Technology is disclosed for context sensitive synchronization of a distributed cloud-based file system across multiple devices and for providing seamless merging of conflicting data objects. In some embodiments, data objects of a user are stored across multiple computing devices associated with a user, e.g., mobile computing devices such as a tablet, a laptop, or a smartphone, and/or at server systems, e.g., cloud-based storage servers, in a distributed cloud-based storage system. The described technology intelligently synchronizes the data objects based on context and manages potential conflicts.