Encryption - Crypto 101
https://tryhackme.com/room/encryptioncrypto101
Task 1: What will this room cover?
I'm ready to learn about encryption
No answer needed
Task 2: Key terms
Ciphertext - The result of encrypting a plaintext, encrypted data
Cipher - A method of encrypting or decrypting data. Modern ciphers are cryptographic, but there are many non cryptographic ciphers like Caesar.
Plaintext - Data before encryption, often text but not always. Could be a photograph or other file
Encryption - Transforming data into ciphertext, using a cipher.
Encoding - NOT a form of encryption, just a form of data representation like base64. Immediately reversible.
Key - Some information that is needed to correctly decrypt the ciphertext and obtain the plaintext.
Passphrase - Separate to the key, a passphrase is similar to a password and used to protect a key.
Asymmetric encryption - Uses different keys to encrypt and decrypt.
Symmetric encryption - Uses the same key to encrypt and decrypt
Brute force - Attacking cryptography by trying every different password or every different key
Cryptanalysis - Attacking cryptography by finding a weakness in the underlying maths
Alice and Bob - Used to represent 2 people who generally want to communicate. They’re named Alice and Bob because this gives them the initials A and B.
I agree not to complain too much about how theory heavy this room is.
No answer needed
Are SSH keys protected with a passphrase or a password?
passphrase
Task 3: Why is Encryption important?
Cryptography is used to protect confidentiality, ensure integrity, ensure authenticity. You use cryptography every day most likely, and you’re almost certainly reading this now over an encrypted connection.
What does SSH stand for?
Secure Shell
How do webservers prove their identity?
certificates
What is the main set of standards you need to comply with if you store or process payment card details?
PCI-DSS
Task 4: Crucial Crypto Maths
What's 30 % 5?
0
What's 25 % 7
4
What's 118613842 % 9091
3565
Task 5: Types of Encryption
The two main categories of Encryption are symmetric and asymmetric.
Symmetric encryption uses the same key to encrypt and decrypt the data. Examples of Symmetric encryption are DES (Broken) and AES. These algorithms tend to be faster than asymmetric cryptography, and use smaller keys (128 or 256 bit keys are common for AES, DES keys are 56 bits long).
Asymmetric encryption uses a pair of keys, one to encrypt and the other in the pair to decrypt. Examples are RSA and Elliptic Curve Cryptography. Normally these keys are referred to as a public key and a private key. Data encrypted with the private key can be decrypted with the public key, and vice versa. Your private key needs to be kept private, hence the name. Asymmetric encryption tends to be slower and uses larger keys, for example RSA typically uses 2048 to 4096 bit keys.
RSA and Elliptic Curve cryptography are based around different mathematically difficult (intractable) problems, which give them their strength. More about RSA later.
Should you trust DES? Yea/Nay
Nay
What was the result of the attempt to make DES more secure so that it could be used for longer?
Triple DES
Is it ok to share your public key? Yea/Nay
Yea
Task 6: RSA - Rivest Shamir Adleman
The math(s) side
RSA is based on the mathematically difficult problem of working out the factors of a large number. It’s very quick to multiply two prime numbers together, say 17*23 = 391, but it’s quite difficult to work out what two prime numbers multiply together to make 14351 (113x127 for reference).
The attacking side
The maths behind RSA seems to come up relatively often in CTFs, normally requiring you to calculate variables or break some encryption based on them. The wikipedia page for RSA seems complicated at first, but will give you almost all of the information you need in order to complete challenges.
There are some excellent tools for defeating RSA challenges in CTFs, and my personal favorite is https://github.com/Ganapati/RsaCtfTool which has worked very well for me. I’ve also had some success with https://github.com/ius/rsatool.
The key variables that you need to know about for RSA in CTFs are p, q, m, n, e, d, and c.
“p” and “q” are large prime numbers, “n” is the product of p and q.
The public key is n and d, the private key is n and e.
“m” is used to represent the message (in plaintext) and “c” represents the ciphertext (encrypted text).
