Upgrading from older version - skip majors or no?

Hi,

I have a system running version 10 that I might be upgrading to 14 one of these days. I understand it's "supported", (?) but I've seen a direct upgrade of that magnitude varyingly described as "fine", "...but not recommended" and "absolutely not". So, which is it? It's a fairly simple server, primarily acting as a web server, with PHP and MySQL.

I don't remember having seen any rationale behind the non recommendations, except for some bug that required upgrading to 12.4 before proceeding. Which versions does that bug affect?

Are there any known issues that might occur from skipping versions? Let's assume I shouldn't skip versions, then, what should the upgrade path be? Any key checkpoints, or should one just do one major at a time?

Regardless of which, should I update to the latest minor version before proceeding, or is the latest patch enough?
 
I have a system running version 10 that I might be upgrading to 14 one of these days.
How's the disk partitioned? You're very likely to run out of disk space. I wouldn't upgrade such an old version, recommend doing a clean reinstall.
It's a fairly simple server, primarily acting as a web server, with PHP and MySQL.
Entirely different can of worms you can and will run into. We're talking PHP 5.x to PHP 8.3, MySQL 5.0 to MySQL 8.0?

I don't remember having seen any rationale behind the non recommendations, except for some bug that required upgrading to 12.4 before proceeding.
There have been plenty of bugs that got fixed with freebsd-update(8) since FreeBSD 10.

Are there any known issues that might occur from skipping versions?
Yes, various bugs in freebsd-update(8), running out of disk space (due to partitions being too small).
 
How's the disk partitioned? You're very likely to run out of disk space.
You mean because of the number of patches needing download?

Code:
$ gpart show
=>      34  83886013  da0  GPT  (40G)
        34         6       - free -  (3.0K)
        40      1024    1  freebsd-boot  (512K)
      1064       984       - free -  (492K)
      2048   4194304    2  freebsd-swap  (2.0G)
   4196352  79687680    3  freebsd-zfs  (38G)
  83884032      2015       - free -  (1.0M)
Some 30 GB free on zfs root.

I've got the PHP stuff covered. Was just emphasizing that the setup is fairly basic. I imagine that upgrades might be more prone to issues the more complex the system.

There have been plenty of bugs that got fixed with freebsd-update(8) since FreeBSD 10.
How should one reason about this then, in a general sense? Like, even if I were to upgrade from a much more recent version, say 13.0, there could exist severe bugs. Another way to phrase the question is to what extent is upgrading from old versions supported? When does it start becoming a bad idea?
 
As SirDice already recommended: NFO, RFB (nuke from orbit, rebuild from backup)

A clean new install and importing user data from backup will be much faster and less troublesome than dealing with all the fallout such a huge update step (or many small steps) would cause. We are talking about at least 8 years of missed updates - that is, if you referring to "10" as the latest release from that tree, 10.4, which went EOL in 2017. If you actually are running 10.0 we are at almost 12 years...
 
Something else I just thought of, how about the hardware itself? Is it just as old as the OS it's running? So ~10 years or even older? It might be worthwhile to invest in some new hardware too. While I have no problems running the latest FreeBSD versions on some really old (10-15 years) Supermicro hardware in my homelab, this stuff is exceptionally power hungry compared to more recent models. You get way more bang for your buck with new hardware and it'll run much cheaper too.

Added benefit of building a new machine next to the old one, you can keep the old one running while you're fixing any issues that might arise with all new versions of everything. You're not pressed for time when everything will be offline while you attempt to upgrade or reinstall.
 
Normally I would say anything greater than FreeBSD 8.0-RELEASE give it a try. That was the introduction to ada(4) disk driver from ad.

But you mentioned ZFS. That did go through massive change in the stated timeframe... Booting off ZFS?

Any disk based problem areas I would be wary. UEFI install or LegacyBIOS would be a contributing factor too.
If it is using LegacyBIOS method it would be a good time to change that.

freebsd-boot looks a little small to convert to UEFI..
 
You mean because of the number of patches needing download?
No, I was more worried about the partitioning. Older versions used a different set up with /, /usr, /var and /tmp split up into different partitions and filesystems. I installed 10.1 in a VM a couple of minutes ago to check, and your partition output showed it too, that switch to a 'single' partition must have happened before 10.0. I just can't remember when this was. But it looks like you're in the clear.
 
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