Stunnel and Squid on FreeBSD 11

I don’t like to use untrusted networks. When I have to use such a network, e.g. an open WiFi network, I use a TLS encrypted tunnel connection to encrypt all web traffic that travels through the untrusted network. I’m using a simple stunnel/ Squid setup for this. My setup consists of three components:

  • Stunnel (server mode)
  • Squid proxy
  • Stunnel (client mode)

What is stunnel?

Stunnel is an OSS project that uses OpenSSL to encrypt traffic. The website describes Stunnel as follows:

Stunnel is a proxy designed to add TLS encryption functionality to existing clients and servers without any changes in the programs’ code. Its architecture is optimized for security, portability, and scalability (including load-balancing), making it suitable for large deployments.

How it works

The traffic flow looks like this:

The browser connects to the Stunnel client on 127.0.0.1:8080. This is done by configuring 127.0.0.1:8080 as proxy server in the browser. The traffic enters the tunnel on the client-side, and Stunnel opens a connection to the server-side. You can use any port, as long as it is unused on the server-side. I use 443/tcp. The connection is encrypted using TLS, and the connection is authenticated by a pre-shared key (PSK). On the server, the traffic leaves the tunnel, and the connection attempt of the client is directed to the Squid proxy, which listens on 127.0.0.1:3128 for connections. Summarized, my browser connectes the Squid proxy on my FreeBSD host over a TLS encrypted connection.

Installation and configuration on FreeBSD

Stunnel and Squid can be installed using pkg install .

The configuration files are located under /usr/local/etc/stunnel and /usr/local/etc/squid. After the installation of stunnel, an additional directory for the PID file must be created. Stunnel is not running with root privileges, thus it can’t create its PID file in /var/run.

The stunnel.conf is pretty simple. I’m using a Let’s Encrypt certificate on the server-side. If you like, you can create your own certificate using OpenSSL. But I prefer Let’s Encrypt.

The psk.txt contains the pre-shared key. The same file must be located on the client-side. The file itself it pretty simple – username:passphrase. Make sure that the PSK file is not group- and world-readable!

The squid.conf is also pretty simple. Make sure that Squid only listens on localhost! I disabled the access log. I simply don’t need it, because I’m the only user. And I don’t have to rotate another logfile. Some ACLs of Squid are now implicitly active. There is no need to configure localhsot or 127.0.0.1 as a source, if you want to allow http access only from localhost. Make sure, that all requests are only allowed from localhost!

To enable stunnel and squid in the /etc/rc.conf, add the following lines to your /etc/rc.conf. The stunnel_pidfile  option tells Stunnel, where it should create its PID file.

Make sure that you have initialized the Squid cache dir, before you start squid. Initialize the cache dir, and start Squid and Stunnel on the server-side.

Installation and configuration on Windows

On the client-side, you have to install Stunnel. You can fine installer files for Windows on stunnel.org. The config of the client is pretty simple. The psk.txt contain the same username and passphrase as on the server-side. The file must be located in the same directory as the stunnel.conf on the client.

Test your connection

Start Stunnel on your client and configure 127.0.0.1:8080 as proxy in your browser. If you access https://www.whatismyip.com, you should see the IP address of your server, not the IP address of your local internet connection.

You can check the encrypted connection with Wireshark on the client-side, or with tcpdump on the server-side.

Please note, that the connection is only encrypted until it hits your server. Traffic that leaves your server, e.g. HTTP requests, are unencrypted. It is only an encrypted connection to your proxy, not and encrypted end-2-end connection.

Stunnel and Squid on FreeBSD 11
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Patrick Terlisten
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Patrick Terlisten

vcloudnine.de is the personal blog of Patrick Terlisten. Patrick has nearly 2 decades of experience in IT, especially in the areas infrastructure, cloud, automation and industrialization. Patrick was selected as VMware vExpert (2014 - 2017), as well as PernixData PernixPro.

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