Freebsd Version 14 Upgrade Process

I just went through quite a few FreeBSD 14 upgrades over the past month and just thought I'd note down the process. I also run quite a few jails on my FreeBSD hosts and also noted down what has been working for me. Seems like this information is very rarely documented across the internet so hopefully this helps someone out there!

Major Version Upgrade

Upgrade Host OS

Follow the guide below to upgrade a FreeBSD system to the latest OS version

First download the needed patching files
```
freebsd-update upgrade -r 14.0-RELEASE
```
Once completed install the new version with
```
freebsd-update install
```
Now reboot the system
```
reboot
```
Now run step 2. again
```
freebsd-update install
```
Now we need to reinstall pkg and all installed packages.
- Upgrade PKG with
```
pkg-static install -f pkg
```
- Upgrade installed packages with
```
pkg upgrade -f
```
Then we need to remove any old binaries, run freebsd-update install again
Finally run one last reboot and then run uname -r to confirm we are on the latest version

Upgrade Jail OS

Follow the guide below to upgrade a FreeBSD jail to the latest OS version

First download the needed patching files

freebsd-update upgrade -j "jail_name" -r 14.0-RELEASE

Once completed install the new version with
```
freebsd-update -j "jail_name" install
```
Now reboot the jail with
```
service jail restart "jail_name"
```
Now run freebsd-update -j "jail_name" install again.
```
freebsd-update -j "jail_name" install
```
Now we need to reinstall pkg and all installed packages.
- Upgrade PKG with
```
jexec "jail_name" pkg-static install -f pkg
```
- Upgrade installed packages with
```
jexec "jail_name" pkg upgrade -f
```
Then we need to remove any old binaries, run freebsd-update -j "jail_name" install again.
Finally run one last service restart and then run jexec "jail_name" uname -r to confirm we are on the latest version

Final Notes

Again, this is very straight to the point but for some reason hard to find information that's laid out so clean.

Happy upgrading!