Securing a Virtual Private Network

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A virtual private network (VPN) allows a connection to a private network over a public network. VPNs provide remote access to an internal network for mobile users. Firewall ACLs include rules to allow VPN traffic based on the tunneling protocol. If you’re planning to take the Security+ exam, you should have a basic understanding of implementing common protocols and services.

For example, can you answer this question?

Q. A network administrator needs to open a port on a firewall to support a VPN using PPTP. What ports should the administrator open?

A. UDP 47

B. TCP 50

C. TCP 1723

D. UDP 1721

More, do you know why the correct answer is correct and the incorrect answers are incorrect? The answer and explanation is available at the end of this post.

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Virtual Private Network Over Open Wireless

Public wireless hot spots typically have little or no security. Their goal is to provide users with free wireless access and often include a warning indicating that the network doesn’t have any security. Attackers with wireless sniffers can typically capture any traffic sent over the network.

The best protection for users, especially when entering confidential data, such as usernames and passwords, is to ensure data is encrypted. One method is to ensure that connections are using Hypertext Transfer Protocol Secure (HTTPS) connections.

Another method is to use a VPN service that provides secure VPN connections over open wireless connections. For example, Private Internet Access and TunnelBear are two applications that provide this service, and applications are available for most platforms, including smartphones.

Securing Virtual Private Network Channel

Using TLS and SSL

Some tunneling protocols use either Secure Sockets Layer (SSL) or Transport Layer Security (TLS) to secure the VPN channel. As an example, Secure Socket Tunneling Protocol (SSTP) encrypts VPN traffic using SSL over port 443. Using port 443 provides a lot of flexibility for many administrators and rarely requires opening additional firewall ports. It is a useful alternative when the VPN tunnel must go through a device using NAT, and IPsec is not feasible. OpenVPN and OpenConnect are two open source applications that can use TLS to create a secure channel.

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Online access includes all of the content from the

CompTIA Security+: Get Certified Get Ahead: SY0-401 Study Guide

  • Introduction
  • About the exam (including types of questions and strategies for performance-based questions)
  • 100 question pre-assessment exam
  • Mastering Security Basics (full content from Chapter 1 of the study guide including the exam topic review and 20 practice test questions)
  • Exploring Control Types and Methods (full content from Chapter 2 of the study guide including the exam topic review and 20 practice test questions)
  • Understanding Basic Network Security (full content from Chapter 3 of the study guide including the exam topic review and 20 practice test questions)
  • Securing Your Network (full content from Chapter 4 of the study guide including the exam topic review and 20 practice test questions)
  • Securing Hosts and Data (full content from Chapter 5 of the study guide including the exam topic review and 20 practice test questions)
  • Understanding Malware and Social Engineering (full content from Chapter 6 of the study guide including the exam topic review and 20 practice test questions)
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  • Managing Risk (full content from Chapter 8 of the study guide including the exam topic review and 20 practice test questions)
  • Preparing for Business Continuity (full content from Chapter 9 of the study guide including the exam topic review and 20 practice test questions)
  • Understanding Cryptography (full content from Chapter 10 of the study guide including the exam topic review and 20 practice test questions)
  • Exploring Operational Security (full content from Chapter 11 of the study guide including the exam topic review and 20 practice test questions)
  • 100 question post-assessment exam
  • Security+ Acronyms

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Test your readiness with these quality materials

Random 100-question tests

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34 Simulated Performance-based Questions

Eight sets of performance-based questions with multiple questions in each set. These questions help you understand and prepare for performance based questions.

22 Realistic Performance-based Questions

Two new sets of performance-based questions with a total of 22 questions. These new questions use a new testing engine that includes realistic drag and drop, matching, sorting, and fill in the blank questions.

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Using PPTP

Many Microsoft implementations used Point-to-Point Tunneling Protocol (PPTP) for VPNs. PPTP uses Microsoft’s Point-to-Point Encryption to create the secure channel, but PPTP is rarely used today because of known vulnerabilities. PPTP uses TCP port 1723.

Remember this

L2TP is a VPN tunneling protocol and it is commonly combined with IPsec (as L2TP/IPsec). L2TP uses UDP port 1701. PPTP uses TCP port 1723.

