diff --git a/lib/vagrant/errors.rb b/lib/vagrant/errors.rb
index 8fe7d9e71..b706145df 100644
--- a/lib/vagrant/errors.rb
+++ b/lib/vagrant/errors.rb
@@ -816,6 +816,22 @@ module Vagrant
       error_key(:unimplemented_provider_action)
     end
 
+    class UploadInvalidCompressionType < VagrantError
+      error_key(:upload_invalid_compression_type)
+    end
+
+    class UploadMissingExtractCapability < VagrantError
+      error_key(:upload_missing_extract_capability)
+    end
+
+    class UploadMissingTempCapability < VagrantError
+      error_key(:upload_missing_temp_capability)
+    end
+
+    class UploadSourceMissing < VagrantError
+      error_key(:upload_source_missing)
+    end
+
     class VagrantInterrupt < VagrantError
       error_key(:interrupted)
     end
@@ -968,6 +984,10 @@ module Vagrant
       error_key(:power_off, "vagrant.actions.vm.export")
     end
 
+    class WinRMInvalidCommunicator < VagrantError
+      error_key(:winrm_invalid_communicator)
+    end
+
     class WSLVagrantVersionMismatch < VagrantError
       error_key(:wsl_vagrant_version_mismatch)
     end
diff --git a/plugins/commands/upload/command.rb b/plugins/commands/upload/command.rb
new file mode 100644
index 000000000..a6a408990
--- /dev/null
+++ b/plugins/commands/upload/command.rb
@@ -0,0 +1,236 @@
+require 'optparse'
+require "rubygems/package"
+
+module VagrantPlugins
+  module CommandUpload
+    class Command < Vagrant.plugin("2", :command)
+
+      VALID_COMPRESS_TYPES = [:tgz, :zip].freeze
+
+      def self.synopsis
+        "upload to machine via communicator"
+      end
+
+      def execute
+        options = {}
+
+        opts = OptionParser.new do |o|
+          o.banner = "Usage: vagrant upload [options] <source> [destination] [name|id]"
+          o.separator ""
+          o.separator "Options:"
+          o.separator ""
+
+          o.on("-t", "--temporary", "Upload source to temporary directory") do |t|
+            options[:temporary] = t
+          end
+
+          o.on("-c", "--compress", "Use gzip compression for upload") do |c|
+            options[:compress] = c
+          end
+
+          o.on("-C", "--compression-type=TYPE", "Type of compression to use (#{VALID_COMPRESS_TYPES.join(", ")})") do |c|
+            options[:compression_type] = c.to_sym
+            options[:compress] = true
+          end
+        end
+
+        argv = parse_options(opts)
+        return if !argv
+
+        case argv.size
+        when 3
+          source, destination, guest = argv
+        when 2, 1
+          source = argv[0]
+          if @env.active_machines.map(&:first).map(&:to_s).include?(argv[1])
+            guest = argv[1]
+          else
+            destination = argv[1]
+          end
+        else
+          raise Vagrant::Errors::CLIInvalidUsage, help: opts.help.chomp
+        end
+
+        # NOTE: We do this to handle paths on Windows like: "..\space dir\"
+        # because the final separater acts to escape the quote and ends up
+        # in the source value.
+        source = source.sub(/["']$/, "")
+        destination ||= File.basename(source)
+
+        if File.file?(source)
+          type = :file
+        elsif File.directory?(source)
+          type = :directory
+        else
+          raise Vagrant::Errors::UploadSourceMissing,
+            source: source
+        end
+
+        with_target_vms(guest, single_target: true) do |machine|
+          if options[:temporary]
+            if !machine.guest.capability?(:create_tmp_path)
+              raise Vagrant::Errors::UploadMissingTempCapability
+            end
+            extension = File.extname(source) if type == :file
+            destination = machine.guest.capability(:create_tmp_path, type: type, extension: extension)
+          end
+
+          if options[:compress]
+            compression_setup!(machine, options)
+            @env.ui.info(I18n.t("vagrant.commands.upload.compress",
+              source: source,
+              type: options[:compression_type]
+            ))
+            destination_decompressed = destination
+            destination = machine.guest.capability(:create_tmp_path, type: :file, extension: ".#{options[:compression_type]}")
+            source_display = source
+            source = options[:compression_type] == :zip ? compress_source_zip(source) : compress_source_tgz(source)
+          end
+
+          @env.ui.info(I18n.t("vagrant.commands.upload.start",
+            source: source,
+            destination: destination
+          ))
+
+          # If the source is a directory, attach a `/.` to the end so we
+          # upload the contents to the destination instead of within a
+          # folder at the destination
+          if File.directory?(source) && !source.end_with?(".")
+            upload_source = File.join(source, ".")
+          else
+            upload_source = source
+          end
+
+          machine.communicate.upload(upload_source, destination)
+
+          if options[:compress]
+            @env.ui.info(I18n.t("vagrant.commands.upload.decompress",
+              destination: destination_decompressed,
+              type: options[:compression_type]
+            ))
+            machine.guest.capability(options[:decompression_method], destination, destination_decompressed, type: type)
+            destination = destination_decompressed
+            FileUtils.rm(source)
+            source = source_display
+          end
+        end
+
+        @env.ui.info(I18n.t("vagrant.commands.upload.complete",
+          source: source,
+          destination: destination
+        ))
+
+        # Success, exit status 0
+        0
+      end
+
+      # Setup compression options and validate host and guest have capability
+      # to handle compression
+      #
+      # @param [Vagrant::Machine] machine Vagrant guest machine
+      # @param [Hash] options Command options
+      def compression_setup!(machine, options)
+        if !options[:compression_type]
+          if machine.guest.capability_host_chain.first[0] == :windows
+            options[:compression_type] = :zip
+          else
+            options[:compression_type] = :tgz
+          end
+        end
+        if !VALID_COMPRESS_TYPES.include?(options[:compression_type])
+          raise Vagrant::Errors::UploadInvalidCompressionType,
+            type: options[:compression_type],
+            valid_types: VALID_COMPRESS_TYPES.join(", ")
+        end
+        options[:decompression_method] = "decompress_#{options[:compression_type]}".to_sym
+        if !machine.guest.capability?(options[:decompression_method])
+          raise Vagrant::Errors::UploadMissingExtractCapability,
+            type: options[:compression_type]
+        end
+      end
+
+      # Compress path using zip into temporary file
+      #
+      # @param [String] path Path to compress
+      # @return [String] path to compressed file
+      def compress_source_zip(path)
+        require "zip"
+        zipfile = Tempfile.create(["vagrant", ".zip"])
+        zipfile.close
+        if File.file?(path)
+          source_items = [path]
+        else
+          source_items = Dir.glob(File.join(path, "**", "**", "*"))
+        end
+        c_dir = nil
+        Zip::File.open(zipfile.path, Zip::File::CREATE) do |zip|
+          source_items.each do |source_item|
+            next if File.directory?(source_item)
+            trim_item = source_item.sub(path, "").sub(%r{^[/\\]}, "")
+            dirname = File.dirname(trim_item)
+            zip.mkdir dirname if c_dir != dirname
+            c_dir = dirname
+            zip.get_output_stream(trim_item) do |f|
+              source_file = File.open(source_item, "rb")
+              while data = source_file.read(2048)
+                f.write(data)
+              end
+            end
+          end
+        end
+        zipfile.path
+      end
+
+      # Compress path using tar and gzip into temporary file
+      #
+      # @param [String] path Path to compress
+      # @return [String] path to compressed file
+      def compress_source_tgz(path)
+        tarfile = Tempfile.create(["vagrant", ".tar"])
