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Cracking Encrypted PDFs – Part 1

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In this series of blog posts, I’ll explain how I decrypted the encrypted PDFs shared by John August (John wanted to know how easy it is to crack encrypted PDFs, and started a challenge).

Here is how I decrypted the “easy” PDF (encryption_test).

  • Cracking of PDF files encrypted with 40-bit keys usually takes a few minutes if you use Elcomsoft’s Enterprise edition of Advanced PDF Password Recovery. This is because it attacks the encryption key instead of attempting to guess the password. Other PDF password crackers will take 1-2 days to crack 40 bit encrypted PDFs.
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  • How to Print Protected PDF Files. By: Nick Davis. Share; Share on Facebook; Portable Document Format (PDF) files are sent, received and opened by people around the world everyday. The PDF format allows any computer user to open and view a document created on any platform including Windows, Mac and Linux. The files are compact, easily emailed.

From John’s blog post, I know the password is random and short. So first, let’s check out how the PDF is encrypted.

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pdfid.py confirms the PDF is encrypted (name /Encrypt):

pdf-parser.py can tell us more:

The encryption info is in object 26:

From this I can conclude that the standard encryption filter was used. This encryption method uses a 40-bit key (usually indicated by a dictionary entry: /Length 40, but this is missing here).

PDFs can be encrypted for confidentiality (requiring a so-called user password /U) or for DRM (using a so-called owner password /O). PDFs encrypted with a user password can only be opened by providing this password. PDFs encrypted with a owner password can be opened without providing a password, but some restrictions will apply (for example, printing could be disabled).

QPDF can be used to determine if the PDF is protected with a user password or an owner password:

This output (invalid password) tells us the PDF document is encrypted with a user password.

I’ve written some blog posts about decrypting PDFs, but because we need to perform a brute-force attack here (it’s a short random password), this time I’m going to use hashcat to crack the password.

First we need to extract the hash to crack from the PDF. I’m using pdf2john.py to do this. Remark that John the Ripper (Jumbo version) is now using pdf2john.pl (a Perl program), because there were some issues with the Python program (pdf2john.py). For example, it would not properly generate a hash for 40-bit keys when the /Length name was not specified (like is the case here). However, I use a patched version of pdf2john.py that properly handles default 40-bit keys.

Here’s how we extract the hash:

This format is suitable for John the Ripper, but not for hashcat. For hashcat, just the hash is needed (field 2), and no other fields.

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Let’s extract field 2 (you can use awk instead of csv-cut.py):

I’m storing the output in file “encryption_test – CONFIDENTIAL.hash”.

And now we can finally use hashcat. This is the command I’m using:

I’m using the following options:

  • –potfile-path=encryption_test.pot : I prefer using a dedicated pot file, but this is optional
  • -m 10400 : this hash mode is suitable to crack the password used for 40-bit PDF encryption
  • -a 3 : I perform a brute force attack (since it’s a random password)
  • ?a?a?a?a?a?a : I’m providing a mask for 6 alphanumeric characters (I want to brute-force passwords up to 6 alphanumeric characters, I’m assuming when John mentions a short password, it’s not longer than 6 characters)
  • -i : this incremental option makes that the set of generated password is not only 6 characters long, but also 1, 2, 3, 4 and 5 characters long

And here is the result:

The recovered password is 1806. We can confirm this with QPDF:

Conclusion: PDFs protected with a 4 character user password using 40-bit encryption can be cracked in a couple of seconds using free, open-source tools.

FYI, I used the following GPU: GeForce GTX 980M, 2048/8192 MB allocatable, 12MCU

Update: this is the complete blog post series:

      • Cracking Encrypted PDFs – Part 1: cracking the password of a PDF and decrypting it (what you are reading now)
      • Cracking Encrypted PDFs – Part 2: cracking the encryption key of a PDF
      • Cracking Encrypted PDFs – Part 3: decrypting a PDF with its encryption key
      • Cracking Encrypted PDFs – Conclusion: don’t use 40-bit keys

Short Bytes: Forgetting PDF passwords is something that happens to us all the time. In this article, I’m here with the 5 best free PDF password remover software that will help you instantly. Take a look.

