No one warned me that context sensitive menus require bit sizes to match. This means that shell extensions (like GPGee) which only supply a 32-bit version will not install on your right-click menu on a 64-bit version of Windows. GPGee, apparently, isn't really updating their software since about 2006 or so, and thus I had to go looking for a new GUI front-end for my gpg processes.

GPGshell:

GPGshell is a graphical interface for GnuPG (GNU Privacy Guard). It requires an already working installation of GnuPG v1.4.x (v1.4.9 or later), because it does not have any cryptographic code itself, and some basic knowledge about the GnuPG command-lines and functions. Included translations: CS, DE, FI, EN, ES, IT, NL, NO, PL, RU, SV, ZH Additional or updated GPGshell-related files (incl. translations) may be available here.

GPGshell suffers the same "no 64-bit version" issue, but it's not just a shell extension, there is a key manager, a system-tray bit, and a tool bar for quick encrypt/sign/decrypt in addition to the shell extensions (which don't work on my 64-bit Windows). It's not perfect, but it should save me a ton of typing. Interestingly it says it requires 1.4.9 or later, but it seems to work with my v1.2.3. Why don't I upgrade? For some crazy reason the command line switches changed dramatically in 1.4.9 and I have programs that I've written that work with the v1.2.3 command line switches, and I haven't gotten around to re-writing my stuff so until I do I'll have to put up with a warning each time I run GPGshell. Still easier than dropping to a command line...