How about doing just that, to automate entering a password in Outlook so that emails can be collected from Exchange (which would require the mail user's password to be entered if Exchange was restarted) with Outlook running in a Windows VM on a Linux box, and a custom app processing the emails and POSTing them to an API on the Linux host, where they were processed to extract structured data out of attachments?

That wasn't a fragile system AT ALL.