diff --git a/api/v1beta1/owner_role.go b/api/v1beta1/owner_role.go
index 25ff22d2..dc73309d 100644
--- a/api/v1beta1/owner_role.go
+++ b/api/v1beta1/owner_role.go
@@ -12,12 +12,37 @@ const (
 	ClusterRoleNamesAnnotation = "clusterrolenames.capsule.clastix.io"
 )
 
-func (in OwnerSpec) GetRoles(tenant Tenant) []string {
+// GetRoles read the annotation available in the Tenant specification and if it matches the pattern
+// clusterrolenames.capsule.clastix.io/${KIND}.${NAME} returns the associated roles.
+// Kubernetes annotations and labels must respect RFC 1123 about DNS names and this could be cumbersome in two cases:
+// 1. identifying users based on their email address
+// 2. the overall length of the annotation key that is exceeding 63 characters
+// For emails, the symbol @ can be replaced with the placeholder __AT__.
+// For the latter one, the index of the owner can be used to force the retrieval.
+func (in OwnerSpec) GetRoles(tenant Tenant, index int) []string {
 	for key, value := range tenant.GetAnnotations() {
-		if key == fmt.Sprintf("%s/%s.%s", ClusterRoleNamesAnnotation, strings.ToLower(in.Kind.String()), strings.ToLower(in.Name)) {
+		if !strings.HasPrefix(key, fmt.Sprintf("%s/", ClusterRoleNamesAnnotation)) {
+			continue
+		}
+
+		for symbol, replace := range in.convertMap() {
+			key = strings.ReplaceAll(key, symbol, replace)
+		}
+
+		nameBased := key == fmt.Sprintf("%s/%s.%s", ClusterRoleNamesAnnotation, strings.ToLower(in.Kind.String()), strings.ToLower(in.Name))
+
+		indexBased := key == fmt.Sprintf("%s/%d", ClusterRoleNamesAnnotation, index)
+
+		if nameBased || indexBased {
 			return strings.Split(value, ",")
 		}
 	}
 
 	return []string{"admin", "capsule-namespace-deleter"}
 }
+
+func (in OwnerSpec) convertMap() map[string]string {
+	return map[string]string{
+		"__AT__": "@",
+	}
+}
diff --git a/controllers/tenant/rolebindings.go b/controllers/tenant/rolebindings.go
index 9b65ba87..96682047 100644
--- a/controllers/tenant/rolebindings.go
+++ b/controllers/tenant/rolebindings.go
@@ -61,8 +61,8 @@ func (r *Manager) syncRoleBindings(ctx context.Context, tenant *capsulev1beta1.T
 	// getting requested Role Binding keys
 	keys := make([]string, 0, len(tenant.Spec.Owners))
 	// Generating for dynamic tenant owners cluster roles
-	for _, owner := range tenant.Spec.Owners {
-		for _, clusterRoleName := range owner.GetRoles(*tenant) {
+	for index, owner := range tenant.Spec.Owners {
+		for _, clusterRoleName := range owner.GetRoles(*tenant, index) {
 			cr := r.ownerClusterRoleBindings(owner, clusterRoleName)
 
 			keys = append(keys, hashFn(cr))
@@ -103,8 +103,8 @@ func (r *Manager) syncAdditionalRoleBinding(ctx context.Context, tenant *capsule
 
 	var roleBindings []capsulev1beta1.AdditionalRoleBindingsSpec
 
-	for _, owner := range tenant.Spec.Owners {
-		for _, clusterRoleName := range owner.GetRoles(*tenant) {
+	for index, owner := range tenant.Spec.Owners {
+		for _, clusterRoleName := range owner.GetRoles(*tenant, index) {
 			roleBindings = append(roleBindings, r.ownerClusterRoleBindings(owner, clusterRoleName))
 		}
 	}