A reconnaissance and assessment (RA) tool can receive base information about the network, such as basic network information and details about an entity and personnel associated with network. The RA tool can utilize the base information to perform reconnaissance procedures on the network to identify the attack surface of the network. The RA tool can perform reconnaissance on the network, itself, and on other external sources, such as third party databases, search engines, and partner networks. Once the attack surface is identified, the RA tool can automatically perform appropriate security assessments on the attack surface. Additionally, if additional information is determined about the network during the security assessments, the RA tool can perform additional reconnaissance and security assessments based on the additional information.