1. You should install the meta package for your kernel flavor, e.g. 
virtualbox-ose-modules-generic, which will always depend on the latest 
available version, e.g. currently virtualbox-ose-modules-2.6.24-18-generic (or 
-19-generic in hardy-proposed)
2. Yes, the package wasn't following the kernel, due to missing time on my side 
or "un-announced" security updates (which weren't in hardy-proposed before). 
virtualbox-ose-modules will likely switch to using DKMS, which would make those 
manual uploads unnecessary (AFAIK). Jeff Schroeder is currently looking into 
this.
3. Having to manually run "sudo depmod" after booting the "target kernel", if 
you've installed the modules on a different before, has been reported in bug 
239062. A proposed fix is available, and waiting for an ACK to get it into 
Hardy.
4. virtualbox-ose cannot depend on virtualbox-ose-modules, because this causes 
apt to always install the first possible variant currently (see bug 152405 for 
the depend-wish and bug 188579 for the consequence of it).
5. Make sure to install the correct flavor, e.g. installing v-o-m-386 on a 
generic system is likely to break your system, because of missing kernel 
modules (bug 226960).

Currently, the v-o-m package in hardy-proposed matches the kernel
package therein, so it's likely that the next kernel update will go
smoother (except if 3. gets not approved for fixing).

I'm assigning the bug to virtualbox-ose-modules and mark it as Invalid.
Please refer to the above mentioned bugs for the particular issues.

** Changed in: virtualbox-ose-modules (Ubuntu)
Sourcepackagename: None => virtualbox-ose-modules
     Assignee: (unassigned) => Daniel Hahler (blueyed)
       Status: Confirmed => Invalid

-- 
Kernel updates break VirtualBox support
https://bugs.launchpad.net/bugs/212217
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