diff --git a/archive/tar.go b/archive/tar.go
index db27c0e90dc6..eca6316b02d0 100644
--- a/archive/tar.go
+++ b/archive/tar.go
@@ -19,6 +19,7 @@ package archive
 import (
 	"archive/tar"
 	"context"
+	"fmt"
 	"io"
 	"os"
 	"path/filepath"
@@ -29,6 +30,7 @@ import (
 	"time"
 
 	"github.com/containerd/containerd/log"
+	"github.com/containerd/containerd/pkg/userns"
 	"github.com/containerd/continuity/fs"
 	"github.com/pkg/errors"
 )
@@ -376,6 +378,10 @@ func createTarFile(ctx context.Context, path, extractDir string, hdr *tar.Header
 	// Lchown is not supported on Windows.
 	if runtime.GOOS != "windows" {
 		if err := os.Lchown(path, hdr.Uid, hdr.Gid); err != nil {
+			err = fmt.Errorf("failed to Lchown %q for UID %d, GID %d: %w", path, hdr.Uid, hdr.Gid, err)
+			if errors.Is(err, syscall.EINVAL) && userns.RunningInUserNS() {
+				err = fmt.Errorf("%w (Hint: try increasing the number of subordinate IDs in /etc/subuid and /etc/subgid)", err)
+			}
 			return err
 		}
 	}