diff --git a/cmd/cloudflared/tunnel/cmd.go b/cmd/cloudflared/tunnel/cmd.go
index 8514d60e..beb328de 100644
--- a/cmd/cloudflared/tunnel/cmd.go
+++ b/cmd/cloudflared/tunnel/cmd.go
@@ -215,7 +215,12 @@ func Init(v string, s, g chan struct{}) {
 
 func createLogger(c *cli.Context, isTransport bool) (logger.Service, error) {
 	loggerOpts := []logger.Option{}
-	logPath := c.String(logDirectoryFlag)
+
+	logPath := c.String("logfile")
+	if logPath != "" {
+		logPath = c.String(logDirectoryFlag)
+	}
+
 	if logPath != "" {
 		loggerOpts = append(loggerOpts, logger.DefaultFile(logPath))
 	}
@@ -833,12 +838,17 @@ func tunnelFlags(shouldHide bool) []cli.Flag {
 			Hidden:  shouldHide,
 		}),
 		altsrc.NewStringFlag(&cli.StringFlag{
-			Name:    logDirectoryFlag,
-			Aliases: []string{"logfile"}, // This flag used to be called logfile when it was a single file
-			Usage:   "Save application log to this directory for reporting issues.",
+			Name:    "logfile",
+			Usage:   "Save application log to this file for reporting issues.",
 			EnvVars: []string{"TUNNEL_LOGFILE"},
 			Hidden:  shouldHide,
 		}),
+		altsrc.NewStringFlag(&cli.StringFlag{
+			Name:    logDirectoryFlag,
+			Usage:   "Save application log to this directory for reporting issues.",
+			EnvVars: []string{"TUNNEL_LOGDIRECTORY"},
+			Hidden:  shouldHide,
+		}),
 		altsrc.NewIntFlag(&cli.IntFlag{
 			Name:   "ha-connections",
 			Value:  4,
diff --git a/socks/connection_handler_test.go b/socks/connection_handler_test.go
index 8fb9dda3..40bc9d87 100644
--- a/socks/connection_handler_test.go
+++ b/socks/connection_handler_test.go
@@ -6,6 +6,7 @@ import (
 	"net"
 	"net/http"
 	"testing"
+	"time"
 
 	"github.com/stretchr/testify/assert"
 	"golang.org/x/net/proxy"
@@ -58,7 +59,6 @@ func startTestServer(t *testing.T, httpHandler func(w http.ResponseWriter, r *ht
 
 	// start the servers
 	go http.ListenAndServe(":8085", mux)
-
 }
 
 func respondWithJSON(w http.ResponseWriter, v interface{}, status int) {
@@ -78,6 +78,7 @@ func OkJSONResponseHandler(w http.ResponseWriter, r *http.Request) {
 
 func TestSocksConnection(t *testing.T) {
 	startTestServer(t, OkJSONResponseHandler)
+	time.Sleep(100 * time.Millisecond)
 	b := sendSocksRequest(t)
 	assert.True(t, len(b) > 0, "no data returned!")