Transparency Layer Drops Out of PDF Export

I have an InDesign CS3 layout. I have placed grayscale tiff at 100% as the background, and I have a small image in the foreground covering about a 1/4 of the background image, screened back to 40%.
When I export to PDF at "Press Quality", the small screened image appears fine. But when I export to "Smallest File Size", the foreground image drops out. Why is this happening?

I think we need a screen shot...

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