Best way to upgrade from debian squeeze to jessie

Question

I have an old dedicated server and want to upgrade it to the latest OS version.

I'm searching for the best way to upgrade from Debian 6 Squeeze => Debian 8.6 Jessie.

Answer 1

First, keep in mind that things can break when upgrading from one Debian version to another. I have performed many upgrades and I have seen it going without a glitch, but also seen it resulting on an unworkable machine. I would advise you to first make an image of your current installation in case things go really wrong (a good tool for that is clonezilla - I use it all the time and it works great).

That being said, I would advise you to update from squeeze to wheezy first (see link) and then from wheezy to jessie (see link).

Again, keep in mind this can go wrong and have an image of the installation made before upgrading.