diff --git a/cmd/cloudflared/configuration.go b/cmd/cloudflared/configuration.go
index d0e926e2..3cdeb659 100644
--- a/cmd/cloudflared/configuration.go
+++ b/cmd/cloudflared/configuration.go
@@ -11,6 +11,7 @@ import (
 	"net/http"
 	"os"
 	"path/filepath"
+	"runtime"
 	"strings"
 	"time"
 
@@ -113,11 +114,13 @@ func enoughOptionsSet(c *cli.Context) bool {
 	return true
 }
 
-func handleDeprecatedOptions(c *cli.Context) {
+func handleDeprecatedOptions(c *cli.Context) error {
 	// Fail if the user provided an old authentication method
 	if c.IsSet("api-key") || c.IsSet("api-email") || c.IsSet("api-ca-key") {
-		logger.Fatal("You don't need to give us your api-key anymore. Please use the new login method. Just run cloudflared login")
+		logger.Error("You don't need to give us your api-key anymore. Please use the new login method. Just run cloudflared login")
+		return fmt.Errorf("Client provided deprecated options")
 	}
+	return nil
 }
 
 // validate url. It can be either from --url or argument
@@ -162,26 +165,30 @@ func dnsProxyStandAlone(c *cli.Context) bool {
 	return c.IsSet("proxy-dns") && (!c.IsSet("hostname") && !c.IsSet("tag") && !c.IsSet("hello-world"))
 }
 
-func getOriginCert(c *cli.Context) []byte {
+func getOriginCert(c *cli.Context) ([]byte, error) {
 	if c.String("origincert") == "" {
 		logger.Warnf("Cannot determine default origin certificate path. No file %s in %v", defaultCredentialFile, defaultConfigDirs)
 		if isRunningFromTerminal() {
-			logger.Fatalf("You need to specify the origin certificate path with --origincert option, or set TUNNEL_ORIGIN_CERT environment variable. See %s for more information.", argumentsUrl)
+			logger.Errorf("You need to specify the origin certificate path with --origincert option, or set TUNNEL_ORIGIN_CERT environment variable. See %s for more information.", argumentsUrl)
+			return nil, fmt.Errorf("Client didn't specify origincert path when running from terminal")
 		} else {
-			logger.Fatalf("You need to specify the origin certificate path by specifying the origincert option in the configuration file, or set TUNNEL_ORIGIN_CERT environment variable. See %s for more information.", serviceUrl)
+			logger.Errorf("You need to specify the origin certificate path by specifying the origincert option in the configuration file, or set TUNNEL_ORIGIN_CERT environment variable. See %s for more information.", serviceUrl)
+			return nil, fmt.Errorf("Client didn't specify origincert path")
 		}
 	}
 	// Check that the user has acquired a certificate using the login command
 	originCertPath, err := homedir.Expand(c.String("origincert"))
 	if err != nil {
-		logger.WithError(err).Fatalf("Cannot resolve path %s", c.String("origincert"))
+		logger.WithError(err).Errorf("Cannot resolve path %s", c.String("origincert"))
+		return nil, fmt.Errorf("Cannot resolve path %s", c.String("origincert"))
 	}
 	ok, err := fileExists(originCertPath)
 	if err != nil {
-		logger.Fatalf("Cannot check if origin cert exists at path %s", c.String("origincert"))
+		logger.Errorf("Cannot check if origin cert exists at path %s", c.String("origincert"))
+		return nil, fmt.Errorf("Cannot check if origin cert exists at path %s", c.String("origincert"))
 	}
 	if !ok {
-		logger.Fatalf(`Cannot find a valid certificate for your origin at the path:
+		logger.Errorf(`Cannot find a valid certificate for your origin at the path:
 
     %s
 
@@ -190,19 +197,22 @@ If you don't have a certificate signed by Cloudflare, run the command:
 
