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OK, well, apparently there are a LOT of different ways to attach a file to an item (action), but not all them result in an attachment that will sync.

One method that does NOT work is selecting the item, chosing Edit, Attach File. One method that DOES work is Option-Click-and-Drag the file right onto an action. This was tweeted to me by @shrop on Twitter. (Twitter is now faster than all support desks and even Google at solving problems.)