Quick update:

Adobe's senior support and dev have confirmed the issue does exists in the files we have sent them which uses this particular illustration. They believe this issue is due to the file being created in the older 32 bit version of Illustrator before the transition to the 32 and 64 bit versions of Illustrator and no longer scales properly as today's version is only 64 bit.

They have logged this as a feature request and but will not be categorized as a bug at this time.

Since 24.3, resizing certain complex grouped objects while maintaining the ratio using Command + Return with one x or y dimension is not working properly.

Example:
1. take an affected complex grouped drawing
2. enter a different dimension (higher or lower) in the "x" dimension box
3. press "Command + Enter" to attempt to make the "y" dimension box update with the new dimension with the correct ratio

Here is an example of an affected vector drawing made with an older version of Illustrator so you can see the issue:
https://shared-assets.adobe.com/link/aad814dc-21e1-489f-5cd2-fb20f2fc802c

Result: for objects affected by this issue, it generally makes it taller and does not conform to the usual set ratio.

This is very hard to replicate as it only affects very specific objects but curious if this is affecting anyone else.

As you can see in the screenshot, when pressing "Command + Enter" with a 3" width, the height changes to 3.5947" as opposed to maintaining the expected square size.

We have confimed and replicated this issue with the same AI file on another Mac using version 24.3. Yet, another Mac using 24.23 is not affected by this issue.

Notes:
- caps lock is not pressed
- there are no hidden objects or guides
- snap to grid or pixel is not active
- only affects very specific objects created in versions before 24.3

Bug History:
- Details originally shared here: https://community.adobe.com/t5/illustrator/resizing-object-with-x-or-y-dimension-with-command-return-is-not-working-reliably/m-p/11393180?page=1#M190748
- Adobe has since confirmed this issue and recommended to use 24.2.3 to alleviate this issue