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I have four optional buttons. The file or amortization is required to be uploaded only if either Loan (One of the four option buttons) is selected or Bond is selected. Another words user must upload amortization for both Loan and Bond options.

I cannot use submit button rules, as this form can be submitted without the file attachment if one of the other two remaining option buttons is selected. Any suggestions?

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You can leverage Conditional Validation

Select the FileUpload control and choose Rules -> New Validation

Under Condition -> Click None and Add the two conditions which validates whether Loan is selected or Bond is selected.

http://designshare.wordpress.com/2011/01/11/creating-conditonally-required-fields-in-infopath/

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