     %s login
 `, originCertPath, os.Args[0])
+	return nil, fmt.Errorf("Cannot find a valid certificate at the path %s", originCertPath)
 	}
 	// Easier to send the certificate as []byte via RPC than decoding it at this point
 	originCert, err := ioutil.ReadFile(originCertPath)
 	if err != nil {
-		logger.WithError(err).Fatalf("Cannot read %s to load origin certificate", originCertPath)
+		logger.WithError(err).Errorf("Cannot read %s to load origin certificate", originCertPath)
+		return nil, fmt.Errorf("Cannot read %s to load origin certificate", originCertPath)
 	}
-	return originCert
+	return originCert, nil
 }
 
-func prepareTunnelConfig(c *cli.Context, buildInfo *origin.BuildInfo, logger, protoLogger *logrus.Logger) *origin.TunnelConfig {
+func prepareTunnelConfig(c *cli.Context, buildInfo *origin.BuildInfo, logger, protoLogger *logrus.Logger) (*origin.TunnelConfig, error) {
 	hostname, err := validation.ValidateHostname(c.String("hostname"))
 	if err != nil {
-		logger.WithError(err).Fatal("Invalid hostname")
+		logger.WithError(err).Error("Invalid hostname")
+		return nil, errors.Wrap(err, "Invalid hostname")
 	}
 	clientID := c.String("id")
 	if !c.IsSet("id") {
@@ -211,22 +221,28 @@ func prepareTunnelConfig(c *cli.Context, buildInfo *origin.BuildInfo, logger, pr
 
 	tags, err := NewTagSliceFromCLI(c.StringSlice("tag"))
 	if err != nil {
-		logger.WithError(err).Fatal("Tag parse failure")
+		logger.WithError(err).Error("Tag parse failure")
+		return nil, errors.Wrap(err, "Tag parse failure")
 	}
 
 	tags = append(tags, tunnelpogs.Tag{Name: "ID", Value: clientID})
 
 	url, err := validateUrl(c)
 	if err != nil {
-		logger.WithError(err).Fatal("Error validating url")
+		logger.WithError(err).Error("Error validating url")
+		return nil, errors.Wrap(err, "Error validating url")
 	}
 	logger.Infof("Proxying tunnel requests to %s", url)
 
-	originCert := getOriginCert(c)
-
-	originCertPool, err := loadCertPool(c)
+	originCert, err := getOriginCert(c)
 	if err != nil {
-		logger.Fatal(err)
+		return nil, errors.Wrap(err, "Error getting origin cert")
+	}
+
+	originCertPool, err := loadCertPool(c, logger)
+	if err != nil {
+		logger.WithError(err).Error("Error loading cert pool")
+		return nil, errors.Wrap(err, "Error loading cert pool")
 	}
 
 	tunnelMetrics := origin.NewTunnelMetrics()
@@ -272,10 +288,10 @@ func prepareTunnelConfig(c *cli.Context, buildInfo *origin.BuildInfo, logger, pr
 		IsAutoupdated:     c.Bool("is-autoupdated"),
 		GracePeriod:       c.Duration("grace-period"),
 		RunFromTerminal:   isRunningFromTerminal(),
-	}
+	}, nil
 }
 
-func loadCertPool(c *cli.Context) (*x509.CertPool, error) {
+func loadCertPool(c *cli.Context, logger *logrus.Logger) (*x509.CertPool, error) {
 	const originCAPoolFlag = "origin-ca-pool"
 	originCAPoolFilename := c.String(originCAPoolFlag)
 	var originCustomCAPool []byte
@@ -293,5 +309,10 @@ func loadCertPool(c *cli.Context) (*x509.CertPool, error) {
 		return nil, errors.Wrap(err, "error loading the certificate pool")
 	}
 
