Passwords - A Cracking Christmas (TryHackMe) 🧑‍🎄🎉

This challenge drops us back into the shifting world between Easter and Christmas, where the once‑stable systems of The Best Festival Company begin behaving strangely. Hidden deep within the servers, Sir Carrotbane stumbles upon a collection of encrypted PDF and ZIP files labelled “North Pole Asset List.” Rumours spread that these archives could contain fragments of Santa’s master gift registry — secrets that King Malhare could use to tip the festive balance in his favour.

At first, I genuinely struggled to get into the flow. It’s been a while since I was this hands‑on with cyber tasks, and switching between theory, Security+, and other study paths had made my practical skills feel a bit rusty. But once I started breaking down the steps, the challenge became fun — almost nostalgic. As things began to make sense again, I found myself really enjoying the process.

Sir Carrotbane now takes on the role of uncovering weak passwords, breaking poor encryption, and learning how easily sensitive data can leak when protectors rely on flawed password choices. The question becomes: can the Elves adapt quickly enough to secure their secrets, or will weak passwords expose the North Pole to chaos?

Introduction

The Story

With time between Easter and Christmas being destabilised, the once-quiet systems of The Best Festival Company began showing traces of encrypted data buried deep within their servers. Sir Carrotbane, stumbled upon a series of locked PDF and ZIP files labelled “North Pole Asset List.” Rumours spread that these could contain fragments of Santa’s master gift registry, critical information that could help Malhare control the festive balance between both worlds.

Sir Carrotbane sets out to crack the encryption, learning how weak passwords can expose even the most guarded secrets. Can the Elves adapt fast and prevent their secrets from being discovered?

Learning Objectives

• How password-based encryption protects files such as PDFs and ZIP archives.

• Why weak passwords make encrypted files vulnerable.

• How attackers use dictionary and brute-force attacks to recover passwords.

• A hands-on exercise: cracking the password of an encrypted file to reveal its contents.

• The importance of using strong, complex passwords to defend against these attacks.

A few simple points to remember:

• The strength of protection depends almost entirely on the password. Short or common passwords can be guessed; long, random passwords are far harder to break.

• Different file formats use different algorithms and key derivation methods. For example, PDF encryption and ZIP encryption differ in details (how the key is derived, salt use, number of hash iterations). That affects how easy or hard cracking is.

• Many consumer tools still support legacy or weak modes (particularly older ZIP encryption). That makes some encrypted archives much easier to attack than modern, well-implemented schemes.

• Encryption protects data confidentiality only. It does not prevent someone with access to the encrypted file from trying to guess the password offline.

To make it simple, encryption makes the contents unreadable unless the correct password is known. If the password is weak, an attacker can simply try likely passwords until one works.

Attacks Against Encrypted Files

How Attackers Recover Weak Passwords

Attackers don't usually try to "break" the encryption itself because that would take far too long with modern cryptography. Instead, they focus on guessing the password that protects the file. The two most common ways of doing this are dictionary attacks and brute-force (or mask) attacks.

Dictionary Attacks

In a dictionary attack, the attacker uses a predefined list of potential passwords, known as a wordlist, and tests each one until the correct password is found. These wordlists often contain leaked passwords from previous breaches, common substitutions like password123, predictable combinations of names and dates, and other patterns that people frequently use. Because many users choose weak or common passwords, dictionary attacks are usually fast and highly effective.

Mask Attacks

Brute-force and mask attacks go one step further. A brute-force attack systematically tries every possible combination of characters until it finds the right one. While this guarantees success eventually, the time it takes grows exponentially with the length and complexity of the password.

Mask attacks aim to reduce that time by limiting guesses to a specific format. For example, trying all combinations of three lowercase letters followed by two digits.

By narrowing the search space, mask attacks strike a balance between speed and thoroughness, especially when the attacker has some idea of how the password might be structured.

Practical tips attackers use (and defenders should know about):

• Start with a wordlist (fast wins). Common lists: rockyou.txt, common-passwords.txt.

• If the wordlist fails, move to targeted wordlists (company names, project names, or data from the target).

• If that fails, try mask or incremental attacks on short passwords (e.g. ?l?l?l?d?d = three lowercase letters + two digits, which is used as a password mask format by password cracking tools).

• Use GPU-accelerated cracking when possible; it dramatically speeds up attacks for some algorithms.

• Keep an eye on resource use: cracking is CPU/GPU intensive. That behaviour can be detected on a monitored endpoint.