CompTIA Security+ Study Guide (SY0-401)

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Site-to-Site VPNs

A site-to-site VPN includes two VPN servers that act as gateways for two networks separated geographically. For example, an organization can have two locations. One is its headquarters and the other is a remote office. It can use two VPN servers to act as gateways to connect the networks at the two locations together.

A benefit of the site-to-site model is that it connects both networks without requiring additional steps on the part of the user. Users in the remote office can connect to servers in the headquarters location as easily as if the servers were in the remote office. Connecting to the remote server may be slower than connecting to a local server, but otherwise it’s transparent to end users.

In contrast, in a host-to-gateway model, the end user makes the direct connection to the VPN server and is very much aware of the process.


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Over 440 realistic Security+ practice test questions

All questions include explanations so you'll know why the correct answers are correct,

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Multiple quiz formats to let you use these questions based on the way you learn.
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- Performance Based Question - Set 1

You'll see a graphic explaining what you might be required to do on the actual exam to match different types of security to mobile devices and servers in a data center. You'll then have two questions that test your knowledge and ability to correctly answer the questions. This question also includes a link to a graphic showing the end solution for the overall performance based question simulation.

- Performance Based Question - Set 2

You'll see a graphic explaining what you might be required to do on the actual exam to match different types of attacks with the name of the attack type. You'll then have five questions that test your knowledge and ability to correctly answer the questions. This question also includes a link to a graphic showing the end solution for the overall performance based question simulation.

- Performance Based Question - Set 3

You'll see a graphic showing a network with computers and servers separated by a firewall. The firewall is used to control traffic between the computers and users using rules within an access control list (ACL).  You'll have three questions that test your knowledge and ability to correctly identify the relevant components of the rule. The incorrect answers and explanation provide you with insight into how to correctly answer this type of question on the actual exam.

- Performance Based Question - Set 4

You'll see a graphic explaining what you might be required to do on the actual exam related to what a forensic analyst would do during an investigation. You'll then have two questions that test your knowledge and ability to correctly answer the questions. This question also includes a link to a graphic showing the end solution for the overall performance based question simulation.

- Performance Based Question - Set 5

You'll see a graphic explaining what you might be required to do on the actual exam to match protocols and ports. You'll then have seven questions that test your knowledge and ability to correctly answer the questions. This question also includes a link to a graphic showing the end solution for the overall performance based question simulation.

- Performance Based Question - Set 6

You'll see a list of security controls along with a graphic showing devices and locations within an organization, along with instructions on what you might be required to do on the actual exam to match the controls with the devices and locations. You'll then have four questions that test your knowledge and ability to correctly answer the questions. This question also includes a link to a graphic showing the end solution for the overall performance based question simulation.

- Performance Based Question - Set 7

You'll see a list of authentication methods and authentication factors along with instructions on what you might be required to do on the actual exam to match the authentication methods with the authentication factors. You'll then have six questions that test your knowledge and ability to correctly answer the questions. This set also includes a link to a graphic showing the end solution for the overall performance based question simulation.

- Performance Based Question - Set 8

You'll see a graphic explaining what you might be required to do on the actual exam to match different types of attacks with the name of the attack type. You'll then have five questions that test your knowledge and ability to correctly answer the questions. This is similar to Set 2 but expands on the possibilities. The set also includes a link to a page showing the end solution for the overall performance based question simulation.

New - Performance Based Question - Set 9

New questions recently added using a different testing engine. See a demo here. This set includes drag and drop and matching questions on ports.

New - Performance Based Question - Set 10

A random set of 20 performance-based questions using drag and drop, matching, sorting, and fill in-the blank. This set includes performance-based questions on RAID.

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Get the full bank of Security+ Practice Test Questions

Q. A network administrator needs to open a port on a firewall to support a VPN using PPTP. What ports should the administrator open?

A. UDP 47

B. TCP 50

C. TCP 1723

D. UDP 1721

Answer is C. A virtual private network (VPN) using Point-to-Point Tunneling Protocol (PPTP) requires Transmission Control Protocol (TCP) port 1723 open.

It would also need protocol ID 47 open, but the protocol ID is not a port.

Internet Protocol security (IPsec) uses protocol ID 50.

See Chapter 4 of the CompTIA Security+: Get Certified Get Ahead: SY0-401 Study Guide for more information on remote access.

You might also like to view the Implementing VPNs blog post.

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