The latest upgrades (e.g. 1.5.5=>1.5.6, or 1.5.6=>1.5.7 when it comes out) will break the OpenVPN configuration, but the upgrade process will not, provided the "preserve settings box" is checked.
I'm not too concerned about this, because these are experimental releases, not stable releases -- i.e. people SHOULD know better than to expect stability here. When this feature is in a stable branch, yes things should be stable between releases.
My comments are not fact more a suggestion/question
What I did was install 1.5.5+ then made backup. I then upgraded version and found that things where not working as expected so I downgraded to the exact version and reinstalled from the backup.
I had hoped that the VPN would still work but It didn't. I have assumed that the first 5 - 10 minute encryption files gets wiped..............
While we are on the topic of VPN i've something else to share
I have two or more gargoyle OpenVPN servers and one PC client I would like to use to connect to them all (remote-access) . The problem is that they all use the same ca.crt file name