I think what is happening is that the first password screen is from the preboot environment (before the encryption of the HDD is released), then the main OS boots (you see the progress bar) and finally you log in to the main OS.
Somehow your password as known to the preboot environment did not get changed when you updated your password in the main OS. As such the preboot OS is not able to log you into the main OS once it is booted as it does not know the new password.
I'm not certain of the solution, but I'd start troubleshooting by resetting my OS 'new' password to the old one.
Check that you can log in with just one password
Then change your password back to the new password (or another one). Hopefully that will write both 'preboot' and 'main os' copies of the password.