Here is yet another (and quite possibly, the best) way to upload files: the Document Unpackager. It’s a Building Block that allows you to upload a .zip file containing multiple files and folders, while preserving that file and folder structure within Blackboard.
To get started, create a .zip file using WinZip (Windows) or by compressing the files/folders (Mac: Select all files, CTRL + click, choose “Compress [files]“).
Then, go to or create a content area (or folder) in your course. Select Document Package.
Select the .zip file and hit Submit. Your files and folders will automatically be populated as individual items in the content area.
For step-by-step instructions (including how to zip files on the Mac and PC) with screenshots, check out Vanderbilt’s guide to the Document Unpackager.