If you are authorized to upload documents, when you click the Upload Documents button, you are presented with a file dialogue. Select the file (or files) you wish to upload and click Open.
Apply one comment to all files
When you are uploading multiple files you will see this checkbox. If left unchecked you will be prompted to add a comment to each file being uploaded. If you want to use the same comment for all files being uploaded, then check this box and you are only prompted once for a comment that will be applied to each file.
When you click Yes you are prompted for file comments. In the screen below user chose to add a comment on each file being uploaded. Finish entering comments for each file and click Yes to upload files to work request.
Apply the same comments to all files
Apply a separate comment for each file
Alternatively you can also drag and drop files from your computer to the Docs tab then follow the prompts to add comments and save.