Hi,

First, a warning: I am by no means a "security expert" and I have
very little experience with Mac OS X, which I only use at my
workplace (and only because my employer didn't let me use a
GNU/Linux workstation...).

However and for what it's worth:

On Tue, Nov 06, 2018 at 06:48:07AM -0500, Nicholas Papadonis wrote:
> I noticed that there are two OSX packages for GPG:
> 
>           Mac GPG Installer from the gpgtools project
>           GnuPG for OS X Installer for GnuPG

There's a third possibility, which is the one I use: install the GnuPG
provided by the MacPorts project [1].

Install MacPorts and then simply run:

  $ port install gnupg2

MacPorts packagers seem keen to provide the latest versions and to
update their ports quickly when upstream publishes a new release.
For example, Libgcrypt was updated to version 1.8.4 the day after
that version was released.


> I'm considering using the Mac Mail.app

I tried to build the Mail.app plugin from the gpgtools project,
but failed. I don't remember what the problem was, just that I
gave up.

I am currently using alternatively Neomutt (also installed through
MacPorts), which natively supports GnuPG, and Thunderbird with
Enigmail. Everything is working fine, including smartcard support.
Whether this is a "better integrated" solution than using Mail.app
I cannot tell.

Hope that helps a bit.

Damien

[1] https://www.macports.org/

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