During a CTF game, we came across very-very old systems. Turns out, it is not that easy to hack those dinosaur old systems, because modern tools like Metasploit do not have sploits for those old boxes and of course our "133t h4cking skillz" are useless without Metasploit... :)

The rules for the hack are the following:

I have chosen Windows 95 for this task. First, I had to get a genuine Windows 95 installer, so I visited the Microsoft online shop and downloaded it from their official site.

I installed it in a virtualized environment (remember, you need a boot floppy to install from the CD), and it hit me with a serious nostalgia bomb after watching the installer screens. "Easier to use", "faster and more efficient", "high-powered performance", "friendly", "intuitive interface". Who does not want that? :)

Now that I have a working Windows 95 box, setting up the TCP/IP is easy, let's try to hack it!

My first tool is always nmap. Let's scan the box! Below I'm showing the interesting parts from the result:

PORT      STATE           SERVICE       VERSION
139/tcp   open            netbios-ssn
137/udp   open|filtered   netbios-ns
138/udp   open|filtered   netbios-dgm
Running: Microsoft Windows 3.X|95
OS details: Microsoft Windows for Workgroups 3.11 or Windows 95
TCP Sequence Prediction: Difficulty=25 (Good luck!)
IP ID Sequence Generation: Broken little-endian incremental

The first exciting thing to note is that there is no port 445! Port 445 is only since NT 4.0. If you check all the famous windows sploits (e.g., MS03-026, MS08-067), all of them use port 445 and named pipes. But there are no named pipes on Windows 95!

Because I'm a Nessus monkey, let's run a free Nessus scan on it!

Only one critical vulnerability found:

Microsoft Windows NT 4.0 Unsupported Installation Detection

Thanks for nothing, Nessus! But at least it was for free.

Next, I tried GFI Languard, nothing. It detected the machine as Win95, the opened TCP port, and some UDP ports as open (false-positive), and that's all...

Let's try another free vulnerability scanner tool, Nexpose. The results are much better:

I think the following vulnerabilities are useless for me at the moment:

But we have two interesting vulns:

The vulnerability description at MS side:

For example if the password is "Password" (without quotes) and the client sends the password "P" (without quotes) and the length of 1, the client is authenticated. To find the rest of the password, the attacker increments the length to 2 and starts guessing the second letter until he reaches "PA" and gets authenticated again. As share passwords in Windows 95 are not case sensitive, "Pa" and "PA" will also be accepted. The attacker can continue to increment the length and guessing the next letter one-by-one until he gets the full "PASSWORD" (as the maximum length is 8 characters).

I believe all characters between ALT+033 and ALT+255 can be used in the share password in Windows 95, but as it is case insensitive, we have 196 characters to use, and a maximum length of 8 characters. In worst case this means that we can guess the full password in 1568 requests. The funny thing is that the share password is not connected to (by default) any username/account, and it cannot be locked via brute force.

Luckily there is a great tool which can exploit this vulnerability:

Let's check this tool in action:

W00t w00t, it brute forced the password in less then 2 seconds!

Looking at a wireshark dump we can see how it is done:

As you can see, in the middle of the dump we can see that it already guessed the part "PASS" and it is brute-forcing the fifth character, it founds that "W" is the correct fifth character, and starts brute-forcing the sixth character.

If we are lucky with the CTF, the whole C:\ drive is shared with full read-write access, and we can write our team identifier into the c:\flag.txt. But what if we want remote code execution? Stay tuned, this is going to be the topic of the next part of this post.