PGP practice thread

Hope this Thread is still alive :slight_smile:

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=rzJv
-----END PGP MESSAGE-----
1 Like

Worked just fine! Thanks for participating and bringing some life to thread.

Wow it’s been 7 Months.
I would also like to see a Kryptey practice thread for a more practical-ish encryption (since it uses Signal protocol) but yeah

1 Like

PGP will always be king, in my humble opinion. As cumbersome as UI/UX might be, undisputable OG. Love me some PGP-only conversations.

Hope I’m not too late to the party:

-----BEGIN PGP PUBLIC KEY BLOCK-----

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=3R3t
-----END PGP PUBLIC KEY BLOCK-----

1 Like
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=bJxx
-----END PGP MESSAGE-----
-----BEGIN PGP MESSAGE-----

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=Muk8
-----END PGP MESSAGE-----

Public key:

-----BEGIN PGP PUBLIC KEY BLOCK-----

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=dXL1
-----END PGP PUBLIC KEY BLOCK-----


1 Like
-----BEGIN PGP MESSAGE-----

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1 Like

Former.
Not finding a key for you. Most likely on my end.

Do you mean on the keyserver? I didn’t publish this one because it’s just a throwaway for practicing :sweat_smile: not sure if you noticed the “email” attached to my key haha

1 Like

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-----END PGP MESSAGE-----

-----BEGIN PGP MESSAGE-----
Version: Mailvelope v6.1.0
Comment: https://mailvelope.com

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-----END PGP MESSAGE-----

It’s fine to learn how PGP works from historical PoV, every good cypherpunk should knows their roots. But I’m going to have to be that guy and give some unwelcome advice.

It’s the case many intelligence agencies are performing https://en.wikipedia.org/wiki/Harvest_now,\_decrypt_later attacks, where they collect all messages as they transit through the backbone of the Internet.

In the video below, Snowden talks about how the largest intelligence services can own any modern phone the minute it connects to their network.

And the video below he talks about breaking into computers being done daily.

PGP lacks a fundamentally important property called Forward secrecy - Wikipedia which means that if someone hacks your device, they can steal your PGP private key, and use it to decrypt all those messages harvested from the backbone.

Another major issue is, it uses digital signatures for messages and thus lacks deniable authentication, meaning only you have the key that signs messages you send. That makes it impossible for you to deny what you wrote. Modern messaging uses Message Authentication Codes (MACs) for message signing which means both the sender and the recipient has the key to sign and verify some message. This makes it impossible for your contact to cryptographically prove they did not forge the conversation. I’ve never heard any court care about this but still, it should be done when it can be done, and PGP fundamentally can’t do it because there’s no session.

PGP is also documented to be hard to use


For the purpose of secure messaging, PGP was superseded over 20 years ago with the OTR protocol by Goldberg and Borisov, two very well known cypherpunks.

OTR provided both forward secrecy and break-in key recovery (future secrecy), but it required a synchronous session, i.e. that both are online at the same time.

Signal protocol improved on OTR by ensuring per-message forward secrecy even without round trips of OTR’s Diffie-Hellman ratchet. It handled cross-platform chats seamlessly and supports groups with sizes that are at the edge of what can be expected to have reasonable expectation of privacy.


So as someone who’s been to and who’s organized a few crypto-parties let me say that you should move towards newer, better tools as soon as you nail the basics of PGP.

If you want a trip down the memory lane, you should also check the OTR-plugin for Pidgin, to see what we had to deal with back in the day, in terms of usability; manually enabling E2EE every time, almost impossible cross-platform usage etc. OTR’s 1536-bit keys are considered outdated these days, the modern recommendation is 3072 bits. So don’t actually use it in production.

So what to actually learn?

  1. Signal with usernames (gold standard for day-to-day conversations), how to check safety numbers, how to help friend check common contact’s safety number from safety-number halves.
  2. Cwtch and Ricochet Refresh for metadata-resistant conversation over Tor. For situations where you need to hide from everyone who you’re even talking to.
  3. OnionShare for secure file sharing and maybe dissident blog hosting, and Tor Browser on how to access said Onion Service blog.

PGP still has one good use purpose. You should learn to digitally sign files with it: it comes handy if you ever want to release software or official statements or whatever.

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PGP isn’t the best option for that either, there’s Sigstore, Minisign, and Kryptor

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Yeah I would absolutely prefer Denis’ Minisign, but the thing is it’s not bundled by AFAIK any Linux distro, which is a decent requirement for verifying software signatures.

