Jolly Roger’s Security Thread for Beginners


Jolly Roger’s Security Thread for Beginners

Jolly Roger’s Security Thread for Beginners

By: Jolly Roger


Greetings comrades.

Through my research I have put together some security measures that should be considered by everyone. The reason I put this together is mainly for the newbies of this forum. But if I can help anyone out, then I am grateful for this. I would like to start out by saying, if you are reading like, you are likely a Silk Road user. If this is the case, then the #1 thing you must be using to even access this form is Tor. Tor will provide you with a degree of anonymity by using an 128­bit AES (Advanced Encryption Standard). There has been some debate as to whether or not the NSA can crack this code, and the answer is likely yes. This is why, you should never send anything over Tor that you aren't comfortable sharing with the entire world unless you are using some sort of PGP encryption which we will talk about later.

Communication from your computer, to the internet relies on an entry node which basically "enters your computer" into the Tor network. This entry node communicates with your computer, this entry node knows your IP address. The entry node then passes your encrypted request onto the relay node. The relay node communicates with the entry node and the exit node but does not know your computer's IP address. The exit node, is where your request is decrypted and sent to the internet. The exit node does not know your computer's IP, only the IP of the relay node. Using this model of 3 nodes it makes it harder, but not impossible to correlate your request to your original IP address.

The problem comes obviously when you are entering plain text into TOR because anybody can set up an exit node. The FBI can set up an exit node, the NSA, or any other foreign government, or any malicious person who may want to steal your information. You should not be entering any sensitive data into any websites, especially when accessing them over TOR. If any of the nodes in the chain are compromised, and some likely are, and the people in charge of those compromised nodes have the computing power to decrypt your request, then you better hope it wasn't anything sensitive.

So what can we do to fix this? Well, luckily we are now having more and more servers that are offering something called Hidden services. You can easily recognize these services by the address .onion. These services offer what's called end­to­end encryption. What this does is take the power out of the compromised exit nodes and put them back in your hands. The web server of the hidden service now becomes your exit node, which means the website you are visiting is the one decrypting your message, not some random exit node ran by a potential attacker. Remember, the exit node has the key to decrypt your request. The exit node can see what you are sending in clear text once they decrypt it. So if you are entering your name and address into a field, the exit node has your information. If you are putting a credit card, a bank account, your real name, even your login information, then you are compromising your identity.

Another step you can take, is to only visit websites that use something called HTTP Secure. You can tell if the website you are visiting is using HTTP Secure by the prefix at the beginning of the address. If you see hxxps:// then your website is using HTTP Secure. What this does is encrypts your requests so that only the server can decrypt them, and not somebody eavesdropping on your communication such as a compromised Tor exit node. This is another form of end­to­end encryption. If somebody were to intercept your request over HTTP Secure, they would see encrypted data and would have to work to decrypt it.

Another reason you want to use HTTPS whenever possible, is that malicious Tor nodes can damage or alter the contents passing through them in an insecure fashion and inject malware into the connection. This is particularly easier when you are sending requests in plain text, but HTTPS reduces this possibility. You must be made aware however, that HTTPS can also be currently cracked depending on the level of the key used to encrypt it. When you visit a website using HTTPS, you are encrypting your request using their public key and they are decrypting it using their private key. This is how cryptography works. A public key is provided to those who want to send an encrypted message and the only one who can decrypt is the one with the private key.

Unfortunately, many websites today are still using private keys that are only 1,024 bits long which in today's world are no longer enough. So you need to make sure you find out which level of encryption the website you are visiting uses, to make sure they are using at a minimum 2,048, if not 4,096 bits. Even doing all of this unfortunately is not enough, because we have another problem. What happens if the web server itself has become compromised? Maybe your TOR nodes are clean, maybe you have used HTTPS for all your requests, but the web server itself of the website you are visiting has been compromised. Well then all your requests are again, as good as plain text.

With that being said, this will conclude the first post in this series of the steps we can take to protect our privacy online, to remain anonymous and maintain our freedom.


So keep in mind that if you are a user of Silk Road, or any other form of activism, you never want to enter any identifying details about yourself online. Make it so that even if the NSA intercepted and decrypted, or compromised Silk Road that the only information they have against you is your username and password. How safe is that username and password? Does your password contain any identifying information? Is it the same password that you use for your personal email? Does it contain a name of somebody you know personally? Always keep all of these factors in mind.

Another step you must take, especially when communicating with other users on sites such as Silk Road is using PGP encryption. This is not always possible, such as in cases when you are logging into a website, filling out a form, logging into an email, etc.. Consider any type of information you enter into a website using plain text possibly compromised. Never put anything sensitive is any type of plain text format online. PGP comes into play because it uses a very strong method of encryption called cryptography. PGP stands for Pretty Good Privacy, and it is used for encrypting, decrypting and signing texts, e­mails, files, directories, and whole disk partitions and to increase the security of e­mail communications.

