You can import multiple documents and folders in bulk by using Documents Cloud Uploader, a Java multi-platform desktop application.
This app supports two import methods:
Import folder content. Using this method, you can quickly import the contents (files and folders) of a local folder from your computer. The imported documents will have the Title set to their file/folder name. The folder structure will be preserved. Only documents of type Folder and File can be imported by using this method. Also, it does not support importing metadata attributes like Description or Current Revision. This method is recommended to be used when you just installed the Documents app and you want to move your existing project files to Jira Cloud or to migrate the files from your previous document management system other than Documents for Jira Server/Data Center.
Import documents with metadata. This method is based on an input CSV file, which must contain the metadata attributes (like Title, Description, Revision Notes, etc.) of the items to be imported along with the local path to their corresponding file from the local disk that has to be imported. It supports importing documents of the types Folder, File and URL. This method is recommended to be used when migrating Documents data from Jira Server (or Data Center) to Jira Cloud - in this case, the CSV file along with the files and folders to be imported are easily generated by bulk downloading in Documents for Jira Server.
IMPORTANT!
The user running the import via Documents Cloud Uploader must have administrative permissions over the Jira project that serves as the app repository (see Configuring the app repository).
The migration of documents of type "Wiki" is currently not supported.
The most common scenarios of using these import methods are described below.