I do enter the current password. When it asks for a new password I enter one. When I press enter, it goes right back to asking for the username/password. The new password doesn’t work at this point.

I have the same problem. I log in successfully, it asks to enter a new password. After I enter a new one it goes back to the start asking me to log in

You can try removing the encrypted password in the /etc/shadow file which will result in no password for the root account.

Now try to set a new password. I think that should work.

Let me know if it helps.

Woet was right however it never clicked what I was doing wrong. Thanks again.

I have the same problem, somebody know how to fix it please?

Solution!!!

https://www.digitalocean.com/community/tutorials/how-to-use-the-digitalocean-console-to-access-your-droplet

Here password generator https://www.plerdy.com/password-generator/