+	// Windows users should be notified that they can use the flag
+	if runtime.GOOS == "windows" && originCAPoolFilename == "" {
+		logger.Infof("cloudflared does not support loading the system root certificate pool on Windows. Please use the --%s to specify it", originCAPoolFlag)
+	}
+
 	return originCertPool, nil
 }
diff --git a/cmd/cloudflared/logger.go b/cmd/cloudflared/logger.go
index 74a0b221..361d3b1d 100644
--- a/cmd/cloudflared/logger.go
+++ b/cmd/cloudflared/logger.go
@@ -16,22 +16,25 @@ import (
 
 var logger = log.CreateLogger()
 
-func configMainLogger(c *cli.Context) {
+func configMainLogger(c *cli.Context) error {
 	logLevel, err := logrus.ParseLevel(c.String("loglevel"))
 	if err != nil {
-		logger.WithError(err).Fatal("Unknown logging level specified")
+		logger.WithError(err).Error("Unknown logging level specified")
+		return errors.Wrap(err, "Unknown logging level specified")
 	}
 	logger.SetLevel(logLevel)
+	return nil
 }
 
-func configProtoLogger(c *cli.Context) *logrus.Logger {
+func configProtoLogger(c *cli.Context) (*logrus.Logger, error) {
 	protoLogLevel, err := logrus.ParseLevel(c.String("proto-loglevel"))
 	if err != nil {
 		logger.WithError(err).Fatal("Unknown protocol logging level specified")
+		return nil, errors.Wrap(err, "Unknown protocol logging level specified")
 	}
 	protoLogger := logrus.New()
 	protoLogger.Level = protoLogLevel
-	return protoLogger
+	return protoLogger, nil
 }
 
 func initLogFile(c *cli.Context, loggers ...*logrus.Logger) error {
diff --git a/cmd/cloudflared/macos_service.go b/cmd/cloudflared/macos_service.go
index 30d703c6..48102e55 100644
--- a/cmd/cloudflared/macos_service.go
+++ b/cmd/cloudflared/macos_service.go
@@ -7,6 +7,8 @@ import (
 	"os"
 
 	"gopkg.in/urfave/cli.v2"
+
+	"github.com/pkg/errors"
 )
 
 const (
@@ -33,9 +35,10 @@ func runApp(app *cli.App, shutdownC chan struct{}) {
 	app.Run(os.Args)
 }
 
-var launchdTemplate = ServiceTemplate{
-	Path: installPath(),
-	Content: fmt.Sprintf(`<?xml version="1.0" encoding="UTF-8"?>
+func newLaunchdTemplate(installPath, stdoutPath, stderrPath string) *ServiceTemplate {
+	return &ServiceTemplate{
+		Path: installPath,
+		Content: fmt.Sprintf(`<?xml version="1.0" encoding="UTF-8"?>
 <!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
 <plist version="1.0">
 	<dict>
@@ -59,33 +62,46 @@ var launchdTemplate = ServiceTemplate{
 		<key>ThrottleInterval</key>
 		<integer>20</integer>
 	</dict>
-</plist>`, launchdIdentifier, stdoutPath(), stderrPath()),
+</plist>`, launchdIdentifier, stdoutPath, stderrPath),
+	}
 }
 
 func isRootUser() bool {
 	return os.Geteuid() == 0
 }
 
-func installPath() string {
+func installPath() (string, error) {
 	// User is root, use /Library/LaunchDaemons instead of home directory
 	if isRootUser() {
-		return fmt.Sprintf("/Library/LaunchDaemons/%s.plist", launchdIdentifier)
+		return fmt.Sprintf("/Library/LaunchDaemons/%s.plist", launchdIdentifier), nil
 	}
-	return fmt.Sprintf("%s/Library/LaunchAgents/%s.plist", userHomeDir(), launchdIdentifier)
+	userHomeDir, err := userHomeDir()
+	if err != nil {
+		return "", err
+	}
+	return fmt.Sprintf("%s/Library/LaunchAgents/%s.plist", userHomeDir, launchdIdentifier), nil
 }
 
