Hello Madison,
It’s not a glitch in our system. It’s a glitch in your memory ;-)
You are not entering the right password for the file in question, so it asks you for it. You then re-enter the same password you used to sign in with – but that has already been tried, so we inform you that it’s no use re-entering a password you’re already signed in with and that we’ve already tried, and failed, to open the file with.
You need to remember the password originally used to encrypt the file. Remember that a password reset does NOT give you access to previously encrypted files. It only allows you to sign in to the system, and the new password is used to encrypt new files.