SSL support with Apache and Proxytunnel

Question

I'm inside a strict corporate environment. https traffic goes out via an internal proxy (for this example it's 10.10.04.33:8443) that's smart enough to block ssh'ing directly to ssh.glakspod.org:443.

I can get out via proxytunnel. I set up an apache2 VirtualHost at ssh.glakspod.org:443 thus:

ServerAdmin [email protected] ServerName ssh.glakspod.org

    <!-- Proxy Section -->
    <!-- Used in conjunction with ProxyTunnel -->
    <!-- proxytunnel -q -p 10.10.04.33:8443 -r ssh.glakspod.org:443 -d %host:%port -->
    ProxyRequests on
    ProxyVia on
    AllowCONNECT 22
    <Proxy *>
            Order deny,allow
            Deny from all
            Allow from 74.101
    </Proxy>

So far so good: I hit the Apache proxy with a CONNECT and then PuTTY and my ssh server shake hands and I'm off to the races.

There are, however, two problems with this setup:

1. The internal proxy server can sniff my CONNECT request and also see that an SSH handshake is taking place. I want the entire connection between my desktop and ssh.glakspod.org:443 to look like HTTPS traffic no matter how closely the internal proxy inspects it.

2. I can't get the VirtualHost to be a regular https site while proxying. I'd like the proxy to coexist with something like this: SSLEngine on SSLProxyEngine on SSLCertificateFile /path/to/ca/samapache.crt SSLCertificateKeyFile /path/to/ca/samapache.key SSLCACertificateFile /path/to/ca/ca.crt

   DocumentRoot /mnt/wallabee/www/html
   <Directory /mnt/wallabee/www/html/>
           Options Indexes FollowSymLinks MultiViews
           AllowOverride None
           Order allow,deny
           allow from all
   </Directory>
   
   <!-- Need a valid client cert to get into the sanctum -->
   <Directory /mnt/wallabee/www/html/sanctum>
           SSLVerifyClient require
           SSLOptions +FakeBasicAuth +ExportCertData
           SSLVerifyDepth 1
   </Directory>
   

So my question is: How to I enable SSL support on the ssh.glakspod.org:443 VirtualHost that will work with ProxyTunnel?

I've tried various combinations of proxytunnel's -e, -E, and -X flags without any luck.

The only lead I've found is Apache Bug No. 29744, but I haven't been able to find a patch that will install cleanly on Ubuntu Jaunty's Apache version 2.2.11-2ubuntu2.6.

Thanks in advance.

Answer 1

I pieced together the answer from the proxytunnel-users mailing list.

First, looking at the Apache bugreport number 29744, the attachment containing the patch for my version of Apache, 2.2.11-2ubuntu2.6, was hidden because it was considered obsolete. Clicking on the "Show Obsolete" link in the lower-right corner of the attachments box revealed the patch.

So I did an apt-get source apache2 on my jaunty box, patched the source, did a debuild . . . ate some cereal . . . and then did a dpkg -i *.deb on everything I built.

Now those two separate Apache snippets above live together in harmony.

The last piece of the puzzle is how to call proxytunnel. Here's what worked:

proxytunnel -q -X -p 10.10.04.33:8443 -r ssh.glakspod.org:443 -d %host:%port ServerAliveInterval 30

Hope this helps someone else down the line!