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I part-own and manage a co-located server that is running Ubuntu 6.06 LTS server edition.

I realise that the version we use is supported until June 2011 (https://wiki.ubuntu.com/Releases) but I'm thinking of upgrading to 8.04 LTS.

This would be mainly to get the benefit of newer versions of software and also to hopefully resolve some problems we are having with software RAID.

Is it sensible to do an upgrade from a version that old or should I just do a fresh installation?

Upgrading would of course be better for me than doing a fresh installation as it would require less downtime.

But I had a bad experience with the desktop version of Ubuntu when an upgrade left me with a box that wouldn't boot successfully. Was this just bad luck or am I right to be wary?

A few things to note:
The server is patched and up to date security wise.
I'd take a full backup to a separate partition before doing the upgrade.

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It's worth pointing out that next April's release will most likely be a LTS. You might want to wait 9 months. –  David Pashley Aug 9 '09 at 8:04
    
Just as a follow up, we're buying a new server and running it in parallel. This will allow us to migrate services/data bit by bit. So no need to do a scary upgrade now. –  Darren Greaves Oct 18 '11 at 9:47

3 Answers 3

up vote 3 down vote accepted

Dump your install into a VMWWare/Virtualbox/... and then upgrade. This will give you a test environment, so you can see if anything has gone wrong. If things seem okay, upgrade your real machine.

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I also always do critical updates/upgrades in a VM. –  ThorstenS Aug 9 '09 at 9:20
    
This is an excellent idea, thanks! –  Darren Greaves Aug 10 '09 at 10:08

Funny you should ask, as I've spent the afternoon upgrading around 8-10 Dapper boxes to Hardy, without a hitch.

If you're considering reinstalling, why not attempt an upgrade, and if it goes wrong, reinstall.

The method I used was to install update-manager-core and then run:

# do-release-upgrade

Just follow the prompts and a little while later you're upgraded to Hardy.

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Seconded. Dapper -> Hardy updates with do-release-upgrade are generaly so easy they make me nervous. I keep waiting for the other shoe to drop. –  Insyte Aug 9 '09 at 4:43
    
The only problem I've had is do-release-upgrade sometimes not liking something about my local mirror, so have to point my sources.list back at an official mirror and run it again. –  David Pashley Aug 9 '09 at 8:03
    
Thanks for this. To save people looking it up, Dapper = 6.06 and Hardy = 8.04. I always forget which name relates to which numerical version. –  Darren Greaves Aug 10 '09 at 10:10

It's Oct 2011 -- Now that 6.06 LTS AND 8.04 3 LTS have gone into EOL, the upgrade is anything but smooth. The problem is (1) that the /etc/apt/sources.list must be changed from us.archive.ubuntu.com to old-releases.ubuntu.com and (2) that the upgrade process rewrites the apt/sources.list file, removing the "old-releases" changes that you made !! The result is a half-done upgrade that can't find apt files because they no longer exist at us.ubuntu, but instead exist at old-releases.ubuntu. Canonical should have NEVER moved those sources from us. to old-releases. Launchpad has https://answers.launchpad.net/ubuntu/+source/update-manager/+question/62184 and https://answers.launchpad.net/ubuntu/+source/update-manager/+question/166342

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