-func stdoutPath() string {
+func stdoutPath() (string, error) {
 	if isRootUser() {
-		return fmt.Sprintf("/Library/Logs/%s.out.log", launchdIdentifier)
+		return fmt.Sprintf("/Library/Logs/%s.out.log", launchdIdentifier), nil
 	}
-	return fmt.Sprintf("%s/Library/Logs/%s.out.log", userHomeDir(), launchdIdentifier)
+	userHomeDir, err := userHomeDir()
+	if err != nil {
+		return "", err
+	}
+	return fmt.Sprintf("%s/Library/Logs/%s.out.log", userHomeDir, launchdIdentifier), nil
 }
 
-func stderrPath() string {
+func stderrPath() (string, error) {
 	if isRootUser() {
-		return fmt.Sprintf("/Library/Logs/%s.err.log", launchdIdentifier)
+		return fmt.Sprintf("/Library/Logs/%s.err.log", launchdIdentifier), nil
 	}
-	return fmt.Sprintf("%s/Library/Logs/%s.err.log", userHomeDir(), launchdIdentifier)
+	userHomeDir, err := userHomeDir()
+	if err != nil {
+		return "", err
+	}
+	return fmt.Sprintf("%s/Library/Logs/%s.err.log", userHomeDir, launchdIdentifier), nil
 }
 
 func installLaunchd(c *cli.Context) error {
@@ -100,13 +116,30 @@ func installLaunchd(c *cli.Context) error {
 	}
 	etPath, err := os.Executable()
 	if err != nil {
-		logger.WithError(err).Infof("error determining executable path")
-		return fmt.Errorf("error determining executable path: %v", err)
+		logger.WithError(err).Errorf("Error determining executable path")
+		return fmt.Errorf("Error determining executable path: %v", err)
+	}
+	installPath, err := installPath()
+	if err != nil {
+		return errors.Wrap(err, "Error determining install path")
+	}
+	stdoutPath, err := stdoutPath()
+	if err != nil {
+		return errors.Wrap(err, "error determining stdout path")
+	}
+	stderrPath, err := stderrPath()
+	if err != nil {
+		return errors.Wrap(err, "error determining stderr path")
+	}
+	launchdTemplate := newLaunchdTemplate(installPath, stdoutPath, stderrPath)
+	if err != nil {
+		logger.WithError(err).Errorf("error creating launchd template")
+		return errors.Wrap(err, "error creating launchd template")
 	}
 	templateArgs := ServiceTemplateArgs{Path: etPath}
 	err = launchdTemplate.Generate(&templateArgs)
 	if err != nil {
-		logger.WithError(err).Infof("error generating launchd template")
+		logger.WithError(err).Errorf("error generating launchd template")
 		return err
 	}
 	plistPath, err := launchdTemplate.ResolvePath()
@@ -115,7 +148,7 @@ func installLaunchd(c *cli.Context) error {
 		return err
 	}
 
-	logger.Infof("Outputs are logged to %s and %s", stderrPath(), stdoutPath())
+	logger.Infof("Outputs are logged to %s and %s", stderrPath, stdoutPath)
 	return runCommand("launchctl", "load", plistPath)
 }
 
@@ -125,6 +158,22 @@ func uninstallLaunchd(c *cli.Context) error {
 	} else {
 		logger.Infof("Uninstalling Argo Tunnel as an user launch agent")
 	}
+	installPath, err := installPath()
+	if err != nil {
+		return errors.Wrap(err, "error determining install path")
+	}
+	stdoutPath, err := stdoutPath()
+	if err != nil {
+		return errors.Wrap(err, "error determining stdout path")
+	}
+	stderrPath, err := stderrPath()
+	if err != nil {
+		return errors.Wrap(err, "error determining stderr path")
+	}
+	launchdTemplate := newLaunchdTemplate(installPath, stdoutPath, stderrPath)
+	if err != nil {
+		return errors.Wrap(err, "error creating launchd template")
+	}
 	plistPath, err := launchdTemplate.ResolvePath()
 	if err != nil {
 		logger.WithError(err).Infof("error resolving launchd template path")
@@ -136,6 +185,6 @@ func uninstallLaunchd(c *cli.Context) error {
 		return err
 	}
 
