Right now to attach files "attach from sharepoint" in a task you can only attach one at a time. It has been requested to be able to attach multiple files at a time. To clarify, this is when you are in a task and "attach from sharepoint" you are limited to one at a time.
Hi Shelby! Thanks so much for your submission! This idea was a duplicate of an idea that was already in this portal, so we’ve merged the two together! Your vote and notes were automatically added to the other idea. Check out the merged idea #281. Thank you again for your feedback and for voting!