Shift Constraint is not working properly when editing proportionally or duplicating using Option drag Shift command. Illustrator v. 29.6.1
Shift Constraint is not working properly when editing proportionally or when duplicating using Option drag Shift command. I'm surprised that as many updates as we are required to do, that the glitches and bugs are so prevalent than they used to be before constant updating. I'm beginning to think that updating isn't really about making the product better, but to keep folks paying their subscriptions.

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Steve commented
In this video I'm holding down the shift key, and dragging at a 45 degree angle from the center of the triangle (origin point shown) while using the scale tool.
I like to use the scale tool in some situations, especially when duplicating and scaling at the same time. I like my smart guides and use them too for some situations and ease of use.
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Steve, please tell more.
Does it happen with or without Smart Guides?
What options do you have enabled in Preferences > Smart Guides?
Does it behave the same way when you use Selection tool (using Bounding Box’s handles), Scale tool, Free Transform tool?
Can you record a short video to show exactly how it works when you try?