I don't believe this. I've configured or customised dozens of packages
on my system - in the sense that I've changed options in the GUI, or
told them what my name was, or given them login details. None of them
had upgrade problems. Examples: ekiga, banshee, grip, iPodder, listen,
scite, gnucash, openoffice.org, gftp, gimp...

This sort of question during the upgrade process is entirely
unacceptable for a normal user. Aunt Tillie/my grandma/Joe Public
wouldn't have a clue what to do. They aren't going to be merging
configuration files by hand.

And, in fact, in the "what do I do?" dialog, neither answer is the
"safe" answer - you risk either losing all your settings, or the
application breaking because some new compulsory configuration option
does not have a value.

-- 
Dapper -> Edgy failure: sbackup configuration file has conflicts
https://launchpad.net/bugs/63354

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