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Mac OS X 10.13.3
AI CC 2015.3.1
With text selected with "Normal Selection Tool" menu item "Create Outlines" is grayed out even though the shortcut "Shift+Cmd+O" still works.
This came to light when attempting to automate a task by calling the menu item directly.
Can anyone confirm this "bug"?
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Have you tried different fonts? Does this happen to all fonts? Have you tried just expanding it?
I have not had this issue. But that crazy it does that to you. If you have the creative cloud suit, you should be able to update to the latest version of Illustrator CC 2018 (22.1.0.312). There are some great new features.
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Oh boy, I won't go into my experience with CC 2018.
My workaround is to only use the keyboard shortcut. It is sporadic. If I determine a pattern I'll post it here.
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Have you tried trashing preferences?