Admin User Redirect Loops with Secure Pages - Self Signed Certificate

Question

Problem

I'm trying to mimic my production environment on my dev server.

(Setup: LEMP server, Ubuntu Server LTS 12.04)

On my production site I use an SSL certificate from Gandi, it all works fine.

On my dev environment I created one myself following the instructions here:

I'm using the Secure Pages module to secure the admin area however when I enable HTTPS for a role (Administrator) I get a re-direct loop for all my pages which locks me out of my site.

HTTPS does however work fine for single pages.

Any ideas what I could be doing wrong? Could this be a config thing?

Instructions I used to generate an SSL

sudo openssl genrsa -des3 -out server.key 1024
sudo openssl req -new -key server.key -out server.csr
// Leave all options blank, except put 192.168.1.95 address into common
sudo cp server.key server.key.org
sudo openssl rsa -in server.key.org -out server.key
sudo openssl x509 -req -days 365 -in server.csr -signkey server.key -out server.crt

Possible Relevant Nginx Config

/etc/nginx/sites-available/mysite

 server {
      listen 443;

        root /srv/www/mysite/public
        ...
        ...
        ssl on;
        ssl_certificate /etc/nginx/ssl/testssl.crt;
        ssl_certificate_key /etc/nginx/ssl/testssl.key;

        location / {
           index  index.html index.htm index.php;
           error_page 404 = @drupal;
        }

        location ~ \.php$ {
            try_files $uri =404;
            include /etc/nginx/fastcgi_params;
            if ($uri !~ "^/default/files/") {
                fastcgi_pass 127.0.0.1:9000;
            }
            fastcgi_index index.php;
            fastcgi_param SCRIPT_FILENAME /srv/www/mysite/public$fastcgi_script_name;
        }

        location @drupal {
            rewrite ^(.*)$ /index.php?q=$1 last;
        }