CompTIA PenTest+ TTT VM Readme file Author: Lee McWhorter (lee@mcwhortertechnologies.com) This Readme provides information about the VirtualBox Virtual Machines provided as part of the CompTIA PenTest+ Train the Trainer (TTT) series held during the summer of 2018. PROVIDED: All provided VMs are setup on Host-only with no gateway and on the 192.168.13.x network. VirtualBox in effect acts as a switch and all can connect via this virtual Host-only network. They all use the Net-Server VM at 192.168.13.250 as DNS server for the test.test 'domain.' PenTest+_TTT_VM_Kali is assigned the IP of 192.168.13.13 and also has a second NAT interface set up by DHCP. (Uses standard Kali root/toor as username/pw). This is the full, standard version of the importable VM. The only thing that has been changed is the networking. PenTest+_TTT_VM_Dev-Client was built using Ubuntu Desktop 18.04 and is assigned the IP of 192.168.13.150 (Uses victim/victim as username/pw for main user which can sudo). Also has a Dev Account (dev/dev) for scripting/development work and testing. This VM has Python3, Ruby, BASH, and PowerShell as well as the Visual Studio Code editor. PenTest+_TTT_VM_Net-Server was built using Ubuntu Server 16.04 and is assigned the IP of 192.168.13.250 (Uses mail-admin/mail-admin as username/pw for main user which can sudo). It has EMAIL, DNS, and HTTP services and DNS records for a test.test 'domain.' Also has two other users: victim (victim/victim) and victim2 (victim2/victim2). PenTest+_TTT_VM_Meta2 is assigned the IP of 192.168.13.251 (Uses standard msfadmin/msfadmin as username/pw). It is a full version of Metasploitable2, converted to Virtualbox format using the provided VMWare VM files. NOT PROVIDED: A Win10-Target VM can be built using the Windows 10 Enterprise 90 trial download, if no other older version of Windows is available. Older version are better for showing more exploits, but the only 'free' Windows version at this time is the Windows 10 Enterprise trial. Make sure this VM is also on Host-only before first boot and make a local account using: Username/PW: victim/victim Assign this VM the IP address of 192.168.13.100 Use 192.168.13.250 as DNS and no gateway Set up Mail app using Add Account and then at bottom of Account Type, Advanced Settings. Fill out whole form as appropriate, uncheck Sending requires Auth and Require SSL boxes. Should get an initial email from mail-admin when you first connect.