And yes, I have renamed /root/.digitalocean_password. Also does it from sudo. I set the password and flushed privileges yesterday.

root@web01:~# mv /root/.digitalocean_password /root/.digitalocean_password.good
root@web01:~# mysql -u root wordpress
Reading table information for completion of table and column names
You can turn off this feature to get a quicker startup with -A

Welcome to the MySQL monitor.  Commands end with ; or \g.
Your MySQL connection id is 1207
Server version: 5.7.24-0ubuntu0.18.04.1 (Ubuntu)

Copyright (c) 2000, 2018, Oracle and/or its affiliates. All rights reserved.

Oracle is a registered trademark of Oracle Corporation and/or its
affiliates. Other names may be trademarks of their respective
owners.

Type 'help;' or '\h' for help. Type '\c' to clear the current input statement.

mysql> ^DBye
root@web01:~# logout
cdevidal@web01:~$ sudo mysql -u root wordpress
Reading table information for completion of table and column names
You can turn off this feature to get a quicker startup with -A

Welcome to the MySQL monitor.  Commands end with ; or \g.
Your MySQL connection id is 1208
Server version: 5.7.24-0ubuntu0.18.04.1 (Ubuntu)

Copyright (c) 2000, 2018, Oracle and/or its affiliates. All rights reserved.

Oracle is a registered trademark of Oracle Corporation and/or its
affiliates. Other names may be trademarks of their respective
owners.

Type 'help;' or '\h' for help. Type '\c' to clear the current input statement.

mysql>