Stunnel/Troubleshooting

Having issues getting stunnel client and server to connect.

Have been following this Digital Ocean guide: https://www.digitalocean.com/community/tutorials/how-to-set-up-an-ssl-tunnel-using-stunnel-on-ubuntu

Problem Description

Currently trying to create an stunnel connection from client to server.

Here is the client stunnel.conf (Mac):

output  = /var/log/stunnel4/stunnel.log
cert    = /usr/local/etc/stunnel/stunnel.fullchain.pem
key     = /usr/local/etc/stunnel/stunnel.key.pem
client  = yes
debug   = 7
[ssh]
accept  = 127.0.0.1:22
connect = 92.126.102.36:8000

Here is the server stunnel.conf (Ubuntu):

output  = /var/log/stunnel4/stunnel.log
cert    = /etc/stunnel/stunnel.fullchain.pem
key     = /etc/stunnel/stunnel.key.pem
client  = no
debug   = 7
[ssh]
accept = 8000
connect = 127.0.0.1:22

The debug level of 7 is maximum and gives a more detailed description of what's happening in the log file.

Server behavior

On the server, starting the stunnel client using the following steps:

Check the stunnel conf:

$ cat /etc/stunnel/stunnel.conf

Open port 8000 if needed:

$ iptables -A INPUT -p tcp --dport 8000 -j ACCEPT

Stop previous stunnel instances and start a new one:

$ killall stunnel && stunnel

Look at the last few lines of the log to verify it is running correctly and bound to port 8000:

$ tail /var/log/stunnel4/stunnel.log
...
2017.03.29 04:59:15 LOG5[ui]: Configuration successful
2017.03.29 04:59:15 LOG7[ui]: Listening file descriptor created (FD=7)
2017.03.29 04:59:15 LOG7[ui]: Service [ssh] (FD=7) bound to 0.0.0.0:8000

Client behavior

When the stunnel command is run on the client,