+        tarfile.close
+        tarfile = File.open(tarfile.path, "wb+")
+        tgzfile = Tempfile.create(["vagrant", ".tgz"])
+        tgzfile.close
+        tgzfile = File.open(tgzfile.path, "wb")
+        tar = Gem::Package::TarWriter.new(tarfile)
+        tgz = Zlib::GzipWriter.new(tgzfile)
+        if File.file?(path)
+          tar.add_file(File.basename(path), File.stat(path).mode) do |io|
+            File.open(path, "rb") do |file|
+              while bytes = file.read(4096)
+                io.write(bytes)
+              end
+            end
+          end
+        else
+          Dir.glob(File.join(path, "**/**/*")).each do |item|
+            rel_path = item.sub(path, "")
+            item_mode = File.stat(item).mode
+
+            if File.directory?(item)
+              tar.mkdir(rel_path, item_mode)
+            else
+              tar.add_file(rel_path, item_mode) do |io|
+                File.open(item, "rb") do |file|
+                  while bytes = file.read(4096)
+                    io.write(bytes)
+                  end
+                end
+              end
+            end
+          end
+        end
+        tar.close
+        tarfile.rewind
+        while bytes = tarfile.read(4096)
+          tgz.write bytes
+        end
+        tgz.close
+        tgzfile.close
+        tarfile.close
+        File.delete(tarfile.path)
+        tgzfile.path
+      end
+    end
+  end
+end
diff --git a/plugins/commands/upload/plugin.rb b/plugins/commands/upload/plugin.rb
new file mode 100644
index 000000000..ec1c64804
--- /dev/null
+++ b/plugins/commands/upload/plugin.rb
@@ -0,0 +1,17 @@
+require "vagrant"
+
+module VagrantPlugins
+  module CommandUpload
+    class Plugin < Vagrant.plugin("2")
+      name "upload command"
+      description <<-DESC
+      The `upload` command uploads files to guest via communicator
+      DESC
+
+      command("upload") do
+        require File.expand_path("../command", __FILE__)
+        Command
+      end
+    end
+  end
+end
diff --git a/plugins/commands/winrm/command.rb b/plugins/commands/winrm/command.rb
new file mode 100644
index 000000000..dd19109db
--- /dev/null
+++ b/plugins/commands/winrm/command.rb
@@ -0,0 +1,69 @@
+require 'optparse'
+
+require "vagrant/util/safe_puts"
+
+module VagrantPlugins
+  module CommandWinRM
+    class Command < Vagrant.plugin("2", :command)
+      include Vagrant::Util::SafePuts
+
+      def self.synopsis
+        "executes commands on a machine via WinRM"
+      end
+
+      def execute
+        options = {
+          command: [],
+          shell: :powershell
+        }
+
+        opts = OptionParser.new do |o|
+          o.banner = "Usage: vagrant winrm [options] [name|id]"
+          o.separator ""
+          o.separator "Options:"
+          o.separator ""
+
+          o.on("-c", "--command COMMAND", "Execute a WinRM command directly") do |c|
+            options[:command] << c
+          end
+
+          o.on("-e", "--elevated", "Run with elevated credentials") do |e|
+            options[:elevated] = true
+          end
+
+          o.on("-s", "--shell SHELL", [:powershell, :cmd], "Use specified shell (powershell, cmd)") do |s|
+            options[:shell] = s
+          end
+        end
+
+        argv = parse_options(opts)
+        return if !argv
+
+        with_target_vms(argv, single_target: true) do |machine|
+          if machine.config.vm.communicator != :winrm
+            raise Vagrant::Errors::WinRMInvalidCommunicator
+          end
+
+          opts = {
+            shell: options[:shell],
+            elevated: !!options[:elevated]
+          }
+
+          options[:command].each do |cmd|
+            begin
+              machine.communicate.execute(cmd, opts) do |type, data|
+                io = type == :stderr ? $stderr : $stdout
+                safe_puts(data, io: io, printer: :print)
+              end
+            rescue VagrantPlugins::CommunicatorWinRM::Errors::WinRMBadExitStatus
+              return 1
+            end
+          end
+        end
+
+        # Success, exit status 0
+        0
+      end
+    end
+  end
+end
diff --git a/plugins/commands/winrm/plugin.rb b/plugins/commands/winrm/plugin.rb
new file mode 100644
index 000000000..5a578ff4f
--- /dev/null
+++ b/plugins/commands/winrm/plugin.rb
@@ -0,0 +1,17 @@
+require "vagrant"
+
+module VagrantPlugins
+  module CommandWinRM
+    class Plugin < Vagrant.plugin("2")
+      name "winrm command"
+      description <<-DESC
+      The `winrm` command executes commands on a machine via WinRM
+      DESC
+
+      command("winrm") do
+        require File.expand_path("../command", __FILE__)
+        Command
+      end
+    end
+  end
+end
diff --git a/plugins/commands/winrm_config/command.rb b/plugins/commands/winrm_config/command.rb
new file mode 100644
index 000000000..995eccf55
--- /dev/null
+++ b/plugins/commands/winrm_config/command.rb
@@ -0,0 +1,125 @@
+require 'optparse'
+require "vagrant/util/safe_puts"
+require_relative "../../communicators/winrm/helper"
+
+module VagrantPlugins
+  module CommandWinRMConfig
+    class Command < Vagrant.plugin("2", :command)
+      include Vagrant::Util::SafePuts
+
+      def self.synopsis
+        "outputs WinRM configuration to connect to the machine"
+      end
+
+      def convert_win_paths(paths)
+        paths.map! { |path| Vagrant::Util::Platform.format_windows_path(path, :disable_unc) }
+      end
+
+      def execute
+        options = {}
+
+        opts = OptionParser.new do |o|
+          o.banner = "Usage: vagrant winrm-config [options] [name|id]"
+          o.separator ""
+          o.separator "Options:"
+          o.separator ""
+
+          o.on("--host NAME", "Name the host for the config") do |h|
+            options[:host] = h
+          end
+        end
+
+        argv = parse_options(opts)
+        return if !argv
+
+        with_target_vms(argv) do |machine|
+          winrm_info = CommunicatorWinRM::Helper.winrm_info(machine)
+          raise Vagrant::Errors::WinRMNotRead if winrm_info.nil?
+
+          rdp_info = get_rdp_info(machine) || {}
+
+          variables = {
+            host_key: options[:host] || machine.name || "vagrant",
+            rdp_host: rdp_info[:host] || winrm_info[:host],
+            rdp_port: rdp_info[:port],
+            rdp_user: rdp_info[:username],
+            rdp_pass: rdp_info[:password],
+            winrm_host: winrm_info[:host],
+            winrm_port: winrm_info[:port],
+            winrm_user: machine.config.winrm.username,
+            winrm_password: machine.config.winrm.password
+          }
+
+          template = "commands/winrm_config/config"
+          config = Vagrant::Util::TemplateRenderer.render(template, variables)
+          machine.ui.machine("winrm-config", config)
+          safe_puts(config)
+          safe_puts
+        end
+
+        # Success, exit status 0
+        0
+      end
+
+      protected
+
+      # Generate RDP information for machine
+      #
+      # @param [Vagrant::Machine] machine Guest machine
+      # @return [Hash, nil]
+      def get_rdp_info(machine)
+        rdp_info = {}
+        if machine.provider.capability?(:rdp_info)
+          rdp_info = machine.provider.capability(:rdp_info)
+          rdp_info ||= {}
+        end
+
+        ssh_info = machine.ssh_info || {}
+
+        if !rdp_info[:username]
+          username = ssh_info[:username]
+          if machine.config.vm.communicator == :winrm
+            username = machine.config.winrm.username
+          end
+          rdp_info[:username] = username
+        end
+
+        if !rdp_info[:password]
+          password = ssh_info[:password]
+          if machine.config.vm.communicator == :winrm
+            password = machine.config.winrm.password
+          end
+          rdp_info[:password] = password
+        end
+
+        rdp_info[:host] ||= ssh_info[:host]
+        rdp_info[:port] ||= machine.config.rdp.port
+        rdp_info[:username] ||= machine.config.rdp.username
+
+        if rdp_info[:host] == "127.0.0.1"
+          # We need to find a forwarded port...
