Re: Most secure GPG combination for Mac OS X

2018-11-06 Thread Nicholas Papadonis
comments
On Tue, Nov 6, 2018 at 7:54 AM Damien Goutte-Gattat <
dgouttegat...@incenp.org> wrote:

> 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].
>
>
This raises another question about the security of the ports project
itself.  I read that Homebrew had some security issues, a majority which
come from the installer making /usr/local/bin writable by users other than
root.  This allows an unprivileged application to inject a malicious binary
there, for instance sudo.  /usr/local/bin is first in the search path and
therefore the administrator password could be captured.  I also read
Macports may not have this security issue because the installer runs as
root and all installations run as root.


> 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.
>
> Thanks for the suggestion.  I'm hoping to clear up my security questions
on Macports as well.  I suspect there could be many security holes based
upon the tool chain to compile the ports and all hands involved in the
source trees.

Nicholas

>
> > 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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Re: Most secure GPG combination for Mac OS X

2018-11-06 Thread Ralph Seichter
* Nicholas Papadonis:

> I'm considering using the Mac Mail.app, however am interested if
> Thunderbird is better integrated from a security standpoint.

Apple's on-board Mail requires a plugin to encrypt/decrypt messages.
While GPG Suite (https://gpgtools.org) provides said plugin, it is no
longer free to use. Once the trial period runs out, you won't be able to
encrypt, sign or verify unless you pay for a "support plan".

I suggest you go for Thunderbird plus Enigmail, unless you are really
keen on using Apple software.

If you're willing to stray off the beaten path, you may also want to
evaluate the Notmuch mail system (https://notmuchmail.org). I use EMACS
as a frontend for Notmuch, meaning that I have powerful GPG integration
provided by the editor, but there are other UIs as well.

-Ralph

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Re: Most secure GPG combination for Mac OS X

2018-11-06 Thread stefan . claas

Am 06.11.2018 12:48 schrieb Nicholas Papadonis:

Does anyone have suggestions on the most secure and reviewed
combination for bits for sending secure email on OS X?

I noticed that there are two OSX packages for GPG:

  Mac GPG Installer from the gpgtools project
  GnuPG for OS X Installer for GnuPG

Is any one preferred, have more eyes reviewing source, better release
management in terms of security concerns?  Any details?  Am I better
off building from source?


Well, i never have read that GnuPG had a security audit, regardless
of platform used, nor the plug-ins for various apps.

For example recently Enigmal for Thunderbird had a fatal security
bug which send encrypted email unencrypted under Windows.

You can build from source, which i did also in the past or use for
example MacPorts GnuPG distribution.


I'm considering using the Mac Mail.app, however am interested if
Thunderbird is better integrated from a security standpoint.  At the
lowest level, my assumption is that the command line tools can be used
to encrypt / decrypt blocks of text, which I will also be interested
in using.


I used Mail.app in the past too and later switched to 
Thunderbird/Eingmail.


Currently i use the GnuPG package from Patrick Brunschwieg (Enigmail
developer) in combination with Claws-Mail (MacPorts). I also use GnuPG
often as commandline tool.


Appreciate a security experts guidance immersing myself into more
secure communication.


While i am no security expert and only a Mac dummie i like the fact that
one can build from source and use it on an off-line computer, even
if the email received is in PGP/MIME format, because scripts are 
available

which allows a conversion.

Regards
Stefan

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Re: Most secure GPG combination for Mac OS X

2018-11-06 Thread Damien Goutte-Gattat via Gnupg-users
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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Most secure GPG combination for Mac OS X

2018-11-06 Thread Nicholas Papadonis
Does anyone have suggestions on the most secure and reviewed combination
for bits for sending secure email on OS X?

I noticed that there are two OSX packages for GPG:

  Mac GPG Installer from the gpgtools project
  GnuPG for OS X Installer for GnuPG

Is any one preferred, have more eyes reviewing source, better release
management in terms of security concerns?  Any details?  Am I better off
building from source?

I'm considering using the Mac Mail.app, however am interested if
Thunderbird is better integrated from a security standpoint.  At the lowest
level, my assumption is that the command line tools can be used to encrypt
/ decrypt blocks of text, which I will also be interested in using.

Appreciate a security experts guidance immersing myself into more secure
communication.

(ps please reply to my personal email as well, for some reasons my
subscription request won't go through.  Maybe for accepting that the
confirmation is sent through an insecure channel. :| )

Thank you,
Nicholas
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