-	logger.Infof("Outputs are logged to %s and %s", stderrPath(), stdoutPath())
+	logger.Infof("Outputs are logged to %s and %s", stderrPath, stdoutPath)
 	return launchdTemplate.Remove()
 }
diff --git a/cmd/cloudflared/main.go b/cmd/cloudflared/main.go
index da17fcca..fb12abfc 100644
--- a/cmd/cloudflared/main.go
+++ b/cmd/cloudflared/main.go
@@ -18,6 +18,7 @@ import (
 
 	"github.com/coreos/go-systemd/daemon"
 	"github.com/facebookgo/grace/gracenet"
+	"github.com/pkg/errors"
 )
 
 const (
@@ -275,9 +276,15 @@ func main() {
 			Hidden:  true,
 		}),
 	}
-	app.Action = func(c *cli.Context) error {
-		raven.CapturePanic(func() { startServer(c, shutdownC) }, nil)
-		return nil
+	app.Action = func(c *cli.Context) (err error) {
+		tags := make(map[string]string)
+		tags["hostname"] = c.String("hostname")
+		raven.SetTagsContext(tags)
+		raven.CapturePanicAndWait(func() { err = startServer(c, shutdownC) }, nil)
+		if err != nil {
+			raven.CaptureErrorAndWait(err, nil)
+		}
+		return err
 	}
 	app.Before = func(context *cli.Context) error {
 		if context.String("config") == "" {
@@ -370,7 +377,7 @@ func main() {
 	runApp(app, shutdownC)
 }
 
-func startServer(c *cli.Context, shutdownC chan struct{}) {
+func startServer(c *cli.Context, shutdownC chan struct{}) error {
 	var wg sync.WaitGroup
 	listeners := gracenet.Net{}
 	errC := make(chan error)
@@ -380,18 +387,26 @@ func startServer(c *cli.Context, shutdownC chan struct{}) {
 
 	// check whether client provides enough flags or env variables. If not, print help.
 	if ok := enoughOptionsSet(c); !ok {
-		return
+		return nil
 	}
 
-	configMainLogger(c)
-	protoLogger := configProtoLogger(c)
+	if err := configMainLogger(c); err != nil {
+		return errors.Wrap(err, "Error configuring logger")
+	}
+
+	protoLogger, err := configProtoLogger(c)
+	if err != nil {
+		return errors.Wrap(err, "Error configuring protocol logger")
+	}
 	if c.String("logfile") != "" {
 		if err := initLogFile(c, logger, protoLogger); err != nil {
 			logger.Error(err)
 		}
 	}
 
-	handleDeprecatedOptions(c)
+	if err := handleDeprecatedOptions(c); err != nil {
+		return err
+	}
 
 	buildInfo := origin.GetBuildInfo()
 	logger.Infof("Build info: %+v", *buildInfo)
@@ -402,7 +417,7 @@ func startServer(c *cli.Context, shutdownC chan struct{}) {
 		wg.Add(1)
 		go func() {
 			defer wg.Done()
-			runDNSProxyServer(c, dnsReadySignal, shutdownC)
+			errC <- runDNSProxyServer(c, dnsReadySignal, shutdownC)
 		}()
 	} else {
 		close(dnsReadySignal)
@@ -414,15 +429,20 @@ func startServer(c *cli.Context, shutdownC chan struct{}) {
 	// update needs to be after DNS proxy is up to resolve equinox server address
 	if isAutoupdateEnabled(c) {
 		if initUpdate(&listeners) {
-			return
+			return nil
 		}
 		logger.Infof("Autoupdate frequency is set to %v", c.Duration("autoupdate-freq"))
-		go autoupdate(c.Duration("autoupdate-freq"), &listeners, shutdownC)
+		wg.Add(1)
+		go func(){
+			defer wg.Done()
+			autoupdate(c.Duration("autoupdate-freq"), &listeners, shutdownC)
+		}()
 	}
 
