capability?).and_return(false)
+    guest_caps.each do |cap|
+      allow(guest).to receive(:capability?).with(cap).and_return(true)
+      allow(guest).to receive(:capability).with(cap, any_args).and_return(true)
+    end
+  end
+
+  describe ".usable?" do
+    context "without supporting capabilities" do
+      it "is not usable" do
+        expect(subject.usable?(machine)).to be(false)
+      end
+
+      it "raises exception when raise_error enabled" do
+        expect{subject.usable?(machine, true)}.to raise_error(
+          VagrantPlugins::SyncedFolderSMB::Errors::SMBNotSupported)
+      end
+    end
+
+    context "with smb not installed" do
+      let(:host_caps){ [:smb_installed] }
+
+      it "is not usable" do
+        expect(host).to receive(:capability).with(:smb_installed).and_return(false)
+        expect(subject.usable?(machine)).to be(false)
+      end
+    end
+
+    context "with smb installed" do
+      let(:host_caps){ [:smb_installed] }
+
+      it "is usable" do
+        expect(subject.usable?(machine)).to be(true)
+      end
+    end
+  end
+
+  describe ".prepare" do
+    let(:host_caps){ [:smb_start, :smb_prepare] }
+
+    context "without credentials provided" do
+      before do
+        expect(machine.env.ui).to receive(:ask).and_return('username')
+        expect(machine.env.ui).to receive(:ask).and_return('password')
+      end
+
+      it "should prompt for credentials" do
+        subject.prepare(machine, folders, options)
+      end
+
+      it "should set credential information into all folder options" do
+        subject.prepare(machine, folders, options)
+        expect(folders['/first/path'][:smb_username]).to eq('username')
+        expect(folders['/first/path'][:smb_password]).to eq('password')
+        expect(folders['/second/path'][:smb_username]).to eq('username')
+        expect(folders['/second/path'][:smb_password]).to eq('password')
+      end
+
+      it "should start the SMB service if capability is available" do
+        expect(host).to receive(:capability).with(:smb_start, any_args)
+        subject.prepare(machine, folders, options)
+      end
+    end
+
+    context "with credentials provided" do
+      context "in single share entry" do
+        let(:folders){ {'/first/path' => {}, '/second/path' => {smb_username: 'smbuser', smb_password: 'smbpass'}} }
+
+        it "should not prompt for credentials" do
+          expect(machine.env.ui).not_to receive(:ask)
+          subject.prepare(machine, folders, options)
+        end
+
+        it "should add existing credentials to folder options without" do
+          subject.prepare(machine, folders, options)
+          expect(folders['/first/path'][:smb_username]).to eq('smbuser')
+          expect(folders['/first/path'][:smb_password]).to eq('smbpass')
+        end
+      end
+
+      context "in both entries" do
+        let(:folders){ {'/first/path' => {smb_username: 'user', smb_password: 'pass'},
+          '/second/path' => {smb_username: 'smbuser', smb_password: 'smbpass'}} }
+
+        it "should not modify existing credentials" do
+          subject.prepare(machine, folders, options)
+          expect(folders['/first/path'][:smb_username]).to eq('user')
+          expect(folders['/first/path'][:smb_password]).to eq('pass')
+          expect(folders['/second/path'][:smb_username]).to eq('smbuser')
+          expect(folders['/second/path'][:smb_password]).to eq('smbpass')
+        end
+
+        it "should register passwords with scrubber" do
+          expect(Vagrant::Util::CredentialScrubber).to receive(:sensitive).with('pass')
+          expect(Vagrant::Util::CredentialScrubber).to receive(:sensitive).with('smbpass')
+          subject.prepare(machine, folders, options)
+        end
+      end
+    end
+  end
+
+  describe ".enable" do
+    it "fails when guest does not support capability" do
+      expect{
+        subject.enable(machine, folders, options)
+      }.to raise_error(Vagrant::Errors::GuestCapabilityNotFound)
+    end
+
+    context "with guest capability supported" do
+      let(:guest_caps){ [:mount_smb_shared_folder, :choose_addressable_ip_addr] }
+      let(:host_caps){ [:configured_ip_addresses] }
+
+      it "should attempt to install smb on guest" do
+        expect(guest).to receive(:capability?).with(:smb_install).and_return(true)
+        expect(guest).to receive(:capability).with(:smb_install, any_args)
+        subject.enable(machine, folders, options)
+      end
+
+      it "should request host IP addresses" do
+        expect(host).to receive(:capability).with(:configured_ip_addresses)
+        subject.enable(machine, folders, options)
+      end
+
+      it "should determine guest accessible address" do
+        expect(guest).to receive(:capability).with(:choose_addressable_ip_addr, any_args)
+        subject.enable(machine, folders, options)
+      end
+
+      it "should error if no guest accessible address is available" do
+        expect(guest).to receive(:capability).with(:choose_addressable_ip_addr, any_args).and_return(nil)
+        expect{ subject.enable(machine, folders, options) }.to raise_error(
+          VagrantPlugins::SyncedFolderSMB::Errors::NoHostIPAddr)
+      end
+
+      it "should default owner and group to ssh username" do
+        subject.enable(machine, folders, options)
+        expect(folders["/first/path"][:owner]).to eq("sshuser")
+        expect(folders["/first/path"][:group]).to eq("sshuser")
+        expect(folders["/second/path"][:owner]).to eq("sshuser")
+        expect(folders["/second/path"][:group]).to eq("sshuser")
+      end
+
+      it "should set the host address in folder options" do
+        expect(guest).to receive(:capability).with(:choose_addressable_ip_addr, any_args).and_return("ADDR")
+        subject.enable(machine, folders, options)
+        expect(folders["/first/path"][:smb_host]).to eq("ADDR")
+        expect(folders["/second/path"][:smb_host]).to eq("ADDR")
+      end
+
+      context "with smb_host option set" do
+        let(:folders){ {"/first/path" => {smb_host: "ADDR"}, "/second/path" => {}} }
+
+        it "should not update the value" do
+          expect(guest).to receive(:capability).with(:choose_addressable_ip_addr, any_args).and_return("OTHER")
+          subject.enable(machine, folders, options)
+          expect(folders["/first/path"][:smb_host]).to eq("ADDR")
+          expect(folders["/second/path"][:smb_host]).to eq("OTHER")
+        end
+      end
+
+      context "with owner and group set" do
+        let(:folders){ {"/first/path" => {owner: "smbowner"}, "/second/path" => {group: "smbgroup"}} }
+
+        it "should not update set owner or group" do
+          subject.enable(machine, folders, options)
+          expect(folders["/first/path"][:owner]).to eq("smbowner")
+          expect(folders["/first/path"][:group]).to eq("sshuser")
+          expect(folders["/second/path"][:owner]).to eq("sshuser")
+          expect(folders["/second/path"][:group]).to eq("smbgroup")
+        end
+      end
+    end
+  end
+
+  describe ".cleanup" do
+    context "without supporting capability" do
+      it "does nothing" do
+        subject.cleanup(machine, options)
+      end
+    end
+
+    context "with supporting capability" do
+      let(:host_caps){ [:smb_cleanup] }
+
+      it "runs cleanup" do
+        expect(host).to receive(:capability).with(:smb_cleanup, any_args)
+        subject.cleanup(machine, options)
+      end
+    end
+  end
+end
diff --git a/website/source/docs/synced-folders/smb.html.md b/website/source/docs/synced-folders/smb.html.md
index 6b88857e4..58206ad9a 100644
--- a/website/source/docs/synced-folders/smb.html.md
+++ b/website/source/docs/synced-folders/smb.html.md
@@ -19,17 +19,50 @@ SMB is built-in to Windows machines and provides a higher performance
 alternative to some other mechanisms such as VirtualBox shared folders.
 
