The technology disclosed enables metadata-based policy enforcement for requests that do not include metadata relevant to a policy. In a particular example, a method provides, in a network security system interposed between clients and a cloud application, receiving an incoming request from a client directed towards the cloud application. In response to determining that the incoming request lacks metadata for enforcement of a policy, the method includes transmitting a synthetic request to obtain the metadata from the cloud application and receiving a response to the synthetic request. The response provides the metadata. The method further includes applying the policy to the incoming request based on the metadata.