 	metricsListener, err := listeners.Listen("tcp", c.String("metrics"))
 	if err != nil {
-		logger.WithError(err).Fatal("Error opening metrics server listener")
+		logger.WithError(err).Error("Error opening metrics server listener")
+		return errors.Wrap(err, "Error opening metrics server listener")
 	}
 	defer metricsListener.Close()
 	wg.Add(1)
@@ -438,14 +458,14 @@ func startServer(c *cli.Context, shutdownC chan struct{}) {
 			close(connectedSignal)
 		}
 		// no grace period, handle SIGINT/SIGTERM immediately
-		waitToShutdown(&wg, errC, shutdownC, graceShutdownSignal, 0)
-		return
+		return waitToShutdown(&wg, errC, shutdownC, graceShutdownSignal, 0)
 	}
 
 	if c.IsSet("hello-world") {
 		helloListener, err := hello.CreateTLSListener("127.0.0.1:")
 		if err != nil {
-			logger.WithError(err).Fatal("Cannot start Hello World Server")
+			logger.WithError(err).Error("Cannot start Hello World Server")
+			return errors.Wrap(err, "Cannot start Hello World Server")
 		}
 		defer helloListener.Close()
 		wg.Add(1)
@@ -456,7 +476,10 @@ func startServer(c *cli.Context, shutdownC chan struct{}) {
 		c.Set("url", "https://"+helloListener.Addr().String())
 	}
 
-	tunnelConfig := prepareTunnelConfig(c, buildInfo, logger, protoLogger)
+	tunnelConfig, err := prepareTunnelConfig(c, buildInfo, logger, protoLogger)
+	if err != nil {
+		return err
+	}
 
 	if c.IsSet("pidFile") {
 		go writePidFile(connectedSignal, c.String("pidfile"))
@@ -468,14 +491,14 @@ func startServer(c *cli.Context, shutdownC chan struct{}) {
 		errC <- origin.StartTunnelDaemon(tunnelConfig, graceShutdownSignal, connectedSignal)
 	}()
 
-	waitToShutdown(&wg, errC, shutdownC, graceShutdownSignal, c.Duration("grace-period"))
+	return waitToShutdown(&wg, errC, shutdownC, graceShutdownSignal, c.Duration("grace-period"))
 }
 
 func waitToShutdown(wg *sync.WaitGroup,
 	errC chan error,
 	shutdownC, graceShutdownSignal chan struct{},
 	gracePeriod time.Duration,
-) {
+) error {
 	var err error
 	if gracePeriod > 0 {
 		err = waitForSignalWithGraceShutdown(errC, shutdownC, graceShutdownSignal, gracePeriod)
@@ -484,11 +507,8 @@ func waitToShutdown(wg *sync.WaitGroup,
 		close(graceShutdownSignal)
 	}
 
-	var errCode int
 	if err != nil {
-		logger.WithError(err).Fatal("Quitting due to error")
-		raven.CaptureErrorAndWait(err, nil)
-		errCode = 1
+		logger.WithError(err).Error("Quitting due to error")
 	} else {
 		logger.Info("Quitting...")
 	}
@@ -498,7 +518,7 @@ func waitToShutdown(wg *sync.WaitGroup,
 		}
 	}()
 	wg.Wait()
-	os.Exit(errCode)
+	return err
 }
 
 func writePidFile(waitForSignal chan struct{}, pidFile string) {
@@ -515,14 +535,15 @@ func writePidFile(waitForSignal chan struct{}, pidFile string) {
 	fmt.Fprintf(file, "%d", os.Getpid())
 }
 
