diff --git a/lib/vagrant/action/builtin/ssh_run.rb b/lib/vagrant/action/builtin/ssh_run.rb
index 3572507a8..2ac41dffa 100644
--- a/lib/vagrant/action/builtin/ssh_run.rb
+++ b/lib/vagrant/action/builtin/ssh_run.rb
@@ -47,7 +47,10 @@ module Vagrant
             # Add an extra space to the command so cmd.exe quoting works
             # properly
             command = "#{shell} /C #{command} "
-            env[:tty] = false
+          elsif shell == "powershell"
+            command = "$ProgressPreference = \"SilentlyContinue\"; #{command}"
+            command = Base64.strict_encode64(command.encode("UTF-16LE", "UTF-8"))
+            command = "#{shell} -encodedCommand #{command}"
           else
             command = "#{shell} -c '#{command}'"
           end
@@ -57,10 +60,11 @@ module Vagrant
           opts[:extra_args] ||= []
 
           # Allow the user to specify a tty or non-tty manually, but if they
-          # don't then we default to a TTY
+          # don't then we default to a TTY unless they are using WinSSH
           if !opts[:extra_args].include?("-t") &&
               !opts[:extra_args].include?("-T") &&
-              env[:tty]
+              env[:tty] &&
+              env[:machine].config.vm.communicator != :winssh
             opts[:extra_args] << "-t"
           end
 
diff --git a/test/unit/vagrant/action/builtin/ssh_run_test.rb b/test/unit/vagrant/action/builtin/ssh_run_test.rb
index 39a51aaf1..49053afeb 100644
--- a/test/unit/vagrant/action/builtin/ssh_run_test.rb
+++ b/test/unit/vagrant/action/builtin/ssh_run_test.rb
@@ -93,11 +93,12 @@ describe Vagrant::Action::Builtin::SSHRun do
     before do
       expect(vm).to receive(:communicator).and_return(:winssh)
       expect(config).to receive(:winssh).and_return(winssh)
+      env[:tty] = nil
     end
 
     it "should use the WinSSH shell for running ssh commands" do
       ssh_info = { foo: :bar }
-      opts = {:extra_args=>["-t", "foo -c 'dir'"], :subprocess=>true}
+      opts = {:extra_args=>["foo -c 'dir'"], :subprocess=>true}
 
       expect(ssh_klass).to receive(:exec).
         with(ssh_info, opts)
@@ -106,23 +107,42 @@ describe Vagrant::Action::Builtin::SSHRun do
       env[:ssh_run_command] = "dir"
       described_class.new(app, env).call(env)
     end
-  end
 
-  context "when shell is cmd" do
-    before do
-      expect(ssh).to receive(:shell).and_return('cmd')
+    context "when shell is cmd" do
+      before do
+        expect(winssh).to receive(:shell).and_return('cmd')
+      end
+
+      it "should use appropriate options for cmd" do
+        ssh_info = { foo: :bar }
+        opts = {:extra_args=>["cmd /C dir "], :subprocess=>true}
+
+        expect(ssh_klass).to receive(:exec).
+          with(ssh_info, opts)
+
+        env[:ssh_info] = ssh_info
+        env[:ssh_run_command] = "dir"
+        described_class.new(app, env).call(env)
+      end
     end
 
-    it "should use appropriate options for cmd" do
-      ssh_info = { foo: :bar }
-      opts = {:extra_args=>["cmd /C dir "], :subprocess=>true}
+    context "when shell is powershell" do
+      before do
+        expect(winssh).to receive(:shell).and_return('powershell')
+      end
 
-      expect(ssh_klass).to receive(:exec).
-        with(ssh_info, opts)
+      it "should base64 encode the command" do
+        ssh_info = { foo: :bar }
+        encoded_command = "JABQAHIAbwBnAHIAZQBzAHMAUAByAGUAZgBlAHIAZQBuAGMAZQAgAD0AIAAiAFMAaQBsAGUAbgB0AGwAeQBDAG8AbgB0AGkAbgB1AGUAIgA7ACAAZABpAHIA"
+        opts = {:extra_args=>["powershell -encodedCommand #{encoded_command}"], :subprocess=>true}
 
-      env[:ssh_info] = ssh_info
-      env[:ssh_run_command] = "dir"
-      described_class.new(app, env).call(env)
+        expect(ssh_klass).to receive(:exec).
+          with(ssh_info, opts)
+
+        env[:ssh_info] = ssh_info
+        env[:ssh_run_command] = "dir"
+        described_class.new(app, env).call(env)
+      end
     end
   end
 end