Exercise

You will find the files for this section in the Desktop directory of the machine. Switch to it by running cd Desktop in your terminal.

1. Confirm the File Type

Use the file command or open the file with a hex viewer. This helps pick the right tool.

File Command

ubuntu@tryhackme:~/Desktop$ file flag.pdf
ubuntu@tryhackme:~/Desktop$ file flag.zip

If it's a PDF, proceed with PDF tools. If it's a ZIP, proceed with ZIP tools.

2. Tools to Use (pick one based on file type)

• PDF: pdfcrack, john (via pdf2john)

• ZIP: fcrackzip, john (via zip2john)

• General: john (very flexible) and hashcat (GPU acceleration, more advanced)

3. Try a Dictionary Attack First (fast, often successful)

Example: PDF with pdfcrack and rockyou.txt:

PdfCrack Command

ubuntu@tryhackme:~/Desktop$ pdfcrack -f flag.pdf -w /usr/share/wordlists/rockyou.txt 
PDF version 1.7
Security Handler: Standard
V: 2
R: 3
P: -1060
Length: 128
Encrypted Metadata: True
FileID: 3792b9a3671ef54bbfef57c6fe61ce5d
U: c46529c06b0ee2bab7338e9448d37c3200000000000000000000000000000000
O: 95d0ad7c11b1e7b3804b18a082dda96b4670584d0044ded849950243a8a367ff
Average Speed: 29538.5 w/s. Current Word: 's8t8a8r8'
Average Speed: 31068.0 w/s. Current Word: 'toby344'
Average Speed: 30443.7 w/s. Current Word: 'erikowa'
Average Speed: 29519.3 w/s. Current Word: '0848845800'
Average Speed: 29676.4 w/s. Current Word: 'u3904041'
Average Speed: 29339.8 w/s. Current Word: 'spider0187'
Average Speed: 30156.8 w/s. Current Word: 'roermond7'
Average Speed: 30364.8 w/s. Current Word: 'papaopass2'
found user-password: 'XXXXXXXXXX'

Example: using john

• Create a hash that John can understand: zip2john flag.zip > ziphash.txt

Terminal

ubuntu@tryhackme:~/Desktop$ zip2john flag.zip > ziphash.txt

• John will report the recovered password if it finds one.

Terminal

ubuntu@tryhackme:~/Desktop$ john --wordlist=/usr/share/wordlists/rockyou.txt ziphash.txt
Using default input encoding: UTF-8
Loaded 1 password hash (ZIP, WinZip [PBKDF2-SHA1 128/128 AVX 4x])
Cost 1 (HMAC size) is 29 for all loaded hashes
Will run 2 OpenMP threads
Press 'q' or Ctrl-C to abort, almost any other key for status
XXXXXXXXXXX      (flag.zip/flag.txt)     
1g 0:00:02:12 DONE (2025-10-03 08:26) 0.007552g/s 20696p/s 20696c/s 20696C/s winternights..wine23
Use the "--show" option to display all of the cracked passwords reliably
Session completed.

Detection of Indicators and Telemetry

Offline cracking does not hit login services, so lockouts and failed logon dashboards stay quiet. We can detect the work where it runs, on endpoints and jump boxes. The important signals to monitor include:

Process creation: Password cracking has a small set of well-known binaries and command patterns that we can look out for. A mix of process events, file activity, GPU signals, and network touches tied to tooling and wordlists. Our goal is to make the activity obvious without drowning in noise.

• Binaries and aliases: john, hashcat, fcrackzip, pdfcrack, zip2john, pdf2john.pl, 7z, qpdf, unzip, 7za, perl invoking pdf2john.pl.

• Command‑line traits: --wordlist, -w, --rules, --mask, -a 3, -m in Hashcat, references to rockyou.txt, SecLists, zip2john, pdf2john.

• Potfiles and state: ~/.john/john.pot, .hashcat/hashcat.potfile, john.rec.

It's worth noting that on Windows systems, Sysmon Event ID 1 captures process creation with full command line properties, while on Linux, auditd, execve, or EDR sensors capture binaries and arguments.

GPU and Resource Artefacts

GPU cracking is loud. Sudden high utilisation on hosts can be picked up and would need to be investigated.

• nvidia-smi shows long‑running processes named hashcat or john.

• High, steady GPU utilisation and power draw while the fan curve spikes.

• Libraries loaded: nvcuda.dll, OpenCL.dll, libcuda.so, amdocl64.dll.

