Tommy Boy: 1

  • Name: Tommy Boy: 1
  • Date release: 27 Jul 2016


(Size: 1.4 GB)



HOLY SCHNIKES! Tommy Boy needs your help!

The Callahan Auto company has finally entered the world of modern technology and stood up a Web server for their customers to use for ordering brake pads.

Unfortunately, the site just went down and the only person with admin credentials is Tom Callahan Sr. - who just passed away! And to make matters worse, the only other guy with knowledge of the server just quit!

You'll need to help Tom Jr., Richard and Michelle get the Web page restored again. Otherwise Callahan Auto will most certainly go out of business :-(



The primary objective is to restore a backup copy of the homepage to Callahan Auto's server. However, to consider the box fully pwned, you'll need to collect 5 flags strewn about the system, and use the data inside them to unlock one final message.

Other info


  • Size: 1.3GB
  • Hypervisor: Created with VMWare Fusion 8.1.1.
  • Difficulty: ?

Special thanks to


  • Rand0mbytez for testing about 10 versions of this frickin' thing to get the bugs worked out.
  • RobertWinkel for additional detailed testing and suggestions for tweaking the VM for a better overall experience.

  • Filename: TommyBoy1dot0.ova
  • File size: 1.4 GB
  • MD5: E7CBE794995EA7C0344A354F339495D1
  • SHA1: E26272DB76CA014BA8FD523D8AFC06E2C18F847C

  • Format: Virtual Machine (Virtualbox - OVA)
  • Operating System: Linux

  • DHCP service: Enabled
  • IP address: Automatically assign