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I have a small production server running Debian Squeeze, and in order to stay more current with apt packages, I thought I should upgrade the distro. The last time I attempted a distro upgrade was from Sarge to Etch, and for a first timer it went horribly wrong and I ended up installing Squeeze a few months later when it went stable.

I was planning to back up /home, /etc, MySQL databases, but I was unsure if it's generally safe to use apt to go from Squeeze -> Wheezy -> Jessie, or if it's better to use the Windows method and go for a full reinstall.

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I performed a successful update through apt-get dist upgrade after changing the configuration files, but I can tell you from experience that Debian testing is essentially worthless. Enormous breakage webs, constant breakage, patches for shell shock and heartbleed level bugs take literally two weeks, half-baked configurations, and a thousand other reasons. Honestly, Sid is more usable than testing. Even production.

If you want a more modern distro, abandon Debian entirely and use CentOS, Arch, Fedora, etc. Those distros are built for new packages and handle them much, much, much more gracefully. Testing is an afterthought through and through.

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  • Interesting. When I got my server in 2006 I investigated what distro to run, and ended up with Debian. Red Hat has left a bitter taste in my mouth after the amount of security issues it had back in the late 90s, early 2000s, but I'm sure they've come a long, long way since then. Since I already consider a full reinstall, I might explore alternative distros, too.
    – M. A.
    May 29, 2015 at 0:48
  • If you'd rather stay Debian, I can say that I've found Sid better than Jessie all around.
    – Arthur Kay
    May 29, 2015 at 3:47
  • Please notice that "sid" is not a "stable" release, so IMNSHO it's very unfortunate that it has a release-sounding name. @ArthurKay I just read on debians web that "sid" is not getting security updates "in a timely manner" like real releases do. (Currently Mar 2016: wheezy 7.0 and jessie 8.0, but Debian 6.0 squeeze no longer).
    – Simon B.
    Mar 9, 2016 at 10:08

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