Secunia, a security company that tracks known vulnerabilities in software and operating systems, has a downloadable beta of a new free utility that can identify missing Windows patches and outdated, insecure software on your PC.
The Secunia Personal Software Inspector isn't perfect, but it offers a wealth of information about potentially risky old software. And since keeping your system up-to-date is one of the best things you can do to stay safe, it's a pretty useful program.

The company says it can scan for more than 4,200 different programs and determine versions according to the "meta-data of executables and library files." In some cases that might not return the correct version - PSI told me I had an insecure 2.0.0.0 version of Thunderbird installed, but the mail program is already up-to-date at 2.0.0.5. It's possible that the discrepancy is a bug, since this is beta software.
If you click the program name for any listed insecure software, you'll get handy links to patches or newer software versions. You'll also get a link to Secunia's advisory about why your version isn't safe, and explanations for why you might see three versions of the Micromedia Flash Player installed, for instance.

To get all this data, the program communicates with Secunia's servers. According to the privacy statement, the company stores data about your installed programs for up to 12 months, but doesn't collect any personal data beyond their version numbers. It also says it will publish aggregate statistics based on the data. In the past that has been along the lines of "28 percent of all detected applications are insecure."