So today I was working on setting up a trac instance behind a reverse proxy, and found that it could be done quite easily under Apache 2. Apache 2 allows you to set up your reverse proxy in a variety of different ways.
The main thing to note here is that you should never try to ProxyPass/ProxyReverse from port 443 to Port 443. Instead, pass from port 443 to 80 in the back-end. Allow the proxy to handle the SSL authentication for the browser.
If you require a secure connection from the back-end web server to the front-end proxy server, then utilize a VPN, or an SSH tunnel to pass the data; but don’t waste your time trying to make the web server behind your proxy handle the SSL authentication with the browser. The amount of time you’ll spend trying to figure it out, you would have saved to go do something else more fun, like set up a Cacti instance to monitor bandwidth consumption within your home network :)