Pjotr,

Great care was taken during the implementation to ensure that the prompt
is only shown to the user when there is a conflict *in* the
autogenerated section of the menu.lst file.  If you received this
prompt, it's precisely because you have made some changes (using a tool,
or by hand) to this section of your menu.lst, and update-grub cannot
automatically insert the entry for the new kernel without also
destructively overwriting your local changes.

Two of the chief reasons for such conflicts historically are that a user
has modified their boot device setting manually without updating the
"magic" variable in menu.lst, or that a user has added a completely
different boot option within the automanaged block.  Doing either of
these things is a mistake from the standpoint of the update-grub model,
but they're both very common mistakes; and overwriting menu.lst
automatically in these cases will either leave the system unbootable, or
change the default boot order of the system.

Therefore, leaving the existing boot section alone is the correct
default option when a conflict is encountered.  Indeed, none of the
available options are great defaults, and this is really a stopgap
measure until grub2 is ready with a richer config file format that
doesn't require the use of magic config sections; but within those
constraints, the current implementation functions as intended.

Not getting kernel security fixes if the user chooses the default option
is a valid concern, but one that is nevertheless outweighed by the risk
of leaving the system unbootable on upgrade.

In any event, if users are seeing this prompt as a result of using
startupmanager, then a high-priority task needs to be opened on
startupmanager to get *that* tool fixed.

** Changed in: grub (Ubuntu)
       Status: New => Won't Fix

-- 
After a kernel update, I am asked what to do with the old menu.lst. The wrong 
choice is offered by default.
https://bugs.launchpad.net/bugs/238339
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