A computer-implemented method performed by a content management server, comprising one or more computing devices, wherein, via a network, the content management server is communicatively coupled to a personal computing device having a storage device, the method comprising: receiving, over the network from the personal computing device having the storage device, an indication of whether at least a portion of the storage device is protected by disk encryption; wherein the portion of the storage device stores one or more copies of one or more content items, wherein the one or more copies of the one or more content items stored in the portion of the storage device are periodically synchronized with one or more copies of the one or more content items stored at the content management server; determining, based on the receiving the indication, whether the portion of the storage device is protected by disk encryption; and based on determining that the portion of the storage device is not protected by disk encryption, performing one of (a) or (b) instead of sending synchronization data over the network to the personal computing device for synchronizing the one or more copies of the one or more content items stored in the storage device with the one or more copies of the one or more content items stored at the content management server: (a) sending data to the personal computing device for instructing a user of the personal computing device how to enable disk encryption, or (b) sending a command to the personal computing device to automatically enable disk encryption for the storage device. receiving, over the network from the personal computing device having the storage device, an indication of whether at least a portion of the storage device is protected by disk encryption; wherein the portion of the storage device stores one or more copies of one or more content items, wherein the one or more copies of the one or more content items stored in the portion of the storage device are periodically synchronized with one or more copies of the one or more content items stored at the content management server; determining, based on the receiving the indication, whether the portion of the storage device is protected by disk encryption; and based on determining that the portion of the storage device is not protected by disk encryption, performing one of (a) or (b) instead of sending synchronization data over the network to the personal computing device for synchronizing the one or more copies of the one or more content items stored in the storage device with the one or more copies of the one or more content items stored at the content management server: (a) sending data to the personal computing device for instructing a user of the personal computing device how to enable disk encryption, or (b) sending a command to the personal computing device to automatically enable disk encryption for 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, or (b) sending a command to the personal computing device to automatically enable disk encryption for the storage device.