So reading bsdinstall(8), installing an OS in a jail doesn't include the kernel. So when doing freebsd-update -b jail, it only upgrades the userland right?
Yes, because a jail doesn't need a kernel, it runs on the host's kernel.
-b probably assumes there's a "full" install on the destination directory, that would include a kernel. There's a -j option, specifically for jails.
Code:
-b basedir Operate on a system mounted at basedir. (default: /, or
as given in the configuration file.)
Code:
-j jail Operate on the given jail specified by jid or name.
(The version of the installed userland is detected and
the --currently-running option is no more required.)
Either way, it's not going to matter if there's a kernel (/boot/kernel/{...}) inside the jail or not, it's never going to be used. It will only use some disk space, and might be confusing, especially if it's an older kernel.
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