Scale strokes box keeps unchecking
The "Scale Strokes and Effects" box keeps becoming unchecked making it necessary for me to check preferences for each document.

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Jesse Mellon commented
In Adobe Illustrator 29.7.1 on Mac OS, the "Scale Strokes & Effects" setting in Preferences is not sticky. After enabling the checkbox and quitting Illustrator, the setting reverts to unticked when relaunching the app. This happens consistently, regardless of whether a new or existing document is open. Resetting preferences does not resolve the problem. The expected behavior is for the "Scale Strokes & Effects" preference to persist across sessions, but currently it resets after every restart.
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Mike commented
I never actually use settings in transform or properties. I'm kind of old school (Illustrator 88 on a Mac SE) and to be honest never knew they were in those panels so I've never changed the setting in any panel other than preferences.
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This option is a global one, as each option in Preferences is... so toggling it in Properties, or in Transform, or even in Transform Each or Transform effect dialogs (and the last one is bugged because of it) makes this toggled for every document, at the app level.
Mike, please try to watch it closely and see if the behavior you get fits into this paradigm or breaks it.