Network Hints, Light but Useful

Offline cracking does not need the network once wordlists are present. Yet most operators fetch lists and tools first.

• Downloads of large text files named rockyou.txt, or Git clones of popular wordlist repos.

• Package installs, for example apt install john hashcat, detected by EDR package telemetry.

• Tool updates and driver fetches for GPU runtimes.

Unusual File Reads

Repeated reads of files such as wordlists or encrypted files would need analysis.

Detections

Below are some examples of detection rules and hunting queries we can put to use across various environments.

Sysmon:

(ProcessName="C:\Program Files\john\john.exe" OR
 ProcessName="C:\Tools\hashcat\hashcat.exe" OR
 CommandLine="*pdf2john.pl*" OR
 CommandLine="*zip2john*")

Linux audit rules, temporary for an investigation:

auditctl -w /usr/share/wordlists/rockyou.txt -p r -k wordlists_read
auditctl -a always,exit -F arch=b64 -S execve -F exe=/usr/bin/john -k crack_exec
auditctl -a always,exit -F arch=b64 -S execve -F exe=/usr/bin/hashcat -k crack_exec

Sigma style rule, Windows process create for cracking tools:

title: Password Cracking Tools Execution
id: 9f2f4d3e-4c16-4b0a-bb3a-7b1c6c001234
status: experimental
logsource:
  product: windows
  category: process_creation
detection:
  selection_name:
    Image|endswith:
      - '\john.exe'
      - '\hashcat.exe'
      - '\fcrackzip.exe'
      - '\pdfcrack.exe'
      - '\7z.exe'
      - '\qpdf.exe'
  selection_cmd:
    CommandLine|contains:
      - '--wordlist'
      - 'rockyou.txt'
      - 'zip2john'
      - 'pdf2john'
      - '--mask'
      - ' -a 3'
  condition: selection_name or selection_cmd
level: medium

Response Playbook

As security analysts in Wareville, it is important to have a playbook to follow when such incidents occur. The immediate actions to take are:

1. Isolate the host if malicious activity is detected. If it is a lab, tag and suppress.

2. Capture triage artefacts such as process list, process memory dump, nvidia-smi sample output, open files, and the encrypted file.

3. Preserve the working directory, wordlists, hash files, and shell history.

4. Review which files were decrypted. Search for follow‑on access, lateral movement or exfiltration.

5. Identify the origin and intent of the activity. Was this authorised? If not, escalate to the IR team.

6. Remediate the activity, rotate affected keys and passwords, and enforce MFA for accounts.

7. Close with education and correct placement of tools into approved sandboxes.

Answer the questions below

1. What is the flag inside the encrypted PDF?

   file flag.pdf

   file flag.zip

   pdfcrack -f flag.pdf -w /usr/share/wordlists/rockyou.txt

   john --wordlist=/usr/share/wordlists/rockyou.txt pdfhash.txt

   xdg-open flag.pdf

   

   

   

   The screen below will be launched which expects you to enter the password use naughtylist from above

   

   Once you enter the password, the flag will be revealed:

   

2. What is the flag inside the encrypted zip file?

   zip2john flag.zip > ziphash.txt

   john --wordlist=/usr/share/wordlists/rockyou.txt ziphash.txt

   unzip flag.zip

   7z x flag.zip

   cat flag.txt

   the flag.txt file has the flag

   

3. For those who want another challenge, have a look around the VM to get access to the key for Side Quest 2! Accessible through our Side Quest Hub!

4. If you enjoyed this task, feel free to check out the Password Attacks room.

This task was more than just cracking a PDF and ZIP archive — it was a reminder of how powerful (and dangerous) weak passwords can be. I started off rusty and honestly a bit lost, but as soon as the tools and patterns became familiar again, the challenge turned enjoyable. It felt good to get back into practical, hands‑on cyber work after spending so much time in theory.

Through dictionary attacks, hash extraction, testing wordlists, and understanding how various encryption methods behave, the exercise highlighted a simple truth: encryption is only as strong as the password protecting it. PDFs, ZIP files, and other archives can all fall quickly if their passwords are predictable or commonly used.

From an analyst’s perspective, we also saw how offline password cracking behaves, what telemetry it leaves behind, how detection rules can be written, and how defenders can respond to such activity.

By the end of the challenge, both encrypted files were successfully unlocked — proving once more why strong, unique, and complex passwords matter.

And if you’re looking for more practice, the VM even hints at a bonus key for Side Quest 2. For anyone who enjoyed this, the Password Attacks room is a great next step.