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Dragging down the editor only expands the text box to ~50% larger than its popup default size. Manual dragging can extend it to ~100% larger. Basically, dragging is not increasing the textbox size in a 1:1 ratio to amount dragged

Can you rephrase this or maybe add screenshots or something?

Default, Dragged, Manually Adjusted

http://imgur.com/a/ZatT6

This is sort of an annoying thing to fix because I don't know how much room the links are going to take up ahead of time.

The resizing works perfectly well if there are excessive links, dragging and expanding expands only the text box, and the links stay down (a couple get hidden below the scrollbar, but that's fine). The text area expands the same amount as it does in the no-link case (the pictures)

I'm aware, but if I have to decide how large the text box should be knowing only the total size of the window, it's hard to say how large a size I could choose because there could be any number of links and I need to fit them all under the text box.

Yeah, this looks tricky. Might as well let it slide for now then