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: 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. 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.