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Which version of Illustrator are you using?
You need to explain the problem in more detail. I don't see what it sounds like you are trying to describe:
Describe each operation you are performing; every click, tool selection, etc.
In Illustrator, dimensions of rotated bounding boxes do not reflect the measures of the rotated box. They uselessly reflect the mere vertical and horizontal bounds of the rotated box (like an invisible bounding box of a visible bounding box). Canvas, for example, handles this correctly, giving the user the choice between absolute and relative measures.
Sorry, mistake in my original post. I should have said 30 degrees (or anything other than 45).
Example. Create a rectangle and then rotate it 30 degrees. Create a copy of the rectangle and then reflect it 90 degrees vertically. The image below illustrates the new (post-reflection) bounding box on the left. The rectangle height cannot be changed without losing the width dimensions and vice versa.
The second example below illustrates the problem with a stick man created using a number of rounded rectangles.
The bounding boxes for the reflected stickman (on the left) prevent the limbs from being lengthened correctly.
I have never seen anything like that, and it should not be. Your Illy seems to be ill. Maybe it is time for the FAQ #2 cure, if that is enough.
Are you sure, Jacob, that you've never seen something like that?
I can confirm the behaviour Michael is describing in conjunction with reflecting the rotated objects in all AI versions from AI 9 to AI 14.
Helping me, Illy always keeps the Bounding Box following the original X and Y directions of (one of) the original object(s), with an X and Y preference whenever applicable.
Strange. If I use the Reflect Tool (30 deg rotated before 90deg vertical axis reflect) I get the problem, but it returns to normal when applied again.