Users of communication applications may be enabled to select from a user-friendly and efficiently provided list of files that may be of interest to them to attach to a correspondence and send to one or more recipients. For example, the communication application may retrieve information from one or more application programming interfaces (APIs) associated with applications of the user to determine the list of files. The files may be local files or cloud-based files, and a variety of criteria may be used to determine, group, and present the files to the user for selection. Once selected by the user, the files or links to cloud destinations of the files may be attached to the correspondence, where the files or links may be displayed in an attachment well or a body of the correspondence. Permissions associated with the attachments may be set by default, by user configuration, and/or modified by user.