diff --git a/mysql-test/r/acl_roles_admin.result b/mysql-test/r/acl_roles_admin.result
index 591d155003e..ad3d4125252 100644
--- a/mysql-test/r/acl_roles_admin.result
+++ b/mysql-test/r/acl_roles_admin.result
@@ -19,7 +19,7 @@ ERROR 42000: You have an error in your SQL syntax; check the manual that corresp
 grant role1 to foo@localhost with admin option;
 grant role2 to foo@localhost;
 grant role2 to role1;
-grant role3 to role4 with admin option;
+grant role4 to role3 with admin option;
 grant select on *.* to foo@localhost with admin option;
 ERROR 42000: You have an error in your SQL syntax; check the manual that corresponds to your MariaDB server version for the right syntax to use near 'admin option' at line 1
 show grants for foo@localhost;
@@ -33,18 +33,18 @@ Grants for role1
 GRANT USAGE ON *.* TO 'role1'
 GRANT USAGE ON *.* TO 'role2'
 GRANT USAGE ON *.* TO 'role3'
+GRANT USAGE ON *.* TO 'role4'
 GRANT role2 TO 'role1'
 GRANT role3 TO 'role1' WITH ADMIN OPTION
+GRANT role4 TO 'role3' WITH ADMIN OPTION
 show grants for role4;
 Grants for role4
-GRANT USAGE ON *.* TO 'role3'
 GRANT USAGE ON *.* TO 'role4'
-GRANT role3 TO 'role4' WITH ADMIN OPTION
 select * from mysql.roles_mapping;
 Host	User	Role	Admin_option
 	role1	role2	N
 	role1	role3	Y
-	role4	role3	Y
+	role3	role4	Y
 bar	foo	role6	Y
 localhost	foo	role1	Y
 localhost	foo	role2	N
@@ -64,25 +64,26 @@ Grants for role1
 GRANT USAGE ON *.* TO 'role1'
 GRANT USAGE ON *.* TO 'role2'
 GRANT USAGE ON *.* TO 'role3'
+GRANT USAGE ON *.* TO 'role4'
 GRANT role2 TO 'role1'
 GRANT role3 TO 'role1' WITH ADMIN OPTION
+GRANT role4 TO 'role3' WITH ADMIN OPTION
 show grants for role4;
 Grants for role4
-GRANT USAGE ON *.* TO 'role3'
 GRANT USAGE ON *.* TO 'role4'
-GRANT role3 TO 'role4' WITH ADMIN OPTION
 select * from information_schema.applicable_roles;
 GRANTEE	ROLE_NAME	IS_GRANTABLE
 role1	role2	NO
 role1	role3	YES
-role4	role3	YES
+role3	role4	YES
 root@localhost	role1	YES
 root@localhost	role2	YES
 root@localhost	role4	YES
 grant role2 to role1 with admin option;
 revoke role1 from foo@localhost;
-revoke admin option for role3 from role4;
+revoke admin option for role4 from role3;
 revoke admin option for role2 from foo@localhost;
+revoke admin option for role1 from root@localhost;
 show grants for foo@localhost;
 Grants for foo@localhost
 GRANT CREATE USER ON *.* TO 'foo'@'localhost'
@@ -93,22 +94,22 @@ Grants for role1
 GRANT USAGE ON *.* TO 'role1'
 GRANT USAGE ON *.* TO 'role2'
 GRANT USAGE ON *.* TO 'role3'
+GRANT USAGE ON *.* TO 'role4'
 GRANT role2 TO 'role1' WITH ADMIN OPTION
 GRANT role3 TO 'role1' WITH ADMIN OPTION
+GRANT role4 TO 'role3'
 show grants for role4;
 Grants for role4
-GRANT USAGE ON *.* TO 'role3'
 GRANT USAGE ON *.* TO 'role4'
-GRANT role3 TO 'role4'
 select * from mysql.roles_mapping;
 Host	User	Role	Admin_option
 	role1	role2	Y
 	role1	role3	Y
-	role4	role3	N
+	role3	role4	N
 bar	foo	role6	Y
 localhost	foo	role2	N
 localhost	foo	role5	Y
-localhost	root	role1	Y
+localhost	root	role1	N
 localhost	root	role2	Y
 localhost	root	role4	Y
 flush privileges;
@@ -122,20 +123,30 @@ Grants for role1
 GRANT USAGE ON *.* TO 'role1'
 GRANT USAGE ON *.* TO 'role2'
 GRANT USAGE ON *.* TO 'role3'
+GRANT USAGE ON *.* TO 'role4'
 GRANT role2 TO 'role1' WITH ADMIN OPTION
 GRANT role3 TO 'role1' WITH ADMIN OPTION
+GRANT role4 TO 'role3'
 show grants for role4;
 Grants for role4
-GRANT USAGE ON *.* TO 'role3'
 GRANT USAGE ON *.* TO 'role4'
-GRANT role3 TO 'role4'
 select * from information_schema.applicable_roles;
 GRANTEE	ROLE_NAME	IS_GRANTABLE
 role1	role2	YES
 role1	role3	YES
-role4	role3	NO
-root@localhost	role1	YES
+role3	role4	NO
+root@localhost	role1	NO
 root@localhost	role2	YES
 root@localhost	role4	YES
+grant role1 to role4;
+ERROR 28000: Access denied for user 'root'@'localhost'
+grant role1 to role4 with admin option;
+ERROR 28000: Access denied for user 'root'@'localhost'
+grant role3 to role2;
+revoke role3 from role2;
+grant role4 to role2 with admin option;
+revoke role2 from current_user;
+revoke role4 from current_user;
+grant role4 to current_user;
 drop role role1, role2, role3, role4, role5, role6;
 drop user foo@localhost;
diff --git a/mysql-test/t/acl_roles_admin.test b/mysql-test/t/acl_roles_admin.test
index 9568547eaeb..14f63c5ced8 100644
--- a/mysql-test/t/acl_roles_admin.test
+++ b/mysql-test/t/acl_roles_admin.test
@@ -30,7 +30,7 @@ create user bar with admin current_user;
 grant role1 to foo@localhost with admin option;
 grant role2 to foo@localhost;
 grant role2 to role1;
-grant role3 to role4 with admin option;
+grant role4 to role3 with admin option;
 --error ER_PARSE_ERROR
 grant select on *.* to foo@localhost with admin option;
 