For the more technical users, it uses a serial combination of hashing, data compression, symmetric­key cryptography, and finally public­key cryptography. For the less technical users, the process of encrypting messages using PGP is as follows. You create a private key and a public key. The public key is the key you give out to people you want to send you encrypted messages. Your private key, is kept privately by you. This private key is the only key that can unlock messages that were previously locked with your public key.

If you are still confused, think about it like this. Think about a public key that can go around locking boxes that are intended for you. Anyone can lock a box that is intended for you, but you are the only one with the key to unlock the box. Either if the person who sent you a message locked a box (message) with your public key, they themselves can not unlock it. Only the person possessing the private key can unlock it. If you wish to respond to this person, you must use their public key to encrypt the message you intend to send to them. And they themselves, use their own private key to decrypt the message you sent them.

If you are still with me, I am glad I haven't lost you yet. This is called cryptography and was designed so that anybody intercepting your message could not decrypt the message without your private key. Even if you yourself, lose your private key, there is no method of key recovery. You can consider that message locked forever. So how do you use PGP?

Well before we get to that, I want to introduce you to a Live Operating System, which makes using PGP encryption and decryption very easy. A live operating system is an operating system that you can run on top of your current operating system. So for example, if you are a Windows user, you have 2 choices. You can download the live operating system, burn it to a CD or DVD and then boot your computer from that DVD or CD. This will make sure your computer run as if you have this operating system installed on your computer. However, if you remove the CD or DVD and reboot, then your computer will boot as normal. You can also use a USB drive to perform this same feature.

Secondly, you can run this live operating system in what's called a Virtual Box. The benefits of this are that you can run Windows simultaneously as you run this other operating system and you can easily switch back and forth between them without rebooting the computer. Both methods have their pros and cons. The pros of running a live CD boot, are that reduce the risk of having your computer compromised by viruses, malware and keyloggers that rely on Windows vulnerabilities to run.

If you are going to run this OS from a Virtual Box, I suggest downloading Virtual Box from Oracle. Note the hxxps://


Next, the live operating system I would encourage you to use is Tails. Tails can be found at the following website.


The reason I choose Tails, is because it has many of the security features that you require to stay anonymous already installed. Some users are not happy with Tails, but it really is a great operating system loaded with security features. Many I will talk about in this series on security including PGP encryption and decryption. Make sure you download the Tails ISO file from the official Tails website and you can either load it into Virtual Box or burn it to a DVD or load it onto a USB and booting your computer from that drive.

There are plenty of tutorials on how to load Tails into Virtual Box, so I won't go into much detail other than, make sure you run Virtual Box and Tails from a USB drive or SD card. I would suggest a USB drive however for reasons I will explain later. But basically when when Virtual Box runs directly on your hard drive, it creates a virtual hard drive that is uses as a temporary hard drive while Tails is running. Once Tails is closed, this virtual drive is deleted, but it's not permanently deleted. As we know from the power of recovery tools, deleted files are easily recoverable with the right tools. I will talk about how to protect your files from data recovery tools in future posts but for now, just keep Virtual Box and Tails OFF of your hard drive, and load it either on a USB drive or SD card.

The same goes when booting your computer directly into Tails from a DVD or USB stick. Your hard drive will be used to store files used by Tails, so make sure any files that are saved or accessed using Tails are done from a USB stick or SD card, otherwise they will be recoverable. This is why I prefer using a Virtual Box and running both the Virtual Box and Tails inside of it, off of a USB stick. Keep as much as possible off of your actual hard drive. It is possible to shred files beyond recovery, but it's much easier to do this on a 16gb flash drive, then it is a 1 TB hard drive.

Next post we will get back on topic and start learning how to use PGP. The reason I have to take a detour to using Tails is because we will be using Tails for many of the features from here on out, including PGP.


Ok, so by now I am assuming you have Tails running. Let's learn how to use PGP within Tails. First thing you are going to want to do is create your own personal key, which consists of your public key that you can give out to people or post in your profiles online. As mentioned before, this is the key people use to encrypt messages to send to you. Your personal key also consists of your private key which you can use to decrypt messages that are encrypted using your PGP public key.

If you look up to the top right area, you will see a list of icons, and one o them looks like a clipboard. You need to click on that clipboard and click Manage Keys

Next click File ­> New
Select PGP Key and click Continue
Fill out your full name (I suggest you use your online name, not your real name)
Optionally fill out an email and a comment as well.
Next, click Advanced Key Options.
Make sure Encryption type is set to RSA and set key strength to 4096.
Once you have done this, click Create and it will generate your key.

Once you have done this, you can view your personal key by clicking the tab My Personal Keys. You have now created your personal key! To find your PGP public key, you right click on your personal key and click Copy and it will copy your PGP public key to your clipboard, in which you can paste anywhere you wish. A PGP public key will look something like this.