diff --git a/plugins/communicators/winssh/communicator.rb b/plugins/communicators/winssh/communicator.rb
index 208ec0f90..96477ec40 100644
--- a/plugins/communicators/winssh/communicator.rb
+++ b/plugins/communicators/winssh/communicator.rb
@@ -207,7 +207,7 @@ SCRIPT
               @logger.debug("Uploading file #{path} to remote #{dest}")
               upload_file = File.open(path, "rb")
               begin
-                scp.upload!(upload_file, dest)
+                scp.upload!(upload_file, dest, shell: "powershell.exe")
               ensure
                 upload_file.close
               end
@@ -234,3 +234,53 @@ SCRIPT
     end
   end
 end
+
+# This monkey patches Net::SCP#start_command so that we don't apply special
+# shell escaping rules to the remote path when using powershell.exe as a shell.
+# PowerShell also needs single quotes around the remote path if the path has
+# spaces in it.
+#
+# Here is an example of a properly formatted scp command for PowerShell:
+#
+#     scp.exe -t 'c:/destination path'
+#
+module Net
+  class SCP
+    def start_command(mode, local, remote, options={}, &callback)
+      session.open_channel do |channel|
+      
+        if options[:shell].to_s == "powershell.exe"
+          powershell_escaped = remote.gsub(/'/, "''")
+          command = "#{options[:shell]} -c #{scp_command(mode, options)} '#{powershell_escaped}'"
+        elsif options[:shell]
+          escaped_file = shellescape(remote).gsub(/'/) { |m| "'\\''" }
+          command = "#{options[:shell]} -c #{scp_command(mode, options)} #{escaped_file}"
+        else
+          command = "#{scp_command(mode, options)} #{shellescape(remote)}"
+        end
+
+        channel.exec(command) do |ch, success|
+          if success
+            channel[:local   ] = local
+            channel[:remote  ] = remote
+            channel[:options ] = options.dup
+            channel[:callback] = callback
+            channel[:buffer  ] = Net::SSH::Buffer.new
+            channel[:state   ] = "#{mode}_start"
+            channel[:stack   ] = []
+            channel[:error_string] = ''
+
+            channel.on_close                  { |ch| send("#{channel[:state]}_state", channel); raise Net::SCP::Error, "SCP did not finish successfully (#{channel[:exit]}): #{channel[:error_string]}" if channel[:exit] != 0 }
+            channel.on_data                   { |ch, data| channel[:buffer].append(data) }
+            channel.on_extended_data          { |ch, type, data| debug { data.chomp } }
+            channel.on_request("exit-status") { |ch, data| channel[:exit] = data.read_long }
+            channel.on_process                { send("#{channel[:state]}_state", channel) }
+          else
+            channel.close
+            raise Net::SCP::Error, "could not exec scp on the remote host"
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/test/unit/plugins/communicators/winssh/communicator_test.rb b/test/unit/plugins/communicators/winssh/communicator_test.rb
index 7c000f839..99e8a90dc 100644
--- a/test/unit/plugins/communicators/winssh/communicator_test.rb
+++ b/test/unit/plugins/communicators/winssh/communicator_test.rb
@@ -274,7 +274,7 @@ describe VagrantPlugins::CommunicatorWinSSH::Communicator do
     it "uploads a directory if local path is a directory" do
       Dir.mktmpdir('vagrant-test') do |dir|
         FileUtils.touch(File.join(dir, "test-file"))
-        expect(scp).to receive(:upload!).with(an_instance_of(File), /test-file/)
+        expect(scp).to receive(:upload!).with(an_instance_of(File), /test-file/, {shell: "powershell.exe"})
         communicator.upload(dir, 'C:\destination')
       end
     end
@@ -282,7 +282,7 @@ describe VagrantPlugins::CommunicatorWinSSH::Communicator do
     it "uploads a file if local path is a file" do
       file = Tempfile.new('vagrant-test')
       begin
-        expect(scp).to receive(:upload!).with(instance_of(File), 'C:/destination/file')
+        expect(scp).to receive(:upload!).with(instance_of(File), 'C:/destination/file', {shell: "powershell.exe"})
         expect(Vagrant::Util::Platform).to receive(:unix_windows_path).with('C:\destination\file').
           and_call_original
         communicator.upload(file.path, 'C:\destination\file')
@@ -294,7 +294,7 @@ describe VagrantPlugins::CommunicatorWinSSH::Communicator do
     it "raises custom error on permission errors" do
       file = Tempfile.new('vagrant-test')
       begin
-        expect(scp).to receive(:upload!).with(instance_of(File), 'C:/destination/file').
+        expect(scp).to receive(:upload!).with(instance_of(File), 'C:/destination/file', {shell: "powershell.exe"}).
           and_raise("Permission denied")
         expect{ communicator.upload(file.path, 'C:\destination\file') }.to(
           raise_error(Vagrant::Errors::SCPPermissionDenied)
@@ -307,7 +307,7 @@ describe VagrantPlugins::CommunicatorWinSSH::Communicator do
     it "does not raise custom error on non-permission errors" do
       file = Tempfile.new('vagrant-test')
       begin
-        expect(scp).to receive(:upload!).with(instance_of(File), 'C:/destination/file').
+        expect(scp).to receive(:upload!).with(instance_of(File), 'C:/destination/file', {shell: "powershell.exe"}).
           and_raise("Some other error")
         expect{ communicator.upload(file.path, 'C:\destination\file') }.to raise_error(RuntimeError)
       ensure
@@ -585,3 +585,32 @@ describe VagrantPlugins::CommunicatorWinSSH::Communicator do
     end
   end
 end
+
+# Tests for Net::SCP#start_command patch
+describe Net::SCP do
+  include_context "unit"
+
+  let(:session) do
+    double("session",
+           logger: nil)
+  end
+
+  let(:scp){ @scp ||= described_class.new(session) }
+
+  let(:channel) { double("channel") }
+
+  before do
+    allow(session).to receive(:open_channel).and_yield(channel)
+  end
+
+  describe "#start_command" do
+    context "with shell set to powershell.exe" do
+      let(:options) { {:shell => "powershell.exe" } }
+
+      it "escapes single quotes in the destination" do
+        expect(channel).to receive(:exec).with(/C:\/vagrant''s scripts/)
+        scp.start_command("", anything, "C:/vagrant's scripts", options)
+      end
+    end
+  end
+end