Printing to PDF in Paper Space the PDF Mirrored when plotted

So I have rotated the paper space with UCS command like always and have it rotated right. I have line work and text with a TIFF xref of a plan in the background. Everything looks great go to plot and the TIFF in the background is flipped. Not in plot preview just when I plot. The pdf opens with the Tiff flipped.

Very odd I have 2024 SP0

Everything else works well in the release so far. This one is odd.