diff --git a/communicator/ssh/communicator.go b/communicator/ssh/communicator.go
index f39d70898..2427194bd 100644
--- a/communicator/ssh/communicator.go
+++ b/communicator/ssh/communicator.go
@@ -139,13 +139,15 @@ func (c *Communicator) Connect(o terraform.UIOutput) (err error) {
 				"  Private key: %t\n"+
 				"  Certificate: %t\n"+
 				"  SSH Agent: %t\n"+
-				"  Checking Host Key: %t",
+				"  Checking Host Key: %t\n"+
+				"  Target Platform: %s\n",
 			c.connInfo.Host, c.connInfo.User,
 			c.connInfo.Password != "",
 			c.connInfo.PrivateKey != "",
 			c.connInfo.Certificate != "",
 			c.connInfo.Agent,
 			c.connInfo.HostKey != "",
+			c.connInfo.TargetPlatform,
 		))
 
 		if c.connInfo.BastionHost != "" {
@@ -343,7 +345,7 @@ func (c *Communicator) Start(cmd *remote.Cmd) error {
 	session.Stdout = cmd.Stdout
 	session.Stderr = cmd.Stderr
 
-	if !c.config.noPty {
+	if !c.config.noPty && c.connInfo.TargetPlatform != TargetPlatformWindows {
 		// Request a PTY
 		termModes := ssh.TerminalModes{
 			ssh.ECHO:          0,     // do not echo
@@ -425,35 +427,35 @@ func (c *Communicator) UploadScript(path string, input io.Reader) error {
 	if err != nil {
 		return fmt.Errorf("Error reading script: %s", err)
 	}
-
 	var script bytes.Buffer
-	if string(prefix) != "#!" {
+
+	if string(prefix) != "#!" && c.connInfo.TargetPlatform != TargetPlatformWindows {
 		script.WriteString(DefaultShebang)
 	}
-
 	script.ReadFrom(reader)
+
 	if err := c.Upload(path, &script); err != nil {
 		return err
 	}
+	if c.connInfo.TargetPlatform != TargetPlatformWindows {
+		var stdout, stderr bytes.Buffer
+		cmd := &remote.Cmd{
+			Command: fmt.Sprintf("chmod 0777 %s", path),
+			Stdout:  &stdout,
+			Stderr:  &stderr,
+		}
+		if err := c.Start(cmd); err != nil {
+			return fmt.Errorf(
+				"Error chmodding script file to 0777 in remote "+
+					"machine: %s", err)
+		}
 
-	var stdout, stderr bytes.Buffer
-	cmd := &remote.Cmd{
-		Command: fmt.Sprintf("chmod 0777 %s", path),
-		Stdout:  &stdout,
-		Stderr:  &stderr,
+		if err := cmd.Wait(); err != nil {
+			return fmt.Errorf(
+				"Error chmodding script file to 0777 in remote "+
+					"machine %v: %s %s", err, stdout.String(), stderr.String())
+		}
 	}
-	if err := c.Start(cmd); err != nil {
-		return fmt.Errorf(
-			"Error chmodding script file to 0777 in remote "+
-				"machine: %s", err)
-	}
-
-	if err := cmd.Wait(); err != nil {
-		return fmt.Errorf(
-			"Error chmodding script file to 0777 in remote "+
-				"machine %v: %s %s", err, stdout.String(), stderr.String())
-	}
-
 	return nil
 }
 
diff --git a/communicator/ssh/provisioner.go b/communicator/ssh/provisioner.go
index b6fe80a4a..63a753c1a 100644
--- a/communicator/ssh/provisioner.go
+++ b/communicator/ssh/provisioner.go
@@ -29,29 +29,38 @@ const (
 	// DefaultPort is used if there is no port given
 	DefaultPort = 22
 
-	// DefaultScriptPath is used as the path to copy the file to
-	// for remote execution if not provided otherwise.
-	DefaultScriptPath = "/tmp/terraform_%RAND%.sh"
+	// DefaultUnixScriptPath is used as the path to copy the file to
+	// for remote execution on unix if not provided otherwise.
+	DefaultUnixScriptPath = "/tmp/terraform_%RAND%.sh"
+	// DefaultWindowsScriptPath is used as the path to copy the file to
+	// for remote execution on windows if not provided otherwise.
+	DefaultWindowsScriptPath = "C:/windows/temp/terraform_%RAND%.cmd"
 
 	// DefaultTimeout is used if there is no timeout given
 	DefaultTimeout = 5 * time.Minute
+
+	// TargetPlatformUnix used for cleaner code, and is used if no target platform has been specified
+	TargetPlatformUnix = "unix"
+	//TargetPlatformWindows used for cleaner code
+	TargetPlatformWindows = "windows"
 )
 
