diff --git a/internal/app/osd/internal/reg/reg.go b/internal/app/osd/internal/reg/reg.go
index 4e96b3e9f..756d23d76 100644
--- a/internal/app/osd/internal/reg/reg.go
+++ b/internal/app/osd/internal/reg/reg.go
@@ -15,6 +15,7 @@ import (
 	"path/filepath"
 	"strings"
 	"syscall"
+	"time"
 
 	criconstants "github.com/containerd/cri/pkg/constants"
 	"github.com/golang/protobuf/ptypes/empty"
@@ -29,6 +30,7 @@ import (
 	"github.com/talos-systems/talos/pkg/chunker"
 	filechunker "github.com/talos-systems/talos/pkg/chunker/file"
 	"github.com/talos-systems/talos/pkg/constants"
+	"github.com/talos-systems/talos/pkg/retry"
 )
 
 // Registrator is the concrete type that implements the factory.Registrator and
@@ -42,7 +44,21 @@ func (r *Registrator) Register(s *grpc.Server) {
 
 // Kubeconfig implements the osapi.OSDServer interface.
 func (r *Registrator) Kubeconfig(ctx context.Context, in *empty.Empty) (data *osapi.DataReply, err error) {
-	fileBytes, err := ioutil.ReadFile(constants.AdminKubeconfig)
+	var fileBytes []byte
+
+	err = retry.Constant(5*time.Minute, retry.WithUnits(5*time.Second)).Retry(func() error {
+		fileBytes, err = ioutil.ReadFile(constants.AdminKubeconfig)
+		if err != nil {
+			if os.IsNotExist(err) {
+				return retry.ExpectedError(err)
+			}
+
+			return retry.UnexpectedError(err)
+		}
+
+		return nil
+	})
+
 	if err != nil {
 		return
 	}