Constrain (shift key) doesn't work with Smart Guides turned on
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.

I am happy to share that we have fixed this bug in our latest release – 26.3.1 which is available worldwide now.
Going forward, our goal is to fix as many top User-Voice bugs as possible and as frequently as possible. Given the nature of the fixes, some of the bugs will take a longer time to fix, but we are on it.
You can update to the latest release using Creative Cloud desktop App: https://helpx.adobe.com/in/creative-cloud/help/creative-cloud-updates.html
Thank you for all the feedback. Keep it coming!
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Nic commented
super frustrating. anyone have an answer for this?
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Will commented
Maybe this is a new feature, but the shift key no longer constrains scaling, rotating, moving, etc. when using any tool--a feature that was most handy in conjunction with plotting an origin point, and modifying a shape relative to it.
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Jesse commented
When trying to use a shift constrain while moving a node on an object while smart guides are turned on you need to find the exact point where the node would be in order to complete the move. Same thing with scaling (scale tool). Makes you need to turn off smart guides every time you want to use a shift constrain and is very frustrating.
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Marek Domke commented
Do you have the option "Transform Tools" enabled in "Preferences/Smart Guides/Display Options"
I had to reset all settings after updating to v23 and then this was enabled.
With this setting deactivated, the issue was gone! -
Richard Coda commented
Nice going Adobe... break something that works. Please advise when you fix it (make it work the way it used to).
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Lance commented
@Cesar, I know it isn't ideal, in fact it tends to be infuriating, especially since 'smart' guides are usually much less than 'smart'. I find they often try to assist you in aligning your object to something completely unrelated on the other side of the document, especially on a busy artboard(s).
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Cesar commented
@Lance, thank you but unfortunately the workaround of disabling Smart Guides is not a great option. Because, often, Smart Guides are essential to the movement of the section of the object. A Smart Guide will help snap to other objects for alignment or as alignment reference.
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Lance commented
The workaround is to disable smart guides temporarily, ctrl/cmd+U is the keyboard shortcut, or find it in the View menu.
With smart guides on the "shift to constrain" acts really weird, and as you say the user must drag exactly along the line of the angle they wish to use or else the object snaps back to its original position. Turning off smart guides makes the "shift to constrain" work as expected.
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Cesar commented
I've been experienced this issue with Illustrator CC2017 and later.
Illustrator allows a user to use the Direct Selection tool to move a section of an object and constrain the angle of movement by holding down the shift key during the movement. However, older versions of Illustrator didn't require that the movement of the cursor remain exactly on the angle of the desired move. With older versions of Illustrator, a user could simply shift-drag a section of an object with the Direct Selection tool and the section would move regardless of the cursor direction, however, the angle constraints set up in Preferences would be followed. I would like to bring back this behavior. Is this possible?
This video shows the problematic behavior that AI CC2018 exhibits. Notice how the slightest variation in the cursor remaining on the desired angle results in the object's section snapping back to its origin and not moving with the cursor. Requiring that the cursor remain exactly on an angle is far too restrictive for most work.
https://youtu.be/L5mldVbl25Y
Is there a solution for bringing back a less restrictive editing process? -
Herbie commented
Scale tool with constrain (shift key) is now very difficult to use when smart guides is turned on. In all versions prior to 22.0.1, you could easily use the shift key to contain scale when smart guides was on or off. Now, you must be so inhumanly accurate for constrain to work correctly when smart guides are on. It is just *ridiculous* that this bug was introduced now after so many years of Illustrator. Please fix! I should not have to turn smart guides off to use the scale with contain (shift key) effectively.