Thanks. The problem is that the updating process won't go further than that screenshot that I attached. From reading the manual I would expect it to lead to a "install now yes/no button" pop up after that. But it is just stuck there... far longer than 3 minutes.
Sounds like the simplest option is to remove the microSD card and flash it with the latest firmware.
Otherwise, if you're feeling brave, you could SSH into your Chronos and update your package sources. Once your sources are updated to reflect the archived Jessie packages, the Chronos firmware updater should start working for you again.
sudo nano /etc/apt/sources.list.d/backports-debian.list
deb [arch=armel] http://archive.debian.org/debian jessie-backports main contrib non-free
deb [arch=armel] http://archive.debian.org/debian stretch-backports main contrib non-free
sudo nano /etc/apt/sources.list.d/multistrap-debian.list
deb [arch=armel] http://archive.debian.org/debian jessie main contrib non-free
deb-src http://archive.debian.org/debian jessie main contrib non-free
Make sure to run `apt update` after modifying the above two files to reflect those archive.debian.org urls