Back with a vengeance: Constrain (shift key) doesn't work with Smart Guides turned on
This is an older bug that was fixed a while ago but seems to be back with a vengeance.
It is now happening in Adobe Illustrator 28.4 on Mac OS Sonoma 14.4.1.
See this link:
When smart guides are on none of the constrain features (holding down shift) work properly, whether it's rotating, reflecting, etc. It just sort of jumps back to one position, often the original position, and won't move. The little magenta text that lets you know the angle etc. also goes a little crazy and looks like it's trying to display a few different words on top of each other.
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Erwin commented
Hi Egor,
I tried toggling 'Construction Guides' in the preferences but I don't remember that working for me. I tried the latest update 28.4.1 but that didn't fix it. I eventually reverted to Illustator 27.9.3 which does not have this bug.
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Erwin, does the older trick to workaround it work for you — to toggle Construction Guides in Preferences: Smart Guides?