What, another blog so short after the last. Weird.
Had a day off, and finally decided to upgrade my servers with their jails.
I have previously during my vacation upgraded my workstations from 13.2-RELEASE to 14.2-RELEASE. That went without any kind of problems.

doas freebsd-update -r 14.2-RELEASE upgrade install
doas reboot
doas freebsd-update -r 14.2-RELEASE install # i know you don't need to specify version here
doas pkg update && doas pkg upgrade

For the servers it was upgrade from FreeBSD 13.2-RELEASE (EOL 30th june 2024) to 13.5-RELEASE
My main concern was the mailserver jail so i did that last.
Host servers upgraded smoothly.
Went through the jails, starting with my test jail everything went without a problem.
Then came the mail one, and i was slightly nervous...
To my suprise it went without a problem

doas freebsd-update -j mail -r 13.5-RELEASE upgrade install
doas reboot
doas freebsd-update -j mail -r 13.5-RELEASE install
doas pkg -j mail update && doas pkg -j mail upgrade
reboot # a last reboot to see that it works aswell

After that i went to bed, feeling like "ohh nice, that was sooo smooth". Woke up today and realized that something was not exactly working with the mailserver.
I was not receiving mails, kindof a big issue!
Opensmtpd did not start, oops, had not verified this last night. FUDGE!
Apparently there was a problem when upgrading it from 7.3.0 to 7.6.0. No note about this when upgrading the package unfortunately :(
opensmtpd 7.6.0p0 released
Issue1266

The solution seems to be to install some opensmtpd-extras-table-passwd for example. That did not work for me, so i reverted the version back to 7.3.0

While i was looking in mail logs it spewed with spammers trying to login to imap. Thought i would block it in the ipfw firewall rules.
Had a line looking something like this in the middle of my rules file, that is not big at all, like 30 rows:

ipfw add 200 deny tcp from any to any 25 in via re0

I did then copy that row and changed the port, to deny another one. Restarted the ipfw firewall.
Then everything went Really really slow, hitting enter at the prompt took several secounds (literally). What the actual F?
Edited the rules file, again, took literally 5min to open it, comment away a row and save, then restart the service.
After that it was back to normal. WHAT?!?
I did not think to update the 3rd collumn, with a new number. This seems like a bug, will file one. Should be easy to have a checker that looks for that when you start the service.

Other than that, everything went extremely smooth. Considering, 2 servers and 8 jails. This is nothing. Wub FreeBSD.