+          search_port = machine.config.rdp.search_port
+          ports       = nil
+          if machine.provider.capability?(:forwarded_ports)
+            ports = machine.provider.capability(:forwarded_ports)
+          else
+            ports = {}.tap do |result|
+              machine.config.vm.networks.each do |type, netopts|
+                next if type != :forwarded_port
+                next if !netopts[:host]
+                result[netopts[:host]] = netopts[:guest]
+              end
+            end
+          end
+
+          ports = ports.invert
+          port  = ports[search_port]
+          rdp_info[:port] = port
+          return nil if !port
+        end
+
+        rdp_info
+      end
+    end
+  end
+end
diff --git a/plugins/commands/winrm_config/plugin.rb b/plugins/commands/winrm_config/plugin.rb
new file mode 100644
index 000000000..2b0b8e37e
--- /dev/null
+++ b/plugins/commands/winrm_config/plugin.rb
@@ -0,0 +1,17 @@
+require "vagrant"
+
+module VagrantPlugins
+  module CommandWinRMConfig
+    class Plugin < Vagrant.plugin("2")
+      name "winrm-config command"
+      description <<-DESC
+      The `winrm-config` command dumps WinRM configuration information
+      DESC
+
+      command("winrm-config") do
+        require File.expand_path("../command", __FILE__)
+        Command
+      end
+    end
+  end
+end
diff --git a/plugins/guests/bsd/cap/file_system.rb b/plugins/guests/bsd/cap/file_system.rb
new file mode 100644
index 000000000..c14f7b376
--- /dev/null
+++ b/plugins/guests/bsd/cap/file_system.rb
@@ -0,0 +1,77 @@
+module VagrantPlugins
+  module GuestBSD
+    module Cap
+      class FileSystem
+        # Create a temporary file or directory on the guest
+        #
+        # @param [Vagrant::Machine] machine Vagrant guest machine
+        # @param [Hash] opts Path options
+        # @return [String] path to temporary file or directory
+        def self.create_tmp_path(machine, opts)
+          template = "vagrant"
+          cmd = ["mktemp"]
+          if opts[:type] == :directory
+            cmd << "-d"
+          end
+          cmd << "-t"
+          cmd << template
+          tmp_path = ""
+          machine.communicate.execute(cmd.join(" ")) do |type, data|
+            if type == :stdout
+              tmp_path << data
+            end
+          end
+          tmp_path.strip
+        end
+
+        # Decompress tgz file on guest to given location
+        #
+        # @param [Vagrant::Machine] machine Vagrant guest machine
+        # @param [String] compressed_file Path to compressed file on guest
+        # @param [String] destination Path for decompressed files on guest
+        def self.decompress_tgz(machine, compressed_file, destination, opts={})
+          comm = machine.communicate
+          extract_dir = create_tmp_path(machine, type: :directory)
+          cmds = []
+          if opts[:type] == :directory
+            cmds << "mkdir -p '#{destination}'"
+          else
+            cmds << "mkdir -p '#{File.dirname(destination)}'"
+          end
+          cmds += [
+            "tar -C '#{extract_dir}' -xzf '#{compressed_file}'",
+            "mv '#{extract_dir}'/* '#{destination}'",
+            "rm -f '#{compressed_file}'",
+            "rm -rf '#{extract_dir}'"
+          ]
+          cmds.each{ |cmd| comm.execute(cmd) }
+          true
+        end
+
+        # Decompress zip file on guest to given location
+        #
+        # @param [Vagrant::Machine] machine Vagrant guest machine
+        # @param [String] compressed_file Path to compressed file on guest
+        # @param [String] destination Path for decompressed files on guest
+        def self.decompress_zip(machine, compressed_file, destination, opts={})
+          comm = machine.communicate
+          extract_dir = create_tmp_path(machine, type: :directory)
+          cmds = []
+          if opts[:type] == :directory
+            cmds << "mkdir -p '#{destination}'"
+          else
+            cmds << "mkdir -p '#{File.dirname(destination)}'"
+          end
+          cmds += [
+            "unzip '#{compressed_file}' -d '#{extract_dir}'",
+            "mv '#{extract_dir}'/* '#{destination}'",
+            "rm -f '#{compressed_file}'",
+            "rm -rf '#{extract_dir}'"
+          ]
+          cmds.each{ |cmd| comm.execute(cmd) }
+          true
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/guests/bsd/plugin.rb b/plugins/guests/bsd/plugin.rb
index 368765cdf..9a726cfdc 100644
--- a/plugins/guests/bsd/plugin.rb
+++ b/plugins/guests/bsd/plugin.rb
@@ -11,6 +11,21 @@ module VagrantPlugins
         Guest
       end
 
+      guest_capability(:bsd, :create_tmp_path) do
+        require_relative "cap/file_system"
+        Cap::FileSystem
+      end
+
+      guest_capability(:bsd, :decompress_tgz) do
+        require_relative "cap/file_system"
+        Cap::FileSystem
+      end
+
+      guest_capability(:bsd, :decompress_zip) do
+        require_relative "cap/file_system"
+        Cap::FileSystem
+      end
+
       guest_capability(:bsd, :halt) do
         require_relative "cap/halt"
         Cap::Halt
diff --git a/plugins/guests/linux/cap/file_system.rb b/plugins/guests/linux/cap/file_system.rb
new file mode 100644
index 000000000..abff30e37
--- /dev/null
+++ b/plugins/guests/linux/cap/file_system.rb
@@ -0,0 +1,79 @@
+module VagrantPlugins
+  module GuestLinux
+    module Cap
+      class FileSystem
+        # Create a temporary file or directory on the guest
+        #
+        # @param [Vagrant::Machine] machine Vagrant guest machine
+        # @param [Hash] opts Path options
+        # @return [String] path to temporary file or directory
+        def self.create_tmp_path(machine, opts)
+          template = "vagrant-XXXXXX"
+          if opts[:extension]
+            template << opts[:extension].to_s
+          end
+          cmd = ["mktemp", "--tmpdir"]
+          if opts[:type] == :directory
+            cmd << "-d"
+          end
+          cmd << template
+          tmp_path = ""
+          machine.communicate.execute(cmd.join(" ")) do |type, data|
+            if type == :stdout
+              tmp_path << data
+            end
+          end
+          tmp_path.strip
+        end
+
+        # Decompress tgz file on guest to given location
+        #
+        # @param [Vagrant::Machine] machine Vagrant guest machine
+        # @param [String] compressed_file Path to compressed file on guest
+        # @param [String] destination Path for decompressed files on guest
+        def self.decompress_tgz(machine, compressed_file, destination, opts={})
+          comm = machine.communicate
+          extract_dir = create_tmp_path(machine, type: :directory)
+          cmds = []
+          if opts[:type] == :directory
+            cmds << "mkdir -p '#{destination}'"
+          else
+            cmds << "mkdir -p '#{File.dirname(destination)}'"
+          end
+          cmds += [
+            "tar -C '#{extract_dir}' -xzf '#{compressed_file}'",
+            "mv '#{extract_dir}'/* '#{destination}'",
+            "rm -f '#{compressed_file}'",
+            "rm -rf '#{extract_dir}'"
+          ]
+          cmds.each{ |cmd| comm.execute(cmd) }
+          true
+        end
+
+        # Decompress zip file on guest to given location
+        #
+        # @param [Vagrant::Machine] machine Vagrant guest machine
+        # @param [String] compressed_file Path to compressed file on guest
+        # @param [String] destination Path for decompressed files on guest
+        def self.decompress_zip(machine, compressed_file, destination, opts={})
+          comm = machine.communicate
+          extract_dir = create_tmp_path(machine, type: :directory)
+          cmds = []
+          if opts[:type] == :directory
+            cmds << "mkdir -p '#{destination}'"
+          else
+            cmds << "mkdir -p '#{File.dirname(destination)}'"
+          end
+          cmds += [
+            "unzip '#{compressed_file}' -d '#{extract_dir}'",
+            "mv '#{extract_dir}'/* '#{destination}'",
+            "rm -f '#{compressed_file}'",
+            "rm -rf '#{extract_dir}'"
+          ]
+          cmds.each{ |cmd| comm.execute(cmd) }
+          true
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/guests/linux/plugin.rb b/plugins/guests/linux/plugin.rb
index cb0a53c19..e4752571e 100644
--- a/plugins/guests/linux/plugin.rb
+++ b/plugins/guests/linux/plugin.rb
@@ -16,6 +16,21 @@ module VagrantPlugins
         Cap::ChooseAddressableIPAddr
       end
 
+      guest_capability(:linux, :create_tmp_path) do
+        require_relative "cap/file_system"
+        Cap::FileSystem
+      end
+
+      guest_capability(:linux, :decompress_tgz) do
+        require_relative "cap/file_system"
+        Cap::FileSystem
+      end
+
+      guest_capability(:linux, :decompress_zip) do
+        require_relative "cap/file_system"
+        Cap::FileSystem
+      end
+
       guest_capability(:linux, :halt) do
         require_relative "cap/halt"
         Cap::Halt
diff --git a/plugins/guests/solaris/cap/file_system.rb b/plugins/guests/solaris/cap/file_system.rb
new file mode 100644
index 000000000..d697c9db8
--- /dev/null
+++ b/plugins/guests/solaris/cap/file_system.rb
@@ -0,0 +1,77 @@
+module VagrantPlugins
+  module GuestSolaris
+    module Cap
+      class FileSystem
+        # Create a temporary file or directory on the guest
+        #
+        # @param [Vagrant::Machine] machine Vagrant guest machine
+        # @param [Hash] opts Path options
+        # @return [String] path to temporary file or directory
+        def self.create_tmp_path(machine, opts)
+          template = "vagrant-XXXXXX"
+          cmd = ["mktemp"]
+          if opts[:type] == :directory
+            cmd << "-d"
+          end
+          cmd << "-t"
+          cmd << template
+          tmp_path = ""
+          machine.communicate.execute(cmd.join(" ")) do |type, data|
+            if type == :stdout
+              tmp_path << data
+            end
+          end
+          tmp_path.strip
+        end
+
+        # Decompress tgz file on guest to given location
+        #
+        # @param [Vagrant::Machine] machine Vagrant guest machine
+        # @param [String] compressed_file Path to compressed file on guest
+        # @param [String] destination Path for decompressed files on guest
+        def self.decompress_tgz(machine, compressed_file, destination, opts={})
+          comm = machine.communicate
+          extract_dir = create_tmp_path(machine, type: :directory)
+          cmds = []
+          if opts[:type] == :directory
+            cmds << "mkdir -p '#{destination}'"
+          else
+            cmds << "mkdir -p '#{File.dirname(destination)}'"
+          end
+          cmds += [
+            "tar xzf '#{compressed_file}' -C '#{extract_dir}'",
+            "mv '#{extract_dir}'/* '#{destination}'",
+            "rm -f '#{compressed_file}'",
+            "rm -rf '#{extract_dir}'"
+          ]
+          cmds.each{ |cmd| comm.execute(cmd) }
+          true
+        end
+
+        # Decompress zip file on guest to given location
+        #
+        # @param [Vagrant::Machine] machine Vagrant guest machine
+        # @param [String] compressed_file Path to compressed file on guest
+        # @param [String] destination Path for decompressed files on guest
+        def self.decompress_zip(machine, compressed_file, destination, opts={})
+          comm = machine.communicate
+          extract_dir = create_tmp_path(machine, type: :directory)
+          cmds = []
+          if opts[:type] == :directory
+            cmds << "mkdir -p '#{destination}'"
+          else
+            cmds << "mkdir -p '#{File.dirname(destination)}'"
+          end
+          cmds += [
+            "unzip '#{compressed_file}' -d '#{extract_dir}'",
+            "mv '#{extract_dir}'/* '#{destination}'",
+            "rm -f '#{compressed_file}'",
+            "rm -rf '#{extract_dir}'"
+          ]
+          cmds.each{ |cmd| comm.execute(cmd) }
+          true
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/guests/solaris/plugin.rb b/plugins/guests/solaris/plugin.rb
index 83c373100..b8c16df12 100644
--- a/plugins/guests/solaris/plugin.rb
+++ b/plugins/guests/solaris/plugin.rb
@@ -16,6 +16,21 @@ module VagrantPlugins
         Guest
       end
 
+      guest_capability(:solaris, :create_tmp_path) do
+        require_relative "cap/file_system"
+        Cap::FileSystem
+      end
+
+      guest_capability(:solaris, :decompress_tgz) do
+        require_relative "cap/file_system"
+        Cap::FileSystem
+      end
+
+      guest_capability(:solaris, :decompress_zip) do
+        require_relative "cap/file_system"
+        Cap::FileSystem
+      end
+
       guest_capability(:solaris, :change_host_name) do
         require_relative "cap/change_host_name"
         Cap::ChangeHostName
diff --git a/plugins/guests/windows/cap/file_system.rb b/plugins/guests/windows/cap/file_system.rb
new file mode 100644
index 000000000..85a7d4a2f
--- /dev/null
+++ b/plugins/guests/windows/cap/file_system.rb
@@ -0,0 +1,65 @@
+module VagrantPlugins
+  module GuestWindows
+    module Cap
+      class FileSystem
+        # Create a temporary file or directory on the guest
+        #
+        # @param [Vagrant::Machine] machine Vagrant guest machine
+        # @param [Hash] opts Path options
+        # @return [String] path to temporary file or directory
+        def self.create_tmp_path(machine, opts)
+          comm = machine.communicate
+          path = ""
+          cmd = "Write-Output ([System.IO.Path]::Combine([System.IO.Path]::GetTempPath(), " \
+            "[System.IO.Path]::GetRandomFileName())) | Out-String -Width 2048"
+          comm.execute(cmd, shell: :powershell) do |type, data|
+            if type == :stdout
+              path << data
+            end
+          end
+          path.strip!
