Thanks for the continued help. Ping / ssh / tracert all work all fine. I start to think that I should look elswhere for the issue.
The web server is running inside a VM on the OpenVPN Server.
On the OpenVPN Server I included this routing for the web server port:
iptables -t nat -A PREROUTING -p tcp -i em1 --dport 1337 -j DNAT --to-destination <ip of webserver vm>:1337