 <div class="alert alert-info">
-  <strong>Windows only!</strong> SMB is currently only supported
-  when the host machine is Windows. The guest machine can be Windows
-  or Linux.
+  SMB is currently only supported when the host machine is Windows or
+  macOS. The guest machine can be Windows, Linux, or macOS.
 </div>
 
 ## Prerequisites
 
-To use the SMB synced folder type, the machine running Vagrant must be
-a Windows machine with PowerShell version 3 or later installed. In addition to this, the command prompt executing Vagrant
-must have administrative privileges. Vagrant requires these privileges in
-order to create new network folder shares.
+### Windows Host
+
+To use the SMB synced folder type on a Windows host, the machine must have
+PowerShell version 3 or later installed. In addition, when Vagrant attempts
+to create new SMB shares, or remove existing SMB shares, Administrator
+privileges will be required. Vagrant will request these privileges using UAC.
+
+### macOS Host
+
+To use the SMB synced folder type on a macOS host, file sharing must be enabled
+for the local account. Enable SMB file sharing by following the instructions
+below:
+
+* Open "System Preferences"
+* Click "Sharing"
+* Check the "On" checkbox next to "File Sharing"
+* Click "Options"
+* Check "Share files and folders using SMB"
+* Check the "On" checkbox next to your username within "Windows File Sharing"
+* Click "Done"
+
+When Vagrant attempts to create new SMB shares, or remove existing SMB shares,
+root access will be required. Vagrant will request these privileges using
+`sudo` to run the `/usr/sbin/sharing` command. Adding the following to
+the system's `sudoers` configuration will allow Vagrant to manage SMB shares
+without requiring a password each time:
+
+```
+Cmnd_Alias VAGRANT_SMB_ADD = /usr/sbin/sharing -a * -S * -s * -g * -n *
+Cmnd_Alias VAGRANT_SMB_REMOVE = /usr/sbin/sharing -r *
+Cmnd_Alias VAGRANT_SMB_LIST = /usr/sbin/sharing -l
+Cmnd_Alias VAGRANT_SMB_PLOAD = /bin/launchctl load -w /System/Library/LaunchDaemons/com.apple.smb.preferences.plist
+Cmnd_Alias VAGRANT_SMB_DLOAD = /bin/launchctl load -w /System/Library/LaunchDaemons/com.apple.smbd.plist
+Cmnd_Alias VAGRANT_SMB_DSTART = /bin/launchctl start com.apple.smbd
+%admin ALL=(root) NOPASSWD: VAGRANT_SMB_ADD, VAGRANT_SMB_REMOVE, VAGRANT_SMB_LIST, VAGRANT_SMB_PLOAD, VAGRANT_SMB_DLOAD VAGRANT_SMB_DSTART
+```
+
+### Guests
 
 The destination machine must be able to mount SMB filesystems. On Linux
 the package to do this is usually called `smbfs` or `cifs`. Vagrant knows
@@ -75,18 +108,6 @@ shell. Note that you should research if this is the right option for you.
 net config server /autodisconnect:-1
 ```
 
-## Limitations
-
-Because SMB is a relatively new synced folder type in Vagrant, it still
-has some rough edges. Hopefully, future versions of Vagrant will address
-these.
-
-The primary limitation of SMB synced folders at the moment is that they are
-never pruned or cleaned up. Once the folder share is defined, Vagrant never
-removes it. To clean up SMB synced folder shares, periodically run
-`net share` in a command prompt, find the shares you do not want, then
-run `net share NAME /delete` for each, where NAME is the name of the share.
-
 ## Common Issues
 
 ### "wrong fs type" Error