Penetration testing helps to secure networks, and highlights the security issues. In this paper investigate different aspects of penetration testing including tools, attack methodologies, and defense strategies. More specifically, we performed different penetration tests using a private networks, devices, and virtualized systems and tools. We predominately used tools within the Kali Linux suite. The attacks we performed included: smartphone penetration testing, hacking phones Bluetooth, traffic sniffing, hacking WPA Protected Wifi, Man-inthe-Middle attack, spying (accessing a PC microphone), hacking phones Bluetooth, and hacking remote PC via IP and open ports using advanced port scanner. The results are then summarized and discussed. The paper also outlined the detailed steps and methods while conducting these attacks.