The problem is probably something similar to
http://blog.methodmissing.com/2008/1/19/edge-callback-refactorings-attachment_fu/

In my case the method process_attachment defined as a after_validation 
callback doesn't get called for the second attachment of my model.

I replaced beginning of the method:

def after_process_attachment
   if save_attachment?
(...)

I don't know what will it cause other than making my attchements work. 
But they do work now, and I'm glad.

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