Ah, it’s this one again... I know about the trick with disabling the option, mentioned here and there, but I can’t accept is as a solution to myself, because I need this option enabled :)
Thanks for writing back. I think there were other reports on the same topic, will try to find and merge them.

Hey Egor,

I found this old thread from 9 years ago:

https://community.adobe.com/questions-652/snapping-issues-while-holdilidng-shift-793083

The solution was to turn off " Transform tools" in the Smart guides preferences.

It seems to be working now.

I can’t reproduce this on one computer, but suddenly can on a different one!
Both have Windows 10, same exact snap settings... something is very odd. I will test more.
Meanwhile, please locate your preferences, archive the folder, and send it over to the team via sharewithai@adobe.com (mention the link to this report, for tracking, http://illustrator.uservoice.com/forums/601447/suggestions/50935031)
Backup the folder (to restore later, if needed) and try to reset Prefs — very often it magically 'fixes' small problems. I’ll try the same.

Hey Egor,

I downloaded the software you have but the keystrokes are not showing on my recording like yours did. First section of the video is with shift pressed and second section is without the shift pressed.

Thanks,

That’s an important difference and you never stated this previously, but I still can’t reproduce it, no matter what I drag: a point or a segment.
So, please, DO record the exact operation you are doing, as a GIF (I use lightweight LICEcap to grab these), or a video (Sharex or many others).
There should be a difference, and these would help to catch it.

Hey Egor,

I just tested version 29.8.4 and it works fine with this one.

I'm having the issue with version 30.1

I also I replied earlier and I don't see my comment, so here is again:

The issue is when using the white cursor to extend a single edge to the bleed guideline, not when dragging the whole shape with the black cursor. ( I'm on a windows machine right now as well )

Hey Egor,

I'm on a windows machine right now.

I just watched the video you have attached, the issue is not when dragging the entire rectangle to snap.

The issue is using the white cursor and extending a single edge to snap to the bleed.

Try that and let me know if you are having the same results

Thanks!,

Same exact settings, but on Windows, in 30.1 — holding Shift does allow me to snap a rectangle to a bleed guide, pressed before or in the middle of dragging. Odd!
I suppose you can’t test it on a Windows machine, same as I don’t have an access to a Mac currently? It can be the difference...

Hey Egor,

It's happening with all my files, even a new document with a new rectangle in it

Attached is a screenshot of my smart guides settings and screenshots of a new document with a rectangle . as you can see the " pink guideline " for the smart guides is not showing up when using the shift key.

Thanks!

Hector, can you share a test file, please? It seems like this happens only in some specific circumstances.

When dragging the edge of a rectangle while pressing the Shift key the line will not snap to the edge of the bleed guideline, it will only work if I release the Shift key, issue started to happen about a month ago.

I've been doing what you're saying for a while now, but it makes my work less productive. Plus, I lose the precision and agility that smart guides provide.
Please consider correcting this error.

When using the scale tool (o) on any object, with smart guides enabled, it becomes very difficult to get a good result. When scaling the object proportionally by holding down the shift key, the object starts to flicker or have a random proportion.
The problem only appears when I work on MacOS. On Windows I don't have this problem.
This error has persisted for many versions of Illustrator without a solution.

Disabling Transform Tools in Preferences > Smart Guides does make it go away, but it’s a mere workaround

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.

Erwin, does the older trick to workaround it work for you — to toggle Construction Guides in Preferences: Smart Guides?

In Adobe Illustrator 28.4 on Mac OS Sonoma 14.4.1 this very annoying problem seems to be back.... Please fix this.

This is my file

I have the same problem. Any update on this?

Here is the demo