GPG and Outlook

Steven M. Sawczyn steve at
Thu Dec 4 18:41:40 CET 2014

I'm having trouble finding a really suitable way to get GPG and Outlook 2013
working together and would really appreciate some help.  I know of two
solutions and will outline the troubles I'm having with each below.  


GpgOl plugin (included with gpg4win)

*         Does not stay activated, I need to reactivate each time I launch
Outlook 2013.

*         Does not allow me to clear sign a message, I can add an encrypted
signed message to the clear text, but nine times out of ten, that's not what
I want to do.

*         I have two Email accounts configured in Outlook and for some
reason, GpgOL insists on encrypting to my other account even though that
other account is not listed as a recipient anywhere in the message.


Outlook Privacy plugin (beta 18)

*         Installation on Windows 8.1 is tricky because of how the plugin is
signed (at least that's my limited understanding of it).

*         Plugin doesn't encrypt or sign until a message is actually sent so
there's no way to really verify that it's working correctly until it's too

*         Many times I've chosen to encrypt a message only to find that the
plugin sends the message unencrypted.

*         Plugin randomly seems to become deactivated.


If anyone could help with any of this, I'd definitely appreciate it.  As a
stopgap solution, I've thought of possibly using the Windows clipboard to
encrypt/decrypt, however, I can't find an easy way to do this with GPG4win


Thanks in advance,




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