diff --git a/plugins/communicators/winrm/file_manager.rb b/plugins/communicators/winrm/file_manager.rb
new file mode 100644
index 000000000..87a87438c
--- /dev/null
+++ b/plugins/communicators/winrm/file_manager.rb
@@ -0,0 +1,166 @@
+require "log4r"
+
+module VagrantPlugins
+  module CommunicatorWinRM
+
+    # Manages the file system on the remote guest allowing for file tranfer
+    # between the guest and host.
+    class FileManager
+
+      def initialize(shell)
+        @logger = Log4r::Logger.new("vagrant::communication::filemanager")
+        @shell = shell
+      end
+      
+      # Uploads the given file or directory from the host to the guest (recursively).
+      #
+      # @param [String] The source file or directory path on the host
+      # @param [String] The destination file or directory path on the host
+      def upload(host_src_file_path, guest_dest_file_path)
+        @logger.debug("Upload: #{host_src_file_path} -> #{guest_dest_file_path}")
+        if File.directory?(host_src_file_path)
+          upload_directory(host_src_file_path, guest_dest_file_path)
+        else
+          upload_file(host_src_file_path, guest_dest_file_path)
+        end
+      end
+
+      # Downloads the given file from the guest to the host.
+      # NOTE: This currently only supports single file download
+      #
+      # @param [String] The source file path on the guest
+      # @param [String] The destination file path on the host
+      def download(guest_src_file_path, host_dest_file_path)
+        @logger.debug("#{guest_src_file_path} -> #{host_dest_file_path}")
+        
+        output = @shell.powershell("[System.convert]::ToBase64String([System.IO.File]::ReadAllBytes(\"#{guest_src_file_path}\"))")
+        contents = output[:data].map!{|line| line[:stdout]}.join.gsub("\\n\\r", '')
+        out = Base64.decode64(contents)
+        IO.binwrite(host_dest_file_path, out)
+      end
+
+
+      private
+
+      # Recursively uploads the given directory from the host to the guest
+      #
+      # @param [String] The source file or directory path on the host
+      # @param [String] The destination file or directory path on the host
+      def upload_directory(host_src_file_path, guest_dest_file_path)
+        glob_patt = File.join(host_src_file_path, '**/*')
+        Dir.glob(glob_patt).select { |f| !File.directory?(f) }.each do |host_file_path|
+          guest_file_path = guest_file_path(host_src_file_path, guest_dest_file_path, host_file_path)
+          upload_file(host_file_path, guest_file_path)
+        end
+      end
+
+      # Uploads the given file, but only if the target file doesn't exist
+      # or its MD5 checksum doens't match the host's source checksum.
+      #
+      # @param [String] The source file path on the host
+      # @param [String] The destination file path on the guest
+      def upload_file(host_src_file_path, guest_dest_file_path)
+        if should_upload_file?(host_src_file_path, guest_dest_file_path)
+          tmp_file_path = upload_to_temp_file(host_src_file_path)
+          decode_temp_file(tmp_file_path, guest_dest_file_path)
+        else
+          @logger.debug("Up to date: #{guest_dest_file_path}")
+        end
+      end
+
+      # Uploads the given file to a new temp file on the guest
+      #
+      # @param [String] The source file path on the host
+      # @return [String] The temp file path on the guest
+      def upload_to_temp_file(host_src_file_path)
+        tmp_file_path = File.join(guest_temp_dir, "winrm-upload-#{rand()}")
+        @logger.debug("Uploading '#{host_src_file_path}' to temp file '#{tmp_file_path}'")
+        
+        base64_host_file = Base64.encode64(IO.binread(host_src_file_path)).gsub("\n",'')
+        base64_host_file.chars.to_a.each_slice(8000-tmp_file_path.size) do |chunk|
+          out = @shell.cmd("echo #{chunk.join} >> \"#{tmp_file_path}\"")
+          raise_upload_error_if_failed(out, host_src_file_path, tmp_file_path)
+        end
+        
+        tmp_file_path
+      end
+
+      # Moves and decodes the given file temp file on the guest to its
+      # permanent location
+      #
+      # @param [String] The source base64 encoded temp file path on the guest
+      # @param [String] The destination file path on the guest
+      def decode_temp_file(guest_tmp_file_path, guest_dest_file_path)
+        @logger.debug("Decoding temp file '#{guest_tmp_file_path}' to '#{guest_dest_file_path}'")
+        out = @shell.powershell <<-EOH
+          $tmp_file_path = [System.IO.Path]::GetFullPath('#{guest_tmp_file_path}')
+          $dest_file_path = [System.IO.Path]::GetFullPath('#{guest_dest_file_path}')
+
+          if (Test-Path $dest_file_path) {
+            rm $dest_file_path
+          }
+          else {
+            $dest_dir = ([System.IO.Path]::GetDirectoryName($dest_file_path))
+            New-Item -ItemType directory -Force -Path $dest_dir
+          }
+
+          $base64_string = Get-Content $tmp_file_path
+          $bytes = [System.Convert]::FromBase64String($base64_string) 
+          [System.IO.File]::WriteAllBytes($dest_file_path, $bytes)
+        EOH
+        raise_upload_error_if_failed(out, guest_tmp_file_path, guest_dest_file_path)
+      end
+
+      # Checks to see if the target file on the guest is missing or out of date.
+      #
+      # @param [String] The source file path on the host
+      # @param [String] The destination file path on the guest
+      # @return [Boolean] True if the file is missing or out of date
+      def should_upload_file?(host_src_file_path, guest_dest_file_path)
+        local_md5 = Digest::MD5.file(host_src_file_path).hexdigest
+        cmd = <<-EOH
+          $dest_file_path = [System.IO.Path]::GetFullPath('#{guest_dest_file_path}')
+
+          if (Test-Path $dest_file_path) {
+            $crypto_provider = new-object -TypeName System.Security.Cryptography.MD5CryptoServiceProvider
+            try {
+              $file = [System.IO.File]::Open($dest_file_path, [System.IO.Filemode]::Open, [System.IO.FileAccess]::Read)
+              $guest_md5 = ([System.BitConverter]::ToString($crypto_provider.ComputeHash($file))).Replace("-","").ToLower()
+            }
+            finally {
+              $file.Dispose()
+            }
+            if ($guest_md5 -eq '#{local_md5}') {
+              exit 0
+            }
+          }
+          exit 1
+        EOH
+        @shell.powershell(cmd)[:exitcode] == 1
+      end
+
+      # Creates a guest file path equivalent from a host file path
+      #
+      # @param [String] The base host directory we're going to copy from
+      # @param [String] The base guest directory we're going to copy to
+      # @param [String] A full path to a file on the host underneath host_base_dir
+      # @return [String] The guest file path equivalent
+      def guest_file_path(host_base_dir, guest_base_dir, host_file_path)
+        rel_path = File.dirname(host_file_path[host_base_dir.length, host_file_path.length])
+        File.join(guest_base_dir, rel_path, File.basename(host_file_path))
+      end
+
+      def guest_temp_dir
+        @guest_temp ||= (@shell.cmd('echo %TEMP%'))[:data][0][:stdout].chomp
+      end
+
+      def raise_upload_error_if_failed(out, from, to)
+        raise Errors::WinRMFileTransferError,
+          :from => from,
+          :to => to,
+          :message => out.inspect if out[:exitcode] != 0
+      end
+    
+    end #class
+  end
+end
diff --git a/plugins/communicators/winrm/shell.rb b/plugins/communicators/winrm/shell.rb
index e1bbb5da0..63edb22af 100644
--- a/plugins/communicators/winrm/shell.rb
+++ b/plugins/communicators/winrm/shell.rb
@@ -9,6 +9,8 @@ Vagrant::Util::SilenceWarnings.silence! do
   require "winrm"
 end
 
