Thanks, I think I should have enough to reproduce the issue here now (finishing to upgrade my test VM).
If you have a minute, can you try booting your system without your announce-ip script?
Having it "exit 1" seems to disturb ifupdown trying to bring up your loopback device, I'm not sure if something changed in ifupdown's handling of a script failure, but it's probably worth trying without the script and see if that solves it.
Thanks, I think I should have enough to reproduce the issue here now (finishing to upgrade my test VM).
If you have a minute, can you try booting your system without your announce-ip script?
Having it "exit 1" seems to disturb ifupdown trying to bring up your loopback device, I'm not sure if something changed in ifupdown's handling of a script failure, but it's probably worth trying without the script and see if that solves it.