+          if opts[:extension]
+            path << opts[:extension].to_s
+          end
+          if opts[:type] == :directory
+            comm.execute("[System.IO.Directory]::CreateDirectory('#{path}')")
+          end
+          path
+        end
+
+        # Decompress zip file on guest to given location
+        #
+        # @param [Vagrant::Machine] machine Vagrant guest machine
+        # @param [String] compressed_file Path to compressed file on guest
+        # @param [String] destination Path for decompressed files on guest
+        def self.decompress_zip(machine, compressed_file, destination, opts={})
+          comm = machine.communicate
+          extract_dir = create_tmp_path(machine, type: :directory)
+          cmds = []
+          destination = destination.tr("/", "\\")
+          if opts[:type] == :directory
+            cmds << "New-Item -ItemType Directory -Force -Path \"#{destination}\""
+          else
+            d_parts = destination.split("\\")
+            d_parts.pop
+            parent_dir = d_parts.join("\\") + "\\"
+            cmds << "New-Item -ItemType Directory -Force -Path \"#{parent_dir}\""
+          end
+          cmd = "$f = \"#{compressed_file}\"; $d = \"#{extract_dir}\"; "
+          cmd << '$s = New-Object -ComObject "Shell.Application"; $z = $s.NameSpace($f); '
+          cmd << 'foreach($i in $z.items()){ $s.Namespace($d).copyhere($i); }'
+          cmds << cmd
+          cmds += [
+            "Move-Item -Force -Path \"#{extract_dir}\\*\" -Destination \"#{destination}\\\"",
+            "Remove-Item -Path \"#{compressed_file}\" -Force",
+            "Remove-Item -Path \"#{extract_dir}\" -Recurse -Force"
+          ]
+          cmds.each do |cmd|
+            comm.execute(cmd, shell: :powershell)
+          end
+          true
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/guests/windows/plugin.rb b/plugins/guests/windows/plugin.rb
index f7a71e959..76124f6b4 100644
--- a/plugins/guests/windows/plugin.rb
+++ b/plugins/guests/windows/plugin.rb
@@ -34,6 +34,16 @@ module VagrantPlugins
         Cap::Halt
       end
 
+      guest_capability(:windows, :create_tmp_path) do
+        require_relative "cap/file_system"
+        Cap::FileSystem
+      end
+
+      guest_capability(:windows, :decompress_zip) do
+        require_relative "cap/file_system"
+        Cap::FileSystem
+      end
+
       guest_capability(:windows, :mount_virtualbox_shared_folder) do
         require_relative "cap/mount_shared_folder"
         Cap::MountSharedFolder
diff --git a/templates/commands/winrm_config/config.erb b/templates/commands/winrm_config/config.erb
new file mode 100644
index 000000000..9eb269eb1
--- /dev/null
+++ b/templates/commands/winrm_config/config.erb
@@ -0,0 +1,11 @@
+Host <%= host_key %>
+  HostName <%= winrm_host %>
+  User <%= winrm_user %>
+  Password <%= winrm_password %>
+  Port <%= winrm_port %>
+  <% if rdp_port -%>
+  RDPHostName <%= rdp_host %>
+  RDPPort <%= rdp_port %>
+  RDPUser <%= rdp_user %>
+  RDPPassword <%= rdp_pass %>
+  <% end -%>
diff --git a/templates/locales/en.yml b/templates/locales/en.yml
index 530f8f5c3..020805632 100644
--- a/templates/locales/en.yml
+++ b/templates/locales/en.yml
@@ -1462,6 +1462,8 @@ en:
         your current setup. Please verify you have all the proper
         prerequisites for using this shared folder type and try again.
 
+      test_key: |-
+        test value
       triggers_run_fail: |-
         Trigger run failed
       triggers_guest_not_running: |-
@@ -1489,6 +1491,24 @@ en:
         '%{provider}', but this provider doesn't support this action. This
         is probably a bug in either the provider or the plugin calling this
         action, and should be reported.
+      upload_invalid_compression_type: |-
+        The compression type requested for upload (`%{type}`) is not a
+        supported value. Try uploading again using a valid compression
+        type.
+
+          Supported types: %{valid_types}
+      upload_missing_extract_capability: |-
+        The guest does not provide extraction capability for the requested
+        compression type (`%{type}`). Try a different compression type or
+        upload without compression.
+      upload_missing_temp_capability: |-
+        The guest does not provide temporary path capabilities. Please
+        try the upload again without requesting a temporary path.
+      upload_source_missing: |-
+        The source path provided for upload cannot be found. Please validate
+        the source location for upload an try again.
+
+          Source Path: %{source}
       vagrantfile_exists: |-
         `Vagrantfile` already exists in this directory. Remove it before
         running `vagrant init`.
@@ -1685,7 +1705,9 @@ en:
       vm_not_running: |-
         VM must be running to open SSH connection. Run `vagrant up`
         to start the virtual machine.
-      test_key: "test value"
+      winrm_invalid_communicator: |-
+        The winrm command requires a WinRM communicator to be used when connecting
+        to the guest. Please update your configuration and try the command again.
       wsl_vagrant_version_mismatch: |-
         Vagrant cannot currently enable access to manage machines within the Windows
         environment because the version of Vagrant installed on Windows does not
@@ -2025,6 +2047,18 @@ en:
       up:
         upping: |-
           Bringing machine '%{name}' up with '%{provider}' provider...
+      upload:
+        compress: |-
+          Compressing %{source} to %{type} for upload...
+        complete: |-
+          Upload has completed successfully!
+
+            Source: %{source}
+            Destination: %{destination}
+        decompress: |-
+          Decompressing %{type} upload to %{destination}...
