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[X3N]

hackthissite.org
They have pretty cool challenges. The stenography ones completely baffle me though.

[Aquin]

Yeah, I'm working my way through them now.  I gotta say, this is pretty fun stuff!  I've always wanted to learn the specifics of a lot of techniques.  It's a great starting point if you wanna get into this stuff.

Right, I'm gonna try the Advanced challenges now.  Yikes! 

[Riley Adams]

I worked through some of that a while back, fun stuff. I liked the programming challenges, sorta like Project Euler but without the emphasis on math...

[AusGat]

Looks like fun. I just tried a few of the challenges, but I may try some more later. I have always wanted to be a hacker, but I'm busy with other computer stuff.

[nikki]

thanks for this link

i just worked myself through the basic missions, and i feel like a 
now the realistic ones !

[Cthulhu32]

I had an account on there that was ranked pretty high before they had a major server crash and lost half their accounts. That site is not shabby for beginners, I'm actually pretty active in a local security group called dc303 (www.dc303.org) I've done one presentation, and one tetris server hacking challenge for the group so far.

If you're finding those challenges too easy, I'd suggest looking at OverTheWire. Its probably the most realistic/hardcore reversing hacking challenge I know of.

http://www.overthewire.org/wargames/vortex/

Last time I played that, I got stuck on Level 4 and never made it past. Its very challenging, but I enjoy it. Also, NOPs 'R Us post the qualifiers and sometimes the full CTF games for Defcon every year with solutions. Some of them are f'ing impossible, but others are great challenges if you're just getting the hang of reversing and exploiting.

http://nopsr.us/

[Aquin]

Thanks man, I was running out of material on hackthissite.org.  I only have a few challenges left!  I really enjoy the later realistic missions, since it feels like I'm doing something real instead of looking for planted weaknesses.

I also appreciate the attention to detail.  Fake e-mails, cute text, old-school looks, and an overall silly parody of the originals (Yuppers! was a big favourite.)  I'd be surprised to find another website that has that kinda stuff.  It *sucks* that hackthissite doesn't seem to update in that vein anymore. 

[skyy]

"Rise from your grave~~"  

Another site that follows the "figure out what to do approach and solve it!" is this:
http://www.pythonchallenge.com/

Don't let the name fool you, it's mainly aimed for python guys but there is NOTHING stopping you from doing the tasks with what ever you want. Starts off stupidly easy, the later ones you need to read in certain pixels from image and figure out what they mean and after that they just rocketed into "stupidly hard" for me and I got stuck. Too bad I don't remember where I got stuck to Meh. I guess I'll work through them again at some point and try to finish it this time!

So basically any language goes for solving. Reading in images, reading pixels, shifting chars and doing basic calculations + few other things.