CTFs involving RSA
Crypto CTF challenges often present you with a set of these values, and you need to break the encryption and decrypt a message to retrieve the flag.
There’s a lot more maths to RSA, and it gets quite complicated fairly quickly. If you want to learn the maths behind it, I recommend reading MuirlandOracle’s blog post here: https://muirlandoracle.co.uk/2020/01/29/rsa-encryption/.
p = 4391, q = 6659. What is n?
29239669
I understand enough about RSA to move on, and I know where to look to learn more if I want to.
No answer needed
Task 7: Establishing Keys Using Asymmetric Cryptography
A very common use of asymmetric cryptography is exchanging keys for symmetric encryption.
Asymmetric encryption tends to be slower, so for things like HTTPS symmetric encryption is better.
But the question is, how do you agree a key with the server without transmitting the key for people snooping to see?
Metaphor time
Imagine you have a secret code, and instructions for how to use the secret code. If you want to send your friend the instructions without anyone else being able to read it, what you could do is ask your friend for a lock.
Only they have the key for this lock, and we’ll assume you have an indestructible box that you can lock with it.
If you send the instructions in a locked box to your friend, they can unlock it once it reaches them and read the instructions.
After that, you can communicate in the secret code without risk of people snooping.
In this metaphor, the secret code represents a symmetric encryption key, the lock represents the server’s public key, and the key represents the server’s private key.
You’ve only used asymmetric cryptography once, so it’s fast, and you can now communicate privately with symmetric encryption.
The Real World
In reality, you need a little more cryptography to verify the person you’re talking to is who they say they are, which is done using digital signatures and certificates. You can find a lot more detail on how HTTPS (one example where you need to exchange keys) really works from this excellent blog post. https://robertheaton.com/2014/03/27/how-does-https-actually-work/
I understand how keys can be established using Public Key (asymmetric) cryptography.
No answer needed
Task 8: Digital signatures and Certificates
What's a Digital Signature?
Digital signatures are a way to prove the authenticity of files, to prove who created or modified them. Using asymmetric cryptography, you produce a signature with your private key and it can be verified using your public key. As only you should have access to your private key, this proves you signed the file. Digital signatures and physical signatures have the same value in the UK, legally.
The simplest form of digital signature would be encrypting the document with your private key, and then if someone wanted to verify this signature they would decrypt it with your public key and check if the files match.
Certificates - Prove who you are!
Certificates are also a key use of public key cryptography, linked to digital signatures. A common place where they’re used is for HTTPS. How does your web browser know that the server you’re talking to is the real tryhackme.com?
The answer is certificates. The web server has a certificate that says it is the real tryhackme.com. The certificates have a chain of trust, starting with a root CA (certificate authority). Root CAs are automatically trusted by your device, OS, or browser from install. Certs below that are trusted because the Root CAs say they trust that organisation. Certificates below that are trusted because the organisation is trusted by the Root CA and so on. There are long chains of trust. Again, this blog post explains this much better than I can. https://robertheaton.com/2014/03/27/how-does-https-actually-work/
You can get your own HTTPS certificates for domains you own using Let’s Encrypt for free. If you run a website, it’s worth setting it up.
What company is TryHackMe's certificate issued to?
Cloudflare
Task 9: SSH Authentication
ssh-keygen is the program used to generate pairs of keys most of the time.
The ~/.ssh folder is the default place to store these keys for OpenSSH. The authorized_keys (note the US English spelling) file in this directory holds public keys that are allowed to access the server if key authentication is enabled.
ssh -i keyNameGoesHere user@host is how you specify a key for the standard Linux OpenSSH client.
I recommend giving this a go yourself. Deploy a VM, like Learn Linux and try to add an SSH key and log in with the private key.
No answer needed
Download the SSH Private Key attached to this room.
No answer needed
What algorithm does the key use?
