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Is there a website I can log into that will can check various exploits on my system, and basically tell me if it's patched up-to-date?

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I think you would be better of by installing Nessus on your own computer. Nessus is free for home use and have a commercial version available too, and it lets you actively probe servers with a wide range of plugins.

Check it out: http://www.nessus.org/nessus/

Also.. could you trust a public webpage that probed your computer for errors? Setting up such a server would probably mean lots of problems for the host, since it would trigger IDS-alerts from other network providers. And you have no guarantee that they won't abuse their findings.

EDIT: Didn't know that they had changed the license on the plugin-feeds. Thanks K. Brian Kelley. Still worth it though. Superb software.

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The plug-ins update is only free if you're a home user. If you're corporate, it's not any longer. nessus.org/plugins/index.php?view=feed – K. Brian Kelley May 28 '09 at 13:18
This is the same software that many professional security companies use to audit networks. It is very powerful. – Brent May 28 '09 at 14:02
I agree, it is a shame they changed the licensing, but they became corporate and you can't blame them. The cost isn't bad, either. However, as soon as they went that direction, we started looking at other pay solutions like eEye's and Qualys. – K. Brian Kelley May 28 '09 at 19:02
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Also, you can try XSpider

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Qualys (http://www.qualys.com) provides a service that does this, but as with my comment to Commander Keen, it's not free. Qualys is generally recognized, too, having spoken with several IDS/IPS providers who also provide security monitoring services. The advantage with Qualys is you can get an appliance for inside your network, but you can also schedule a scan from one of their devices on the Internet.

There are also solutions like McAfee Secure (formerly HackerSafe) which provide those type of scanning services automatically.

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Secunia has some more advanced remote and local services but in this case, their free tool PSI thoroughly checks for unpatched software on a consumer level.

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Qualys offers that (not free), but you can get a free trial:

http://www.qualys.com/products/trials/

There is also a little project that I am developing (free) to look for leaking data on a web site: http://sucuri.net/?page=scan

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