@@ -54,8 +54,9 @@ select * from information_schema.applicable_roles;
 
 grant role2 to role1 with admin option;
 revoke role1 from foo@localhost;
-revoke admin option for role3 from role4;
+revoke admin option for role4 from role3;
 revoke admin option for role2 from foo@localhost;
+revoke admin option for role1 from root@localhost;
 
 --sorted_result
 show grants for foo@localhost;
@@ -75,6 +76,22 @@ show grants for role4;
 --sorted_result
 select * from information_schema.applicable_roles;
 
+# Now, root@localhost don't have admin option for role1:
+--error ER_ACCESS_DENIED_NO_PASSWORD_ERROR
+grant role1 to role4;
+--error ER_ACCESS_DENIED_NO_PASSWORD_ERROR
+grant role1 to role4 with admin option;
+# but role3 is grantable
+grant role3 to role2;
+revoke role3 from role2;
+
+# now, a diamond
+grant role4 to role2 with admin option;
+revoke role2 from current_user;
+revoke role4 from current_user;
+grant role4 to current_user;
+
+
 ########################################
 # cleanup
 ########################################
diff --git a/sql/sql_acl.cc b/sql/sql_acl.cc
index 842d3cf8275..19863d009c1 100644
--- a/sql/sql_acl.cc
+++ b/sql/sql_acl.cc
@@ -5322,6 +5322,67 @@ static void append_user(String *str, const char *u, const char *h)
   str->append('\'');
 }
 
+struct IS_GRANTABLE_DATA
+{
+  ACL_ROLE *role;
+  bool grantable;
+};
+
+static void can_grant_role_callback(ACL_ROLE *unuser __attribute__((unused)),
+                                    ACL_ROLE *grantee, void *context_data)
+{
+  IS_GRANTABLE_DATA *data= (IS_GRANTABLE_DATA*)context_data;
+  for (uint i= 0; i < grantee->role_grants.elements; i++)
+  {
+    ACL_ROLE *r= *(dynamic_element(&grantee->role_grants, i, ACL_ROLE**));
+
+    if (r == data->role)
+    {
+      ROLE_GRANT_PAIR *pair=
+        find_role_grant_pair(&grantee->user, &empty_lex_str, &r->user);
+      if (pair->with_admin)
+        data->grantable= true;
+    }
+  }
+}
+
+
+/*
+  One can only grant a role if SELECT * FROM I_S.APPLICABLE_ROLES shows this
+  role as grantable.
+  
+  What this really means - we need to traverse role graph for the current user
+  looking for our role being granted with the admin option.
+*/
+static bool can_grant_role(THD *thd, ACL_ROLE *role)
+{
+  Security_context *sctx= thd->security_ctx;
+  ACL_USER *grantee= find_user_no_anon(sctx->priv_host, sctx->priv_user, true);
+  if (!grantee)
+    return false;
+
+  LEX_STRING host= { grantee->host.hostname, grantee->hostname_length };
+  IS_GRANTABLE_DATA data= { role, false };
+
+  for (uint i= 0; i < grantee->role_grants.elements; i++)
+  {
+    ACL_ROLE *r= *(dynamic_element(&grantee->role_grants, i, ACL_ROLE**));
+
+    if (r == role)
+    {
+      ROLE_GRANT_PAIR *pair=
+        find_role_grant_pair(&grantee->user, &host, &r->user);
+      if (pair->with_admin)
+        return true;
+    }
+
+    traverse_role_graph(r, &data, NULL, NULL, NULL, can_grant_role_callback);
+    if (data.grantable)
+      return true;
+  }
+  return false;
+}
+
 
 bool mysql_grant_role(THD *thd, List <LEX_USER> &list, bool revoke)
 {
@@ -5371,6 +5432,15 @@ bool mysql_grant_role(THD *thd, List <LEX_USER> &list, bool revoke)
     DBUG_RETURN(TRUE);
   }
 
+  if (!can_grant_role(thd, role))
+  {
+    mysql_mutex_unlock(&acl_cache->lock);
+    mysql_rwlock_unlock(&LOCK_grant);
+    my_error(ER_ACCESS_DENIED_NO_PASSWORD_ERROR, MYF(0),
+             thd->security_ctx->priv_user, thd->security_ctx->priv_host);
+    DBUG_RETURN(TRUE);
+  }
+
   if (open_and_lock_tables(thd, &tables, FALSE, MYSQL_LOCK_IGNORE_TIMEOUT))
   {                                             // Should never happen
     mysql_mutex_unlock(&acl_cache->lock);