+        start: |-
+          Uploading %{source} to %{destination}
       validate:
         success: |-
           Vagrantfile validated successfully.
diff --git a/test/unit/plugins/commands/upload/command_test.rb b/test/unit/plugins/commands/upload/command_test.rb
new file mode 100644
index 000000000..c8077d710
--- /dev/null
+++ b/test/unit/plugins/commands/upload/command_test.rb
@@ -0,0 +1,242 @@
+require File.expand_path("../../../../base", __FILE__)
+require Vagrant.source_root.join("plugins/commands/upload/command")
+
+describe VagrantPlugins::CommandUpload::Command do
+  include_context "unit"
+  include_context "virtualbox"
+
+  let(:iso_env) do
+    # We have to create a Vagrantfile so there is a root path
+    env = isolated_environment
+    env.vagrantfile("")
+    env.create_vagrant_env
+  end
+
+  let(:guest)   { double("guest", capability_host_chain: guest_chain) }
+  let(:host)    { double("host", capability_host_chain: host_chain) }
+  let(:machine) { iso_env.machine(iso_env.machine_names[0], :dummy) }
+  let(:communicator) { double("communicator") }
+  let(:host_chain){ [[]] }
+  let(:guest_chain){ [[]] }
+
+  let(:argv)     { [] }
+  let(:config) {
+    double("config")
+  }
+
+  subject { described_class.new(argv, iso_env) }
+
+  before do
+    allow(machine).to receive(:communicate).and_return(communicator)
+    allow(machine).to receive(:config).and_return(config)
+    allow(subject).to receive(:with_target_vms)
+  end
+
+  it "should raise invalid usage error by default" do
+    expect { subject.execute }.to raise_error(Vagrant::Errors::CLIInvalidUsage)
+  end
+
+  context "when three arguments are provided" do
+    let(:argv) { ["source", "destination", "guest"] }
+
+    before { allow(File).to receive(:file?).and_return(true) }
+
+    it "should use third argument as name of guest" do
+      expect(subject).to receive(:with_target_vms).with("guest", any_args)
+      subject.execute
+    end
+
+    it "should use first argument as source and second as destination" do
+      allow(subject).to receive(:with_target_vms) { |&block| block.call machine }
+      expect(communicator).to receive(:upload).with("source", "destination")
+      subject.execute
+    end
+  end
+
+  context "when two arguments are provided" do
+    let(:argv) { ["source", "ambiguous"] }
+    let(:active_machines) { [] }
+
+    before do
+      allow(File).to receive(:file?).and_return(true)
+      allow(iso_env).to receive(:active_machines).and_return(active_machines)
+    end
+
+    it "should use the the second argument as destination when not a machine name" do
+      allow(subject).to receive(:with_target_vms) { |&block| block.call machine }
+      expect(communicator).to receive(:upload).with("source", "ambiguous")
+      subject.execute
+    end
+
+    context "when active machine matches second argument" do
+      let(:active_machines) { [["ambiguous"]] }
+
+      it "should use second argument as guest name and generate destination" do
+        allow(subject).to receive(:with_target_vms).with("ambiguous", any_args) { |&block| block.call machine }
+        expect(communicator).to receive(:upload).with("source", "source")
+        subject.execute
+      end
+    end
+  end
+
+  context "when single argument is provided" do
+    let(:argv) { ["item"] }
+
+    before do
+      allow(File).to receive(:file?)
+      allow(File).to receive(:directory?)
+    end
+
+    it "should check if source is a file" do
+      expect(File).to receive(:file?).with("item").and_return(true)
+      subject.execute
+    end
+
+    it "should check if source is a directory" do
+      expect(File).to receive(:directory?).with("item").and_return(true)
+      subject.execute
+    end
+
+    it "should raise error if source is not a directory or file" do
+      expect { subject.execute }.to raise_error(Vagrant::Errors::UploadSourceMissing)
+    end
+
+    context "when source path ends with double quote" do
+      let(:argv) { [".\\item\""] }
+
+      it "should remove trailing quote" do
+        expect(File).to receive(:file?).with(".\\item").and_return(true)
+        subject.execute
+      end
+    end
+
+    context "when source path ends with single quote" do
+      let(:argv) { ['.\item\''] }
+
+      it "should remove trailing quote" do
+        expect(File).to receive(:file?).with(".\\item").and_return(true)
+        subject.execute
+      end
+    end
+
+    context "when source is a directory" do
+      before do
+        allow(File).to receive(:file?).with("item").and_return(false)
+        allow(File).to receive(:directory?).with("item").and_return(true)
+        allow(communicator).to receive(:upload)
+        allow(subject).to receive(:with_target_vms) { |&block| block.call machine }
+      end
+
+      it "should upload the directory" do
+        expect(communicator).to receive(:upload).with(/item/, anything)
+        subject.execute
+      end
+
+      it "should append separator and dot to source path for upload" do
+        expect(communicator).to receive(:upload).with("item/.", anything)
+        subject.execute
+      end
+    end
+
+    context "when source is a file" do
+      before do
+        allow(File).to receive(:file?).with("item").and_return(true)
+        allow(communicator).to receive(:upload)
+        allow(subject).to receive(:with_target_vms) { |&block| block.call machine }
+        allow(machine).to receive(:guest).and_return(guest)
+        allow(machine).to receive(:env).and_return(double("env", host: host))
+        allow(guest).to receive(:capability?).and_return(true)
+        allow(guest).to receive(:capability)
+      end
+
+      it "should upload the file" do
+        expect(communicator).to receive(:upload).with("item", anything)
+        subject.execute
+      end
+
+      it "should name destination after the source" do
+        expect(communicator).to receive(:upload).with("item", "item")
+        subject.execute
+      end
+
+      context "when temporary option is set" do
+        before { argv << "-t" }
+
+        it "should get temporary path for destination from guest" do
+          expect(guest).to receive(:capability).with(:create_tmp_path, any_args).and_return("TMP_PATH")
+          expect(communicator).to receive(:upload).with("item", "TMP_PATH")
+          subject.execute
+        end
+      end
+
+      context "when compress option is set" do
+        before do
+          argv << "-c"
+          allow(guest).to receive(:capability).with(:create_tmp_path, any_args).and_return("TMP")
+          allow(subject).to receive(:compress_source_zip).and_return("COMPRESS_SOURCE")
+          allow(subject).to receive(:compress_source_tgz).and_return("COMPRESS_SOURCE")
+          allow(FileUtils).to receive(:rm).with("COMPRESS_SOURCE")
+        end
+
+        it "should check for guest decompression" do
+          expect(guest).to receive(:capability?).with(:decompress_tgz).and_return(true)
+          subject.execute
+        end
+
+        it "should compress the source" do
+          expect(subject).to receive(:compress_source_tgz).with("item").and_return("COMPRESS_SOURCE")
+          subject.execute
+        end
+
+        it "should cleanup compressed source" do
+          expect(FileUtils).to receive(:rm).with("COMPRESS_SOURCE")
+          subject.execute
+        end
+
+        it "should upload the compressed source" do
+          expect(communicator).to receive(:upload).with("COMPRESS_SOURCE", anything)
+          subject.execute
+        end
+
+        it "should upload compressed source to temporary location" do
+          expect(communicator).to receive(:upload).with("COMPRESS_SOURCE", "TMP")
+          subject.execute
+        end
+
+        it "should have guest decompress file" do
+          expect(guest).to receive(:capability).with(:decompress_tgz, "TMP", any_args)
+          subject.execute
+        end
+
+        it "should provide destination for guest decompression of file" do
+          expect(guest).to receive(:capability).with(:decompress_tgz, "TMP", "item", any_args)
+          subject.execute
+        end
+
+        it "should provide the destination type for guest decompression" do
+          expect(guest).to receive(:capability).with(:decompress_tgz, "TMP", "item", hash_including(type: :file))
+          subject.execute
+        end
+
+        context "with compression type set to zip" do
+          before { argv << "-C" << "zip" }
+
+          it "should test guest for decompression capability" do
+            expect(guest).to receive(:capability?).with(:decompress_zip).and_return(true)
+            subject.execute
+          end
+
+          it "should compress source using zip" do
+            expect(subject).to receive(:compress_source_zip)
+            subject.execute
+          end
+
+          it "should have guest decompress file using zip" do
