When sending email with 2 attachments using gpg4win 2.0.1 and Outlook 2007 (encrypt and sign), the email seems to be sent OK, but then the second attachment is always corrupted and cannot be opened by recepient. The first attachment and body of the message are fine.
GpgOL is the compomponent of Gpg4win2 which enhances Outlook. So you should check if this problem is already reported and if not, please
report it. See hints in http://gpg4win.de/reporting-bugs.html