I'm on Win CC2020 and still have this issue. BUT... Smart Guides is the culprit! It seems to be that the shift-constrain is fighting against smart guides. Turn off Smart Guides and the issue goes away.

Come on Adobe, sort it out...

Same problem here, I thought I had changed something wrong in settings but I see more people have this problem.
I have tried a couple of things, nothing worked.
Very annoying.

Has anyone installed the latest update with Mojave installed?

As part of a broad focus shift at Adobe, Mr. Singh probably switched to the company’s marketing staff ;-)

Not sure about them really investigating. Mr. Singh asked me to do a screenshare session to investigate further and after scheduling a date I never heard back from him. That was in January.

Are we any closer to a solution here??? Because it seems as though, somehow... it's getting worse! I don't know how that could be, but it seems really worse than it was last week. With as much as we pay for this software suite, why are such serious problems making their way to users??? I'm not a beta tester but rather someone trying to use your software to do my job. What's going on??? I'm attaching a .mov file in case you need another example of this insane rotate tool's behavior.

Same issue here for several years now it's atrocious. Behavior is normal with smart guides off— but I always need them on!

I can confirm Martin Hasliens behavior.

This have been acting weird for me too. It happened after I enabled "Transform Tools" in Edit → Preferences → Smart Guides… "Transform Tools". This setting is usually off by default.

It snaps to the optional angles defined below it. I cannot remember if it used to be this buggy, but after exporting, then reset, then import my settings, it seems to work better as far as I can remember. Although still buggy.

The snapping is still a little weird, but nonetheless snaps to the defined angles like you expect — and turning it off makes it only snap rotation to 45 degrees like the default behaviour you would expect.

Here's a demonstration https://i.thevirt.us/01/S5j0h.mp4

Not fixed for me either, but to be honest, I don’t care anymore – bye.

Nope, for me it hasn't.

Raghuveer,
Part of the problem is that it's taken ***over a year*** to respond to this bug report!

The bug has already been fixed.

I am having the same problem and it's making me crazy. 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.

My rotate tool is not working. Cannot get the anchor point to stick. Please fix this1

I have the same issue on Windows since AI 23, but not only when dragging something.

It is very annoying for now, trying to rotate an object for 90 degrees with enabled smart guides throught holding the shift key. It mostly becomes stuck somewhere.

I think it would be better to top prioritize the shift constrain feature over the smart guides behaviour so, that the handling in this combination would ignore the smart guides snapping.

High Sierra
AI 23.0.1

when dragging with shift to constrain angle, smartguides snap the dragged shape back to it's starting point if you slight deviate from the constraining angle.

strange..

Anything new? Almost ONE YEAR since introducing this bug?

same here, super annoying

I have the exact same issue! Makes it really unusable and annoying.