Unlocking Word Docs: The Comedy of Cracking Passwords with Python

Hot Take:

Looks like Microsoft Word wanted to join the exclusive “Fort Knox of Office Files” club, but ended up being more like “The Great Escape” for hackers. Yes, they have document protection, but it’s more like a “suggestion box” for determined cyber sleuths!

Key Points:

• Word documents can be protected using the w:documentProtection element in the word/settings.xml file.
• The hash algorithm for protected Word docs is the same as for OOXML spreadsheets, but the password encoding differs.
• A legacy algorithm preprocesses the password before it’s repeatedly hashed, making tools like hashcat ineffective.
• Python implementations can be used to decode the password preprocessing.
• With the right salt and password, calculated hashes can match stored hashes, confirming the password.

Cracking the Code: Document Protection in Word

If you thought your “super-secret” Microsoft Word document was safe with its fancy w:documentProtection element, think again. Apparently, it’s more like putting a “Do Not Enter” sign on an open field. The hash algorithm might be the same as for OOXML spreadsheets, but don’t get too comfy. Your favorite password-cracking tool, hashcat, won’t be of much help here. Why? Because Microsoft decided to take a trip down memory lane and use a legacy algorithm to preprocess the password. It’s like they found an old recipe book and stuck to it, no matter how outdated it is.

Python Saves the Day (Again)

Good news for those who love a good Python script! There’s a Python implementation floating around that can help decode this archaic password preprocessing method. So, if you’re not afraid of a little coding, you can take a peek behind the curtain and see how your Word document password gets prepped before hashing.

Matrix Magic: The Encryption Matrix

Ready for some fun with matrices? The encryption process involves an array of high-order word lists and a complex encryption matrix. It’s like a Sudoku puzzle, but instead of numbers, you’re dealing with hex values. The password is encoded, sliced, diced, and finally dressed up in a hex string ready for hashing. It’s a lot of work for something that’s supposed to keep your document safe, but hey, who doesn’t love a good encryption challenge?

Hashing It Out

Once the password is properly encoded, it’s time for the hashing marathon. The password (now in its hex-string glory) gets hashed with a salt using SHA-512, and then hashed again. And again. And again—100,000 times, to be exact. It’s like running a marathon 100,000 times to ensure no one else can catch up. With the right salt and password, you can calculate the hash and see if it matches what’s stored. If it does, congrats, you’ve cracked the code!

But Is It Worth It?

So, what’s the takeaway here? Microsoft Word document protection is a bit of a mixed bag. Sure, it adds a layer of security, but if someone’s determined enough (and has a penchant for Python scripts and hashing marathons), they can break through. It’s a reminder that no matter how secure something seems, there’s always someone out there ready to take on the challenge. So, maybe think twice before using Word’s built-in protection for your top-secret files. Or, you know, just add another layer of security for good measure.

In conclusion, while Microsoft Word’s document protection might look impressive on the surface, it has its vulnerabilities. With some coding know-how and patience, those barriers can be bypassed. So, stay vigilant and combine multiple security measures to keep your document fortress strong!