In a post Heartbleed world, implementation of SSL is being scrutinized like never before (at least in my short years of experience in information security). Even though Microsoft/IIS implementations were hardly, if at all, affected by Heartbleed, they do often suffer from other common SSL vulnerabilities. This is particularly true of Microsoft Server 2003 R2 / IIS 6.5 and older setups.

Back in the olden days (you know, like 5 – 10 years ago…) before massive Chinese super-computers, NSA spying programs, and 30-core processors, a 48-Bit SSL cipher may have been considered sufficient as the length of time it would take to brute-force decrypt collected data was significant on the hardware of the day. No so much anymore.

Fast forward to today, many environments still have aging servers sitting around from a bygone era whose weak implementation of SSL pose a security risk. It is time to turn off archaic SSL ciphers on these old boxes and strengthen your connection security.

So… before you read any further, you need to check a few things to find out if this article is relevant to you.

First, do you host any websites in IIS that use SSL? (i.e. do they have “HTTPS” preceding the URL?) (more…)