diff --git a/cmd/cloudflared/access/carrier.go b/cmd/cloudflared/access/carrier.go
index 722cc0c1..506c57c6 100644
--- a/cmd/cloudflared/access/carrier.go
+++ b/cmd/cloudflared/access/carrier.go
@@ -6,6 +6,7 @@ import (
 	"strings"
 
 	"github.com/cloudflare/cloudflared/carrier"
+	"github.com/cloudflare/cloudflared/cmd/cloudflared/cliutil"
 	"github.com/cloudflare/cloudflared/cmd/cloudflared/config"
 	"github.com/cloudflare/cloudflared/h2mux"
 	"github.com/cloudflare/cloudflared/logger"
@@ -67,7 +68,7 @@ func ssh(c *cli.Context) error {
 
 	logger, err := logger.New(logger.DefaultFile(logDirectory), logger.LogLevelString(logLevel))
 	if err != nil {
-		return errors.Wrap(err, "error setting up logger")
+		return cliutil.PrintLoggerSetupError("error setting up logger", err)
 	}
 
 	// get the hostname from the cmdline and error out if its not provided
diff --git a/cmd/cloudflared/cliutil/errors.go b/cmd/cloudflared/cliutil/errors.go
index f197c335..afbb6fdb 100644
--- a/cmd/cloudflared/cliutil/errors.go
+++ b/cmd/cloudflared/cliutil/errors.go
@@ -2,8 +2,10 @@ package cliutil
 
 import (
 	"fmt"
+	"log"
 
 	"github.com/cloudflare/cloudflared/logger"
+	"github.com/pkg/errors"
 	"gopkg.in/urfave/cli.v2"
 )
 
@@ -39,3 +41,15 @@ func ErrorHandler(actionFunc cli.ActionFunc) cli.ActionFunc {
 		return err
 	}
 }
+
+// PrintLoggerSetupError returns an error to stdout to notify when a logger can't start
+func PrintLoggerSetupError(msg string, err error) error {
+	l, le := logger.New()
+	if le != nil {
+		log.Printf("%s: %s", msg, err)
+	} else {
+		l.Errorf("%s: %s", msg, err)
+	}
+
+	return errors.Wrap(err, msg)
+}
diff --git a/cmd/cloudflared/main.go b/cmd/cloudflared/main.go
index 561af284..3a318e2d 100644
--- a/cmd/cloudflared/main.go
+++ b/cmd/cloudflared/main.go
@@ -6,6 +6,7 @@ import (
 	"time"
 
 	"github.com/cloudflare/cloudflared/cmd/cloudflared/access"
+	"github.com/cloudflare/cloudflared/cmd/cloudflared/cliutil"
 	"github.com/cloudflare/cloudflared/cmd/cloudflared/config"
 	"github.com/cloudflare/cloudflared/cmd/cloudflared/tunnel"
 	"github.com/cloudflare/cloudflared/cmd/cloudflared/updater"
@@ -165,16 +166,15 @@ func handleError(err error) {
 
 // cloudflared was started without any flags
 func handleServiceMode(shutdownC chan struct{}) error {
+	defer log.SharedWriteManager.Shutdown()
 	logDirectory, logLevel := config.FindLogSettings()
 
 	logger, err := log.New(log.DefaultFile(logDirectory), log.LogLevelString(logLevel))
 	if err != nil {
-		return errors.Wrap(err, "error setting up logger")
+		return cliutil.PrintLoggerSetupError("error setting up logger", err)
 	}
 	logger.Infof("logging to directory: %s", logDirectory)
 
-	defer log.SharedWriteManager.Shutdown()
-
 	// start the main run loop that reads from the config file
 	f, err := watcher.NewFile()
 	if err != nil {
diff --git a/cmd/cloudflared/tunnel/cmd.go b/cmd/cloudflared/tunnel/cmd.go
index 84195b12..8514d60e 100644
--- a/cmd/cloudflared/tunnel/cmd.go
+++ b/cmd/cloudflared/tunnel/cmd.go
@@ -235,7 +235,7 @@ func createLogger(c *cli.Context, isTransport bool) (logger.Service, error) {
 func StartServer(c *cli.Context, version string, shutdownC, graceShutdownC chan struct{}) error {
 	logger, err := createLogger(c, false)
 	if err != nil {
-		return errors.Wrap(err, "error setting up logger")
+		return cliutil.PrintLoggerSetupError("error setting up logger", err)
 	}
 
 	_ = raven.SetDSN(sentryDSN)
@@ -478,7 +478,7 @@ func StartServer(c *cli.Context, version string, shutdownC, graceShutdownC chan
 func Before(c *cli.Context) error {
 	logger, err := createLogger(c, false)
 	if err != nil {
-		return errors.Wrap(err, "error setting up logger")
+		return cliutil.PrintLoggerSetupError("error setting up logger", err)
 	}
 
 	if c.String("config") == "" {
diff --git a/logger/create.go b/logger/create.go
index 58f7d603..085bde08 100644
--- a/logger/create.go
+++ b/logger/create.go
@@ -141,7 +141,7 @@ func ParseLevelString(lvl string) ([]Level, error) {
 		return []Level{FatalLevel}, nil
 	case "error":
 		return []Level{FatalLevel, ErrorLevel}, nil
-	case "info":
+	case "info", "warn":
 		return []Level{FatalLevel, ErrorLevel, InfoLevel}, nil
 	case "debug":
 		return []Level{FatalLevel, ErrorLevel, InfoLevel, DebugLevel}, nil
diff --git a/tunneldns/tunnel.go b/tunneldns/tunnel.go
index e85d0a26..4a4faf45 100644
--- a/tunneldns/tunnel.go
+++ b/tunneldns/tunnel.go
@@ -8,6 +8,7 @@ import (
 	"sync"
 	"syscall"
 
+	"github.com/cloudflare/cloudflared/cmd/cloudflared/cliutil"
 	"github.com/cloudflare/cloudflared/cmd/cloudflared/config"
 	"github.com/cloudflare/cloudflared/logger"
 	"github.com/cloudflare/cloudflared/metrics"
@@ -31,7 +32,7 @@ func Run(c *cli.Context) error {
 	logDirectory, logLevel := config.FindLogSettings()
 	logger, err := logger.New(logger.DefaultFile(logDirectory), logger.LogLevelString(logLevel))
 	if err != nil {
-		return errors.Wrap(err, "error setting up logger")
+		return cliutil.PrintLoggerSetupError("error setting up logger", err)
 	}
 
 	metricsListener, err := net.Listen("tcp", c.String("metrics"))