Using stunnel and TinyProxy to obfuscate HTTP traffic

Using stunnel to create an SSL tunnel to a TinyProxy HTTP proxy

Written by Benjamin Cane on 2017-04-15 14:30:00 | 9 min read

Recently there has been a lot of coverage in both tech and non-tech news outlets about internet privacy and how to prevent snooping both from service providers and governments. In this article I am going to show one method of anonymizing internet traffic; using a TLS enabled HTTP/HTTPS Proxy.

In this article we will walk through using stunnel to create a TLS tunnel with an instance of TinyProxy on the other side.

How does this help anonymize internet traffic

TinyProxy is an HTTP & HTTPS proxy server. By setting up a TinyProxy instance on a remote server and configuring our HTTP client to use this proxy. We can route all of our HTTP & HTTPS traffic through that remote server. This is a useful technique for getting around network restrictions that might be imposed by ISP's or Governments.

However, it's not enough to simply route HTTP/HTTPS traffic to a remote server. This in itself does not add any additional protection to the traffic. In fact, with an out of the box TinyProxy setup, all of the HTTP traffic to TinyProxy would still be unencrypted, leaving it open to packet capture and inspection. This is where stunnel comes into play.

I've featured it in earlier articles but for those who are new to stunnel, stunnel is a proxy that allows you to create a TLS tunnel between two or more systems. In this article we will use stunnel to create a TLS tunnel between the HTTP client system and TinyProxy.

By using a TLS tunnel between the HTTP client and TinyProxy our HTTP traffic will be encrypted between the local system and the proxy server. This means anyone trying to inspect HTTP traffic will be unable to see the contents of our HTTP traffic.

This technique is also useful for reducing the chances of a man-in-the-middle attack to HTTPS sites.

I say reducing because one of the caveats of this article is, while routing our HTTP & HTTPS traffic through a TLS tunneled HTTP proxy will help obfuscate and anonymize our traffic. The system running TinyProxy is still susceptible to man-in-the-middle attacks and HTTP traffic snooping.

Essentially, with this article, we are not focused on solving the problem of unencrypted traffic, we are simply moving our problem to a network where no one is looking. This is essentially the same approach as VPN service providers, the advantage of running your own proxy is that you control the proxy.

Now that we understand the end goal, let's go ahead and get started with the installation of TinyProxy.

Installing TinyProxy

The installation of TinyProxy is fairly easy and can be accomplished using the apt-get command on Ubuntu systems. Let's go ahead and install TinyProxy on our future proxy server.

server: $ sudo apt-get install tinyproxy

Once the apt-get command finishes, we can move to configuring TinyProxy.

Configuring TinyProxy

By default TinyProxy starts up listening on all interfaces for a connection to port 8888. Since we don't want to leave our proxy open to the world, let's change this by configuring TinyProxy to listen to the localhost interface only. We can do this by modifying the Listen parameter within the /etc/tinyproxy.conf file.



Replace With:


Once complete, we will need to restart the TinyProxy service in order for our change to take effect. We can do this using the systemctl command.

server: $ sudo systemctl restart tinyproxy

After systemctl completes, we can validate that our change is in place by checking whether port 8888 is bound correctly using the netstat command.

server: $ netstat -na
Active Internet connections (servers and established)
Proto Recv-Q Send-Q Local Address           Foreign Address         State      
tcp        0      0*               LISTEN

Based on the netstat output it appears TinyProxy is setup correctly. With that done, let's go ahead and setup stunnel.

Installing stunnel

Just like TinyProxy, the installation of stunnel is as easy as executing the apt-get command.

server: $ sudo apt-get install stunnel

Once apt-get has finished we will need to enable stunnel by editing the /etc/default/stunnel4 configuration file.


# Change to one to enable stunnel automatic startup


# Change to one to enable stunnel automatic startup

By default on Ubuntu, stunnel is installed in a disabled mode. By changing the ENABLED flag from 0 to 1 within /etc/default/stunnel4, we are enabling stunnel to start automatically. However, our configuration of stunnel does not stop there.

Our next step with stunnel, will involve defining our TLS tunnel.

TLS Tunnel Configuration (Server)

By default stunnel will look in /etc/stunnel for any files that end in .conf. In order to configure our TLS stunnel we will be creating a file named /etc/stunnel/stunnel.conf. Once created, we will insert the following content.

accept =
connect =
cert = /etc/ssl/cert.pem
key = /etc/ssl/key.pem

The contents of this configuration file are fairly straight forward, but let's go ahead and break down what each of these items mean. We will start with the accept option.

The accept option is similar to the listen option from TinyProxy. This setting will define what interface and port stunnel will listen to for incoming connections. By setting this to we are defining that stunnel should listen on all interfaces on port 3128.

