diff --git a/pkg/cri/sbserver/podsandbox/sandbox_run.go b/pkg/cri/sbserver/podsandbox/sandbox_run.go
index 7d4228d67..ed8f1aef7 100644
--- a/pkg/cri/sbserver/podsandbox/sandbox_run.go
+++ b/pkg/cri/sbserver/podsandbox/sandbox_run.go
@@ -25,6 +25,7 @@ import (
 	v1 "github.com/containerd/nri/types/v1"
 	"github.com/containerd/typeurl"
 	"github.com/davecgh/go-spew/spew"
+	"github.com/hashicorp/go-multierror"
 	"github.com/opencontainers/selinux/go-selinux"
 	runtime "k8s.io/cri-api/pkg/apis/runtime/v1"
 
@@ -46,6 +47,10 @@ func init() {
 		"github.com/containerd/cri/pkg/store/sandbox", "Metadata")
 }
 
+type CleanupErr struct {
+	error
+}
+
 // Start creates resources required for the sandbox and starts the sandbox.  If an error occurs, Start attempts to tear
 // down the created resources.  If an error occurs while tearing down resources, a zero-valued response is returned
 // alongside the error.  If the teardown was successful, a nil response is returned with the error.
@@ -55,6 +60,7 @@ func (c *Controller) Start(ctx context.Context, id string) (cin sandbox.Controll
 	defer func() {
 		if retErr != nil && cleanupErr != nil {
 			log.G(ctx).WithField("id", id).WithError(cleanupErr).Errorf("failed to fully teardown sandbox resources after earlier error: %s", retErr)
+			retErr = multierror.Append(retErr, CleanupErr{cleanupErr})
 		}
 	}()
 
diff --git a/pkg/cri/sbserver/sandbox_run.go b/pkg/cri/sbserver/sandbox_run.go
index 76a28ac9f..58701b8f7 100644
--- a/pkg/cri/sbserver/sandbox_run.go
+++ b/pkg/cri/sbserver/sandbox_run.go
@@ -28,6 +28,7 @@ import (
 
 	"github.com/containerd/go-cni"
 	"github.com/containerd/typeurl"
+	"github.com/hashicorp/go-multierror"
 	"github.com/sirupsen/logrus"
 	runtime "k8s.io/cri-api/pkg/apis/runtime/v1"
 
@@ -232,9 +233,16 @@ func (c *criService) RunPodSandbox(ctx context.Context, r *runtime.RunPodSandbox
 	ctrl, err := controller.Start(ctx, id)
 	if err != nil {
 		sandbox.Container, _ = c.client.LoadContainer(ctx, id)
-		if ctrl.SandboxID == "" && ctrl.Pid == 0 && ctrl.CreatedAt.IsZero() && len(ctrl.Labels) == 0 {
-			// if resp is a non-nil zero-value, an error occurred during cleanup
-			cleanupErr = fmt.Errorf("failed to cleanup sandbox")
+		var cerr podsandbox.CleanupErr
+		if errors.As(err, &cerr) {
+			cleanupErr = fmt.Errorf("failed to cleanup sandbox: %w", cerr)
+
+			// Strip last error as cleanup error to handle separately
+			if merr, ok := err.(*multierror.Error); ok {
+				if errs := merr.WrappedErrors(); len(errs) > 0 {
+					err = errs[0]
+				}
+			}
 		}
 		return nil, fmt.Errorf("failed to start sandbox %q: %w", id, err)
 	}