Setting up & Using Encrypted Email in Mac Mail

I have a client that needs to set up encrypted email on her MacBook Pro running Snow Leopard. I have no experience with setting up or using encryption. I'm trying to figure it out on my MacBook before I set it up for the client.

I downloaded & installed GPGMail on my MacBook. When I go into Mac Mail preferences I now see a new tab called GPGMail. There is a Keys section and there is a field labeled "Default Personal Key" but there doesn't seem to be any way to modify that field. And what would I even put in there?

I believe there needs to be both a private and public key used in this setup. But I don't know how to go about this.

Also, is GPGMail the best way to set up encrypted email on a Mac?
anuneznycAsked:
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John-Charles-HerzbergCommented:
This one is good also.

http://www.macupdate.com/app/mac/31072/encrypt-mail

Encrypt Mail... As Businesses rely increasingly on electronic mail to correspond with co-workers, colleagues and their customers, more sensitive and confidential information is transferred over Internet, and the need for email privacy becomes omnipresent. This is especially true with the high volume of businesses sending invoices as PDF attachments as well as other personal documents. Now more than ever, encryption is the only solution to protect email correspondence from prying eyes.

What is Encrypt Mail?
Perfect for both personal and business use, Encrypt Mail is an easy-to-use client for sending encrypted emails and encrypted attachments. Mac based recipients will receive a DMG password protected file. Windows and more...
WHAT'S NEW
Version 2.0:
Gives the user the ability to compose messages with encrypted files for Mail
User interface changes making the application more intuitive and easy to use
Various code optimizations and improvements to product stability
REQUIREMENTS
PPC / Intel, Mac OS X 10.5 or later.
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anuneznycAuthor Commented:
JCH, thanks for that info. I'm going to try setting up GPGMail first & see if I can get that to work.
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John-Charles-HerzbergCommented:
GPGMail is good.  If you need more help just ask.  - Have a good weekend.
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anuneznycAuthor Commented:
OK, just tried installing GPGMail on client's MacBook Pro. It said it installed successfully. However, when I open up Mac Mail and go in Mail preferences, there isn't a new tab called GPGMail like there is on my MacBook. Why would that be??
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John-Charles-HerzbergCommented:
I found this at : https://github.com/GPGTools/GPGMail/wiki/Not-working-anymore-after-an-OS-update

In case the GPGMail bundle gets deactivated you've several options:

Try to autofix the installed bundle by installing the GPGTools System Preference Pane.
https://github.com/GPGTools/GPGTools_Preferences

Run this script in the terminal. https://github.com/GPGTools/GPGTools_Preferences/blob/master/scripts/fix_gpgmail.sh

Move the bundle from "Bundles (Disabled)" to "Bundles" and copy and paste the following lines into the terminal:

bundle="$HOME/Library/Mail/Bundles/GPGMail.mailbundle"
uuid1=`defaults read "/Applications/Mail.app/Contents/Info" "PluginCompatibilityUUID"`
uuid2=`defaults read "/System/Library/Frameworks/Message.framework/Resources/Info" "PluginCompatibilityUUID"`
defaults write "$bundle/Contents/Info" "SupportedPluginCompatibilityUUIDs" -array-add "$uuid1"
defaults write "$bundle/Contents/Info" "SupportedPluginCompatibilityUUIDs" -array-add "$uuid2"
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anuneznycAuthor Commented:
Thanks! Let me give that a try.
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anuneznycAuthor Commented:
I'm not 100% on this. Am I copying & pasting the contents of this link into a text doc when I then save as a script file and then run it from the command prompt? https://github.com/GPGTools/GPGTools_Preferences/blob/master/scripts/fix_gpgmail.sh

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anuneznycAuthor Commented:
Saved that script on that link as fix_gpgmail.sh in the user's home directory.
Ran chmod +x on it to make it executable.
Typed in the name at command prompt and got a "command not found" error.

I'm ready to give up here.
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John-Charles-HerzbergCommented:
Have you tried downloading the file from https://github.com/GPGTools/GPGTools_Preferences/blob/master/scripts/fix_gpgmail.sh under the downlaod tabe. I found 3 fix file in the zip file. I have attached the file also. fix-gpgmail.sh
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anuneznycAuthor Commented:
Thanks, but the file you emailed me got same error: command not found.

Is there another program available that integrates w/ Mail?? Encrypt Mail is no good as it is a separate program. GPGMail would have been perfect, if only it would work!!
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John-Charles-HerzbergCommented:
Do you have the GPGTools in System Preferences?  If so will it open?  How did you generate the keys?

Thanks
JC
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anuneznycAuthor Commented:
Yes to your first 2 questions.

I haven't generated any keys yet. No point in generating keys if the interface (inside Mac Mail) is not available to client when they go to compose an encrypted email, right?

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bstaudConnect With a Mentor CEOCommented:
anuneznyc:
"command not found" error

From what you described, I believe the script you wrote is in a folder not included in your executable search path. You can check where executables are found by using
echo $PATH

The cure is to say ./scriptname
(that's dot-slash-scriptname) for it to look in the current directory.
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bstaudCEOCommented:
anunexnyc:

"GPGMail would have been perfect, if only it would work!!"

From the fix you mentioned, I would say GPG is Not Ready for Prime Time.
I would not like to think that all my encrypted mail would depend on me finding some obscure patch every time a version changed.
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anuneznycAuthor Commented:
In looking for an alternative, I came across this link:
http://blog.davingranroth.com/2010/12/signing-and-encrypting-e-mail-on-mac-os-x-10-6-using-self-signed-certificates/

However, in following the directions and sending some test emails, it seems like this is only good for sending 'signed' emails, but they don't seem to be encrypted. At least when I sent some test emails to my Yahoo mail account, they came through normally except that they had a "This sender is DomainKeys verified."
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anuneznycAuthor Commented:
Thanks.
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