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.
Even though this issue was resolved previously, the problem is back. If you do have it now — please upvote this newer report, so the team can evaluate the problem’s severity.
The more votes it gets, the faster we’ll get it fixed once and for all. Thanks!
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Erwin made a separate report about this started to happen again:
http://illustrator.uservoice.com/forums/601447/suggestions/48243365 - 
      
Erwin
    
 commented
    
  In Adobe Illustrator 28.4 on Mac OS Sonoma 14.4.1 this very annoying problem seems to be back.... Please fix this.
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Related to this problem:
https://illustrator.uservoice.com/forums/601447/suggestions/46248568 - 
      
DPR023
    
 commented
    
  It's back in 27.0 on Windows 10
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It works, I confirm. Fixed, finally!
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Pam
    
 commented
    
  I just started a new job and this glitch is making it almost impossible to work efficiently! It's taking me FOREVER to complete simple tasks. Please fix asap. Illustrator 26.1 on Monterey 12.3
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Diana Rich
    
 commented
    
  This issue just started for me. I'm on Catalina 10.15.7 and Illustrator 26.1. Really a pain.
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Lindsey
    
 commented
    
  Shift+Drag still buggy in Illustrator 26.1. Sometimes works sometimes doesn't. When it doesn't I usually get a ding sound. And a green thing pops up for a second.
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Another demo with the workaround
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The workaround would be to disable Construction Guides option for Smart Guides in Preferences. This does 'fix' the issue, but in fact it does not. The team (at least a part of it) knows about the issue.
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I also attach two GIFs that show how it used to work (fine), and how it does work now, in several latest releases (not OK).
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It’s a known bug, and I believe it is fixed in the Beta.
Can you check it and see if it works fine for you?
If not, please provide more details — how do you scale exactly? which snapping options are enabled for you? If possible, please record a video to make sure we talk about the same thing. - 
      
~Woody
    
 commented
    
  It used to be that holding the shift key while scaling would scale no matter which direction you dragged... now I've got to try to follow a smart guide.
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Kai
    
 commented
    
  The issue still persists even in V25.4.1. Really bad for workflows requiring pixel-perfect accuracy. Adobe please fix this
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Mark Gould commented
I am still having this problem with 25.4.1. Disabling Transform Tools in Smart Guides preferences helps resolve the problem, but checking it continues to disallow moving the point or points when shift-dragging.
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Scott R
    
 commented
    
  Shift+drag continues to be erratic here. Enabling/disabling Transform Tools does not appear to be a reliable fix. Same shift+drag issue seems to be plaguing Photoshop as well.
Illustrator 25.3.1, Big Sur 11.5Edit: May be worth noting that the erratic behavior consistently manifests itself during option+drag copy actions
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jan
    
 commented
    
  Dear admin, I wonder this bug occur in different Mac OS?
I have one Mac illustrator fixed, but one still not fixed (25.3.1)
The bug still occur in OS Big Sur 11.4 - 
      
Kristian
    
 commented
    
  Still not fixed 25.2.3
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Justin
    
 commented
    
  @jan - I've had the 'Transform Tools' check box (in Preferences / Smart Guides) turned off all this time to avoid this bug. Your comment actually reminded me about this issue so this morning, I've turned 'Transform Tools' back on and so far, it looks like it's working correctly now (version 25.2.1).
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jan
    
 commented
    
  Hi there, I wonder this problem is still happen in the latest version V25.2.1
This function is so important. I nearly use this everyday.
And this bug was reported in Jun 2020, but after 9 months still not got fixed?
I can't believe that.