Hi,

>    * ruby: remove Breaks/Conflicts/Replaces against old interpreter packages
>      as this will force the removal of old interpreters from users' systems
>      (Closes: #740733)
>      .
>      The following upgrade scenarios from wheezy were tested, still work fine,
>      and leave the old interpreters alone:
>      - ruby
>      - ruby + ruby1.8
>      - ruby + apt-listbugs
>      - ruby + ruby1.8 + apt-listbugs
>      - ruby1.8 + apt-listbugs

I've just run into a scenario not listed above in which left me
without /usr/bin/ruby afterwards. This scenario is likely not
happening during an dist-upgrade from Wheezy to Jessie as it's planned
now, but may still hit other people who are running unstable.

After I've read this changelog entry, I installed glark (which is
currently ruby1.8 only) again to notice when there's an updated
version working with a newer release of Ruby.

Afterwards, how-can-i-help threw strange errors:

/usr/lib/ruby/vendor_ruby/debian.rb:24:in `require': no such file to load -- 
debian_version (LoadError)
        from /usr/lib/ruby/vendor_ruby/debian.rb:24
        from /usr/bin/how-can-i-help:20:in `require'
        from /usr/bin/how-can-i-help:20
E: Problem executing scripts DPkg::Post-Invoke '[ ! -e /usr/bin/how-can-i-help 
] || /usr/bin/how-can-i-help'

I noticed that /usr/bin/ruby points back to ruby1.8:

update-alternatives: using /usr/bin/ruby1.8 to provide /usr/bin/ruby (ruby) in 
auto mode

I'm not sure if this is a bug in update-alternatives as it seems to
happily overwrite a file which was installed by a package -- I would
expect that it should prevent that.

At least I think, it's worthwile to consider Marga's idea of uploading
ruby1.8 once more to remove that call to update-alternatives to
prevent this kind of issue.

Another option I can imagine is to keep the update-alternatives
mechanism for one more release but with just one alternative.

... or make update-alternatives not to overwrite package-installed
files. That's dpkg-divert's job.

I'm neither sure where to actually file a bug report for that issue
nor which severity it should have (I can imagine everything, from
minor to grave -- as it deletes a file installed by another package).
Any advice or comment is appreciated.

                Regards, Axel
-- 
 ,''`.  |  Axel Beckert <a...@debian.org>, http://people.debian.org/~abe/
: :' :  |  Debian Developer, ftp.ch.debian.org Admin
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