Didier Stevens

TL;DR: PDFs protected with 40-bit keys can not guarantee confidentiality, even with strong passwords. When you protect your PDFs with a password, you have to encrypt your PDFs with strong passwords and use long enough keys. The PDF specification has evolved over time, and with it, the encryption options you have. There are many encryption options today, you are no longer restricted to 40-bit keys. You can use 128-bit or 256-bit keys too.

There is a trade-off too: the more advanced encryption option you use, the more recent the PDF reader must be to support the encryption option you selected. Older PDF readers are not able to handle 256-bit AES for example.

Since each application capable of creating PDFs will have different options and descriptions for encryption, I can not tell you what options to use for your particular application. There are just too many different applications and versions. But if you are not sure if you selected an encryption option that will use long enough keys, you can always check the /Encrypt dictionary of the PDF you created, for example with my pdf-parser (in this example /Length 128 tells us a 128-bit key is used):

Or you can use QPDF to encrypt an existing PDF (I’ll publish a blog post later with encryption examples for QPDF).

But don’t use 40-bit keys, unless confidentiality is not important to you:

I first showed (almost 4 years ago) how PDFs with 40-bit keys can be decrypted in minutes, using a commercial tool with rainbow tables. This video illustrates this.

Later I showed how this can be done with free, open source tools: Hashcat and John the Ripper. But although I could recover the encryption key using Hashcat, I still had to use a commercial tool to do the actual decryption with the key recovered by Hashcat.

Today, this is no longer the case: in this series of blog posts, I show how to recover the password, how to recover the key and how to decrypt with the key, all with free, open source tools.

Overview of the complete blog post series:

• • Cracking Encrypted PDFs – Part 1: cracking the password of a PDF and decrypting it
  • 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 (what you are reading now)

I performed a brute-force attack on the password of an encrypted PDF and a brute-force attack on the key of (another) encrypted PDF, both PDFs are part of a challenge published by John August.

The encryption key is derived from the password. it’s not just based on the password only, but also on metadata. This implies that different PDFs encrypted with the same user password, will have different encryption keys.

When you recover the user password of an encrypted PDF, you can just use it with PDF readers like Adobe Reader: they will ask you for the password, you provide it and the PDF will be decrypted and rendered.

But when you recover the key of an encrypted PDF, you can not use it with PDF reader: there is no feature that will allow you to input a key in stead of a password. The only method I knew to decrypt a PDF document with its encryption key, was to use Elcomsoft’s PDF cracking tool:

Now I worked out a second method: I modified the source code of QPDF so that it will accept encryption keys too. It’s a quick and dirty hack, I did not add a new option to QPDF but I “hijacked” the –password option. If the value to the option –password starts with string “key:”, then QPDF will not derive the key from the provided password, but it will use the key provided as hexadecimal characters. Here is how I use it to decrypt the “tough” PDF:

I also made a small modification to the –show-encryption option, to display the encryption key:

Update: I had an email exchange with Jay Berkenbilt, the author of QPDF, and he will look into this patch and possibly add a new key option to QPDF.

If you are interested in my modified version of QPDF, you can find the modified source code files and Windows binaries here:

qpdf-patched.zip (https)
MD5: 57E1A5A232E12B45D0A927181A1E8C3B
SHA256: 6F17E095B38AE72F229A6662216DDCE86057D2BA1C567B07FEF78B8A93413495

Update: this is the complete blog post series:

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

After cracking the “easy” PDF of John’s challenge, I’m cracking the “tough” PDF (harder_encryption).

Using the same steps as for the “easy” PDF, I confirm the PDF is encrypted with a user password using 40-bit encryption, and I extract the hash.

Since the password is a long random password, a brute-force attack on the password like I did in the first part will take too long. That’s why I’m going to perform a brute-force attack on the key: using 40-bit encryption means that the key is just 5 bytes long, and that will take about 2 hours on my machine. The key is derived from the password.

I’m using hashcat again, but this time with hash mode 10410 in stead of 10400.
This is the command I’m using:

hashcat-4.0.0\hashcat64.exe --potfile-path=harder_encryption.pot -m 10410 -a 3 -w 3 "harder_encryption - CONFIDENTIAL.hash" ?b?b?b?b?b

I’m using the following options:

• –potfile-path=harder_encryption.pot : I prefer using a dedicated pot file, but this is optional
• -m 10410 : this hash mode is suitable to crack the key used for 40-bit PDF encryption
• -a 3 : I perform a brute force attack (since it’s a key, not a password)
• -w 3 : I’m using a workload profile that is supposed to speed up cracking on my machine
• ?b?b?b?b?b : I’m providing a mask for 5 bytes (I want to brute-force keys that are 40 bits long, i.e. 5 bytes)

And here is the result:

The recovered key is 27ce78c81a. I was lucky, it took about 15 minutes to recover this key (again, using GPU GeForce GTX 980M, 2048/8192 MB allocatable, 12MCU). Checking the complete keyspace whould take a bit more than 2 hours.

Now, how can we decrypt a PDF with the key (in stead of the password)? I’ll explain that in the next blog post.

Want a hint? Take a look at my Tweet!

Update: this is the complete blog post series:

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

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).

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

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.

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:

hashcat-4.0.0\hashcat64.exe --potfile-path=encryption_test.pot -m 10400 -a 3 -i "encryption_test - CONFIDENTIAL.hash" ?a?a?a?a?a?a

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