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Woah i just did something cool. I dont know if you knew this but i started thinking why some keys where there and some where not when i open gpg keychain acess. so i copied a public key from a vendor and i pasted it in text edit. i saved it under their name. then i opened up gpg key chain access and clicked import and searched for the text edit file. and it imported the key info! and now it seem to be permanently  on the list of imported keys! i guess it still doesnt explain why sometimes even if you want to sign with your key nothing comes up. but anyway hope it helps. i think it ha to do with the connection to the server but who knows

SSBD, Here is a tutorial by Guru which helps with a lot of problems for those using a Mac.

You would be a lot better off using Gpg4usb, which works on Windows, Mac and Linux OS.

Download link  - http://gpg4usb.cpunk.de/download.html

Tutorial by astor - http://32yehzkk7jflf6r2.onion/gpg4usb/

It's a great piece of software, simple yet robust.


This is a tutorial written by former member Guru that should help you. 


This is a known issue with the standard build. What you want to do is install the latest nightly build, per the following instructions (originally written by Guru)

GPGTools is highly version dependent -- depending on which version of OS X
you have, it may or may not work as expected.  If you have Leopard (10.5)
then you're pretty much out of luck. Your only option then will be using
the command-line.

If you have Snow Leopard (10.6), Lion (10.7) or Mountain Lion (10., the
following instructions should be sufficient to allow you to get up and
running.

Download and install GPGTools: http://nightly.gpgtools.org/GPGTools_Installer-trunk.dmg

Once you have installed GPGTools,  what you want to do is to go into
System Preferences --> Keyboard --> Services.

Scroll down until you find the following entries. Be sure to put a check
mark in the boxes to activate each keyboard shortcut.

Keyboard shortcuts:

OpenPGP: Decrypt Selection:             Shift-Command-D

OpenPGP: Encrypt Selection:             Shift-Command-E

OpenPGP: Import Key from Selection:     Shift-Command-I

OpenPGP: Insert My Fingerprint:         Shift-Command-F

OpenPGP: Insert My Key:                 Shift-Command-K

OpenPGP: Sign Selection:                Shift-Command-R

OpenPGP: Verify Signature of Selection: Shift-Control-V

Remember, these shortcuts only operate on highlighted or selected text.

N.B.: To properly be able to import PGP into GPGChain (via TextEdit) you
need to change the default on TextEdit from .rtf to plain text. You can do
that through the Format menu, or you can go through the main configuration
menu, accessible by using Command-comma. Ensure the plain text radio button
is selected.

Also ensure that the following are UNCHECKED in TextEdit preferences:
smart quotes, smart dashes, smart links.

To select text within TextEdit, use Command-A to highlight the entire
document, or use your mouse to selection the section that you want to
verify/sign/encrypt/decrypt. It is highly recommended that you use only
plain-text, as opposed to Rich Text (.rtf) format. Use Command-comma to
bring up Preferences and ensure that the plain text radio button is
checked.

Once your text is highlighted in TextEdit, (by pressing Comand-A) you then
encrypt using Shift-Command-E. You will then be presented with a list of
keys to encrypt to, that you have added to your PGP keyring:

Other Commands You May Need:
============================

OpenPGP: Decrypt File:                   Control-Command-D

OpenPGP: Encrypt File:                   Control-Command-E

OpenPGP: Sign File:                      Control-Command-S

OpenPGP: Verify Signature of File:       Control-Command-V


Once you have setup these shortcuts, you can begin using GPG.

To encrypt a message to someone using GPG, you first need a copy of the
recipient's PGP public key.

Once you have located someone's PGP public key, you should copy and paste
it into Text Edit. Save the PGP key to a file; you can call the file,
import.asc (or import.txt), for example. This saved file will usually be
found in the Documents folder.

Launch GPG Keychain Access from the Applications folder. click on the
Import icon in the upper left hand corner. GPG Keychain Access will then
prompt you for the name of the file which contains the key to import. It
will usually show you a list of files in the Documents folder. Click on the
file named import.asc (or import.txt), and click ok. The PGP public key
will then be imported into your PGP keyring.

To encrypt a message to a person, the message must be contained in a
TextEdit document. Use Command-A to highlight the entire document. Then
use Shift-Command-E to encrypt. GPG will pop-up a list of public keys in
your PGP keyring. Each key will have a little checkbox beside it which you
can check, to select that particular key. If you were encrypting a message
to me, you would put a check in the box beside my PGP key (Guru@SR).

When you click on OK, the plaintext (unencrypted) message in TextEdit will
be replaced with the encrypted message. You can then copy and paste the
encrypted message to enter it into a form on Silk Road, or anywhere else
that it needs to go.

To decrypt a message sent to you by other people, you need to copy that
message to the clipboard, and paste it into a Text Edit document. Again use
Command-A to highlight all the encrypted message. Then use Shift-Command-D
to decrypt the message. If the message is encrypted to your PGP public key,
you will be prompted to enter your passphrase. Once the correct passphrase
has been entered, and you click OK, then the message will be decrypted,
and the decrypted text will be placed in the Text Edit document, replacing
the encrypted message that was there previously.