Hackfail.htb [top] (2026)

You are www-data . The group tech owns that folder. You aren't in tech ... user1 is. And you have a user1 hash from the Flask database? No. But you do have an LFI via the debugger that lets you read /home/user1/.ssh/id_rsa .

This article explores the typical architecture, attack vectors, and lessons learned from engaging with the "hackfail" challenge, providing a roadmap for those looking to sharpen their penetration testing skills. hackfail.htb

======================================= hackfail.htb "Where exploits come to die... slowly." ======================================= You are www-data

Because DEBUG=True and you have a SECRET_KEY , you can craft a Flask session cookie that forces a server-side template inclusion. A known exploit chain: Use the secret key to sign a cookie with a malicious session value that reads files. user1 is

flask-unsign --sign --cookie "'user': '__import__(\"os\").popen(\"cat /etc/machine-id\").read()'" --secret 'supersecret-fail-key-2023'