I have quite a lot of Raspberry Pis out there in the wild and quite some of them are still running on a Raspbian that is based on Debian 8 ‘Jessie’. I have no incentive, from an application point of view, to upgrade them to a new Debian version because you are never save from side effects. I speak from experience. Last time it broke my channel bonding redundancy setup. Another option is to re-install and configure the applications I use on a fresh install. But that’s not a trivial 5 minute task either.
This has become a bit of a concern to me because the current Raspberry Pi images are based on Debian 9 ‘Stretch’ and there isn’t a firm commitment on any official Raspberry Pi web page that I could find out how long security fixes will be provided for Debian 8 based Raspbian.