+            expect(guest).to receive(:capability).with(:decompress_zip, any_args)
+            subject.execute
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/test/unit/plugins/commands/winrm/command_test.rb b/test/unit/plugins/commands/winrm/command_test.rb
new file mode 100644
index 000000000..5481296b8
--- /dev/null
+++ b/test/unit/plugins/commands/winrm/command_test.rb
@@ -0,0 +1,95 @@
+require File.expand_path("../../../../base", __FILE__)
+
+require Vagrant.source_root.join("plugins/commands/winrm/command")
+
+describe VagrantPlugins::CommandWinRM::Command do
+  include_context "unit"
+  include_context "virtualbox"
+
+  let(:iso_env) do
+    # We have to create a Vagrantfile so there is a root path
+    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(:communicator) { double("communicator") }
+
+  let(:argv)     { [] }
+  let(:config) {
+    double("config",
+      vm: double("vm-config", communicator: communicator_name))
+  }
+  let(:communicator_name) { :winrm }
+
+  subject { described_class.new(argv, iso_env) }
+
+  before do
+    allow(machine).to receive(:communicate).and_return(communicator)
+    allow(machine).to receive(:config).and_return(config)
+    allow(subject).to receive(:with_target_vms) { |&block| block.call machine }
+    allow(communicator).to receive(:execute)
+  end
+
+  it "should exit successfully when no command is provided" do
+    expect(subject.execute).to eq(0)
+  end
+
+  context "with command provided" do
+    let(:argv){ ["-c", "dir"] }
+
+    it "should execute the command via the communicator" do
+      expect(communicator).to receive(:execute).with("dir", any_args)
+      subject.execute
+    end
+
+    it "should execute with default shell" do
+      expect(communicator).to receive(:execute).with(anything, hash_including(shell: :powershell))
+      subject.execute
+    end
+
+    it "should execute without elevated privileges" do
+      expect(communicator).to receive(:execute).with(anything, hash_including(elevated: false))
+      subject.execute
+    end
+
+    context "with elevated option set" do
+      let(:argv) { ["-c", "dir", "-e"] }
+
+      it "should execute with elevated privileges" do
+        expect(communicator).to receive(:execute).with(anything, hash_including(elevated: true))
+        subject.execute
+      end
+    end
+
+    context "with shell option set" do
+      let(:argv) { ["-c", "dir", "-s", "cmd"] }
+
+      it "should execute with custom shell" do
+        expect(communicator).to receive(:execute).with(anything, hash_including(shell: :cmd))
+        subject.execute
+      end
+    end
+  end
+
+  context "with multiple command provided" do
+    let(:argv) { ["-c", "dir", "-c", "dir2"] }
+
+    it "should execute multiple commands via the communicator" do
+      expect(communicator).to receive(:execute).with("dir", any_args)
+      expect(communicator).to receive(:execute).with("dir2", any_args)
+      subject.execute
+    end
+  end
+
+  context "with invalid communicator configured" do
+    let(:communicator_name) { :ssh }
+
+    it "should raise an error" do
+      expect { subject.execute }.to raise_error(Vagrant::Errors::WinRMInvalidCommunicator)
+    end
+  end
+end
diff --git a/test/unit/plugins/commands/winrm_config/command_test.rb b/test/unit/plugins/commands/winrm_config/command_test.rb
new file mode 100644
index 000000000..95d3be329
--- /dev/null
+++ b/test/unit/plugins/commands/winrm_config/command_test.rb
@@ -0,0 +1,143 @@
+require File.expand_path("../../../../base", __FILE__)
+
+require Vagrant.source_root.join("plugins/commands/winrm_config/command")
+require Vagrant.source_root.join("plugins/communicators/winrm/helper")
+
+describe VagrantPlugins::CommandWinRMConfig::Command do
+  include_context "unit"
+  include_context "virtualbox"
+
+  let(:iso_env) do
+    # We have to create a Vagrantfile so there is a root path
+    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(:argv)     { [] }
+  let(:winrm_info) {{
+    host: "testhost.vagrant.dev",
+    port: 1234
+  }}
+  let(:config) {
+    double("config",
+      winrm: double("winrm-config", username: "vagrant", password: "vagrant"),
+      rdp: rdp_config,
+      vm: double("vm-config", communicator: :winrm)
+    )
+  }
+
+  let(:rdp_config) { double("rdp-config", port: 9876) }
+
+  subject { described_class.new(argv, iso_env) }
+
+  before do
+    allow(machine).to receive(:config).and_return(config)
+    allow(VagrantPlugins::CommunicatorWinRM::Helper).to receive(:winrm_info).and_return(winrm_info)
+    allow(subject).to receive(:with_target_vms) { |&block| block.call machine }
+  end
+
+  describe "execute" do
+    it "prints out the winrm config for the given machine" do
+      output = ""
+      allow(subject).to receive(:safe_puts) do |data|
+        output += data if data
+      end
+
+      subject.execute
+
+      expect(output).to eq(<<-WINRMCONFIG)
+Host #{machine.name}
+  HostName testhost.vagrant.dev
+  User vagrant
+  Password vagrant
+  Port 1234
+  RDPHostName testhost.vagrant.dev
+  RDPPort 9876
+  RDPUser vagrant
+  RDPPassword vagrant
+      WINRMCONFIG
+    end
+
+    context "with host option set" do
+      let(:argv) { ["--host", "my-host"]}
+
+      it "should use custom host name in config output" do
+        output = ""
+        allow(subject).to receive(:safe_puts) do |data|
+          output += data if data
+        end
+
+        subject.execute
+
+        expect(output).to eq(<<-WINRMCONFIG)
+Host my-host
+  HostName testhost.vagrant.dev
+  User vagrant
+  Password vagrant
+  Port 1234
+  RDPHostName testhost.vagrant.dev
+  RDPPort 9876
+  RDPUser vagrant
+  RDPPassword vagrant
+      WINRMCONFIG
+      end
+    end
+
+    context "when no RDP port is configured" do
+      let(:rdp_config) {  double("rdp-config", port: nil) }
+
+      it "should not include any RDP configuration information" do
+        output = ""
+        allow(subject).to receive(:safe_puts) do |data|
+          output += data if data
+        end
+
+        subject.execute
+        expect(output).not_to include("RDP")
+      end
+    end
+
+    context "when provider has rdp_info capability" do
+      let(:rdp_info) {
+        {host: "provider-host", port: 9999, username: "pvagrant", password: "pvagrant"}
+      }
+
+      before do
+        allow(machine.provider).to receive(:capability?).with(:rdp_info).and_return(true)
+        allow(machine.provider).to receive(:capability).with(:rdp_info).and_return(rdp_info)
+      end
+
+      it "should use provider RDP information" do
+        output = ""
+        allow(subject).to receive(:safe_puts) do |data|
+          output += data if data
+        end
+
+        subject.execute
+        expect(output).to include("RDPPort 9999")
+        expect(output).to include("RDPHostName provider-host")
+        expect(output).to include("RDPUser pvagrant")
+        expect(output).to include("RDPPassword pvagrant")
+      end
+
+      context "when provider rdp_info does not include host" do
+        before { rdp_info[:host] = nil }
+
+        it "should use winrm host" do
+          output = ""
+          allow(subject).to receive(:safe_puts) do |data|
+            output += data if data
+          end
+
+          subject.execute
+          expect(output).to include("RDPHostName testhost.vagrant.dev")
+        end
+      end
+    end
+  end
+end
diff --git a/test/unit/plugins/guests/bsd/cap/file_system_test.rb b/test/unit/plugins/guests/bsd/cap/file_system_test.rb
new file mode 100644
index 000000000..7e7d528d6
--- /dev/null
+++ b/test/unit/plugins/guests/bsd/cap/file_system_test.rb
@@ -0,0 +1,127 @@
+require_relative "../../../../base"
+
+describe "VagrantPlugins::GuestBSD::Cap::FileSystem" do
+  let(:caps) do
+    VagrantPlugins::GuestBSD::Plugin
+      .components
+      .guest_capabilities[:bsd]
+  end
+
+  let(:machine) { double("machine", communicate: comm) }
+  let(:comm) { double("comm") }
+
+  before { allow(comm).to receive(:execute) }
+
+  describe ".create_tmp_path" do
+    let(:cap) { caps.get(:create_tmp_path) }
+    let(:opts) { {} }
+
+    it "should generate path on guest" do
+      expect(comm).to receive(:execute).with(/mktemp/)
+      cap.create_tmp_path(machine, opts)
+    end
+
+    it "should capture path generated on guest" do
+      expect(comm).to receive(:execute).with(/mktemp/).and_yield(:stdout, "TMP_PATH")
+      expect(cap.create_tmp_path(machine, opts)).to eq("TMP_PATH")
+    end
+
+    it "should strip newlines on path" do
+      expect(comm).to receive(:execute).with(/mktemp/).and_yield(:stdout, "TMP_PATH\n")
+      expect(cap.create_tmp_path(machine, opts)).to eq("TMP_PATH")
+    end
+
+    context "when type is a directory" do
+      before { opts[:type] = :directory }
+
+      it "should create guest path as a directory" do
