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Hey!
I use both apps together and I always select (using Rectangle or Command+A) and copy an image onto a layer and paste it into Illustrator. For example: when I want to know faster the exact proportion of a placeholder in a graphic mockup, then I just adjust the lines in Illustrator before copying it back to Photoshop.
Since the last update this trick is no longer working and sometimes it does.
MacOS M1 16Gb.
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Hi @andreischneider let's see what we can do about this.
Let's make sure we're in a default state and there are no stale settings somewhere:
Restore your preferences using this manual method:
https://helpx.adobe.com/photoshop/using/preferences.html#Manually 
Does it work correctly?
If that doesn't solve it, you can quit Photoshop and put the Settings folder back.
It may help if we could see your Photoshop System Info. Launch Photoshop, and select Help >System Info...and copy/paste the text in a reply.
Thank you,
Cory