Unwanted bounding box resets

I'm having a rather infuriating issue with Bounding Box resets.
Image here:
http://img848.imageshack.us/i/unled3j.jpg/
Sorry—I can’t get it to show up in this message.
The first row of the linked image shows a roughly isometric view of a machine decal, followed by straight on views of a red box and a newer version of the decal.
To turn this new decal into a similar perspective, I normally:
1-rotate the decal using the black/closed arrow hovering over a corner handle
2-use the Free Transform tool on the rotated side handle of the bounding box to skew the rotated image
The second row shows what happens to the red box and its Bounding Box after rotation.I would normally use the handle that had been the middle right to Free Transform this object
The third row shows the new decal rotated. It's bounding box has reset itself automatically and is no longer useful with the Free Transform tool.
These two objects are on the same document, so I'm guessing the Bounding Box reset has something to do with some attribute of the new decal. Whatever it is, an operation that normally take 10 seconds has become suddenly impossible. Anybody know what to do to fix this?
Thanks.
Matt
http://img848.imageshack.us/i/unled3j.jpg/

I had this problem as well, and it was driving me crazy. This happens when you have multiple objects sellected that have bounding boxes set at different rotations. They can be grouped or ungrouped, it makes no difference, and the bounding box will automatically reset. I found that resetting the bounding box (before applying the transform) fixes the problem. This seems counter intuitive, because the bounding box doesn't look like it needs to be reset. It already appears straight, so there is no noticable change after applying the reset bounding box command. However, afterwards the bounding box will stay in the correctly rotated position because all objects have the same bounding box rotation.

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