Ok two issues that I'm not sure how to solve.
I have an OpenVPN server set-up and it's purely used for DNS resolution. DNS servers are pushed from the server to the clients upon connection. Actual traffic goes through the client default gateway.
First Issue
Tunnelblick on Mac connects without issue and sets the new DNS server (or servers if I have add an additional one in). Before I upgraded Tunnelblick to the latest version no DNS resolution would occur at all effectively meaning no internet. I upgraded to the latest version of Tunnelblick and DNS resolution worked for a bit before stopping. I tried playing around with the Set nameserver option but no difference (other than one option simply mean local DNS was used rather than the OpenVPN pushed DNS). Not really sure what else to try here. Looking at the logs I can see the below when it's attempting to use the VPN but I don't know what they mean.
2018-10-28 15:28:38 us=867876 UDP WRITE [62] to [AF_INET] XX.XX.XXX.XX:11194: P_ACK_V1 kid=0 sid=50fbe417 cd8a5571 [ ]
2018-10-28 15:28:38 us=868024 UDP write returned 62
2018-10-28 15:28:38 us=868164 event_wait returned 1
2018-10-28 15:28:38 us=868306 read from TUN/TAP returned 72
2018-10-28 15:28:38 us=868407 tls_prepend_opcode_v2
2018-10-28 15:28:38 us=868526 event_wait returned 1
2018-10-28 15:28:38 us=868651 UDP WRITE [96] to [AF_INET]XX.XX.XXX.XX:11194: P_DATA_V2 kid=0 DATA 00000000 00000119 a497afe9 f6e96d01 5e6fe305 2e5d971f e69d2b3b 4d55a15[more...]
2018-10-28 15:28:38 us=868804 UDP write returned 96
2018-10-28 15:28:38 us=878944 event_wait returned 1
2018-10-28 15:28:38 us=879105 UDP read returned 93
Second Issue
On the iOS device it works fine (same config as above - different cert) and all DNS goes through the VPN. I have two pushed DNS servers and the client always uses the first one. If I take the first DNS server offline I would have thought that it would fallback to the second pushed DNS server - which would logically make sense. Instead it simply starts using the local DNS rather than any pushed DNS. Again not sure how to fix this.