+        expect(comm).to receive(:execute).with(/-d/)
+        cap.create_tmp_path(machine, opts)
+      end
+    end
+  end
+
+  describe ".decompress_tgz" do
+    let(:cap) { caps.get(:decompress_tgz) }
+    let(:comp) { "compressed_file" }
+    let(:dest) { "path/to/destination" }
+    let(:opts) { {} }
+
+    before { allow(cap).to receive(:create_tmp_path).and_return("TMP_DIR") }
+    after{ cap.decompress_tgz(machine, comp, dest, opts) }
+
+    it "should create temporary directory for extraction" do
+      expect(cap).to receive(:create_tmp_path)
+    end
+
+    it "should extract file with tar" do
+      expect(comm).to receive(:execute).with(/tar/)
+    end
+
+    it "should extract file to temporary directory" do
+      expect(comm).to receive(:execute).with(/TMP_DIR/)
+    end
+
+    it "should remove compressed file from guest" do
+      expect(comm).to receive(:execute).with(/rm .*#{comp}/)
+    end
+
+    it "should remove extraction directory from guest" do
+      expect(comm).to receive(:execute).with(/rm .*TMP_DIR/)
+    end
+
+    it "should create parent directories for destination" do
+      expect(comm).to receive(:execute).with(/mkdir -p .*to'/)
+    end
+
+    context "when type is directory" do
+      before { opts[:type] = :directory }
+
+      it "should create destination directory" do
+        expect(comm).to receive(:execute).with(/mkdir -p .*destination'/)
+      end
+    end
+  end
+
+  describe ".decompress_zip" do
+    let(:cap) { caps.get(:decompress_zip) }
+    let(:comp) { "compressed_file" }
+    let(:dest) { "path/to/destination" }
+    let(:opts) { {} }
+
+    before { allow(cap).to receive(:create_tmp_path).and_return("TMP_DIR") }
+    after{ cap.decompress_zip(machine, comp, dest, opts) }
+
+    it "should create temporary directory for extraction" do
+      expect(cap).to receive(:create_tmp_path)
+    end
+
+    it "should extract file with zip" do
+      expect(comm).to receive(:execute).with(/zip/)
+    end
+
+    it "should extract file to temporary directory" do
+      expect(comm).to receive(:execute).with(/TMP_DIR/)
+    end
+
+    it "should remove compressed file from guest" do
+      expect(comm).to receive(:execute).with(/rm .*#{comp}/)
+    end
+
+    it "should remove extraction directory from guest" do
+      expect(comm).to receive(:execute).with(/rm .*TMP_DIR/)
+    end
+
+    it "should create parent directories for destination" do
+      expect(comm).to receive(:execute).with(/mkdir -p .*to'/)
+    end
+
+    context "when type is directory" do
+      before { opts[:type] = :directory }
+
+      it "should create destination directory" do
+        expect(comm).to receive(:execute).with(/mkdir -p .*destination'/)
+      end
+    end
+  end
+end
diff --git a/test/unit/plugins/guests/linux/cap/file_system_test.rb b/test/unit/plugins/guests/linux/cap/file_system_test.rb
new file mode 100644
index 000000000..aa7c0340c
--- /dev/null
+++ b/test/unit/plugins/guests/linux/cap/file_system_test.rb
@@ -0,0 +1,127 @@
+require_relative "../../../../base"
+
+describe "VagrantPlugins::GuestLinux::Cap::FileSystem" do
+  let(:caps) do
+    VagrantPlugins::GuestLinux::Plugin
+      .components
+      .guest_capabilities[:linux]
+  end
+
+  let(:machine) { double("machine", communicate: comm) }
+  let(:comm) { double("comm") }
+
+  before { allow(comm).to receive(:execute) }
+
+  describe ".create_tmp_path" do
+    let(:cap) { caps.get(:create_tmp_path) }
+    let(:opts) { {} }
+
+    it "should generate path on guest" do
+      expect(comm).to receive(:execute).with(/mktemp/)
+      cap.create_tmp_path(machine, opts)
+    end
+
+    it "should capture path generated on guest" do
+      expect(comm).to receive(:execute).with(/mktemp/).and_yield(:stdout, "TMP_PATH")
+      expect(cap.create_tmp_path(machine, opts)).to eq("TMP_PATH")
+    end
+
+    it "should strip newlines on path" do
+      expect(comm).to receive(:execute).with(/mktemp/).and_yield(:stdout, "TMP_PATH\n")
+      expect(cap.create_tmp_path(machine, opts)).to eq("TMP_PATH")
+    end
+
+    context "when type is a directory" do
+      before { opts[:type] = :directory }
+
+      it "should create guest path as a directory" do
+        expect(comm).to receive(:execute).with(/-d/)
+        cap.create_tmp_path(machine, opts)
+      end
+    end
+  end
+
+  describe ".decompress_tgz" do
+    let(:cap) { caps.get(:decompress_tgz) }
+    let(:comp) { "compressed_file" }
+    let(:dest) { "path/to/destination" }
+    let(:opts) { {} }
+
+    before { allow(cap).to receive(:create_tmp_path).and_return("TMP_DIR") }
+    after{ cap.decompress_tgz(machine, comp, dest, opts) }
+
+    it "should create temporary directory for extraction" do
+      expect(cap).to receive(:create_tmp_path)
+    end
+
+    it "should extract file with tar" do
+      expect(comm).to receive(:execute).with(/tar/)
+    end
+
+    it "should extract file to temporary directory" do
+      expect(comm).to receive(:execute).with(/TMP_DIR/)
+    end
+
+    it "should remove compressed file from guest" do
+      expect(comm).to receive(:execute).with(/rm .*#{comp}/)
+    end
+
+    it "should remove extraction directory from guest" do
+      expect(comm).to receive(:execute).with(/rm .*TMP_DIR/)
+    end
+
+    it "should create parent directories for destination" do
+      expect(comm).to receive(:execute).with(/mkdir -p .*to'/)
+    end
+
+    context "when type is directory" do
+      before { opts[:type] = :directory }
+
+      it "should create destination directory" do
+        expect(comm).to receive(:execute).with(/mkdir -p .*destination'/)
+      end
+    end
+  end
+
+  describe ".decompress_zip" do
+    let(:cap) { caps.get(:decompress_zip) }
+    let(:comp) { "compressed_file" }
+    let(:dest) { "path/to/destination" }
+    let(:opts) { {} }
+
+    before { allow(cap).to receive(:create_tmp_path).and_return("TMP_DIR") }
+    after{ cap.decompress_zip(machine, comp, dest, opts) }
+
+    it "should create temporary directory for extraction" do
+      expect(cap).to receive(:create_tmp_path)
+    end
+
+    it "should extract file with zip" do
+      expect(comm).to receive(:execute).with(/zip/)
+    end
+
+    it "should extract file to temporary directory" do
+      expect(comm).to receive(:execute).with(/TMP_DIR/)
+    end
+
+    it "should remove compressed file from guest" do
+      expect(comm).to receive(:execute).with(/rm .*#{comp}/)
+    end
+
+    it "should remove extraction directory from guest" do
+      expect(comm).to receive(:execute).with(/rm .*TMP_DIR/)
+    end
+
+    it "should create parent directories for destination" do
+      expect(comm).to receive(:execute).with(/mkdir -p .*to'/)
+    end
+
+    context "when type is directory" do
+      before { opts[:type] = :directory }
+
+      it "should create destination directory" do
+        expect(comm).to receive(:execute).with(/mkdir -p .*destination'/)
+      end
+    end
+  end
+end
diff --git a/test/unit/plugins/guests/solaris/cap/file_system_test.rb b/test/unit/plugins/guests/solaris/cap/file_system_test.rb
new file mode 100644
index 000000000..6f7288aad
--- /dev/null
+++ b/test/unit/plugins/guests/solaris/cap/file_system_test.rb
@@ -0,0 +1,127 @@
+require_relative "../../../../base"
+
+describe "VagrantPlugins::GuestSolaris::Cap::FileSystem" do
+  let(:caps) do
+    VagrantPlugins::GuestSolaris::Plugin
+      .components
+      .guest_capabilities[:solaris]
+  end
+
+  let(:machine) { double("machine", communicate: comm) }
+  let(:comm) { double("comm") }
+
+  before { allow(comm).to receive(:execute) }
+
+  describe ".create_tmp_path" do
+    let(:cap) { caps.get(:create_tmp_path) }
+    let(:opts) { {} }
+
+    it "should generate path on guest" do
+      expect(comm).to receive(:execute).with(/mktemp/)
+      cap.create_tmp_path(machine, opts)
+    end
+
+    it "should capture path generated on guest" do
+      expect(comm).to receive(:execute).with(/mktemp/).and_yield(:stdout, "TMP_PATH")
+      expect(cap.create_tmp_path(machine, opts)).to eq("TMP_PATH")
+    end
+
+    it "should strip newlines on path" do
+      expect(comm).to receive(:execute).with(/mktemp/).and_yield(:stdout, "TMP_PATH\n")
+      expect(cap.create_tmp_path(machine, opts)).to eq("TMP_PATH")
+    end
+
+    context "when type is a directory" do
+      before { opts[:type] = :directory }
+
+      it "should create guest path as a directory" do
+        expect(comm).to receive(:execute).with(/-d/)
+        cap.create_tmp_path(machine, opts)
+      end
+    end
+  end
+
+  describe ".decompress_tgz" do
+    let(:cap) { caps.get(:decompress_tgz) }
+    let(:comp) { "compressed_file" }
+    let(:dest) { "path/to/destination" }
+    let(:opts) { {} }
+
+    before { allow(cap).to receive(:create_tmp_path).and_return("TMP_DIR") }
+    after{ cap.decompress_tgz(machine, comp, dest, opts) }
