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penetration testing
Computing has to be the fastest moving industry there is. Every day there is at least one new software product. This is hard enough to keep up with if you are looking after one Operating System, let alone more - and as a PenTester you are interested in them all !

How on earth do you keep up to date ? ( And I'm perfectly open to suggestion here ... My e-mail inbox is bursting at the seams. )

These are your options :

1) Printed media - books, magazines, newsletters etc.
These are the slowest of all sources, however, this doesn't mean that you should discount them - just because something is old doesn't mean it will no longer be an issue - just look at Tom Jones... You will discover over time that a significant number of the vulnerabilities that you discover have been known, and patched for some time - just who ever you are testing overlooked / didn't patch / couldn't patch.

2) Electronic media - Mailing lists, web sites, newsletters etc.
This is where I get a great deal of information - subscribe to advisory lists, bug disclosure list, Security discussions, software mailing list, os mailing lists, and more - and then write some mail filters ! This brings a LOT of information in, and a lot of it is complete and utter garbage. But hidden in it all are the bits of gold that will get you a long way.
There are also databases which you can search for vulnerabilities, these can be very useful, although occasionally somewhat limited in what you can search on. I'm currently trying, with Perl, to create a database of all of the vulnerability alert e-mails that I have received over the last two years - this in combination with SQL will, I hope finally give me what I really want !

3) DIY ( Do It Yourself ... )
This is for all of you guys with loads of time on your hands and/or being paid to take time to find vulnerabilities. I think that these people are great, and I think, like many things, that this is something that everyone should take the time to learn how to do. ( Read the rest of TestingReflections for this ! ) The rest of us though are too busy trying to make a living ( or writing blogs :P ) to do this.

All of the above are of value, and keeping yourself up-to-date is no mean feat ! Try keeping a notebook / diary of things as you come accross them - the action of writing things down always help me to remember, and it is ( sadly ) often still easier to flick back through a notebook than it is to find one e-mail in 5000. You can also make notes against the vulnerabilities that you come accross most often, this will make testing for these obvious and common problems much quicker and easier, and will eventually get 90% done in the first 5 minutes !

Here are some links to consider:
Secunia Security Advisories
CERT
Insecure.org
SecurityFocus
Bugtraq

That should keep you busy for a while :)