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PGP Tutorial For OS X

Full credit goes to MLP_is_my_OPSEC for writing this tutorial – Thanks for publishing and giving your permission to repost!

Part 0 – Introduction

Here’s my basic guide for PGP on OS X. The OS in question is OS X 10.9 Mavericks, but it should still work for other versions. As for the tool itself, we’ll be using GPG Suite Beta 5. This is my first time using OS X in… years. If you see anything I’m doing wrong, or could be done easier, feel free to correct me in the comments.

If you’ve done your research, you’ll see it’s not recommended to do anything darknet related on OS X, but I’m not going to go over the details here. You’ve obviously made your decision.

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Part 1 – Installing the software

Like I said above, we’ll be using GPG Suite Beta 5. If you’re curious and want to see the source code, you can do so here.

  1. Head on over to https://gpgtools.org, and download ‘GPG Suite Beta 5’ UAQo3Ca[1]
  2. Open the file you downloaded, you should see this screen. Double click on ‘Install’ dV8D0FZ[1]
  3. Follow the installation process. If successful, you should see this screen. You can now close the window m8qytPb[1]

Part 2 – Creating your keypair

GPG Suite actually makes this a super simple process. Just like the Linux guide, we’ll be using 4096 bit length for encryption.

  1. Open up GPG Keychain, you should be greeted by this beautiful window 1xvho3K[1]
  2. Click ‘New’ at the top left of the window JH57cE5[1]
  3. You should see a small popup. Click the arrow beside ‘Advanced options’, make sure the key length is 4096. For our purposes, we’ll uncheck ‘key expires’. Put your username where it says ‘full name’, fill out what you want for email, and create a secure passphrase. Check the picture for an example on how to fill it out. When complete, click ‘Generate key’ UPn7xO4[1]
  4. GPG Keychain will begin generating your key. Move the mouse around, mash keys in a text editor, have something downloading. Do random stuff to create entropy for a secure key. 1oFPI10[1]
  5. annndddddd we’re done! J0HkvZG[1]

Part 3 – Setting up the environment

This is where OS X differs from other platforms. The suite itself doesn’t provide a window to encrypt/decrypt messages, so we need to enable some options.

  1. Go into system preferences, open up ‘Keyboard’ EYKyVkn[1]
  2. You should see this window. Click the ‘Keyboard Shortcuts’ tab at the top, then ‘Services’ in the left pane. Scroll down in the right pane to the subsection labeled ‘Text’, and to the OpenPGP options. Here you can create keyboard shortcuts. We’ll uncheck everything OpenPGP that’s under ‘Text’, and delete their shortcuts. Now we’ll enable ‘Decrypt’, ‘Encrypt’, and ‘Import key’. Create keyboard shortcuts for these if you wish. Check the picture to make sure you’re doing everything correctly. You can now close the window. 2vQlkq8[1]

Part 4 – Obtaining your public key

This part is super simple.

  1. Open up GPG Keychain, select your key
  2. At the top of the window, click ‘Export’ pvVfw2V[1]
  3. Give it a name, make sure ‘include secret key in exported file’ is unchecked, and click ‘save’ xwjzDoI[1]
  4. Open your text editor of choice, browse to where you saved the key, open it
  5. There it is. Copy and paste this on your market profile to make it easier for people to contact you RJhHUWx[1]

Part 5 – Obtaining your private key

Again, super simple.

  1. Open up GPG Keychain, select your key
  2. At the top of the window, click ‘Export’
  3. Keep the file name it gives you, check ‘Include secret key in exported file’, then click save QSLfhqW[1]

Keep this file in a safe place, and don’t forget your passphrase. You’re fucked without it!

Part 6 – Importing a public key

This is really easy.

  1. Find the key you want to import.
  2. Copy everything from ‘—–BEGIN PGP PUBLIC KEY BLOCK—–‘ to ‘—–END PGP PUBLIC KEY BLOCK—–‘ nH6MBYc[1]
  3. Paste it into your favourite text editor, highlight everything, right click, go to ‘Services’, then ‘OpenPGP: Import key’ Uq40mv1[1]
  4. You’ll see this window pop up confirming the key has been imported, click ‘Ok’ CWv0ySL[1]
  5. Open up GPG Keychain just to confirm the key is there zQYRK9c[1]

Part 7 – Importing a private key

Again, really easy.

  1. Open GPG Keychain, click ‘Import’ at the top o7XMOBq[1]
  2. Browse to where your key is, click it, then click ‘Open’. It should have a .asc file extension yUTGU3o[1]
  3. You’ll see this pop up confirming your key has been imported. Click ‘Close’ 5Cadwt8[1]

Part 8 – Encrypting a message

  1. Open your text editor of choice, write your message
  2. Highlight the message, right click, ‘Services’, ‘OpenPGP: Encrypt’ LWjLFfL[1]
  3. A window should appear. Select who you’re sending it to, sign it with your key if you wish, click ‘Ok’ g4UyC6Y[1]
  4. Copy everything, and send it to the recipient AFGqEOx[1]

Part 9 – Decrypting a message

Pretty much the same process as encrypting

  1. Open your text editor of choice, paste the message
  2. Highlight everything, right click, ‘Services’, ‘OpenPGP: Decrypt’ u2wWMtA[1]
  3. A window should pop up. Enter your passphrase, then click ‘Ok’ gL2nnbq[1]
  4. aannnddddd there’s your message zNX94M7[1]

Part 10 – Conclusion

That wasn’t too hard, was it? Like I said in the intro, you shouldn’t be using OS X for DNM activities due to privacy issues, but I won’t go into it. This took forever to complete because OS X is a bitch to get running properly in a virtual machine. A guide for Windows will be coming next week!

17 comments

  1. “If you’ve done your research, you’ll see it’s not recommended to do anything darknet related on OS X, but I’m not going to go over the details here.”

    I can only presume you’re recommending Tails, not Windows. What vulnerability are you talking about? If you’re going to make a sweeping statement like that, at least provide a link, because I can find nothing on this.

  2. Agreed with the above statement ^^^.

    Care to explain?

    Using a VPN and ensuring no DNS leaks (unlike Windows OS X doesn’t leak up the anus, although you need to be careful as always….)…what privacy concerns are we talking about? Secret NSA backdoors forced by Apple to be added to their code?

  3. Puzzled newbie

    Whats with Step 8. (Encrypt your Message ) ??
    It just says: “Copy everything, and send it to the recipient”…
    How exactly do you send it to the recipient ? All this step does is encrypt the text.

  4. hello
    i cannot decrpt message from public pgp it say : Decrypt failed!
    code=0 everythings works exept that…does anyone can help me thanks

  5. So I’m trying to figure out if I should do this on my mac or not can someone please help me out (new to this and don’t wanna get in any problems)

  6. This guide is for PGP and show GPGtools
    PGP and GPG are not the same thing…
    http://www.differencebetween.net/technology/software-technology/difference-between-pgp-and-gpg/

  7. Very useful guide, thanks to the writer.

  8. part 3 step 2. I dont have decrypt encrypt and import. Only encrypt decrypt selection and import key from selection. What should I do??

  9. Omg you just saved my fucking life. Thank you soooo much

  10. HI,

    When import my keys, a window announce me : “1 key treated and 0 keys imported”

    I checked up many times the keyboard configuration and it’s the same according to the tutorial.

    Part 6.4 is okay, and nothing about the part 6.7

    COuld you help me?

    Mac Os el capitan

  11. I don’t know why do a forum because you DON T ASWER when we ask a question.
    My question is the same Just Sayin, but youv DIDN’T Answer Him.

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