diff --git a/internal/core/helpers_test.go b/internal/core/helpers_test.go
index 7a70cc3ad..508b858e2 100644
--- a/internal/core/helpers_test.go
+++ b/internal/core/helpers_test.go
@@ -62,6 +62,19 @@ func testGuestConfig(name string) *component.ConfigData {
 	}
 }
 
+// Set communicator name in vm configuration
+func testCommunicatorConfig(name string) *component.ConfigData {
+	return &component.ConfigData{
+		Data: map[string]interface{}{
+			"vm": &component.ConfigData{
+				Data: map[string]interface{}{
+					"communicator": name,
+				},
+			},
+		},
+	}
+}
+
 // Generate a synced folder plugin
 func syncedFolderPlugin(t *testing.T, name string) *plugin.Plugin {
 	return plugin.TestPlugin(t,
diff --git a/internal/core/target.go b/internal/core/target.go
index 4278afde9..858029808 100644
--- a/internal/core/target.go
+++ b/internal/core/target.go
@@ -145,11 +145,12 @@ func (t *Target) Communicate() (c core.Communicator, err error) {
 		c = i.(core.Communicator)
 		return
 	}
-	rawCommunicatorName, err := t.vagrantfile.GetValue("vm", "communicator")
-	if err != nil {
-		return nil, err
-	}
 	communicatorName := ""
+	rawCommunicatorName, err := t.vagrantfile.GetValue("vm", "communicator")
+	// If there is an error getting the communicator, default to using the ssh communicator
+	if err != nil {
+		communicatorName = "ssh"
+	}
 	if rawCommunicatorName == nil {
 		communicatorName = "ssh"
 	} else {
diff --git a/internal/core/target_test.go b/internal/core/target_test.go
index e67b838a4..4f3b7bd8b 100644
--- a/internal/core/target_test.go
+++ b/internal/core/target_test.go
@@ -3,7 +3,9 @@ package core
 import (
 	"testing"
 
+	"github.com/hashicorp/vagrant-plugin-sdk/component"
 	"github.com/hashicorp/vagrant-plugin-sdk/core"
+	"github.com/hashicorp/vagrant/internal/plugin"
 	"github.com/hashicorp/vagrant/internal/server/proto/vagrant_server"
 	"github.com/stretchr/testify/require"
 )
@@ -64,3 +66,46 @@ func TestTargetSpecializeBad(t *testing.T) {
 		t.Errorf("Should not specialize to an unsupported type")
 	}
 }
+
+func TestTargetConfigedCommunicator(t *testing.T) {
+	type test struct {
+		config *component.ConfigData
+		errors bool
+	}
+
+	tests := []test{
+		{config: testCommunicatorConfig("winrm"), errors: false},
+		{config: testSyncedFolderConfig([]*testSyncedFolder{}), errors: false},
+		{config: testCommunicatorConfig("idontexist"), errors: true},
+	}
+	communicatorMockSSH := BuildTestCommunicatorPlugin("ssh")
+	communicatorMockWinRM := BuildTestCommunicatorPlugin("winrm")
+
+	pluginManager := plugin.TestManager(t,
+		plugin.TestPlugin(t,
+			communicatorMockSSH,
+			plugin.WithPluginName("ssh"),
+			plugin.WithPluginTypes(component.CommunicatorType),
+		),
+		plugin.TestPlugin(t,
+			communicatorMockWinRM,
+			plugin.WithPluginName("winrm"),
+			plugin.WithPluginTypes(component.CommunicatorType),
+		),
+	)
+
+	for _, tc := range tests {
+		tp := TestProject(t, WithPluginManager(pluginManager))
+		tm := TestMachine(t, tp,
+			WithTestTargetConfig(tc.config),
+		)
+		comm, err := tm.Communicate()
+		if tc.errors {
+			require.Error(t, err)
+			require.Nil(t, comm)
+		} else {
+			require.NoError(t, err)
+			require.NotNil(t, comm)
+		}
+	}
+}