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What would be the preferred steps I'd take to upgrade this particular system?

The system is at the moment hosting a production server using VirtualBox (so keeping downtime to a minimum is important.) Ubuntu itself is not hosting anything else -- just VirtualBox.

I am thinking of cloning the production server (not the system that needs upgrading) to a different box that could temporarily host the server during the upgrade process. And later to clone it back to the upgraded system.

I do intend on using the upgraded system the same way as before, not hosting anything but just using VirtualBox.

For the upgrade:

  • Would a clean install be preferred? I tend to think so -- but would love to be proven wrong. (Having to reconfigure the network configuration is the thing I am worried about and not looking forward to.)

  • And -- should I skip 18.04 and go straight to 19.04? (Not sure on this; and again, would this need to be a clean install? Or should I got 17.10 to 18.04 to 19.04?)

  • And should Desktop or Server be installed for a clean install? What would be quicker?

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    Ubuntu 19.04 is a short term release, and the only upgrade path to 19.04 is from 18.10; so 17.10->18.04->18.10->19.04 (skipping releases is unsupported & untested even if possible, unless thru re-install). If you don't want to upgrade every 6-9 months to remain secure; use LTS releases such as Ubuntu 18.04 LTS. Your next upgrade to Ubuntu 18.04 LTS which is a LTS release, and you can jump from that to Ubuntu 20.04 LTS (ie. LTS can release from LTS to next LTS). – guiverc Jul 8 at 22:11
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    in addition to echoing the other comment (clean install + use 18.04 LTS until 20.04 LTS): if you only install the server you will have no desktop environment. So if you don't need a desktop and plan to use the server command line only, then a server install will be much lighter. If you need a desktop, install the flavor that has the DE you want. – Nmath Jul 9 at 3:21
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    From the upgrading Virtualbox perspective (which I do very regularly) there are a few gotchas when going between point releases. I find it's much better to stop all your machines, make sure that they have actually stopped (as some vbox services love to hang around) and then remove virtualbox-X.Y (no need to purge). Then do the upgrade, then reinstall virtualbox-Z.A (because they will probably be different). This is important because vbox has a module it compiles as part of the installation which must match the kernel & vbox version you're running and gets out of date between point releases. – tu-Reinstate Monica-dor duh Jul 9 at 5:30
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I ended up moving the VM to a different box. That worked well, and freed up my Ubuntu system for updating to 18.04 LTS as suggested in the comments. Thank you.

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