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Re: Lenny (Debian 5.0) approaching end of life

On Fri, 6 Jan 2012 19:45:25 -0500
Tony Baldwin <tonybaldwin@gmx.com> wrote:

> On Fri, Jan 06, 2012 at 01:46:38PM -0800, Steven Rosenberg wrote:
> > 
> > The official upgrade process for Lenny to Squeeze was not as easy
> > as a simple dist-upgrade, and I wonder if Lenny-to-Wheezy would be
> > too
> It really amazes me to see anybody say(write) this.
> Having used several distributions (as mentioned), 
> I found the Lenny->Squeeze (my first Debian upgrade) to be amazingly
> easy. Like falling off a log.

Come back and tell us when you've done a dozen servers. Everything in
life is easy and works first time..... except when it doesn't.

Take a brand new clean and basic Debian installation, do an upgrade and
it really should Just Work every time. Take a server which was
originally, say, sarge, and upgrade it, and you roll the dice. It has
had so many configuration changes made, so many extra scripts added, a
few outright bodges, and you really can't be confident that everything
will come through OK. A server upgrade is traumatic, and to be avoided
where possible. The only thing worse is a clean installation, which you
then have to spend a few days fiddling with to get everything working
the way you want.

I'm down to looking after my own server and one for a client, and my
own lenny-to-squeeze upgrade went easily. But I had spent some time
studying the upgrade notes, and I could see significant work there if I
was doing certain things differently. As it was, I was worried about the
FreeRADIUS server, which I had compiled myself, an experience I had no
wish to repeat. The squeeze FreeRADIUS now had SSL support built-in, so
would my hand-compiled version upgrade smoothly? It did, but there was
no way to predict that, and there were still minor quibbles about
switching to a dpkg-registered package from an independent one.

Generally an upgrade *will* break a few things, usually when software
is withdrawn from Debian, though sometimes when there is a major
software version change. My previous upgrade from etch to lenny broke my
mail server, and it took me a few hours and some determined use of dpkg
to get it running again. The problem wasn't the software itself, but
the heavily-modified configuration file, which left aptitude stuck
with a partly-installed package which could neither go further nor be

I have no argument about Debian having a relatively smooth and
well-researched upgrade path. The upgrade can also normally be done with
only one reboot (possibly more after certain preparations, if they were
necessary) with minimal disturbance to users. That's why so many
Internet servers use it. Most recent Windows versions cannot be
upgraded at all, Microsoft being reduced to producing scripts to ease
the migration of users and data to a completely different machine.
While I have dabbled with other Linux distributions in the past, it has
always been easier to clean install a newer version and just copy data.
It's only when a few years' worth of customisation is added that an easy
upgrade becomes really important.


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