The Random File Plugin (http://wordpress.org/extend/plugins/random-file/) definitely doesn´t work with WP Super Cache 0.9.6+.
Before its execution you will notice that WP Super Cache adds the following text:
<!-- No closing html tag. Not caching. -->
and the page is not cached.
This is what I found on the debug log:
2:48:17 /24023/yamopo-2009-yet-another-most-popular-architecture-sites-ranking/ In WP Cache Phase 2
22:48:17 /24023/yamopo-2009-yet-another-most-popular-architecture-sites-ranking/ Setting up WordPress actions
22:48:17 /24023/yamopo-2009-yet-another-most-popular-architecture-sites-ranking/ Created output buffer
22:48:17 /24023/yamopo-2009-yet-another-most-popular-architecture-sites-ranking/ supercache dir: /html/wp-content/cache/supercache/www.archdaily.com/24023/yamopo-2009-yet-another-most-popular-architecture-sites-ranking/
22:48:17 /24023/yamopo-2009-yet-another-most-popular-architecture-sites-ranking/ Output buffer callback
22:48:17 /24023/yamopo-2009-yet-another-most-popular-architecture-sites-ranking/ No closing html tag. Not caching.
I let the author know about this. If you use this plugin check if your website is being cached, caused a high load on mine for a few days...