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290Chapter 7  PKI and Cryptographic Applications

Web Applications

Encryption is widely used to protect web transactions. This is mainly because of the strong movement toward ecommerce and the desire of both ecommerce vendors and consumers to securely exchange financial information (such as credit card information) over the web. We’ll look at the two technologies that are responsible for the small lock icon within web browsers—Secure Sockets Layer (SSL) and Transport Layer Security (TLS).

Secure Sockets Layer (SSL)

SSL was originally developed by Netscape to provide client/server encryption for web traffic sent using the Hypertext Transfer Protocol Secure (HTTPS). Over the years, security researchers discovered a number of critical flaws in the SSL protocol that render it insecure for use today. However, SSL serves as the technical foundation for its successor, Transport Layer Security (TLS), which remains widely used today.

Even though TLS has been in existence for more than a decade, many people still mistakenly call it SSL. When you hear people use the term SSL, that’s a red flag that you should further investigate to ensure that they’re really using the modern, secure TLS and not the outdated SSL.

Transport Layer Security (TLS)

TLS relies on the exchange of server digital certificates to negotiate encryption/decryption parameters between the browser and the web server. TLS’s goal is to create secure communications channels that remain open for an entire web browsing session. It depends on a combination of symmetric and asymmetric cryptography. The following steps are involved:

1.When a user accesses a website, the browser retrieves the web server’s certificate and extracts the server’s public key from it.

2.The browser creates a random symmetric key (known as the ephemeral key), uses the server’s public key to encrypt it, and sends the encrypted symmetric key to the server.

3.The server decrypts the symmetric key using its own private key, and the two systems exchange all future messages using the symmetric encryption key.

This approach allows TLS to leverage the advanced functionality of asymmetric cryptography while encrypting and decrypting the vast majority of the data exchanged using the faster symmetric algorithm.

When TLS was first proposed as a replacement for SSL, not all browsers supported the more modern approach. To ease the transition, early versions of TLS supported downgrading communications to SSL v3.0 when both parties did not support TLS. However, in 2011, TLS v1.2 dropped this backward compatibility.

In 2014, an attack known as the Padding Oracle On Downgraded Legacy Encryption (POODLE) demonstrated a significant flaw in the SSL 3.0 fallback mechanism of TLS. In an effort to remediate this vulnerability, many organizations completely dropped SSL support and now rely solely on TLS security.

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The original version of TLS, TLS 1.0, was simply an enhancement to the SSL 3.0 standard. TLS 1.1, developed in 2006 as an upgrade to TLS 1.0, also contains known security vulnerabilities. TLS 1.2, released in 2008, is now considered the minimum secure option. TLS 1.3, released in 2018, is also secure and adds performance improvements.

It’s important to understand that TLS is not an encryption algorithm itself. It is a framework within which other encryption algorithms may function. Therefore, it isn’t sufficient to verify that a system is using a secure version of TLS. Security professionals must also ensure that the algorithms being used with TLS are secure as well.

Each system supporting TLS provides a listing of the cipher suites that it supports. These are combinations of encryption algorithms that it is willing to use together, and these lists are used by two systems to identify a secure option that both systems support. The cipher suite consists of four components:

■■The key exchange algorithm that will be used to exchange the ephemeral key. For example, a server might support RSA, Diffie–Hellman (abbreviated DH) and Elliptic Curve Diffie Hellman (abbreviated ECDH).

■■The authentication algorithm that will be used to prove the identity of the server and/or client. For example, a server might support RSA, DSA, and ECDSA.

■■The bulk encryption algorithm that will be used for symmetric encryption. For example, a server might support multiple versions of AES and 3DES.

■■The hash algorithm that will be used to create message digests. For example, a server might support different versions of the SHA algorithm.

Cipher suites are usually expressed in long strings that combine each of these four elements. For example, the cipher suite:

TLS_DH_RSA_WITH_AES_256_CBC_SHA384

means that the server supports TLS using Diffie–Hellman key exchange (DH). In this cipher suite, it will perform authentication using the RSA protocol and will perform bulk encryption using AES CBC mode with a 256-bit key. Hashing will take place using the SHA-384 algorithm.

You may also see cipher suites that use DHE or ECDHE key exchange algorithms. The “E” indicates that the Diffie–Hellman (or Elliptic Curve Diffie–Hellman) algorithm uses different, ephemeral keys for each communication to provide forward secrecy and reduce the likelihood of key compromise. The “E” versions of these algorithms provide added security, but this comes at the cost of added computational complexity.

Tor and the Dark Web

Tor, formerly known as The Onion Router, provides a mechanism for anonymously routing traffic across the internet using encryption and a set of relay nodes. It relies on a technology

292Chapter 7  PKI and Cryptographic Applications

known as perfect forward secrecy, where layers of encryption prevent nodes in the relay chain from reading anything other than the specific information they need to accept and forward the traffic. By using perfect forward secrecy in combination with a set of three or more relay nodes, Tor allows for both anonymous browsing of the standard internet, as well as the hosting of completely anonymous sites on the dark web.

Steganography and Watermarking

Steganography is the art of using cryptographic techniques to embed secret messages within another message. Steganographic algorithms work by making alterations to the least significant bits of the many bits that make up image files. The changes are so minor that there is no appreciable effect on the viewed image. This technique allows communicating parties to conceal messages in plain sight—for example, they might embed a secret message within an illustration on an otherwise innocent web page.

It is also possible to embed messages inside larger excerpts of text. This approach is known as a concealment cipher.

Steganographers often embed their secret messages within images or WAV files because these files are often so large that the secret message would easily be missed by even the most observant inspector. Steganography techniques are often used for illegal activities, such as espionage and child pornography.

Steganography can also be used for legitimate purposes, however. Adding digital watermarks to documents to protect intellectual property is accomplished by means of steganography. The hidden information is known only to the file’s creator. If someone later creates an unauthorized copy of the content, the watermark can be used to detect the copy and (if uniquely watermarked files are provided to each original recipient) trace the offending copy back to the source.

Steganography commonly works by modifying the least significant bit (LSB) of a pixel value. For example, each pixel might be described by using three decimal numbers ranging from 0 to 255. One represents the degree of red color in the image, the second represents blue, and the third represents green. If a pixel has a blue value of 64, changing that value to 65 would result in an imperceptible change but does allow the encoding of a bit of steganographic data.

Steganography is an extremely simple technology to use, with free tools openly available on the internet. Figure 7.2 shows the entire interface of one such tool, iSteg. It simply requires that you specify a text file containing your secret message and an image file that you wish to use to hide the message. Figure 7.3 shows an example of a picture with an embedded secret message; the message is impossible to detect with the human eye because the text file was added into the message by modifying only the least significant bits of the file. Those do not survive the printing process, and in fact, even if you examined the original full-color, high-resolution digital images, you would not be able to detect the difference.

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FIGURE 7. 2   Steganography tool

FIGURE 7. 3   Image with embedded message

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