On Tue, Aug 20, 2013 at 03:33:26PM +0100, Ian Jackson wrote:
> Charles Plessy writes ("Re: Dreamhost dumps Debian"):
> > However, one difficulty that was not mentionned in this thread is that if we
> > aim at both long term support and frequent releases, then we need to support
> > users skipping releases or upgrading multiple releases in a row.
> 
> I have done skip upgrades on multiple occasions.  The fallout was
> always manageable.  (The most recent one was etch->squeeze IIRC.)

Why wouldn't you instead:
sed -i s/etch/lenny/ /etc/apt/sources.list
apt-get dist-upgrade
sed -i s/lenny/squeeze/ /etc/apt/sources.list
apt-get dist-upgrade

This costs some machine time, yeah, but to solve that "fallout" costs human
time which is in most cases far more expensive.

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