E.g. https://www.kryptor.co.uk/ has detached signatures that use… kryptor : ) Talk about a bootstrapping problem. Yeah the SHA256 are probably fine, especially if you have the site’s TLS certificate fingerprint pinned somewhere. Oh what’s that? It changes every three months?

age and minisign at least install via apt, which is a bit better. So yeah teaching any those is not a bad idea because when the best one gains popularity, it incentivizes distro vendors to bundle it.

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I don’t believe anyone ever made one for Kleopatra. Maybe this will help. It’s for tails os, but I don’t see what it wouldn’t work on linux as well. Anyway, if you need to edit it, feel free to do so.

Instructions for using Kleopatra on Tails os.

Note – Should be mostly the same for Linux users except for the persistent storage

Basics of PGP Keys, Creating, Encrypting, Decrypting, and Verifying

This guide is meant for people new to PGP. It does not describe advanced techniques such as expiring keys and command line interface.

Part 1 - Configure Persistent Storage in Tails for PGP Key Retention

Part 2 - Creating a Basic Key Pair in Kleopatra

Part 2 (Optional) - Creating a Backup of Your Key Pair in Kleopatra at Key Creation

Part 3 - Exporting your Public Key in Kleopatra

Part 4 - Copying Your Public Key in Cleartext to Post on Other Web Sites or Send to another person

Part 5 - Importing a Public Key Into Your Keyring

Part 6 - Decrypting a Message

Part 7 - Verifying a PGP Signed Message

Part 8 - Encrypting a Message

Part 9 - PGP Signing a Message (To prove you have control of your secret key)

Part 10 - Backing Up Your Secret Key After Creation

Part 11 - Changing an Expiry Date for a Secret Key

Part 1 - Configure Persistent Storage in Tails for PGP Key Retention

Step 1 - In Tails, click Applications - Favorites - Configure persistent volume

Step 2 - In the Setup Tails persistent volume popup, scroll down to GnuPG and slide the button to the right. The background will turn blue when it is enabled.

Step 3 - Click Save.

Step 4 - Fill out a passphrase if you are prompted.

Step 5 - Once completed, click Save and restart Tails.

Step 6 - In the Welcome to Tails window, fill in your Persistent Encrypted Storage passphrase and click Unlock. You should receive a message the persistent storage is unlocked. If the background turns bright blue, you entered the wrong passphrase. Try again.

Step 7 - Once your persistent storage is unlocked, click Start Tails.

Part 2 - Creating a Basic Key Pair in Kleopatra

Step 1 - Start Kleopatra

Step 2 - Click File - New Key Pair

Step 3 - In the Key Pair Creation Wizard – Kleopatra popup, click Create a personal OpenPGP pair

Step 4 - Enter your desired key name on the Name: line

Email – Optional (If using tails, you may not want to add an email)

Step 5 - Click Advanced Settings…

Step 6 - In the Advanced Settings – Kleopatra popup, change RSA from 3072 to 4096. Change + RSA from 3072 to 4096. Uncheck Valid until:, then click OK.

Step 7 - Click Next >, then click Create.

Step 8 - In the popup, enter a passphrase in the Passphrase: line, and repeat the passphrase in the Repeat: line, then click OK.

Step 9 - In the Key Pair Creation Wizard - Kleopatra popup, in the Result area, you should see Key pair created successfully followed by the Fingerprint: for you new private key.

Step 10 - If you want to make a backup of your key pair, go to Part 2 - (Optional) Creating a Backup of Your Key Pair in Kleopatra at Key Creation, now. Otherwise, click Finish.

NOTE - You can back up your secret key later by following the steps in Part 10 - Back Up Your Secret Key After Creation.

Part 2 (Optional) - Creating a Backup of Your Key Pair in Kleopatra at Key Creation

Step 1 - In the Key Pair Creation Wizard - Kleopatra popup, under Next Steps click Make a Backup Of Your Key Pair…

Step 2 - In the Export Secret Key – KLeopatra popup, under Name, double-click Persistent.

Step 3 - Change the File name: to something you will remember as your backup secret key. I use SecretBackup.asc

Step 4 - Click Save

Step 5 - In the Passphrase: popup, enter the passphrase for your secret key, then click OK.

Step 6 - In the Secret Key Export Finished – Kleopatra popup, click OK.

NOTE - You can copy this saved key to a USB drive to have an offline copy on seperate media.

Part 3 - Exporting your Public Key in Kleopatra

Step 1 - In Kleopatra, find your secret key (it will be in bold text).