PFileopen Pdf Crackassword protected PDF files add an extra layer of security to your documents. But, what if you forget the PDF password and you urgently need to access its content? Well, you are at right place as in this article, I’m going to tell you about the 5 best PDF password remover software to crack any protected file.

For those who don’t know, a PDF password remover tool is a computer program that is used to remove or bypass the security layers that don’t allow you to open the password protected PDF files.

On the internet, you’ll come across various programs with names PDF password crackers, password recovery tools/software or password reset tools. Don’t worry, all these have different names, but they perform a similar function.

Also read: How to Crack WinRAR Password Protected Files In Simple Steps

If you search online, you’ll come across plenty of PDF password remover software, but most of them cost you some chunk of money. Here, I’m going to tell you the 5 best and free PDF password remover software that you can use to recover your forgotten password.

Disclaimer: Use these tools to remove the passwords from the files you own and you’ve forgotten their password. Don’t use them for illegal purposes.

I’ll be telling you the benefits and limitations of each tool and which kind of methods these tools employ to break the security of PDF files.:

1. PDFCrack:

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PDFCrack is my favorite PDF password remover software. It’s a password recovery tool that recovers the forgotten password and helps you to access the hidden content.

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It recovers both the user and owner passwords from the password protected files. For those who don’t know, user passwords just restrict the opening of documents and owner passwords put restrictions like printing, changing, copying, comments etc.

This PDF password remover software works fine with PDF files up to version 1.6 protected with 128-bit RC4 encryption. The PDFCrack software deploys brute-force attack to recover the password.

Our rating: 4.5/5

Download here: PDFCrack

2. PDF Password Remover

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PDF Password Remover is a simple tool that removes the PDF owner passwords and works with a simple interface.

The PDF Password Remover software works with PDF files up to version 1.7 level 8 files protected with 128-bit RC4 encryption. This tool is easy to use but it doesn’t work with the PDF files with a user password and higher levels of encryption.

Our rating: 4/5

Download here: PDF Password Remover

3. PDF Unlocker

This PDF password remover software is a basic Windows program designed to unlock a file protected with encryption. This tool is helpful if you just want to break the permission security in the PDF, but it doesn’t remove the user password unless you know it.

PDF Unlocker supports and unlocks PDF files up to version 1.7 level 8 with 128-bit AES encryption.

Actually it’s a PDF password recovery tool as it discovers the actual owner password and you can use a brute-force or a dictionary password attack method.

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Our rating: 3.5/5

Download here: PDF Unlocker

4. PDFCrypt

PDFCrypt is the fifth tool on our free PDF password remover software list. It’s a simple command-line PDF password remover tool that performs the task instantly.

It should be noted that it’s a password remover software and it won’t tell you the user or owner password.

Our rating: 3.5/5

Download here: PDFCrypt

5. PDFMate Free PDF Merger

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I’ve included this free PDF password remover software as apart from cracking the passwords, it works as a PDF joiner, PDF combiner and an image to PDF converter.

With this free software, you can delete the unwanted pages and rearrange them in the desired order in high speed and accuracy.

The software also works as a PDF encrypter and offers you the option to protect your PDF files and set a password.

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Our rating: 3/5

Download here: PDFMate Free PDF Merger

My Recommendation: I recommend using PDFCrack PDF password remover software as it is 100% free and it performs all the desired functions. However, if you don’t want to download the software and do the job online, FreeMyPDF.com is the ultimate website.

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Did you find this list helpful? Which tool do you use for PDF password cracking? Tell us in the comments below.

Also read: How to Crack WinRAR Password Protected Files In Simple Steps