Section 27 - Security Protocols Flashcards

1
Q

What does S/MIME stand for?

A

Secure/Multipurpose Internet Mail Extensions

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2
Q

What is S/MIME?

A

This is a standard that provides cryptographic security for electronic messaging, things like email.

*** This is built into most email clients that you use

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3
Q

S/MIME uses ___ session keys for each email message that’s being sent or received.

A

separate

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4
Q

We can use digital IDs within Outlook or digital signatures within many different programs to give our emails authentication, integrity, and non-repudiation through ___.

A

S/MIME

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5
Q

S/MIME is a way that we can encrypt our emails and their content. The problem with that is…?

A

It also encrypts all of their contents, including malware.

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6
Q

What is “SSL”?

A

Secure Socket Layer

This was a way to start securing the web as we wanted to start doing ecommerce.

*** This is a cryptographic protocol that provided secure internet communications for web browsing, IM, email, VoIP, etc. It was last updated in 1996 at version three so you shouldn’t use it. It was replaced with TLS.

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7
Q

What is “TLS”?

A

Transport Layer Security

*** This is the newer cryptographic protocol that provided secure internet communications. The current version in use is 1.3.

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8
Q

Often times when it comes to SSL and TLS, you’ll find that people will…?

A

Call it SSL even if it’s TLS that you’re using

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9
Q

How does TLS and SSL work?

A

The web browser goes out and gets the server’s public key. It, then, takes that and encrypts a random string of numbers, sends that over to the web server. Once the server gets it, they decrypt it using their private key. They will then create a symmetric tunnel between the two. That tunnel, is SSL or TLS.

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10
Q

How does TLS work in conjunction with HTTPS?

A

If you want to run a secure website, you would tunnel the normal HTTP protocol through a TLS tunnel. Normally you would use HTTP over port 80 but when you tunnel it through SSL or TLS, you’re going to end up putting it on port 443, which is secure HTTP or HTTPS.

For an email, you’d use SMTP and send it over port 25. But if you want to do it securely, you establish a TLS tunnel first. That would establish a TLS tunnel over port 465 instead and your SMTP traffic would go through that tunnel.

You apply this process to IM, file transfer and other stuff.

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11
Q

What is a way that people can attack TLS?

A

Downgrade attack

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12
Q

What is a “downgrade attack”?

A

When a protocol is tricked into using a lower quality version instead of using the higher quality version that it was supposed to.

*** Using a weaker (lower quality) protocol makes it easier to be exploited.

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13
Q

What does it mean to do a “break and inspect”?

A

As a defender of a network, it can be challenging when people use TLS connections because you can’t see what’s going on inside that tunnel. So, with break and inspect, you act as a man-in-the-middle by putting a proxy there. This requires the TLS tunnel to connect to the proxy to be inspected prior to getting to its destination.

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14
Q

What is SSH?

A

Secure Shell

This is a protocol used to tunnel other protocols through.

This creates a secure channel between two computers or network devices and allows one device to control another device.

This was designed to replace Telnet.

*** For example, if you wanted to use your laptop to connect to a server to do remote execution of commands as a system admin, you would use SSH to do that.

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15
Q

Why was SSH designed to replace Telnet?

A

Telnet sends everything in the clear and unencrypted

SSH, on the other hand, allows us to have an encrypted tunnel that protects our data.

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16
Q

SSH is most commonly used as…?

A

A text-based remote control method for anything that you need to be able to get into and do remote control of, things like routers and switches.

17
Q

SSH operates over what port?

A

22

18
Q

What other protocols operate over port 22 aside from SSH?

A

Secure Copy
Secure FTP

*** This is because these both operate in an SSH tunnel. Yes, just like TLS you can create a tunnel for security.

19
Q

What are the three big versions of SSH?

A

Version 1
Version 1.5
Version 2

20
Q

What is a “VPN”?

A

Virtual Private Network

This is a secure connection between two or more computers or devices that aren’t on the same private network, creating a virtual private network.

21
Q

There’s three big VPN’s out there. What are they?

A

PPTP
L2TP
IPSec

22
Q

What is PPTP?

A

Point-to-Point Tunneling Protocol

This is a protocol that encapsulates PPP packets and ultimately sends data out as encrypted traffic

*** PPP is the Point-to-Point Protocol and it was originally used for dial-up connections but it’s used in combination with PPTP over port 1723 to allow servers and devices to connect to a WAN.

23
Q

How is PPTP vulnerable?

A

It uses CHAP based authentication making it vulnerable to attack

24
Q

What is “L2TP”?

A

Layer 2 Tunneling Protocol

This is going to give you a connection between two or more computers or devices that aren’t on the same private network

25
Q

How is L2TP vulnerable?

A

It provides no encryption and no confidentiality by itself.

Therefore, people usually pair it with IPSec to provide that.

26
Q

What is IPSec?

A

Provides us with the encryption and confidentiality when using L2TP which allows the ability to use PKI

27
Q

What port does IPSec operate over?

A

1701

28
Q

IPSec is going to provide confidentiality, integrity and authentication how?

A

Confidentiality - by giving us encryption

Integrity - by using hashing

Authentication - by performing a key exchange

29
Q

What does IKE stand for?

A

Internet Key Exchange

*** This is a method used by IPSec to create a secure tunnel by encrypting the connection between authenticated peers.

30
Q

What are the three different types of key exchanges?

A

Main Mode
Aggressive Mode
Quick Mode

31
Q

What is a Security Association?

A

Also known as “SA”

This is the establishment of secure connections and shared security information using certificates or cryptographic keys

*** Basically, you trust me and I trust you. We’ve shared information and now, we know each other and we’ve verified our identities.

32
Q

What is an “Authentication Header”?

A

Protocol used in IPSec that provides integrity and authentication

A header that is hashed to provide integrity and it’s often used with an ESP.

33
Q

What is an “ESP”?

A

Encapsulating Security Payload

Provides you integrity, confidentiality, and authentication for the packets by encapsulating them and encrypting them.

34
Q

IPSec can be operated in one of two modes. What are they?

A

Transport Mode
Tunnel Mode

35
Q

What is Transport mode in IPSec?

A

This is where there’s a Host-to-Host transport mode using only encryption of the payload of an IP packet but not its header

*** Think of this like a semi-truck. The cab in the front that pulls the trailer, that’s the header, that part’s not encrypted. But everything in that back trailer is encrypted.

36
Q

What is Tunnel mode in IPSec?

A

This creates an end-to-end network tunnel that’s created, that’s going to encrypt the entire IP packet, the payload, and the header.

*** This is used for sending things over the internet instead of transport because everything is protected. Typically on VPN’s because it’s the safest way to send transmissions over untrusted networks.