Can you please provide a screenshot or step-by-step details of what you are trying to do. I ask because it’s working fine for me (see attached screenshot; it’s quite possible that I misinterpreted what you are trying to achieve). Could it be that the negative offset you are applying is greater than the size of the object. In that case, it won’t work. Otherwise it should.
An error occurred while saving the commentKendall commented
I am having the same issue. I wasn't able to follow the steps provided by Pen (not sure how to get a stroke with no fill...) but using the stroke to make an object appear thinner did work. Then I just expanded the shape with fill and stroke, then deleted the part of the shape that used to be the stroke.
We have fixed this bug in our latest release – v 24.2.1 which is available worldwide now. Thanks for your patience on this.
Please note that after upgrading you might still see that Align To sets itself to Align to Key Object. If you see this, please manually set the Align To to the required setting, and this reported bug will not happen again. You’ll need to this one time only.
The reason Align To might get set to Key Object after update is because Ai remembers your last Align To on subsequent launches as well. So, if your last Align To was Key Object before quitting/upgrading, after first multi-selection, it will set itself to Key Object. After you manually change it one-time, it will work fine.
You can update to the latest release using Creative Cloud desktop App: https://helpx.adobe.com/in/creative-cloud/help/creative-cloud-updates.html