Hello my friends,

I've just noticed one of my beloved headless shell boxen is FreeBSD 5.4; its a workhorse I've been neglecting far too long and I'd really like to bring it up to 'current' (say fbsd 8.x). For awhile it was held back by very specific applications I had to support, but I'm in the clear now.

Given the age of the installation, I'm wondering what the recommended upgrade path would be.

ie: This machine has a lot going on .. wiki's (ie: apache et al), mysql databases, mailing lists, and a dozen hand rolled applications. (Hey, someone has to write custom emulators of ancient systems to keep BBSes alive, right?) Naturally, /etc is modified all to hell, and I'm terrified of any automated upgrades for fear random things would just not work later. Especially with the age... Things work great, but I worry about security naturally, and keeping up with patches or installing anything new is a nightmare due to dependancies.

o I should be able to identify most important changes and data; /etc, /home, the kernel build path so I've got the old kernel conf files I used for this machine (yay!), /usr/local was used instead of polluting /usr-proper, etc.

o I'd love if I coudl do an upgrade, and things would still work; I mean, from samba configuration etc and so on, eveyrthign is great. I realize this is unlikely though .. upgrading services likely means conf changes all over the random place, etc.

o Some of the executables on this box are without source but I still need them to run; short of moving them to a VM and doing some voodoo, what are the chances a binary built for fbsd 5.x works fine in 8.x? (earlier fbsd's had the break between gcc versions, but I'm rather hoping thats not a problem here.)
        gcc (GCC) 3.4.2 [FreeBSD] 20040728

        The obvious options are..

1 - upgrade step by step; go from fbsd 5.4 to 6.4 (say) to 7.2 (say) to 8.0

        2 - one big-ass upgrade from 5.4 to 8 (*fear*)

3 - yank the drive, slap a giant new fat drive in there, do a full fbsd 8.0 install, and then migration from old drive as needed

Strikes me most people will recommend (3) -- nice big new drive, no risk of destroying a working machine (can always slap old drive back in), easy migration of service by service, etc and so on. Strikes me as a PITA, but then again .. the others are probably all PITAs as well given the age of the box. Something will break, so maybe its best to just start fresh with a nice new install and go from there.

        *ugh* but that'll teach me to stay on top of it more :)

Aside -- whats the recommended way to stay on top of upgrades anyway? It used to be a tortuous process back 5 years ago, but hopefully things are much more streamlined now .. nightly 'make upgrade' ftw :)

                jeff

--
If everyone would put barbecue sauce on their food, there would be no war.
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