[fChk]

I'm not much of a Debian user, but I do use it when I have to. For example, when setting up a Docker image and the idiosyncrasies of a software are too Debian-centric.

Anyway, for what it's worth, I can confirm that using the method outlined in the OP, it is possible to upgrade from Debain 8 (Jessie) to Debain 9 (Stretch) and from Debain 9 (Stretch) to Debian 10 (Buster) in two consecutive steps.

The only difference between my process and the OP is when it comes to editing the sources.list file:
> For Jessie to Stretch Upgrade:

Code: (Select All)

root@kvm-Post2Host-Phoenix:~# sed -i 's/jessie/stretch/g' /etc/apt/sources.list

> For Stretch to Buster Upgrade:

Code: (Select All)

root@kvm-Post2Host-Phoenix:~# sed -i 's/stretch/buster/g' /etc/apt/sources.list

I achieved this on Phoenix-based VPS-9 which came with Debian Jessie.

Never saw an OS that easy to upgrade!!.. but it felt weird for me to have to manage a non-RedHat-based Linux system.. The naming changes, the assumptions and on and on..

I did ask for an OS change though; the above was just for testing.