PGP Tutorial For OS X

DDW Archive
DeepDotWeb   20 Feb 2015   26

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 http://gpgtools.org, and download ‘GPG Suite Beta 5’
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  2. Open the file you downloaded, you should see this screen. Double click on ‘Install’
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  3. Follow the installation process. If successful, you should see this screen. You can now close the window
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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
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  2. Click ‘New’ at the top left of the window
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  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’
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  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.
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  5. annndddddd we’re done!
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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’
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  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.
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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’
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  3. Give it a name, make sure ‘include secret key in exported file’ is unchecked, and click ‘save’
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  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
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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
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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—–‘
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  3. Paste it into your favourite text editor, highlight everything, right click, go to ‘Services’, then ‘OpenPGP: Import key’
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  4. You’ll see this window pop up confirming the key has been imported, click ‘Ok’
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  5. Open up GPG Keychain just to confirm the key is there
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Part 7 – Importing a private key

Again, really easy.

  1. Open GPG Keychain, click ‘Import’ at the top
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  2. Browse to where your key is, click it, then click ‘Open’. It should have a .asc file extension
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  3. You’ll see this pop up confirming your key has been imported. Click ‘Close’
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Part 8 – Encrypting a message

  1. Open your text editor of choice, write your message
  2. Highlight the message, right click, ‘Services’, ‘OpenPGP: Encrypt’
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  3. A window should appear. Select who you’re sending it to, sign it with your key if you wish, click ‘Ok’
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  4. Copy everything, and send it to the recipient
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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’
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  3. A window should pop up. Enter your passphrase, then click ‘Ok’
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  4. aannnddddd there’s your message
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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!

26 Comments

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  1. March 22, 2018 at 5:43 am Xerex

    Merci !!!! très clair et très utile

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  2. January 7, 2018 at 9:56 am papel

    When i download the PGP program adn created an account: while create an account it doesn’t give the option to create the passphrase while created the account.

    Please someone help.

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  3. December 20, 2017 at 11:30 am Brandon

    I’m trying to communicate with a guy and normally at the top of our communication it says PGPtools blah blah blah, well this guy is now sending me encryptions with the top saying GnuPG V.2, and when i go to copy, paste, and decrypt, it keeps saying Decrypt Failed, (no secret Key) Code=17. Its seriously frustrating the hell out of me that this keeps happening and i have no way to communicate with him now….. Please can someone give me insight on how to mend this issue?

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    • March 8, 2018 at 4:51 am terry

      Try looking up his latest address as you did to get the original address.

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  4. July 19, 2017 at 8:57 am ivy

    Where can I download GPG Keychain?

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    • August 30, 2017 at 5:01 am Mephisto

      If you don’t even have the ability to use a search engine, maybe the DarkNet is not for you.

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  5. June 8, 2017 at 8:50 am Dave Fox

    When I try to get my public key, it just takes me to a box marked verification results and verification failed

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  6. February 12, 2017 at 10:15 am DamienMoi

    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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  7. January 22, 2017 at 6:31 am mathieu

    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

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  8. October 17, 2016 at 8:12 am pinksquirrel

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

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  9. October 14, 2016 at 7:55 am betty

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

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  11. January 30, 2016 at 3:35 am knotknotone

    Very useful guide, thanks to the writer.

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  12. September 26, 2015 at 6:26 am Marker

    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/

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  13. September 16, 2015 at 9:56 am Neeleekesnah010

    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)

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    • March 8, 2018 at 4:49 am terry

      If it was dangerous on a mac,I’d probably know it by now.Use a VPN and tor and you should be alright?In spite of a recent article saying tor was government.It was taken from the navy(US).The providers have to cooperate with FBI and NSA.If you weren’t aware of that,you know nothing.

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  14. August 13, 2015 at 3:18 am Rom012010

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

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  15. July 7, 2015 at 8:26 am 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.

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    • September 20, 2015 at 9:24 am sudon't

      Same way you send any other email. You’re pasting the encrypted contents of the text file into a new email.

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  16. July 7, 2015 at 7:17 am Just Sayin

    Check out every Step #3 and pay close attention to the screen shots. The email address says: [email protected]! and entered in the comment section: jk not jk. Should we be spooked? Does anyone know where this tutorial came from!?

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    • June 3, 2017 at 10:52 am leo

      Just sayin

      if u look at the same line in the screenshot, the sender of the email have an adress in @fbi.gouv

      maybe

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  17. February 26, 2015 at 12:40 am ANON

    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?

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  18. February 25, 2015 at 9:13 am sudon't

    “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.

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    • March 16, 2015 at 6:57 am deepdotcom

      would you care to explain a little about why not on OS X? any useful links you can pass over?

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      • March 16, 2015 at 8:06 am sudon't

        Are you asking me? I’m quoting the author and asking the same question.

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    • April 26, 2015 at 11:39 am mac

      I would like to know as well, because my searches also didn’t reveal anything.

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