Matters are slightly more complicated because the existing squid
packages (both the original squid(v2) and squid3) do not track
squid.conf as a conffile, probably because the example configuration is
generated at build time.

After discussing the matter with several Ubuntu devs, it appears there
are two possible solutions:

1.  On upgrade, if the user had modified the original squid(2)
configuration, raise a debconf dialog box that very loudly warns that
the config may not be compatable after upgrade.

2.  On upgrade, if the user has modified the original squid(2)
configuration, transfer it to the new squid3 location and attempt to
start squid3.  If the config is compatable (that is, does not contain
unsupported config options), squid3 should start successfully.   If the
user was using squid(2) features that are unsupported in squid3, the
proxy will fail to start and cause upgrade errors.

3. Regardless of whether or not previous squid configuration has been
modified, use the default squid3 configuration in all cases and start a
unconfigured proxy.  Perhaps backup the original squid for reference.

In either case, matters are complicated by the fact that the example
squid.conf shipped with either package is not tracked as a conffile by
dpkg (it is generated at build time)  To do any conffile handling
mentioned above, we'll need to hard-code a list of hash sums in
maintainer scripts that cover all previous releases of the squid
package, and perhaps maintain this list over time if updates are SRU'd.

The real question (as slangasek pointed out) is whether its better to
have a broken proxy after dist-upgrade or an uncofigured proxy.

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https://bugs.launchpad.net/bugs/924739

Title:
  after upgrade from oneiric to precise, previous squid config unused,
  cannot be used when relocated

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