Thanks to everyone replaying to this thread. I carefully re-reading as kindly pointed out by Stefan. I ended up implementing this paragraph
Using an /etc/hostname.* file without persist-tun ------------------------------------------------- OpenVPN normally re-creates the tun/tap interface at startup. This has been reported to cause problems with some PF configurations (especially with queueing), if you run into problems with this then OpenVPN should be started from the hostname.* file, e.g.: # cat << EOF > /etc/hostname.tun0 up !LD_LIBRARY_PATH=/usr/local/lib:/usr/lib /usr/local/sbin/openvpn \ --daemon --config /etc/openvpn/server.conf EOF In a hindsight I should have done that before making a noise. I have had at least two OpenVPN/OpenBSD servers servers (30-40 road warriors) for the past eight years. I got spoiled by the painless upgrade process and squeaked on the first sign that something worked tiny bit different than previous release. Best, Predrag