diff --git a/cmd/dockerd/daemon.go b/cmd/dockerd/daemon.go
index fcb7b0b5b2..0359411af1 100644
--- a/cmd/dockerd/daemon.go
+++ b/cmd/dockerd/daemon.go
@@ -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
 }
 
diff --git a/cmd/dockerd/daemon_unix.go b/cmd/dockerd/daemon_unix.go
index 8f74026d2e..a0f1b893b4 100644
--- a/cmd/dockerd/daemon_unix.go
+++ b/cmd/dockerd/daemon_unix.go
@@ -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
diff --git a/internal/test/daemon/daemon.go b/internal/test/daemon/daemon.go
index ebea527d38..bb7236b893 100644
--- a/internal/test/daemon/daemon.go
+++ b/internal/test/daemon/daemon.go
@@ -309,9 +309,7 @@ func (d *Daemon) StartWithLogFile(out *os.File, providedArgs ...string) error {
 			return errors.Errorf("[%s] Daemon exited and never started", d.id)
 		case <-tick:
 			ctx, cancel := context.WithTimeout(context.TODO(), 2*time.Second)
-			req := req.WithContext(ctx)
-
-			resp, err := client.Do(req)
+			resp, err := client.Do(req.WithContext(ctx))
 			cancel()
 			if err != nil {
 				d.log.Logf("[%s] error pinging daemon on start: %v", d.id, err)
@@ -413,12 +411,16 @@ 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() {
-		d.log.Logf("[%s] Daemon stopped", d.id)
+		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
 	}()
@@ -490,7 +492,6 @@ func (d *Daemon) Restart(t testingT, args ...string) {
 // RestartWithError will restart the daemon by first stopping it and then starting it.
 func (d *Daemon) RestartWithError(arg ...string) error {
 	if err := d.StopWithError(); err != nil {
-		d.log.Logf("[%s] Error when stopping daemon: %v", d.id, err)
 		return err
 	}
 	return d.StartWithError(arg...)