diff --git a/hack/preload-images/preload_images.go b/hack/preload-images/preload_images.go
index b41de29548..1c6c858331 100644
--- a/hack/preload-images/preload_images.go
+++ b/hack/preload-images/preload_images.go
@@ -17,6 +17,7 @@ limitations under the License.
 package main
 
 import (
+	"bytes"
 	"flag"
 	"fmt"
 	"os"
@@ -92,7 +93,7 @@ func executePreloadImages() error {
 	defer os.Remove(baseDir)
 
 	if err := os.MkdirAll(baseDir, 0755); err != nil {
-		return err
+		return errors.Wrap(err, "mkdir")
 	}
 	if err := driver.Create(); err != nil {
 		return errors.Wrap(err, "creating kic driver")
@@ -123,7 +124,7 @@ func executePreloadImages() error {
 	}
 	// Create image tarball
 	if err := createImageTarball(); err != nil {
-		return err
+		return errors.Wrap(err, "create tarball")
 	}
 	return copyTarballToHost()
 }
@@ -139,7 +140,7 @@ func createImageTarball() error {
 	cmd := exec.Command("docker", args...)
 	cmd.Stdout = os.Stdout
 	if err := cmd.Run(); err != nil {
-		return errors.Wrap(err, "creating image tarball")
+		return errors.Wrapf(err, "tarball cmd: %s", cmd.Args)
 	}
 	return nil
 }
@@ -149,7 +150,7 @@ func copyTarballToHost() error {
 	cmd := exec.Command("docker", "cp", fmt.Sprintf("%s:/%s", profile, tarballFilename), dest)
 	cmd.Stdout = os.Stdout
 	if err := cmd.Run(); err != nil {
-		return errors.Wrap(err, "copying tarball to host")
+		return errors.Wrapf(err, "cp cmd: %s", cmd.Args)
 	}
 	return nil
 }
@@ -162,9 +163,11 @@ func deleteMinikube() error {
 
 func verifyDockerStorage() error {
 	cmd := exec.Command("docker", "info", "-f", "{{.Info.Driver}}")
+	var stderr bytes.Buffer
+	cmd.Stderr = &stderr
 	output, err := cmd.Output()
 	if err != nil {
-		return err
+		return fmt.Errorf("%v: %v:\n%s", cmd.Args, err, stderr.String())
 	}
 	driver := strings.Trim(string(output), " \n")
 	if driver != dockerStorageDriver {
diff --git a/pkg/drivers/kic/oci/volumes.go b/pkg/drivers/kic/oci/volumes.go
index 115ab51a0a..58c13b9621 100644
--- a/pkg/drivers/kic/oci/volumes.go
+++ b/pkg/drivers/kic/oci/volumes.go
@@ -103,6 +103,7 @@ func allVolumesByLabel(ociBin string, label string) ([]string, error) {
 // to the volume named volumeName
 func ExtractTarballToVolume(tarballPath, volumeName, imageName string) error {
 	cmd := exec.Command(Docker, "run", "--rm", "--entrypoint", "/usr/bin/tar", "-v", fmt.Sprintf("%s:/preloaded.tar:ro", tarballPath), "-v", fmt.Sprintf("%s:/extractDir", volumeName), imageName, "-I", "lz4", "-xvf", "/preloaded.tar", "-C", "/extractDir")
+	glog.Infof("executing: %s", cmd.Args)
 	if out, err := cmd.CombinedOutput(); err != nil {
 		return errors.Wrapf(err, "output %s", string(out))
 	}
@@ -114,6 +115,7 @@ func ExtractTarballToVolume(tarballPath, volumeName, imageName string) error {
 // TODO: this should be fixed as a part of https://github.com/kubernetes/minikube/issues/6530
 func createDockerVolume(profile string, nodeName string) error {
 	cmd := exec.Command(Docker, "volume", "create", nodeName, "--label", fmt.Sprintf("%s=%s", ProfileLabelKey, profile), "--label", fmt.Sprintf("%s=%s", CreatedByLabelKey, "true"))
+	glog.Infof("executing: %s", cmd.Args)
 	if out, err := cmd.CombinedOutput(); err != nil {
 		return errors.Wrapf(err, "output %s", string(out))
 	}