+
+    it "should create temporary directory for extraction" do
+      expect(cap).to receive(:create_tmp_path)
+    end
+
+    it "should extract file with tar" do
+      expect(comm).to receive(:execute).with(/tar/)
+    end
+
+    it "should extract file to temporary directory" do
+      expect(comm).to receive(:execute).with(/TMP_DIR/)
+    end
+
+    it "should remove compressed file from guest" do
+      expect(comm).to receive(:execute).with(/rm .*#{comp}/)
+    end
+
+    it "should remove extraction directory from guest" do
+      expect(comm).to receive(:execute).with(/rm .*TMP_DIR/)
+    end
+
+    it "should create parent directories for destination" do
+      expect(comm).to receive(:execute).with(/mkdir -p .*to'/)
+    end
+
+    context "when type is directory" do
+      before { opts[:type] = :directory }
+
+      it "should create destination directory" do
+        expect(comm).to receive(:execute).with(/mkdir -p .*destination'/)
+      end
+    end
+  end
+
+  describe ".decompress_zip" do
+    let(:cap) { caps.get(:decompress_zip) }
+    let(:comp) { "compressed_file" }
+    let(:dest) { "path/to/destination" }
+    let(:opts) { {} }
+
+    before { allow(cap).to receive(:create_tmp_path).and_return("TMP_DIR") }
+    after{ cap.decompress_zip(machine, comp, dest, opts) }
+
+    it "should create temporary directory for extraction" do
+      expect(cap).to receive(:create_tmp_path)
+    end
+
+    it "should extract file with zip" do
+      expect(comm).to receive(:execute).with(/zip/)
+    end
+
+    it "should extract file to temporary directory" do
+      expect(comm).to receive(:execute).with(/TMP_DIR/)
+    end
+
+    it "should remove compressed file from guest" do
+      expect(comm).to receive(:execute).with(/rm .*#{comp}/)
+    end
+
+    it "should remove extraction directory from guest" do
+      expect(comm).to receive(:execute).with(/rm .*TMP_DIR/)
+    end
+
+    it "should create parent directories for destination" do
+      expect(comm).to receive(:execute).with(/mkdir -p .*to'/)
+    end
+
+    context "when type is directory" do
+      before { opts[:type] = :directory }
+
+      it "should create destination directory" do
+        expect(comm).to receive(:execute).with(/mkdir -p .*destination'/)
+      end
+    end
+  end
+end
diff --git a/test/unit/plugins/guests/windows/cap/file_system_test.rb b/test/unit/plugins/guests/windows/cap/file_system_test.rb
new file mode 100644
index 000000000..ca093399e
--- /dev/null
+++ b/test/unit/plugins/guests/windows/cap/file_system_test.rb
@@ -0,0 +1,85 @@
+require_relative "../../../../base"
+
+describe "VagrantPlugins::GuestWindows::Cap::FileSystem" do
+  let(:caps) do
+    VagrantPlugins::GuestWindows::Plugin
+      .components
+      .guest_capabilities[:windows]
+  end
+
+  let(:machine) { double("machine", communicate: comm) }
+  let(:comm) { double("comm") }
+
+  before { allow(comm).to receive(:execute) }
+
+  describe ".create_tmp_path" do
+    let(:cap) { caps.get(:create_tmp_path) }
+    let(:opts) { {} }
+
+    it "should generate path on guest" do
+      expect(comm).to receive(:execute).with(/GetRandomFileName/, any_args)
+      cap.create_tmp_path(machine, opts)
+    end
+
+    it "should capture path generated on guest" do
+      expect(comm).to receive(:execute).with(/Write-Output/, any_args).and_yield(:stdout, "TMP_PATH")
+      expect(cap.create_tmp_path(machine, opts)).to eq("TMP_PATH")
+    end
+
+    it "should strip newlines on path" do
+      expect(comm).to receive(:execute).with(/Write-Output/, any_args).and_yield(:stdout, "TMP_PATH\r\n")
+      expect(cap.create_tmp_path(machine, opts)).to eq("TMP_PATH")
+    end
+
+    context "when type is a directory" do
+      before { opts[:type] = :directory }
+
+      it "should create guest path as a directory" do
+        expect(comm).to receive(:execute).with(/CreateDirectory/, any_args)
+        cap.create_tmp_path(machine, opts)
+      end
+    end
+  end
+
+  describe ".decompress_zip" do
+    let(:cap) { caps.get(:decompress_zip) }
+    let(:comp) { "compressed_file" }
+    let(:dest) { "path/to/destination" }
+    let(:opts) { {} }
+
+    before { allow(cap).to receive(:create_tmp_path).and_return("TMP_DIR") }
+    after{ cap.decompress_zip(machine, comp, dest, opts) }
+
+    it "should create temporary directory for extraction" do
+      expect(cap).to receive(:create_tmp_path)
+    end
+
+    it "should extract file with zip" do
+      expect(comm).to receive(:execute).with(/copyhere/, any_args)
+    end
+
+    it "should extract file to temporary directory" do
+      expect(comm).to receive(:execute).with(/TMP_DIR/, any_args)
+    end
+
+    it "should remove compressed file from guest" do
+      expect(comm).to receive(:execute).with(/Remove-Item .*#{comp}/, any_args)
+    end
+
+    it "should remove extraction directory from guest" do
+      expect(comm).to receive(:execute).with(/Remove-Item .*TMP_DIR/, any_args)
+    end
+
+    it "should create parent directories for destination" do
+      expect(comm).to receive(:execute).with(/New-Item .*Directory .*to\\"/, any_args)
+    end
+
+    context "when type is directory" do
+      before { opts[:type] = :directory }
+
+      it "should create destination directory" do
+        expect(comm).to receive(:execute).with(/New-Item .*Directory .*destination"/, any_args)
+      end
+    end
+  end
+end
diff --git a/vagrant.gemspec b/vagrant.gemspec
index d67d1e83c..0d804e446 100644
--- a/vagrant.gemspec
+++ b/vagrant.gemspec
@@ -27,6 +27,7 @@ Gem::Specification.new do |s|
   s.add_dependency "net-scp", "~> 1.2.0"
   s.add_dependency "rb-kqueue", "~> 0.2.0"
   s.add_dependency "rest-client", ">= 1.6.0", "< 3.0"
+  s.add_dependency "rubyzip", "~> 1.2.2"
   s.add_dependency "wdm", "~> 0.1.0"
   s.add_dependency "winrm", "~> 2.1"
   s.add_dependency "winrm-fs", "~> 1.0"
diff --git a/website/source/docs/cli/upload.html.md b/website/source/docs/cli/upload.html.md
new file mode 100644
index 000000000..42898da6d
--- /dev/null
+++ b/website/source/docs/cli/upload.html.md
@@ -0,0 +1,30 @@
+---
+layout: "docs"
+page_title: "vagrant upload - Command-Line Interface"
+sidebar_current: "cli-upload"
+description: |-
+  The "vagrant upload" command is used to upload files from the host
+  to a guest machine.
+---
+
+# Upload
+
+**Command: `vagrant upload source [destination] [name|id]`**
+
+This command uploads files and directories from the host to the guest
+machine.
+
+## Options
+
+* `destination` - Path on the guest machine to upload file or directory.
+
+* `source` - Path to file or diretory on host to upload to guest machine.
+
+* `--compress` - Compress the file or directory before uploading to guest machine.
+
+* `--compression-type type` - Type of compression to use when compressing
+  file or directory for upload. Defaults to `zip` for Windows guests and
+  `tgz` for non-Windows guests. Valid values: `tgz`, `zip`.
+
+* `--temporary` - Create a temporary location on the guest machine and upload
+  files to that location.
diff --git a/website/source/docs/cli/winrm.html.md b/website/source/docs/cli/winrm.html.md
new file mode 100644
index 000000000..67eb0ff3b
--- /dev/null
+++ b/website/source/docs/cli/winrm.html.md
@@ -0,0 +1,26 @@
+---
+layout: "docs"
+page_title: "vagrant winrm - Command-Line Interface"
+sidebar_current: "cli-winrm"
+description: |-
+  The "vagrant winrm" command is used execute commands on the remote
+  machine via WinRM
+---
+
+# WinRM
+
+**Command: `vagrant winrm [name|id]`**
+
+Executes the provided command(s) on the guest machine using the
+WinRM communicator. Commands are provided with the `--command`
+option and multiple `--command` flags may be provided for
+executing multiple commands. This command requires the  guest
+machine to be configured with the WinRM communicator.
+
+## Options
+
+* `--command COMMAND` - Command to execute.
+
+* `--elevated` - Run command(s) with elevated credentials.
+
+* `--shell (cmd|powershell)` - Shell to execute commands. Defaults to `powershell`.
diff --git a/website/source/docs/cli/winrm_config.html.md b/website/source/docs/cli/winrm_config.html.md
new file mode 100644
index 000000000..76a44b2cd
--- /dev/null
+++ b/website/source/docs/cli/winrm_config.html.md
@@ -0,0 +1,20 @@
+---
+layout: "docs"
+page_title: "vagrant winrm-config - Command-Line Interface"
+sidebar_current: "cli-winrm_config"
+description: |-
+  The "vagrant winrm-config" command is used to output the WinRM configuration
+  used to connect to the guest machine.
+---
+
+# WinRM Config
+
+**Command: `vagrant winrm-config [name|id]`**
+
+This will output the WinRM configuration used for connecting to
+the guest machine. It requires that the WinRM communicator is in
+use for the guest machine.
+
+## Options
+
+* `--host NAME` - Name of the host for the outputted configuration.