A computer-implemented method performed by a content management system, the content management system comprising one or more server computing devices (106, 108) operatively coupled via a data network to a personal computing device having a storage device, the personal computing device being configured to periodically synchronize copies of one or more synchronized content items stored on the storage device with copies of one or more synchronized content items stored at the content management system, the method comprising the steps of: receiving, by the content management system, over the data network, from the personal computing device having the storage device, an indication of whether the storage device is protected by disk encryption; determining, by the content management system, based on the indication, whether synchronization data should be withheld from the personal computing device, the synchronization data being for synchronizing the copies of the one or more content items stored in the storage device with the copies of the one or more content items stored at the content management system; sending, by the content management system, the synchronization data over the data network to the personal computing device, if the storage device is protected by disk encryption; and performing, by the content management system, at least one of the following operations (a), (b), or (c) instead of sending the synchronization data over the data network to the personal computing device, if the storage device is not protected by disk encryption: (a) sending data to the personal computing device for instructing a user of the personal computing device how to enable disk encryption, (b) sending a command to the personal computing device to automatically enable disk encryption for the storage device, or (c) sending data to the personal computing device identifying one or more content items stored in the storage device to be removed from the storage device. receiving, by the content management system, over the data network, from the personal computing device having the storage device, an indication of whether the storage device is protected by disk encryption; determining, by the content management system, based on the indication, whether synchronization data should be withheld from the personal computing device, the synchronization data being for synchronizing the copies of the one or more content items stored in the storage device with the copies of the one or more content items stored at the content management system; sending, by the content management system, the synchronization data over the data network to the personal computing device, if the storage device is protected by disk encryption; and performing, by the content management system, at least one of the following operations (a), (b), or (c) instead of sending the synchronization data over the data network to the personal computing device, if the storage device is not protected by disk encryption: (a) sending data to the personal computing device for instructing a user of the personal computing device how to enable disk encryption, (b) sending a command to the personal computing device to automatically enable disk encryption for the storage device, or (c) sending data to the personal computing device identifying one or more content items stored in the storage device to be removed from the storage device. (a) sending data to the personal computing device for instructing a user of the personal computing device how to enable disk encryption, (b) sending a command to the personal computing device to automatically enable disk encryption for the storage device, or (c) sending data to the personal computing device identifying one or more content items stored in the storage device to be removed from the storage device.