The connect option is used to tell stunnel what IP and port to connect to. In our case this needs to be the IP and port that TinyProxy is listening on;

An easy way to remember how accept and connect should be configured is that accept is where incoming connections should come from, and connect is where they should go to.

Our next two configuration options are closely related, cert & key. The cert option is used to define the location of an SSL certificate that will be used to establish our TLS session. The key option is used to define the location of the key used to create the SSL certificate.

We will set these to be located in /etc/ssl and in the next step, we will go ahead and create both the key and certificate.

Creating a self-signed certificate

The first step in creating a self-signed certificate is to create an private key. To do this we will use the following openssl command.

server: $ sudo openssl genrsa -out /etc/ssl/key.pem 4096

The above will create a 4096 bit RSA key. From this key, we will create a public certificate using another openssl command. During the execution of this command there will be a series of questions. These questions are used to populate the key with organization information. Since we will be using this for our own purposes we will not worry too much about the answers to these questions.

server: $ sudo openssl req -new -x509 -key /etc/ssl/key.pem -out /etc/ssl/cert.pem -days 1826
You are about to be asked to enter information that will be incorporated
into your certificate request.
What you are about to enter is what is called a Distinguished Name or a DN.
There are quite a few fields but you can leave some blank
For some fields there will be a default value,
If you enter '.', the field will be left blank.
Country Name (2 letter code) [AU]:US
State or Province Name (full name) [Some-State]:Arizona
Locality Name (eg, city) []:Phoenix
Organization Name (eg, company) [Internet Widgits Pty Ltd]
Organizational Unit Name (eg, section) []:
Common Name (e.g. server FQDN or YOUR name) []
Email Address []:[email protected]

Once the questions have been answered the openssl command will create our certificate file.

After both the certificate and key have been created, we will need to restart stunnel in order for our changes to take effect.

server: $ sudo systemctl restart stunnel4

At this point we have finished configuring the proxy server. We now need to setup our client.

Setting up stunnel (client)

Like the proxy server, our first step in setting up stunnel on our client is installing it with the apt-get command.

client: $ sudo apt-get install stunnel

We will also once again need to enabling stunnel within the /etc/default/stunnel4 configuration file.


# Change to one to enable stunnel automatic startup


# Change to one to enable stunnel automatic startup

After enabling stunnel we will need to restart the service with the systemctl command.

client: $ sudo systemctl restart stunnel4

From here we can move on to configuring the stunnel client.

TLS Tunnel Configuration (Client)

The configuration of stunnel in "client-mode" is a little different than the "server-mode" configuration we set earlier. Let's go ahead and add our client configuration into the /etc/stunnel/stunnel.conf file.

client = yes

accept =
connect =
verify = 4
CAFile = /etc/ssl/cert.pem

As we did before, let's break down the configuration options shown above.

The first option is client, this option is simple, as it defines whether stunnel should be operating in a client or server mode. By setting this to yes, we are defining that we would like to use client mode.

We covered accept and connect before and if we go back to our description above we can see that stunnel will accept connections on and then tunnel them to, which is the IP and port that our stunnel proxy server is listening on.

The verify option is used to define what level of certificate validation should be performed. The option of 4 will cause stunnel to verify the remote certificate with a local certificate defined with the CAFile option. In the above example, I copied the /etc/ssl/cert.pem we generated on the server to the client and set this as the CAFile.

These last two options are important, without setting verify and CAFile stunnel will open an TLS connection without necessarily checking the validity of the certificate. By setting verify to 4 and CAFile to the same cert.pem we generated earlier, we are giving stunnel a way to validate the identity of our proxy server. This will prevent our client from being hit with a man-in-the-middle attack.

Once again, let's restart stunnel to make our configurations take effect.

client: $ sudo systemctl restart stunnel4

With our configurations complete, let's go ahead and test our proxy.

Testing our TLS tunneled HTTP Proxy

In order to test our proxy settings we will use the curl command. While we are using a command line web client in this article, it is possible to use this same type of configuration with GUI based browsers such as Chrome or Firefox.

