If you are using SSH by password instead of key, you will see this. What this is, it’s the Linux way of handling a password that has expired. When we set a password for you, we immediately set it to expire so that there exists no plain text record of the password later. Once you enter your password that first time, you see it follow up asking for you to repeat the current password. After you enter it again there, it then prompts you twice for the new password.
Typically when there is a failure at the current password prompt, this is a case of user error. I don’t want to say that it always is, I just want you to be on guard for this as anything else is so uncommon that you should reconsider user error multiple times before going further. It isn’t likely that you’re just doing something obviously wrong, it’s probably subtle and very easy to miss. You may be pasting something that you’re not realizing, like an extra space. Manually typing the password, difficult as it may be, can help to rule this out.
What I do personally, I paste the password into Notepad, tune the font size up, and then add a space between every 4 characters. This way I can focus on reading and typing the password 4 characters at a time without losing my place.
If that still fails, and this is a new droplet, I would recommend creating a new one before troubleshooting further. Something like an immutable shadow file could cause this, and how that occurred at such an early stage would be an interesting topic. If user error is totally ruled out and it continues, there is something wrong with the OS on the droplet and theorizing as to what that might be could prove a difficult task.