Two small suggestions that might help, though both would require largely abandoning the code you've written. One is that instead of using Outlook programmatically, you can connect directly to the Exchange server using the CDO API. I don't know how to do this in current versions, and your Windows box may not have the required libraries, and also it would require you to put your username and password somewhere that your program could find it (or type it into a Tk prompt I guess), but it might be an option. The other thing is that Exchange 2000 and later are configured with IMAP by default, and assuming that's enabled, you can just connect to it from the Linux box using the software of your choice.