Step 2 - Right click on the key, then find and click on Export

NOTE - Do not click Export Secret Keys at this time.

Step 3 - In the Export Certificates – Kleopatra popup, double-click Persistent in the Name list.

Step 4 - Rename the File name: to something you will remember. I use PublicKey.asc (Make it simple so you can easily spot the file), then click Save.

Part 4 - Copying Your Public Key in Cleartext to Post on Other Web Sites or Send to Another Person

Step 1 - Open Applications - Favorites - Files, then click on Persistent in the list on the left side of the window.

Step 2 - Right click the PublicKey.asc file, then click Open With Other Application.

Step 3 - In the Select Application popup, click View All Applications at the bottom.

Step 4 - Under Related Applications, find and double-click on Text Editor. This opens a new Text Editor window with your keyfile in cleartext.

NOTE - If you have another Text Editor window active, the file will open as a new tab.

Step 5 - In Text Editor, click on the PublicKey.asc tab.

Step 6 - Click in the cleartext key, then press Ctrl+A to highlight the entire key. Press Ctrl+C to copy the highlighted key.

Step 7 - Go to the site or message you want to copy your key into, then click in the message/PGP Public Key area and press Ctrl+V to paste the copied key.

Part 5 - Importing a Public Key Into Your Keyring

Step 1 - Highlight the key from -----BEGIN PGP PUBLIC KEY BLOCK----- to -----END PGP PUBLIC KEY BLOCK-----, then press Ctrl+C to copy the key into the clipboard.

Step 2 - In Kleopatra, click Tools - Clipboard - Certificate Import

Step 3 - In the You have imported a new certificate (public key) – Kleopatra popup, you are given the opportunity to mark the certificate as valid. If the certificate is from a trusted source, click Yes and go to step 4. If not, click No and you are done importing the key.

NOTE - If you receive a Certificate Import Result – Kleopatra popup, you already have the certificate in your keyring. You will see Total number processed: 1, Imported 0, and Unchanged 1 in the detailed results. You are done importing the key.

Step 4 - In the Certify Certificate: – Kleopatra popup, set the Certify with: selection to your secret key name, then press Certify.

Step 5 - Enter your secret key passphrase if you are prompted, in the Passphrase: line, then click OK.

Step 6 - In the Certification Succeeded popup, click OK. You are done importing the key.

Part 6 - Decrypting a Message

Step 1 - Highlight the message starting with -----BEGIN PGP MESSAGE----- and through -----END PGP MESSAGE-----, then press Ctrl+C to copy the message.

Step 2 - In Kleopatra, click Tools - Clipboard - Decrypt/Verify. Enter your secret key passphrase if prompted.

Step 3 - Click Applications - Accessories - Text Editor to open a blank Text Editor window.

Step 4 - Click anywhere in the window, and press Ctrl+V to paste the decrypted message.

Step 5 - Read the message

Part 7 - Verifying a PGP Signed Message

Step 1 - Highlight the PGP signed message, beginning with -----BEGIN PGP SIGNED MESSAGE----- and ending with -----END PGP SIGNATURE-----, then press Ctrl+C to copy the message into the clipboard.

Step 2 - In Kleopatra, click Tools - Clipboard - Decrypt/Verify

Step 3 - In the Decrypt/Verify E-Mail – Kleopatra popup, under All operations completed, look for a message with a green-tinted background. Look for Valid signature by , then look below that for the message The signature is valid and the certificate’s validy is ultimately trusted. Then click Finish. The signed message is verified as good.

Step 4- IF the background is red-tinted, the message will say Invalid signature, and the bottom line will say The signature is invalid: Bad signature. This means the signed message has probably been altered. and the signature is bad. Click Finish and do not trust the message or links in the message.

IF the background is not tinted, you might not have the key from the signing certificate (aka other persons Public Key) in your keyring, or you might not have certified that key. Check your keyring for the certificate name, and if you can’t find it go to Part 5 - Importing a Public Key Into Your Keyring.

Part 8 - Encrypting a Message

NOTE - This Part presumes you have imported the Public Key as described in Part 5 - Importing a Public Key Into Your Keyring. If you haven’t imported the message receiver’s Public Key, go to Part 5.

Step 1 - Click Applications - Accessories - Text Editor to open a blank Text Editor window.

Step 2 - Write the message you want to send in the Text Editor window

Step 3 - Press Ctrl+A to highlight the completed message, then press Ctrl+X to cut the message from the window and into the clipboard.

