SOLVED Jail Access over openVPN connection

[pro_trouble]

I have an openVPN server configured on my router and have my clients connecting just fine. The issue I am running into is as follows:

When connected over the VPN using the 'tun' adapter, only 1 of my 4 jails is reachable (plexmediaserver). If I connect with the 'tap' adapter then all of my jails are reachable (plexmediaserver, owncloud, transmission, sonarr). Everything else on my network behaves identically regardless of the configuration (i.e. only those 3 jails can't be reached). if I use the 'tun' adapter and ssh into my freenas I can ping the other jails normally. I've gone through all the settings I can find for the jails and haven't found anything that is different between the jails. As it stands, I have no idea where to keep looking.

This is only really important for ownCloud, since iOS doesn't support the tap interface, i can't connect to the owncloud server over the vpn.

Any thoughts? I have posted both server configurations below if it is of any help. My LAN is on 10.10.10.x.

Any help is appreciated.

TUN configuration:

Code:

daemon
server 10.8.0.0 255.255.255.0
proto udp
port 443
dev tun21
comp-lzo adaptive
keepalive 15 60
verb 3
push "route 10.10.10.0 255.255.255.0"
client-config-dir ccd
client-to-client
duplicate-cn
push "dhcp-option DNS 10.10.10.1"
ca ca.crt
dh dh.pem
cert server.crt
key server.key
status-version 2
status status
topology subnet

TAP Configuration:

Code:

daemon
server-bridge
push "route 0.0.0.0 255.255.255.255 net_gateway"
proto udp
port 444
dev tap22
comp-lzo adaptive
keepalive 15 60
verb 3
duplicate-cn
push "dhcp-option DNS 10.10.10.1"
ca ca.crt
dh dh.pem
cert server.crt
key server.key
status-version 2
status status
topology subnet

 

[Whattteva]

Does your router have a static route set up for the OpenVPN network in its routing table?

 

[pro_trouble]

I've tried with and without a static route with no difference in behavio(u)r. Interestingly, I updated the owncloud plugin and now I can get a ping response over the vpn. I also updated sonarr and didn't get the same effect (i.e. it still doesn't work).

 

[pro_trouble]

My boot USB stick failed this week, so I popped in a new one and reinstalled Freenas, then uploaded the config that I had backed up. Now everything works... I did literally nothing to change or fix the problem.

This unfortunately won't help anyone...