Caitlin
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An error occurred while saving the comment Caitlin commentedNever mind, I found the issue for the saving problem. Some how the save dialog changed the Subsetting drop down to "all glyphs" instead of "use system fonts". That made the files huge.
I have not experienced the second issue today, but did not have any particular solution to it.
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Also having this issue with the latest Illustrator 2020. Very annoying. I swear I saw a thread about it that had been solved, but now I can't find it.