diff --git a/internal/registry/auth.go b/internal/registry/auth.go
index e15a139cb471..4844710e6646 100644
--- a/internal/registry/auth.go
+++ b/internal/registry/auth.go
@@ -8,6 +8,7 @@ import (
 	"strings"
 	"time"
 
+	"github.com/containerd/errdefs/pkg/errhttp"
 	"github.com/containerd/log"
 	"github.com/docker/distribution/registry/client/auth"
 	"github.com/docker/distribution/registry/client/auth/challenge"
@@ -67,7 +68,7 @@ func loginV2(ctx context.Context, authConfig *registry.AuthConfig, endpoint APIE
 
 	if resp.StatusCode != http.StatusOK {
 		// TODO(dmcgowan): Attempt to further interpret result, status code and error code string
-		return "", fmt.Errorf("login attempt to %s failed with status: %d %s", endpointStr, resp.StatusCode, http.StatusText(resp.StatusCode))
+		return "", fmt.Errorf("login attempt to %s failed with status: %d %s: %w", endpointStr, resp.StatusCode, http.StatusText(resp.StatusCode), errhttp.ToNative(resp.StatusCode))
 	}
 
 	return credentialAuthConfig.IdentityToken, nil
diff --git a/internal/registry/auth_test.go b/internal/registry/auth_test.go
new file mode 100644
index 000000000000..44632df42e39
--- /dev/null
+++ b/internal/registry/auth_test.go
@@ -0,0 +1,41 @@
+package registry
+
+import (
+	"context"
+	"net/http"
+	"net/http/httptest"
+	"net/url"
+	"testing"
+
+	"github.com/containerd/errdefs"
+	"github.com/moby/moby/api/types/registry"
+	"gotest.tools/v3/assert"
+	is "gotest.tools/v3/assert/cmp"
+)
+
+func TestLoginV2BasicAuthUnauthorized(t *testing.T) {
+	srv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		user, pass, ok := r.BasicAuth()
+		if !ok || user != "alice" || pass != "secret" {
+			w.Header().Set("WWW-Authenticate", `Basic realm="test"`)
+			http.Error(w, "401 Unauthorized", http.StatusUnauthorized)
+			return
+		}
+		w.WriteHeader(http.StatusOK)
+	}))
+	t.Cleanup(srv.Close)
+
+	u, err := url.Parse(srv.URL)
+	assert.NilError(t, err)
+	endpoint := APIEndpoint{URL: u}
+	ctx := context.Background()
+
+	_, err = loginV2(ctx, &registry.AuthConfig{Username: "alice", Password: "wrong"}, endpoint, "docker-test")
+	assert.ErrorContains(t, err, "401")
+	assert.Check(t, errdefs.IsUnauthorized(err))
+	assert.Check(t, is.ErrorType(err, errdefs.IsUnauthorized))
+
+	token, err := loginV2(ctx, &registry.AuthConfig{Username: "alice", Password: "secret"}, endpoint, "docker-test")
+	assert.NilError(t, err)
+	assert.Check(t, is.Equal("", token))
+}