ISSP - Inter-Solar System Police

ISSP is an intentionally vulnerable Active Directory testing lab. It is designed for myself or others to explore and practice AD exploitation techniques in a controlled environment. In the world of Cowboy Bebop, you are taking the role of Edward Wong Hau Pepelu Tivrusky IV, a brilliant hacker who is trying to infiltrate the ISSP's Active Directory.

How to Deploy

Prerequisites

# - Ansible
# - Packer
# - VirtualBox (for local) 
# - AWS CLI + Terraform (for AWS)

# Install Packer plugins
packer plugin install github.com/hashicorp/virtualbox
packer plugin install github.com/hashicorp/amazon

Option 1: Local Deployment

# build images
cd packer/virtualbox/[jet-dc and spike-clt and ed-atk]
packer build .

# test connectivity and run playbooks
cd ../../../ansible
ansible windows -i virtualbox/inventory.ini -m win_ping
ansible-playbook -i virtualbox/inventory.ini issp.yml

Option 2: AWS Deployment

# configure aws creds
aws configure

# create a keypair for ssh access
aws ec2 create-key-pair --key-name [name] --query 'KeyMaterial' --output text > [name].pem
chmod 400 [name].pem

# build images
cd packer/aws/[jet-dc and ed-atk]
packer build .

# edit terraform/terraform.tfvars to include custom ami etc
nvim terraform/terraform.tfvars

# deploy the infrastructure
cd terraform
terraform init
terraform plan
terraform apply

# edit aws/inventory.ini to include public ip
nvim ../ansible/aws/inventory.ini

# run playbooks
cd ../ansible/aws
ansible-playbook -i inventory.ini issp.yml

Vulnerabilities

inspired by this script

• Weak Password Policy
• Kerberoasting
• AS-REP Roasting
• SMB Signing Disabled
• Privilege Escalation (DNS Admins, Group Nesting)
• Constrained Delegation
• Unconstrained Delegation
• Weak Shares