Systems and methods provide multilevel authorization of workspaces using certificates, where all of the authorization levels may be authorized separately or may instead be authorized at once. A measurement of an IHS (Information Handling System) is calculated based on the identity of the IHS and based on firmware of the IHS. A measurement of the configuration of the IHS is calculated based on information for configuring the IHS for supporting workspaces and also based on the IHS measurement. A measurement of a workspace session is calculated based on properties of a session used to remotely support operation of the workspace by the IHS and also based on the configuration measurement. Workspace session data may by authorized at all three levels by evaluating the session measurement against a reference session measurement.