Before testing however, I will need to set the http_proxy and https_proxy environmental variables. These will tell curl to leverage our proxy server.

client: $ export http_proxy="http://localhost:3128"
client: $ export https_proxy="https://localhost:3128"

With our proxy server settings in place, let's go ahead and execute our curl command.

client: $ curl -v
* Rebuilt URL to:
*   Trying
* Connected to localhost ( port 3128 (#0)
* Establish HTTP proxy tunnel to
> Host:
> User-Agent: curl/7.47.0
> Proxy-Connection: Keep-Alive
< HTTP/1.0 200 Connection established
< Proxy-agent: tinyproxy/1.8.3
* Proxy replied OK to CONNECT request
* found 173 certificates in /etc/ssl/certs/ca-certificates.crt
* found 692 certificates in /etc/ssl/certs
* ALPN, offering http/1.1
* SSL connection using TLS1.2 / ECDHE_ECDSA_AES_128_GCM_SHA256
*    server certificate verification OK
*    server certificate status verification SKIPPED
*    common name: * (matched)
*    server certificate expiration date OK
*    server certificate activation date OK
*    certificate public key: EC
*    certificate version: #3
*    subject: C=US,ST=California,L=Mountain View,O=Google Inc,CN=*
*    start date: Wed, 05 Apr 2017 17:47:49 GMT
*    expire date: Wed, 28 Jun 2017 16:57:00 GMT
*    issuer: C=US,O=Google Inc,CN=Google Internet Authority G2
*    compression: NULL
* ALPN, server accepted to use http/1.1
> GET / HTTP/1.1
> Host:
> User-Agent: curl/7.47.0
> Accept: */*
< HTTP/1.1 301 Moved Permanently
< Location:
< Content-Type: text/html; charset=UTF-8
< Date: Fri, 14 Apr 2017 22:37:01 GMT
< Expires: Sun, 14 May 2017 22:37:01 GMT
< Cache-Control: public, max-age=2592000
< Server: gws
< Content-Length: 220
< X-XSS-Protection: 1; mode=block
< X-Frame-Options: SAMEORIGIN
< Alt-Svc: quic=":443"; ma=2592000; v="37,36,35"
<HTML><HEAD><meta http-equiv="content-type" content="text/html;charset=utf-8">
<H1>301 Moved</H1>
The document has moved
<A HREF="">here</A>.
* Connection #0 to host localhost left intact

From the above output we can see that our connection was routed through TinyProxy.

< Proxy-agent: tinyproxy/1.8.3

And we were able to connect to Google.

<HTML><HEAD><meta http-equiv="content-type" content="text/html;charset=utf-8">
<H1>301 Moved</H1>
The document has moved
<A HREF="">here</A>.

Given these results, it seems we have a working TLS based HTTP/HTTPS proxy. Since this proxy is exposed on the internet what would happen if this proxy was found by someone simply scanning subnets for nefarious purposes.

Securing our tunnel further with PreShared Keys

In theory as it stands today they could use our proxy for their own purposes. This means we need some way to ensure that only our client can use this proxy; enter PreShared Keys.

Much like an API token, stunnel supports an authentication method called PSK or PreShared Keys. This is essentially what it sounds like. A token that has been shared between the client and the server in advance and used for authentication. To enable PSK authentication we simply need to add the following two lines to the /etc/stunnel/stunnel.conf file on both the client and the server.

ciphers = PSK
PSKsecrets = /etc/stunnel/secrets

By setting ciphers to PSK we are telling stunnel to use PSK based authentication. The PSKsecrets option is used to provide stunnel a file that contains the secrets in a clientname:token format.

In the above we specified the /etc/stunnel/secrets file. Let's go ahead and create that file and enter a sample PreShared Key.


Since the /etc/stunnel/secrets file contains sensitive information. Let's ensure that the permissions on the file are set appropriately.

$ sudo chmod 600 /etc/stunnel/secrets

By setting the permissions to 600 we are ensuring only the root user (the owner of the file) can read this file. These permissions will prevent other users from accessing the file and stumbling across our authentication credentials.

After setting permissions we will need to once again restart the stunnel service.

$ sudo systemctl restart stunnel4

With our settings are complete on both the client and server, we now have a reasonably secure TLS Proxy service.


In this article we covered setting up both a TLS and HTTP Proxy. As I mentioned before this setup can be used to help hide HTTP and HTTPS traffic on a given network. However, it is important to remember that while this setup makes the client system a much more tricky target, the proxy server itself could still be targeted for packet sniffing and man-in-the-middle attacks.

The key is to wisely select the location of where the proxy server is hosted.

Have feedback on the article? Want to add your 2 cents? Shoot a tweet out about it and tag @madflojo.

Picture of Benjamin Cane

Benjamin is a Systems Architect working in the financial services industry focused on platforms that require Continuous Availability. He has been working with Linux and Unix for over 10 years now and has recently published his first book; Red Hat Enterprise Linux Troubleshooting Guide.


Identify, capture and resolve common issues faced by Red Hat Enterprise Linux administrators using best practices and advanced troubleshooting techniques

What people are saying:
Excellent, excellent resource for practical guidance on how to troubleshoot a wide variety of problems on Red Hat Linux. I particularly enjoyed how the author made sure to provide solid background and practical examples. I have a lot of experience on Red Hat but still came away with some great practical tools to add to my toolkit. - Amazon Review

Sponsored by