A computing device associated with an entity comprising: one or more processing units; a network interface; a graphics hardware interface; and one or more computer-readable media comprising computer-executable instructions which, when executed by the one or more processing units, cause the computing device to: locally obtain device-identifying information; send a request for a license with the device-identifying information; receive, through the network interface, operating system license data based on the obtained device-identifying information, the received operating system license data comprising both a license for an operating system to be set up on the computing device and initial operating system setup options specific to the entity; automatically set operating system options on the computing device in accordance with the received initial operating system setup options; subsequently present, through the graphics hardware interface in the computing device, a customized directory sign-in, wherein the customized directory sign-in is specified by the received initial operating system setup options; and complete setting up the operating system on the computing device in accordance with subsequent operating system setup options received based on user identifying information provided through the customized directory sign-in, wherein the initial operating system setup options are those operating system operations that the operating system requests a user to set prior to allowing the user to log on to a directory service via the customized directory sign-in and the subsequent operating system setup options are those operating system operations that are set in accordance with user specific settings provided based on the user's login to the directory service. one or more processing units; a network interface; a graphics hardware interface; and one or more computer-readable media comprising computer-executable instructions which, when executed by the one or more processing units, cause the computing device to: locally obtain device-identifying information; send a request for a license with the device-identifying information; receive, through the network interface, operating system license data based on the obtained device-identifying information, the received operating system license data comprising both a license for an operating system to be set up on the computing device and initial operating system setup options specific to the entity; automatically set operating system options on the computing device in accordance with the received initial operating system setup options; subsequently present, through the graphics hardware interface in the computing device, a customized directory sign-in, wherein the customized directory sign-in is specified by the received initial operating system setup options; and complete setting up the operating system on the computing device in accordance with subsequent operating system setup options received based on user identifying information provided through the customized directory sign-in, wherein the initial operating system setup options are those operating system operations that the operating system requests a user to set prior to allowing the user to log on to a directory service via the customized directory sign-in and the subsequent operating system setup options are those operating system operations that are set in accordance with user specific settings provided based on the user's login to the directory service. locally obtain device-identifying information; send a request for a license with the device-identifying information; receive, through the network interface, operating system license data based on the obtained device-identifying information, the received operating system license data comprising both a license for an operating system to be set up on the computing device and initial operating system setup options specific to the entity; automatically set operating system options on the computing device in accordance with the received initial operating system setup options; subsequently present, through the graphics hardware interface in the computing device, a customized directory sign-in, wherein the customized directory sign-in is specified by the received initial operating system setup options; and complete setting up the operating system on the computing device in accordance with subsequent operating system setup options received based on user identifying information provided through the customized directory sign-in, wherein the initial operating system setup options are those operating system operations that the operating system requests a user to set prior to allowing the user to log on to a directory service via the customized directory sign-in and the subsequent operating system setup options are those operating system operations that are set in accordance with user specific settings provided based on the user's login to the directory service.