Odd behaviors like that tend to mean issues with the device or filesystem IMO. Also check the state of the CAPSLOCK key. As that can make your password NOT be what you think it is. If you're running from flash based media, those tend to fail to read-only mode. Or maybe / was mounted read-only so your "changes" never actually wrote to disk. Booting another live distro is one option. So you can fsck that partition, and maybe chroot to it to do whatever admin steps are needed. You'll be root when you're in the chroot initially, even if the chroot is to ubuntu, so be careful.
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