Disclosed herein are embodiments of methods, devices and systems for device fingerprinting and automatic and dynamic software deployment to one or more endpoints on a computer network. The device fingerprinting systems and devices herein are configured to operate with limited data without sitting between network devices and the internet, without monitoring all network traffic, and without limited or no active scanning. The embodiments herein may passively collect information as distributed peers and may perform very limited active scans. In some embodiments, the information is used as an input to a custom hierarchical learning model to fingerprint devices on a network by identifying attributes of the devices such as the operating system family, operating system version, and device role. In some embodiments, a dynamic deployer selection process may be utilized to simply and efficiently deploy software. Some embodiments herein involve end-to-end encryption of credentials in a deployment process.