@@ -91,6 +91,8 @@ func (cli *DaemonCli) start(opts *daemonOptions) (err error) {

 		return err

 	}

+	logrus.Info("Starting up")

+

 	cli.configFile = &opts.configFile

 	cli.flags = opts.flags

@@ -266,6 +268,7 @@ func (cli *DaemonCli) start(opts *daemonOptions) (err error) {

 		return errors.Wrap(errAPI, "shutting down due to ServeAPI error")

 	}

+	logrus.Info("Daemon shutdown complete")

 	return nil

 }

@@ -20,6 +20,7 @@ import (

 	"github.com/docker/docker/pkg/homedir"

 	"github.com/docker/libnetwork/portallocator"

 	"github.com/pkg/errors"

+	"github.com/sirupsen/logrus"

 	"golang.org/x/sys/unix"

 )

@@ -152,6 +153,7 @@ func (cli *DaemonCli) initContainerD(ctx context.Context) (func(time.Duration) e

 			return nil, errors.Wrap(err, "could not determine whether the system containerd is running")

 		}

 		if !ok {

+			logrus.Debug("Containerd not running, starting daemon managed containerd")

 			opts, err := cli.getContainerdDaemonOpts()

 			if err != nil {

 				return nil, errors.Wrap(err, "failed to generate containerd options")

@@ -161,6 +163,7 @@ func (cli *DaemonCli) initContainerD(ctx context.Context) (func(time.Duration) e

 			if err != nil {

 				return nil, errors.Wrap(err, "failed to start containerd")

 			}

+			logrus.Debug("Started daemon managed containerd")

 			cli.Config.ContainerdAddr = r.Address()

 			// Try to wait for containerd to shutdown

@@ -290,41 +290,44 @@ func (d *Daemon) StartWithLogFile(out *os.File, providedArgs ...string) error {

 	d.Wait = wait

+	clientConfig, err := d.getClientConfig()

+	if err != nil {

+		return err

+	}

+	client := &http.Client{

+		Transport: clientConfig.transport,

+	}

+

+	req, err := http.NewRequest("GET", "/_ping", nil)

+	if err != nil {

+		return errors.Wrapf(err, "[%s] could not create new request", d.id)

+	}

+	req.URL.Host = clientConfig.addr

+	req.URL.Scheme = clientConfig.scheme

+

 	ticker := time.NewTicker(500 * time.Millisecond)

 	defer ticker.Stop()

 	tick := ticker.C

+	timeout := time.NewTimer(60 * time.Second) // timeout for the whole loop

+	defer timeout.Stop()

+

 	// make sure daemon is ready to receive requests

-	startTime := time.Now().Unix()

 	for {

 		d.log.Logf("[%s] waiting for daemon to start", d.id)

-		if time.Now().Unix()-startTime > 5 {

-			// After 5 seconds, give up

-			return errors.Errorf("[%s] Daemon exited and never started", d.id)

-		}

+

 		select {

-		case <-time.After(2 * time.Second):

-			return errors.Errorf("[%s] timeout: daemon does not respond", d.id)

+		case <-timeout.C:

+			return errors.Errorf("[%s] Daemon exited and never started", d.id)

 		case <-tick:

-			clientConfig, err := d.getClientConfig()

-			if err != nil {

-				return err

-			}

-

-			client := &http.Client{

-				Transport: clientConfig.transport,

-			}

-

-			req, err := http.NewRequest("GET", "/_ping", nil)

-			if err != nil {

-				return errors.Wrapf(err, "[%s] could not create new request", d.id)

-			}

-			req.URL.Host = clientConfig.addr

-			req.URL.Scheme = clientConfig.scheme

-			resp, err := client.Do(req)

+			ctx, cancel := context.WithTimeout(context.TODO(), 2*time.Second)

+			resp, err := client.Do(req.WithContext(ctx))

+			cancel()

 			if err != nil {

+				d.log.Logf("[%s] error pinging daemon on start: %v", d.id, err)

 				continue

 			}

+

 			resp.Body.Close()

 			if resp.StatusCode != http.StatusOK {

 				d.log.Logf("[%s] received status != 200 OK: %s\n", d.id, resp.Status)

@@ -420,12 +423,16 @@ func (d *Daemon) Stop(t testingT) {

 // If it timeouts, a SIGKILL is sent.

 // Stop will not delete the daemon directory. If a purged daemon is needed,

 // instantiate a new one with NewDaemon.

-func (d *Daemon) StopWithError() error {

+func (d *Daemon) StopWithError() (err error) {

 	if d.cmd == nil || d.Wait == nil {

 		return errDaemonNotStarted

 	}

-

 	defer func() {

+		if err == nil {

+			d.log.Logf("[%s] Daemon stopped", d.id)

+		} else {

+			d.log.Logf("[%s] Error when stopping daemon: %v", d.id, err)

+		}

 		d.logFile.Close()

 		d.cmd = nil

 	}()

@@ -435,12 +442,15 @@ func (d *Daemon) StopWithError() error {

 	defer ticker.Stop()

 	tick := ticker.C

+	d.log.Logf("[%s] Stopping daemon", d.id)

+

 	if err := d.cmd.Process.Signal(os.Interrupt); err != nil {

 		if strings.Contains(err.Error(), "os: process already finished") {

 			return errDaemonNotStarted

 		}

 		return errors.Errorf("could not send signal: %v", err)

 	}

+

 out1:

 	for {

 		select {