Thank you Anac and Chris, appreciate your suggestions:

You said that Tor was running. When combining Tor with VPN, the VPN's
connection type should be TCP, not UDP. Did you check that? 

I did check this...opened the connection to Any/Any but this didn't seem to be 
the issue. I also eliminated TOR for testing and connected directly to the 
sys-net(to also eliminate any sys-firewall potential issues)

Before you go through the trouble of a whole reinstall, you could try
setting your VPN VM to use Fedora 28 instead to see if it works. You can
also perform a reinstall of the Debian template. 

I tried with fedora-28 but also had the same TLS connection error. I ran the 
tests in step 3 as suggested and recieved the following errors with both the 
Debian and Fedora setup:

Fri Sep 14 10:30:53 2018 OpenVPN 2.4.0 x86_64-pc-linux-gnu [SSL (OpenSSL)] 
[LZO] [LZ4] [EPOLL] [PKCS11] [MH/PKTINFO] [AEAD] built on Jul 18 2017
Fri Sep 14 10:30:53 2018 library versions: OpenSSL 1.0.2l  25 May 2017, LZO 2.08
Enter Auth Username: My user name
Enter Auth Password: **************
Fri Sep 14 10:32:34 2018 TCP/UDP: Preserving recently used remote address: 
[AF_INET]208.167.254.76:1198
Fri Sep 14 10:32:34 2018 Socket Buffers: R=[212992->212992] S=[212992->212992]
Fri Sep 14 10:32:34 2018 UDP link local: (not bound)
Fri Sep 14 10:32:34 2018 UDP link remote: [AF_INET]208.x.x.x:port xx
Fri Sep 14 10:32:34 2018 write UDP: Operation not permitted (code=1)
Fri Sep 14 10:32:36 2018 write UDP: Operation not permitted (code=1)
Fri Sep 14 10:32:40 2018 write UDP: Operation not permitted (code=1)
Fri Sep 14 10:32:48 2018 write UDP: Operation not permitted (code=1)
Fri Sep 14 10:33:04 2018 write UDP: Operation not permitted (code=1)
Fri Sep 14 10:33:34 2018 TLS Error: TLS key negotiation failed to occur within 
60 seconds (check your network connectivity)
Fri Sep 14 10:33:34 2018 TLS Error: TLS handshake failed
Fri Sep 14 10:33:34 2018 SIGUSR1[soft,tls-error] received, process restarting
Fri Sep 14 10:33:34 2018 Restart pause, 5 second(s)

Definitely strange considering it was working great for a few months...the good 
news is the kill switch functionality with this solution worked.

Any insight with the errors I recieved? If not I think a reinstall is my best 
course...

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