This reflective paper highlights my first 50 hours as a Cloud Engineer supporting Endpoint Transport at NNWC through AERMOR LLC. It explores my hands-on experience contributing to the Navy’s transition from NMCI to Nautilus systems, where I worked with technologies such as Microsoft Intune, Azure VPN, FlankSpeed, and BMC Helix. The paper connects academic knowledge from my cybersecurity studies at Old Dominion University to real-world challenges, including routing diagnostics, endpoint security, and compliance in a highly regulated DoD environment. It also reflects on the challenges, growth, and professional development gained during this early stage of my internship.