Systems, methods, and non-transitory computer-readable storage media for rotating security keys for an online synchronized content management system client. A client having a first security key as an active security key may send a request to a server for a new security key as a replacement for the first security key. The server may receive the request and generate a candidate security key. The server can issue the candidate security key to the client device. After receiving the candidate security key, the client may send a key receipt confirmation message to the server. In response to the confirmation message, the server may mark the candidate key as the new security key for the client and discard the client's old security key. The server may send an acknowledgment message to the client device. In response, the client may also mark the candidate key as its new active key.