diff --git a/logging/logger.go b/logging/logger.go
index 05237f5696..5e6c485ec1 100644
--- a/logging/logger.go
+++ b/logging/logger.go
@@ -130,6 +130,10 @@ func Setup(config *Config, ui cli.Ui) (hclog.InterceptLogger, *GatedWriter, io.W
 			MaxBytes: logRotateBytes,
 			MaxFiles: config.LogRotateMaxFiles,
 		}
+		if err := logFile.openNew(); err != nil {
+			ui.Error(fmt.Sprintf("Failed to setup logging: %v", err))
+			return nil, nil, nil, false
+		}
 		writers = append(writers, logFile)
 	}
 
diff --git a/logging/logger_test.go b/logging/logger_test.go
index 8c6104b421..49ef9aae96 100644
--- a/logging/logger_test.go
+++ b/logging/logger_test.go
@@ -2,8 +2,10 @@ package logging
 
 import (
 	"encoding/json"
+	"os"
 	"testing"
 
+	"github.com/hashicorp/consul/sdk/testutil"
 	"github.com/mitchellh/cli"
 	"github.com/stretchr/testify/require"
 )
@@ -149,3 +151,64 @@ func TestLogger_SetupLoggerWithJSON(t *testing.T) {
 	require.Contains(jsonOutput, "@message")
 	require.Equal(jsonOutput["@message"], "test warn msg")
 }
+
+func TestLogger_SetupLoggerWithValidLogPath(t *testing.T) {
+	t.Parallel()
+	require := require.New(t)
+
+	tmpDir := testutil.TempDir(t, t.Name())
+	defer os.RemoveAll(tmpDir)
+
+	cfg := &Config{
+		LogLevel:    "INFO",
+		LogFilePath: tmpDir + "/",
+	}
+	ui := cli.NewMockUi()
+
+	logger, gatedWriter, writer, ok := Setup(cfg, ui)
+	require.True(ok)
+	require.NotNil(logger)
+	require.NotNil(gatedWriter)
+	require.NotNil(writer)
+}
+
+func TestLogger_SetupLoggerWithInValidLogPath(t *testing.T) {
+	t.Parallel()
+	require := require.New(t)
+
+	cfg := &Config{
+		LogLevel:    "INFO",
+		LogFilePath: "nonexistentdir/",
+	}
+	ui := cli.NewMockUi()
+
+	logger, gatedWriter, writer, ok := Setup(cfg, ui)
+	require.Contains(ui.ErrorWriter.String(), "no such file or directory")
+	require.False(ok)
+	require.Nil(logger)
+	require.Nil(gatedWriter)
+	require.Nil(writer)
+}
+
+func TestLogger_SetupLoggerWithInValidLogPathPermission(t *testing.T) {
+	t.Parallel()
+	require := require.New(t)
+
+	tmpDir := "/tmp/" + t.Name()
+
+	os.Mkdir(tmpDir, 0000)
+	defer os.RemoveAll(tmpDir)
+
+	cfg := &Config{
+		LogLevel:    "INFO",
+		LogFilePath: tmpDir + "/",
+	}
+	ui := cli.NewMockUi()
+
+	logger, gatedWriter, writer, ok := Setup(cfg, ui)
+	require.Contains(ui.ErrorWriter.String(), "permission denied")
+	require.False(ok)
+	require.Nil(logger)
+	require.Nil(gatedWriter)
+	require.Nil(writer)
+}