Multi step major upgrade - reinstalling packages?

Hi,

I'm going to upgrade from 12.4 via 13.5 to 15.1. I need to reinstall all packages after a major upgrade, but can it wait until 15.1, or is that going to cause issues somewhere along the way?
 
I don't bother with either reinstall nor with reinstalling all packages. Works fine most of the time, but see my thread about my screwed up g+.
 
Yeah, I also would recommend a clean new install.
As drsnx60 said, backup your stuff first, perhaps do a full backup, and then do a new installation, maybe on a fresh drive.
A new installation will take you less than an hour (not counting backing up your data, which you have to do anyway) while those many upgrade steps will take you days. And a zillion things can go wrong while this stunt, since several things changed since 12.4, like default shell changes from csh to sh - overseeing such thing, and you also have a mess to clean up, too.
 
For major updates, I reinstall about ten packages - including kmod.
As for the rest, I've installed misc/compat1?x and left it as is.
I am currently on version 15.1, but I still have dozens of 13.x packages as well as some 11.x and 12.x packages remaining.
 
I would recommend a clean reinstall. Too many things that could go wrong (unless you know what you're doing).
I very much disagree with this as a general advice.

But I partly agree. For a machine with lots of software installed (typically a desktop), very few customizations (no special server-style packages with extensive customization and configuration), and files that are just in user directories and can be backed up and restored, I would agree with re-installing. In such a situation, users should actually move to storing their data in the cloud, and using browser-based apps, and treat their desktop machine as a disposable and stateless device.

On the other hand, for a machine that has complex customization, non-standard software installed, and that other things rely on staying up as much as possible, the correct answer is to upgrade seamlessly in place. And FreeBSD's strength is that upgrades are possible and usually relatively painless and safe, even across major versions. That capability needs to be exercised and maintained, both by individual admins and by the project.

Which category the OP's machine falls in: is up to them to decide.
 
Alright, I appreciate that you're all my seniors here, but that is also part of the crux. This is an inherited web server, and while it's not a particularly complex setup, I don't know which minor customizations might be in place. I am not doing a fresh install unless there is an extremely good reason to do so. Why is upgrading even possible? You're making it sound like the feature is useless. If I had upgraded to each major as they were released, would that have been any better? If yes, why?

Yeah, I also would recommend a clean new install.
As drsnx60 said, backup your stuff first, perhaps do a full backup, and then do a new installation, maybe on a fresh drive.
A new installation will take you less than an hour (not counting backing up your data, which you have to do anyway) while those many upgrade steps will take you days. And a zillion things can go wrong while this stunt, since several things changed since 12.4, like default shell changes from csh to sh - overseeing such thing, and you also have a mess to clean up, too.

I don't see why it should take days? It's two steps. (versions) Waiting a little while for packages to download, and spend a couple of minutes merging some configuration files. Couple of reboots. The data is already backed up automatically. I have already tested the upgrade steps on a cloned machine, and it seems to work fine afterwards. I am changing my shell back to csh.

I didn't realise reinstalling packages was optional. I think that it breaks PHP packages, at least? I will just reinstall all packages. I would just like to know whether I need to perform this step for the intermediate version 13, but it's sounding like the answer is no, then.
 
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