sniffing / brute-forcing http password

Hello
I have an IIS server that uses simple username / password authentication to secure a directory. the username and password are created in windows as local users. it does not use SSL or anything like that.
is there any way someone on the internet may get hold of my username and / or password ? i.e. if they get hold of the username, is there any way / method / tool that would enable them to brute-force their way into the password? if so, where can I find that tool so that I can do some self-tests for vulnerability?
eggster34Asked:
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Rich RumbleConnect With a Mentor Security SamuraiCommented:
Sniffing comes down to access for the most part. A cable modem user, may be able to sniff his/her neighbors traffic if the traffic is broadcast, arp has been poisioned, or the subnet/ip is not segregated well enough. If someone were to hack into, or gain physical access to a ISP's lan or equipment, your traffic could be sniffed. The latter is far less common, but the government is doing it currently, and for some time now.
There are many techniques to sniffing, but it's really about the boundries and access. If your on a company lan, the network adminitrator can sniff what ever port he/she want's to, any time. If it's your co-worker next to you, and they fire up ethereal, cain&abel etc... they might be able to see this info.

Most times brute-force isn't even necessary, there are a lot of protocols that are very very plain-text, and or obusifcated poorly. FTP is plain-text, SMTP is... lot's of stuff that probably should be secured isn't. Sniffing that traffic can be difficult, but there are techniques as I said.
http://en.wikipedia.org/wiki/ARP_spoofing (the links at the bottom, and in the article are good to read also)
http://en.wikipedia.org/wiki/Packet_sniffer
http://en.wikipedia.org/wiki/Man-in-the-middle
-rich
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kaerezCommented:
This method is highly suseptible to sniffing and brute force attacks and a hacker
can sniff the packets and gain entry as in regular http login the passwords are
sent in plain text.

I recomment implementing an SSL certificate, if it's not a corporate web site you
can us www.cacert.org to get great 128 bit certificates.

I hope I answered your question.
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DireOrbAntCommented:
Even with SSL, brute force attacks are highly possible.
The best way arrount it is to lock accouts after x bad tries within a time window.
If the authentication is done on the OS side, you might have those already in place or you should :)
If not, you'll need to code that in your Authentication scheme.
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eggster34Author Commented:
ok. my question is how someone would be able to sniff and brute force the password?
are there any documented methods / tools you can suggest so that I can try, learn and see for myself how it's done?
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kaerezCommented:
You can sniff the packets on a PC using different programs such as Ethereal
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DireOrbAntCommented:
Write a script that connects to your secured site and provide username/password to it.
Loop through requests that will try a u/p until it finds a valid one.

I'm not sure the policy of this site allows us to post links to such tools ;)
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eggster34Author Commented:
kaerez

my server is somewhere on the internet, it's not local. I'm trying to find out how someone on the internet can sniff those packets going back and forth to and from the server.
I know how to sniff packets with ethereal, but as far as I know it only works on a local network segment.

DireOrbAnt, if you know of such tools, please email a link to me to cezmi_at_aycasadikoglu_dot_com
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CoccoBillCommented:
"my server is somewhere on the internet"

I agree with DireOrbAnt, it's against the policies of this site to teach how to crack passwords on websites.
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kaerezCommented:
As mentioned this cannot be tought here that said
for security tests you can sniff packets either at
the server side or your (client) side.
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nociSoftware EngineerCommented:
To name another leak:

If you're going through an Europe based ISP/Site, soon (at the latest januari 1st, 2007) all kinds of traffic are logged and stored
by the various governments this is mandatory for every ISP that wants to stay in business within the EU. So all unencrypted traffic
will be legible by various people in the government. (Theoretically after a warrent has been issued....)
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