I don’t know for certain regarding Laserfiche, but a lot of Image programs, when told to rotate an image are not saving it as a new image with all the pixels in new locations, but instead are saving an instruction that says to display the image rotated when viewed.

If I’m right, then you are adding the textbox to the top-right of the image, but then it rotates it when viewed.

You could probably try to detect this rotation in an SDK Script in Workflow and address the textbox differently if rotated.

Or you could recreate the document (i.e. use Snapshot to “print” back to itself) in the rotated state, prior to running the Workflow.