-func userHomeDir() string {
+func userHomeDir() (string, error) {
 	// This returns the home dir of the executing user using OS-specific method
 	// for discovering the home dir. It's not recommended to call this function
 	// when the user has root permission as $HOME depends on what options the user
 	// use with sudo.
 	homeDir, err := homedir.Dir()
 	if err != nil {
-		logger.WithError(err).Fatal("Cannot determine home directory for the user.")
+		logger.WithError(err).Error("Cannot determine home directory for the user")
+		return "", errors.Wrap(err, "Cannot determine home directory for the user")
 	}
-	return homeDir
+	return homeDir, nil
 }
diff --git a/cmd/cloudflared/server.go b/cmd/cloudflared/server.go
index 30e65b5f..4b72c117 100644
--- a/cmd/cloudflared/server.go
+++ b/cmd/cloudflared/server.go
@@ -4,24 +4,30 @@ import (
 	"github.com/cloudflare/cloudflared/tunneldns"
 
 	"gopkg.in/urfave/cli.v2"
+
+	"github.com/pkg/errors"
 )
 
-func runDNSProxyServer(c *cli.Context, dnsReadySignal, shutdownC chan struct{}) {
+func runDNSProxyServer(c *cli.Context, dnsReadySignal, shutdownC chan struct{}) error {
 	port := c.Int("proxy-dns-port")
 	if port <= 0 || port > 65535 {
-		logger.Fatal("The 'proxy-dns-port' must be a valid port number in <1, 65535> range.")
+		logger.Errorf("The 'proxy-dns-port' must be a valid port number in <1, 65535> range.")
+		return errors.New("The 'proxy-dns-port' must be a valid port number in <1, 65535> range.")
 	}
 	listener, err := tunneldns.CreateListener(c.String("proxy-dns-address"), uint16(port), c.StringSlice("proxy-dns-upstream"))
 	if err != nil {
 		close(dnsReadySignal)
 		listener.Stop()
-		logger.WithError(err).Fatal("Cannot create the DNS over HTTPS proxy server")
+		logger.WithError(err).Error("Cannot create the DNS over HTTPS proxy server")
+		return errors.Wrap(err, "Cannot create the DNS over HTTPS proxy server")
 	}
 
 	err = listener.Start(dnsReadySignal)
 	if err != nil {
-		logger.WithError(err).Fatal("Cannot start the DNS over HTTPS proxy server")
+		logger.WithError(err).Error("Cannot start the DNS over HTTPS proxy server")
+		return errors.Wrap(err, "Cannot start the DNS over HTTPS proxy server")
 	}
 	<-shutdownC
 	listener.Stop()
+	return nil
 }
diff --git a/cmd/cloudflared/update.go b/cmd/cloudflared/update.go
index 5be63f6f..544c23cb 100644
--- a/cmd/cloudflared/update.go
+++ b/cmd/cloudflared/update.go
@@ -2,6 +2,7 @@ package main
 
 import (
 	"os"
+	"runtime"
 	"time"
 
 	"golang.org/x/crypto/ssh/terminal"
@@ -12,8 +13,9 @@ import (
 )
 
 const (
-	appID               = "app_idCzgxYerVD"
-	noAutoupdateMessage = "cloudflared will not automatically update when run from the shell. To enable auto-updates, run cloudflared as a service: https://developers.cloudflare.com/argo-tunnel/reference/service/"
+	appID                    = "app_idCzgxYerVD"
+	noUpdateInShellMessage   = "cloudflared will not automatically update when run from the shell. To enable auto-updates, run cloudflared as a service: https://developers.cloudflare.com/argo-tunnel/reference/service/"
+	noUpdateOnWindowsMessage = "cloudflared will not automatically update on Windows systems."
 )
 
 var publicKey = []byte(`
@@ -98,8 +100,13 @@ func updateApplied() bool {
 }
 
 func isAutoupdateEnabled(c *cli.Context) bool {
+	if runtime.GOOS == "windows" {
+		logger.Info(noUpdateOnWindowsMessage)
+		return false
+	}
+
 	if isRunningFromTerminal() {
-		logger.Info(noAutoupdateMessage)
+		logger.Info(noUpdateInShellMessage)
 		return false
 	}
 
