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updating direct from 5 to 9?



I am helping someone update an i386 system from 5 to 9, which is on the net
but without console (remote hands possible but really want to avoid
that).

Normally I update systems by

  cp -p /netbsd /netbsd.ok # save kernel that worked
  put new kernel in /netbsd
  reboot # now running new kernel and old userland
  unpack sets except etc
  unpack etc/xetc to /usr/netbsd-etc
  merge etcfiles via etcmanage
  reboot

  # skip intermediate reboot if staying on the same branch

and this almost always works, as in I don't remember the last failure
(unless I did something crazy which I did on RPI3).

So two questions:

  Are netbsd-5 boot blocks (bootxx_ffsv1 and /boot) ok to boot 9?   I
  have a dim memory of trouble, but I think was sparc from before 2.0
  booting 4.0.

  Is the 9 kernel expected to run 5?  I am having trouble following the
  config defines, and will try harder, so I mean: Have you taken a 5 box
  and booted a 9 kernel and was it ok (multiuser and sshd) or not ok?

  Does anybody advise 6,7,8,9 in series with 8 reboots?  That seems
  like 4 times as much opportunity for trouble to me.

I also intend to image the system onto a same-vintage box and try it.

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