So, grain of salt and all--like a lot of Javascript bugs this may manifest differently for everyone, but since I've had multiple other folks confirm this behavior, I'm pretty sure I'm not crazy , you might just be lucky. But here's how it works for me, with an example from my art library: You can see here, I'm relatively, uh... persnickety, persnickety is one way of putting it... about organizing my image assets. It might take me a couple weeks, but everything I upload eventually gets sorted into folders, sometimes three or four levels deep. In general, it all works. In this screenshot, I've pulled up a few different ways of accessing these images. Blue boxes are areas where drag-and-drop onto the page works. From the recent uploads, it always works. From the pop-out dialog it always works. (I should have chosen a different view for that just for clarity, but it works regardless of what directory you have open.) Anything nested under at least one folder will always work, and I've got a single example open and highlighted in blue. (And only one, because if I open literally any other folder I hide the recent uploads under miles of images or nested folders.) I also have the search box highlighted in blue, because if you run a search, your results will always work. HOWEVER, I also have some tokens that I reuse over and over again. They're not located in a folder, they're just under root, at the top level in the collection. I have those highlighted in red. Those do not work and have not been drag-and-droppable for me for a couple of months. Note that I am speaking specifically about dragging onto a page. Drag-and-drop rearrangement still works for every item. Workarounds: you can drag the offending images into a folder and it won't fix them immediately, because the javascript isn't rebuilding the broken object in the page's document object model, it's just shuffling the metaphorical deck chairs on your metaphorical Titanic. HOWEVER, if you do that and then reload the page , that does the trick and it should work. Also, you can just search for your item, or given where it is in the UI, it's easy to click on and open up the separate Asset Library dialog box, and you can easily drag and drop out of either of those interfaces. Premium assets are always in folders so I have no idea if there could theoretically be a problem in that view, but it should never actually come up in practice. Web assets are always revealed in search and so they always work, although if you save a web asset to your library (instead of to a folder) it will trigger this bug. You can work around it in all the same ways.