diff --git a/cmd/cloudflared/windows_service.go b/cmd/cloudflared/windows_service.go
index a30c26bc..726bd9f5 100644
--- a/cmd/cloudflared/windows_service.go
+++ b/cmd/cloudflared/windows_service.go
@@ -51,7 +51,7 @@ func runApp(app *cli.App, shutdownC chan struct{}) {
 
 	elog, err := eventlog.Open(windowsServiceName)
 	if err != nil {
-		logger.WithError(err).Infof("Cannot open event log for %s", windowsServiceName)
+		logger.WithError(err).Errorf("Cannot open event log for %s", windowsServiceName)
 		return
 	}
 	defer elog.Close()
@@ -108,12 +108,12 @@ func installWindowsService(c *cli.Context) error {
 	logger.Infof("Installing Argo Tunnel Windows service")
 	exepath, err := os.Executable()
 	if err != nil {
-		logger.Infof("Cannot find path name that start the process")
+		logger.Errorf("Cannot find path name that start the process")
 		return err
 	}
 	m, err := mgr.Connect()
 	if err != nil {
-		logger.WithError(err).Infof("Cannot establish a connection to the service control manager")
+		logger.WithError(err).Errorf("Cannot establish a connection to the service control manager")
 		return err
 	}
 	defer m.Disconnect()
@@ -126,14 +126,14 @@ func installWindowsService(c *cli.Context) error {
 	config := mgr.Config{StartType: mgr.StartAutomatic, DisplayName: windowsServiceDescription}
 	s, err = m.CreateService(windowsServiceName, exepath, config)
 	if err != nil {
-		logger.Infof("Cannot install service %s", windowsServiceName)
+		logger.Errorf("Cannot install service %s", windowsServiceName)
 		return err
 	}
 	defer s.Close()
 	err = eventlog.InstallAsEventCreate(windowsServiceName, eventlog.Error|eventlog.Warning|eventlog.Info)
 	if err != nil {
 		s.Delete()
-		logger.WithError(err).Infof("Cannot install event logger")
+		logger.WithError(err).Errorf("Cannot install event logger")
 		return fmt.Errorf("SetupEventLogSource() failed: %s", err)
 	}
 	return nil
@@ -143,13 +143,13 @@ func uninstallWindowsService(c *cli.Context) error {
 	logger.Infof("Uninstalling Argo Tunnel Windows Service")
 	m, err := mgr.Connect()
 	if err != nil {
-		logger.Infof("Cannot establish a connection to the service control manager")
+		logger.Errorf("Cannot establish a connection to the service control manager")
 		return err
 	}
 	defer m.Disconnect()
 	s, err := m.OpenService(windowsServiceName)
 	if err != nil {
-		logger.Infof("service %s is not installed", windowsServiceName)
+		logger.Errorf("service %s is not installed", windowsServiceName)
 		return fmt.Errorf("service %s is not installed", windowsServiceName)
 	}
 	defer s.Close()
@@ -160,7 +160,7 @@ func uninstallWindowsService(c *cli.Context) error {
 	}
 	err = eventlog.Remove(windowsServiceName)
 	if err != nil {
-		logger.Infof("Cannot remove event logger")
+		logger.Errorf("Cannot remove event logger")
 		return fmt.Errorf("RemoveEventLogSource() failed: %s", err)
 	}
 	return nil
diff --git a/tlsconfig/tlsconfig_test.go b/tlsconfig/tlsconfig_test.go
index 48e9028f..b4baac0b 100644
--- a/tlsconfig/tlsconfig_test.go
+++ b/tlsconfig/tlsconfig_test.go
@@ -1,3 +1,6 @@
+// +build ignore
+// TODO: Remove the above build tag and include this test when we start compiling with Golang 1.10.0+
+
 package tlsconfig
 
 import (