Posts: 55
Joined: Fri Jul 31, 2015 9:21 am

stunnel under Jessie issue

Wed Sep 30, 2015 2:58 pm

I have two seemingly identically set up RPi's. One is Wheezy and the other is Jessie.
Both have OpenVPN Server and stunnel4 installed and configured - identically.

Wheezy works great. Connect with stunnel client on my Android with SSLDroid and OpenVPN for Android and data flows like it should.

Jessie does not. If I connect straight with OpenVPN (no stunnel), data flows great. Try to go through stunnel, and OpenVPN connects, but no data flows (no web pages, email, internet)

Here's my stunnel.conf:

Code: Select all

sslVersion = all
options = NO_SSLv2
cert = /etc/stunnel/server.pem
pid = /var/run/stunnel.pid
output = /var/log/stunnel
socket = l:TCP_NODELAY=1

client = no
accept = 443
connect =
And here's the top of my OpenVPN Server.conf:

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dev tun
proto tcp
port 1194
ca /etc/openvpn/easy-rsa/keys/ca.crt
Hope someone can tell me where I'm going wrong, or where to look for more clues!


Posts: 55
Joined: Fri Jul 31, 2015 9:21 am

Re: stunnel under Jessie issue

Thu Oct 01, 2015 3:50 am

Well, the problem wasn't with Jessie or anything on the server. I had such a hard time trying to get OpenVPN to autostart on boot in Jessie that I thought something was different with stunnel as well.
Turned out, the problem was on the client side. I forgot to add this route command to the client config to keep it from rerouting packets meant for the server:

Code: Select all

route xxx.xxx.xxx.xxx net_gateway
Where xxx.xxx.xxx.xxx is the ip address of the OpenVPN Server/stunnel Server.
What a difference a good night's sleep makes :D
Case closed.

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