Hello Michael


>I am not aware of anyone other than us having implemented this yet.  I
>seem to recall that we discussed this on IRC and came to the conclusion
>that you could simply refuse to install if that file was found.  I


Yep I remember that quick discussion :)
Refusing to install is possible, even if in upgrades sounds like a bad user 
experience
(e.g. think about a do-release-upgrade to a new debian/ubuntu release that 
blocks, and require
a manual user action)


>wonder whether dpkg will even allow you to install a package which>overwrites 
>a file already on the system, assuming you create it too?


I guess not. unless I hack a preinst where I check the file content and I 
delete/overwrite it
manually


>The last would be very welcome of course.  Does that sound reasonable?

I don't think we can handle it that way without many and many hacks :(
refusing to install might be the best thing to do, on both sides
(for you it should be simple as
"dpkg -l |grep virtualbox-guest")

G.
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