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I am on a perfectly configured and functioning Ubuntu 14.04 LTS machine.
LTS versions of Ubuntu are supported for 5 years, so in theory there should be no need to upgrade the whole system before the 5 year deadline. I conceive the whole point of having a LTS system the best choice for those like me who prefer to rely on stability for as long as possible, because they develop software or web application for instance: a system upgrade is always a tricky operation.

Considering that I am aware that when 2019 comes Ubuntu 14.04 will not be supported any more, and that I certainly will want at that time to extend the life of my system, I still do not understand what possibilities and options am I left with.

Will in 2019 I be able to upgrade from 14.04 to 18.04 or it is necessary to upgrade gradually, when time comes, from a LTS to the next one? In other words is it necessary now, or in about three months time, to upgrade from 14.04 to 16.04.1 in order to be able to upgrade in 2018 to 18.04?

What is the best and safest choice I can do?

closed as primarily opinion-based by Charles Green, Ron, Eric Carvalho, user117103, Pilot6 May 6 '16 at 14:17

Many good questions generate some degree of opinion based on expert experience, but answers to this question will tend to be almost entirely based on opinions, rather than facts, references, or specific expertise. If this question can be reworded to fit the rules in the help center, please edit the question.

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    This question seems likely to be marked as looking primarily for an opinion. IMHO, it is often easier to do a full install than an upgrade when the upgrade covers several years development. – Charles Green Apr 22 '16 at 13:11
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    The question boils down to this: Is it possible to skip an LTS upgrade?, and hence is a duplicate. – Ron Apr 22 '16 at 13:22
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I don't know if you'll be able to skip an LTS. I think it most likely you'll need to hop via 16.04. But you can do both those steps in 2019. You don't have to move to 16.04 now. You can, but you don't have to.

There may be an upgrade path plan published for 14.04→18.04 so that might be an option, but it doesn't make any difference in practice. Your job is the same. You're going to change the base and you'll need to test your software on it.

The important lesson to consider here is you can test whenever you like. Leaving that until 14.04s is dying, and finding out you need to do weeks of improvements is probably a bad idea. Doing an untested upgrade on a production system and then finding out it's broken is much worse.

There is nothing stopping you, for example, creating a testing system running whatever version of Ubuntu, that you test on. That will let you know what doesn't work and you can incorporate that into bugfixes, or other plans for when you actually deploy. You can go one further and use "continuous integration" techniques to find out where the problems are, as they happen. I'm not sure how appropriate this is for you though.

  • Of course testing would be fundamental, but the only way I would be able to make a test is to use a live boot. I suppose you are suggesting other ways perhaps beyond my abilities. But you hit the spot, I would like on the one hand test if the upgrade can be done and on the other hand when it is better to do it. – Asarluhi Apr 22 '16 at 13:45
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    A virtual machine (lxc for simple servers, virtualbox for desktops). I'd recommend testing 16.04 as soon as is convenient for you. If you find a load of stuff that needs to be fixed, you can plan to fix that. The more you know ahead of this 2019 deadline, the better equipped you are to meet it. – Oli Apr 22 '16 at 14:48

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