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iPadOS client with OpenVPN Server on RT-AC86U

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SeaConn

Occasional Visitor
Hi Everyone,

I’ve scoured the forums and I’m still baffled as to why I can’t get the OpenVPN Server to work for me. I’m about ready to throw in the towel. First, my setup for my home network is as follows:
  1. RT-AC86U router running latest Merlin build
  2. RT-AC86U manually assigns all clients static local IPs
  3. Diversion and SkyNet are running on RT-AC86U
  4. DNS-over-TLS running through quad9.net
  5. OpenVPN client running on RT-AC86U (PIA with selective routing)
  6. OpenVPN server running on RT-AC86U (on a different UDP port than the PIA-VPN client)
  7. Synology DS916+ file server running on local network with Docker and containers
  8. NAT-free Motorola modem
  9. iPad Pro running OpenVPN Connect App
Goal: I use my iPad Pro for everything these days and would like to be able to connect to the SMB file share on my Synology server while I’m out of the house. Also, I have docker containers running on the Synology server (Sonarr, Radarr, etc.) and would like to be able to access their web GUIs.

The Setup: I recently added an OpenVPN Server to the RT-AC86U. I followed the instructions on these forums, but many of them are deprecated as some of the options have been removed as the firmware has been upgraded. The “Advanced Settings” view looks as follows:

upload_2019-12-29_0-52-10.png


I emailed the auto-generated .opvn file to myself and selected “copy to OpenVPN Connect” in iPadOS through my email to load it up. I noticed I was getting TLS key errors initially, so I enabled the “Username / Password Auth. Only” option on the router. This can probably be fixed by copying the key/cert information into the .opvn file. I am testing using my mobile phone’s hotspot connection with the WiFi turned OFF.

The Result: My iPad and/or iPhone connects to the OpenVPN server and is assigned a Virtual IP of 10.1.2.2. I then see IP addresses with a “C” behind them on the VPN status page of the router (like 192.168.1.14C); however, I cannot get the SMB share in the iOS “Files” app to connect to the Synology NAS, nor can I access the Synology’s docker container web GUIs. The “Net Analyzer” app on the client iOS device shows an IP address of 10.1.2.2 and fails to ping the Synology server.

I get this error in the log file:

“Dec 29 01:10:56 ovpn-server1[12009]: event_wait : Interrupted system call (code=4)”

But other than that, the log file is clean.

Anyone have any suggestions? It seems to me like I have some routing issues.

SeaConn
 

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