Step 4 - In Kleopatra, click Tools - Clipboard – Encrypt

Step 5 - In the Encrypt Mail Message – Kleopatra popup, click Add Recipient…

Step 6 - In the Certificate Selection – Kleopatra popup, scroll through the list of certificates by name to find the receiver’s certificate, click on the certificate name to highlight it, then click OK.

NOTE - You can choose more than one certificate to encrypt for if you want or need to such as when you’re messaging multiple people.

Step 7 - In the Encrypt Mail Message – Kleopatra popup, check the name(s) in the Recipient list, then click Next.

Step 8 - Check the Results for Encryption succeeded, then press OK.

Step 9 - Go to the message you’re sending. Click in the blank area and press Ctrl+V to paste the encrypted message.

NOTE - You can paste the encrypted message in the open Text Editor window if you’re not ready to send it yet.

Part 9 - PGP Signing a Message (To prove you have control of your secret key)

Step 1 - Click Applications - Accessories - Text Editor to open a blank Text Editor window.

Step 2 - Write the message in the Text Editor window.

Step 3 - Press Ctrl+A to highlight the completed message, then press Ctrl+X to cut the message from the window into the clipboard.

Step 4 - In Kleopatra, click Tools - Clipboard - OpenPGP Sign

Step 5 - In the Sign Mail Message – Kleopatra popup, click Change Signing Certificates…

Step 6 - In the Select Signing Certificates – Kleopatra popup, set the OpenPGP Signing Certificate: to your secret key in the drop-down list, then click OK.

Step 7 - Click Next.

Step 8 - Enter your secret key passphrase, then click OK.

Step 9 - You should see a message in blue saying Signing succeeded. Click OK.

Step 10 - Navigate to the place you want to post the PGP signed message, click once in the blank area, then press Ctrl+V to paste the message into the desired spot.

Part 10- Backing Up Your Secret Key After Creation

Step 1 - In Kleopatra, scroll through your certificates (aka keys) until you see your secret key (it will be in bold), then right-click on the key.

Step 2 - In the popup, click Export Secret Keys…

Step 3 In the Export Secret Key – Kleopatra popup, under Name, double-click Persistent.

Step 4 - Change the File name: to something you will remember as your backup secret key. I use SecretBackup.asc

Step 5 - Click Save

Step 6 - In the Passphrase: popup, enter the passphrase for your secret key, then click OK.

Step 7 - In the Secret Key Export Finished – Kleopatra popup, click OK.

NOTE - You can copy this saved key to a USB drive to have an offline copy on seperate media.

Part 11 - Changing an Expiry Date for a Secret Key

READ THIS FIRST - Changing the Expiry Date (aka Valid Until date) will change your Secret and Public Key Pair. Remove your current Public Key from all places that use it for 2FA OR YOU WILL BE LOCKED OUT OF THOSE ACCOUNTS. Also remove the Public Key from all sites, or you will not be able to re-enable 2FA.

Step 1 - Remove your current Public Key from all places using it for 2FA FAILURE TO REMOVE YOUR CURRENT PUBLIC KEY FROM 2FA WILL LOCK YOU OUT OF YOUR ACCOUNTS. FAILURE TO REMOVE YOUR PUBLIC KEY COMPLETELY WILL MEAN YOU CANNOT RE-ENABLE 2FA.

Step 2 - Find your Secret Key in Kleopatra, right click on the key, then click Change Expiry Date…

Step 3 - In the Change Expiry - Kleopatra popup, change the date to Never if you want a “forever” key that never expires.

Step 4 - Click OK

Step 5 - Delete your old Public Key anywhere you have it saved. It is now useless.

Step 6 - Export your new Secret Key as described in Part 10- Backing Up Your Secret Key After Creation, and replace all copies of your old Secret Key with your new one.

Step 7 - Repeat Part 3 - Exporting your Public Key in Kleopatra.

Step 8 - (Optional) Refer to Part 4 - Copying Your Public Key in Cleartext to Post on Other Web Sites as needed to enable 2FA on all the sites you disabled it.

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Did you make it yourself, or what is the source? No screenshots? Just wondering! Thanks.

Sorry, no screenshots. It’s just a guide I had in my notes. Some, I put together and some I believe came from a couple of sources, possibly reddit or maybe dread or both. I don’t remember exactly.

Should I just leave it here or should I make a new guide like the other guy said to do?

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what other guy? a new Linux/Tails OS PGP how-to guide, or something else? my bad, got a bit lost there…

I was asking for screenshots in case you’d like me to add a new entry in my blog with it, so that I myself have both Android and Linux how-to guides in there. OP lists the OpenKeychain one. :+1: