High resolution PDF still generates low resolution drop shadows?

I have created a series of print ads in InDesign CS5.5 to be run in magazines, and at the bottom of the page is the company's logo, with a drop shadow applied to it within InDesign. Nothing strange there. Upon exporting the PDF, I use the Press Quality settings which by default are made to create 300 dpi PDFs. The only changes I make in the settings is adding bleed and crop marks, I don't change anything that could affect the resolution or transparency settings. But still, the magazine's print-technician always replies that the shadows in my document have a low resolution.
Up until now I have told him to not worry and run it anyway, and the results have been fine - I haven't noticed any problems with the quality of the print in the magazine. But it really annoys me that I keep getting these error messages - I want to create perfect PDFs! Why on earth are my shadows ending up as low resolution images?
The only thing I can imagine might be a sign of an issue is under the Advanced-tab in my Export-settings. The Transparency Flattener section (which I, to be honest, am not quite sure what it is) is set to medium resolution, and is greyed out - meaning I can't change it to high resolution. Could this be what is causing it? And if so, how do I fix it?

I don't spend a lot of time with Acrobat's preflight, but it looks like it assumes what the flattener preset will be at output even though it could be anything.
The default Press Quality preset exports live transparency with the flattener grayed out as Medium and it looks like Acrobat preflight considers that even though nothing has been flattened yet. So, here I've made a 3" sqaure box and exported it with Press Quality and prefilght tells me it's roughly 200ppi (which by the way is plenty for a dropshadow):
If I change the preset to High (set the Compatibility to 1.3, which lets you set the flattener to High, then reset compatibility to 1.4):
Then Acrobat's preflight tells me the shadow will have more resolution:

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