 // connectionInfo is decoded from the ConnInfo of the resource. These are the
 // only keys we look at. If a PrivateKey is given, that is used instead
 // of a password.
 type connectionInfo struct {
-	User        string
-	Password    string
-	PrivateKey  string `mapstructure:"private_key"`
-	Certificate string `mapstructure:"certificate"`
-	Host        string
-	HostKey     string `mapstructure:"host_key"`
-	Port        int
-	Agent       bool
-	Timeout     string
-	ScriptPath  string        `mapstructure:"script_path"`
-	TimeoutVal  time.Duration `mapstructure:"-"`
+	User           string
+	Password       string
+	PrivateKey     string `mapstructure:"private_key"`
+	Certificate    string `mapstructure:"certificate"`
+	Host           string
+	HostKey        string `mapstructure:"host_key"`
+	Port           int
+	Agent          bool
+	Timeout        string
+	ScriptPath     string        `mapstructure:"script_path"`
+	TimeoutVal     time.Duration `mapstructure:"-"`
+	TargetPlatform string        `mapstructure:"target_platform"`
 
 	BastionUser        string `mapstructure:"bastion_user"`
 	BastionPassword    string `mapstructure:"bastion_password"`
@@ -106,8 +115,19 @@ func parseConnectionInfo(s *terraform.InstanceState) (*connectionInfo, error) {
 	if connInfo.Port == 0 {
 		connInfo.Port = DefaultPort
 	}
-	if connInfo.ScriptPath == "" {
-		connInfo.ScriptPath = DefaultScriptPath
+	// Set default targetPlatform to unix if it's empty
+	if connInfo.TargetPlatform == "" {
+		connInfo.TargetPlatform = TargetPlatformUnix
+	} else if connInfo.TargetPlatform != TargetPlatformUnix && connInfo.TargetPlatform != TargetPlatformWindows {
+		return nil, fmt.Errorf("target_platform for provisioner has to be either %s or %s", TargetPlatformUnix, TargetPlatformWindows)
+	}
+	// Choose an appropriate default script path based on the target platform. There is no single
+	// suitable default script path which works on both UNIX and Windows targets.
+	if connInfo.ScriptPath == "" && connInfo.TargetPlatform == TargetPlatformUnix {
+		connInfo.ScriptPath = DefaultUnixScriptPath
+	}
+	if connInfo.ScriptPath == "" && connInfo.TargetPlatform == TargetPlatformWindows {
+		connInfo.ScriptPath = DefaultWindowsScriptPath
 	}
 	if connInfo.Timeout != "" {
 		connInfo.TimeoutVal = safeDuration(connInfo.Timeout, DefaultTimeout)
diff --git a/communicator/ssh/provisioner_test.go b/communicator/ssh/provisioner_test.go
index f8e0f77d8..959831544 100644
--- a/communicator/ssh/provisioner_test.go
+++ b/communicator/ssh/provisioner_test.go
@@ -50,7 +50,10 @@ func TestProvisioner_connInfo(t *testing.T) {
 	if conf.Timeout != "30s" {
 		t.Fatalf("bad: %v", conf)
 	}
-	if conf.ScriptPath != DefaultScriptPath {
+	if conf.ScriptPath != DefaultUnixScriptPath {
+		t.Fatalf("bad: %v", conf)
+	}
+	if conf.TargetPlatform != TargetPlatformUnix {
 		t.Fatalf("bad: %v", conf)
 	}
 	if conf.BastionHost != "127.0.1.1" {
diff --git a/terraform/eval_validate.go b/terraform/eval_validate.go
index a84aa3ac9..8f1fd7e08 100644
--- a/terraform/eval_validate.go
+++ b/terraform/eval_validate.go
@@ -161,8 +161,11 @@ var connectionBlockSupersetSchema = &configschema.Block{
 			Type:     cty.String,
 			Optional: true,
 		},
-
 		// For type=ssh only (enforced in ssh communicator)
+		"target_platform": {
+			Type:     cty.String,
+			Optional: true,
+		},
 		"private_key": {
 			Type:     cty.String,
 			Optional: true,
diff --git a/website/docs/provisioners/connection.html.markdown b/website/docs/provisioners/connection.html.markdown
index ffa771ed7..52005876c 100644
--- a/website/docs/provisioners/connection.html.markdown
+++ b/website/docs/provisioners/connection.html.markdown
@@ -123,6 +123,9 @@ block would create a dependency cycle.
 
 * `host_key` - The public key from the remote host or the signing CA, used to
   verify the connection.
+* `target_platform` - The target platform to connect to. Valid values are `windows` and `unix`. Defaults to `unix` if not set.
+
+    If the platform is set to `windows`, the default `script_path` is `c:\windows\temp\terraform_%RAND%.cmd`, assuming [the SSH default shell](https://docs.microsoft.com/en-us/windows-server/administration/openssh/openssh_server_configuration#configuring-the-default-shell-for-openssh-in-windows) is `cmd.exe`. If the SSH default shell is PowerShell, set `script_path` to `"c:/windows/temp/terraform_%RAND%.ps1"`  
 
 **Additional arguments only supported by the `winrm` connection type:**
 
@@ -163,4 +166,4 @@ The `ssh` connection also supports the following fields to facilitate connnectio
 
 * `bastion_certificate` - The contents of a signed CA Certificate. The certificate argument
   must be used in conjunction with a `bastion_private_key`. These can be loaded from
-  a file on disk using the [the `file` function](/docs/configuration/functions/file.html).
\ No newline at end of file
+  a file on disk using the [the `file` function](/docs/configuration/functions/file.html).