Described embodiments enable the automatic uploading and sharing of objects via a content management system (CMS). A user of a client device may request to share an object via a user interface. Prior to the request, the object may be stored in a storage location of the client device that is not synchronized with the CMS. In one embodiment, client software detects a “click-and-drag” operation of an object and provide a sharing element into which an object may be dropped for sharing. The CMS receives the sharing request and may automatically initiate a sharing process comprising receiving the object from the client device, storing the object in the CMS, generating a link to the object, and sending the link to indicated or pre-determined recipient(s). In various embodiments, the objects are synchronized with the CMS and/or organized according to various object parameters within a directory of the CMS.