RSA
Crack the password with John The Ripper and rockyou, what's the passphrase for the key?
locate ssh2john
/usr/share/john/ssh2john.py id_rsa > id_rsa.hash
john id_rsa.hash --wordlist="/usr/share/wordlists/rockyou.txt"
delicious
Task 10: Explaining Diffie Hellman Key Exchange
What is Key Exchange?
Key exchange allows 2 people/parties to establish a set of common cryptographic keys without an observer being able to get these keys. Generally, to establish common symmetric keys.
How does Diffie Hellman Key Exchange work?
Alice and Bob want to talk securely. They want to establish a common key, so they can use symmetric cryptography, but they don’t want to use key exchange with asymmetric cryptography. This is where DH Key Exchange comes in.
Alice and Bob both have secrets that they generate, let’s call these A and B. They also have some common material that’s public, let’s call this C.
We need to make some assumptions. Firstly, whenever we combine secrets/material it’s impossible or very very difficult to separate. Secondly, the order that they're combined in doesn’t matter.
Alice and Bob will combine their secrets with the common material, and form AC and BC. They will then send these to each other, and combine that with their secrets to form two identical keys, both ABC. Now they can use this key to communicate.
Extra Resources
An excellent video if you want a visual explanation is available here. https://www.youtube.com/watch?v=NmM9HA2MQGI
DH Key Exchange is often used alongside RSA public key cryptography, to prove the identity of the person you’re talking to with digital signing. This prevents someone from attacking the connection with a man-in-the-middle attack by pretending to be Bob.
I understand how Diffie Hellman Key Exchange works at a basic level
No answer needed
Task 11: PGP, GPG and AES
What is PGP?
PGP stands for Pretty Good Privacy. It’s a software that implements encryption for encrypting files, performing digital signing and more.
What is GPG?
GnuPG or GPG is an Open Source implementation of PGP from the GNU project. You may need to use GPG to decrypt files in CTFs. With PGP/GPG, private keys can be protected with passphrases in a similar way to SSH private keys. You can attempt to crack this passphrase using John The Ripper and gpg2john.
The man page for GPG can be found online here.
What about AES?
AES, sometimes called Rijndael after its creators, stands for Advanced Encryption Standard. It was a replacement for DES which had short keys and other cryptographic flaws.
AES and DES both operate on blocks of data (a block is a fixed size series of bits).
AES is complicated to explain, and doesn’t seem to come up as often. If you’d like to learn how it works, here’s an excellent video from Computerphile https://www.youtube.com/watch?v=O4xNJsjtN6E
Time to try some GPG. Download the archive attached and extract it somewhere sensible.
No answer needed
You have the private key, and a file encrypted with the public key. Decrypt the file. What's the secret word?
unzip gpg.zip
gpg --import tryhackme.key
gpg message.gpg
cat message
Pineapple
Task 12: The Future - Quantum Computers and Encryption
Quantum computers will soon be a problem for many types of encryption.
Asymmetric and Quantum
While it’s unlikely we’ll have sufficiently powerful quantum computers until around 2030, once these exist encryption that uses RSA or Elliptical Curve Cryptography will be very fast to break. This is because quantum computers can very efficiently solve the mathematical problems that these algorithms rely on for their strength.
AES/DES and Quantum
AES with 128 bit keys is also likely to be broken by quantum computers in the near future, but 256 bit AES can’t be broken as easily. Triple DES is also vulnerable to attacks from quantum computers.
Current Recommendations
The NSA recommends using RSA-3072 or better for asymmetric encryption and AES-256 or better for symmetric encryption. There are several competitions currently running for quantum safe cryptographic algorithms, and it’s likely that we will have a new encryption standard before quantum computers become a threat to RSA and AES.
Learn More about Quantum Computers and Cryptography
If you’d like to learn more about this, NIST has resources that detail what the issues with current encryption is and the currently proposed solutions for these. https://doi.org/10.6028/NIST.IR.8105
I also recommend the book "Cryptography Apocalypse" By Roger A. Grimes, as this was my introduction to quantum computing and quantum safe cryptography.
I understand that quantum computers affect the future of encryption. I know where to look if I want to learn more.
No answer needed
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