diff --git a/pkg/kubelet/dockershim/docker_container.go b/pkg/kubelet/dockershim/docker_container.go
index 283dc644dbd..ac79f3fe64a 100644
--- a/pkg/kubelet/dockershim/docker_container.go
+++ b/pkg/kubelet/dockershim/docker_container.go
@@ -233,6 +233,7 @@ func (ds *dockerService) removeContainerLogSymlink(containerID string) error {
 func (ds *dockerService) StartContainer(containerID string) error {
 	err := ds.client.StartContainer(containerID)
 	if err != nil {
+		err = transformStartContainerError(err)
 		return fmt.Errorf("failed to start container %q: %v", containerID, err)
 	}
 	// Create container log symlink.
diff --git a/pkg/kubelet/dockershim/helpers.go b/pkg/kubelet/dockershim/helpers.go
index 22ab777e6af..c5b99a32d57 100644
--- a/pkg/kubelet/dockershim/helpers.go
+++ b/pkg/kubelet/dockershim/helpers.go
@@ -55,6 +55,10 @@ const (
 var (
 	conflictRE = regexp.MustCompile(`Conflict. (?:.)+ is already in use by container ([0-9a-z]+)`)
 
+	// this is hacky, but extremely common.
+	// if a container starts but the executable file is not found, runc gives a message that matches
+	startRE = regexp.MustCompile(`\\\\\\\"(.*)\\\\\\\": executable file not found`)
+
 	// Docker changes the security option separator from ':' to '=' in the 1.23
 	// API version.
 	optsSeparatorChangeVersion = semver.MustParse(securityOptSeparatorChangeVersion)
@@ -359,6 +363,19 @@ func recoverFromCreationConflictIfNeeded(client libdocker.Interface, createConfi
 	return client.CreateContainer(createConfig)
 }
 
+// transformStartContainerError does regex parsing on returned error
+// for where container runtimes are giving less than ideal error messages.
+func transformStartContainerError(err error) error {
+	if err == nil {
+		return nil
+	}
+	matches := startRE.FindStringSubmatch(err.Error())
+	if len(matches) > 0 {
+		return fmt.Errorf("executable not found in $PATH")
+	}
+	return err
+}
+
 // getSecurityOptSeparator returns the security option separator based on the
 // docker API version.
 // TODO: Remove this function along with the relevant code when we no longer