I can confirm that I have this problem and can do it when I turn off Yoast WordPress SEO temporarily.
Hey thanks, more comprehensive reply than I expected..!
Smush.It limit of 1MB is certainly annoying.
I used EWWW on non-media library assets — rather useful..!
Gonna make EWWW my go-to Image Optimizer from now..!
Ah I see so it means it records which images have been optimized in a table.
Is there any difference between EWW Image Optimizer and Smush.it..?
Ignore me, it was nothing to do with the timeline. Timeline is great btw.