+require_relative "file_manager"
+
 module VagrantPlugins
   module CommunicatorWinRM
     class WinRMShell
@@ -62,31 +64,11 @@ module VagrantPlugins
       end
 
       def upload(from, to)
-        @logger.debug("Uploading: #{from} to #{to}")
-        file_name = (cmd("echo %TEMP%\\winrm-upload-#{rand()}"))[:data][0][:stdout].chomp
-        powershell <<-EOH
-          if(Test-Path #{to}) {
-            rm #{to}
-          }
-        EOH
-        Base64.encode64(IO.binread(from)).gsub("\n",'').chars.to_a.each_slice(8000-file_name.size) do |chunk|
-          out = cmd("echo #{chunk.join} >> \"#{file_name}\"")
-        end
-        powershell <<-EOH
-          mkdir $([System.IO.Path]::GetDirectoryName(\"#{to}\"))
-          $base64_string = Get-Content \"#{file_name}\"
-          $bytes  = [System.Convert]::FromBase64String($base64_string)
-          $new_file = [System.IO.Path]::GetFullPath(\"#{to}\")
-          [System.IO.File]::WriteAllBytes($new_file,$bytes)
-        EOH
+        FileManager.new(self).upload(from, to)
       end
 
       def download(from, to)
-        @logger.debug("Downloading: #{from} to #{to}")
-        output = powershell("[System.convert]::ToBase64String([System.IO.File]::ReadAllBytes(\"#{from}\"))")
-        contents = output[:data].map!{|line| line[:stdout]}.join.gsub("\\n\\r", '')
-        out = Base64.decode64(contents)
-        IO.binwrite(to, out)
+        FileManager.new(self).download(from, to)
       end
 
       protected