A computing system includes a control unit configured to determine a usage context including a capability of a device, a usage time and a device location associated with the device, and a user context of one or more users with access to the device; analyze a privacy risk level of a resource based on a resource content included in the resource, a metadata concerning the resource, a collective input regarding the resource, and the usage context; and generate one or more options for sharing the resource with the device based on the privacy risk level and the usage context.