Windows Server 2008R2 – Monitoring Available Entropy

Yes, this can be done. There is documentation on the Atlassian site about this:

http://confluence.atlassian.com/display/JIRA/Integrating+JIRA+with+IIS

Another possibility if you are looking to reverse proxy the request is to use Application Request Routing (a supported IIS add-on): http://www.iis.net/download/ApplicationRequestRouting.

Your system gathers some "real" random numbers by keeping an eye about different events: network activity, hardware random number generator (if available; for example VIA processors usually has a "real" random number generator), and so on. If feeds those to kernel entropy pool, which is used by /dev/random. Applications which need some extreme security tend to use /dev/random as their entropy source, or in other words, the randomness source.

If /dev/random runs out of available entropy, it's unable to serve out more randomness and the application waiting for the randomness stalls until more random stuff is available. The example I've seen during my career is that Cyrus IMAP daemon wanted to use /dev/random for the randomness and its POP sessions wanted to generate the random strings in APOP connections from /dev/random. In a busy environment there were more login attempts than traffic for feeding the /dev/random -> everything stalled. In that case I installed rng-tools and activated the rngd it had -- that shoveled semi-random numbers from /dev/urandom to /dev/random in case /dev/random ran out of "real" entropy.