TLDR: Can I use a Thunderbird plugin for PGP like Enigmail to encrypt archived email from before I started using it on my current emails?

So I do not have access to a Unix box at the moment (please do not remind me about virtual machines, I know what they are and cannot use one right now). In short, I wanna encrypt old emails with PGP before archival. I wanna archive them this way to push them out to GMail and not worry about housing them somewhere other than my own turf. Found a cool howto for a Linux box here which I could pair up with OfflineIMAP to do the rest once the local copies are encrypted, but that would obviously require a non-Windows box with Maildir support (Windows cannot handle Maildir because ; is not allowed in the filename). So anyone got this working for a simple GUI operation for the time being within Thunderbird? I need to clear out a mail box for an impending quota.

EDIT 1: I would also like to avoid something sloppy and annoying like compiling Cygwin then find out it will not handle Maildir format still and will take lots of tweaking for the OfflineIMAP script to bother working. Kthxbai.

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