Syngress - How to Cheat at Securing Windows 2000 Server TCP-IP Connections.pdf
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How to Cheat at Securing Windows 2000 TCP/IP
How to Cheat at Securing Windows 2000 TCP/IP
How to Cheat at Securing Windows 2000
TCP/IP
Copyright 2003 by Syngress Publishing,
all rights reserved
How to Cheat at Being a Windows 2000 System Administrator __
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defined.
TOPIC 1: A TCP/IP Primer ______________________________________________ 5
IP Address Classes and Subnets ________________________________________ 5
Subnets and Routing__________________________________________________ 5
TOPIC 2: The OSI Model ________________________________________________ 7
Seven Layers of the Networking World __________________________________ 7
TOPIC 3: The TCP/IP Protocol Suite_______________________________________ 8
TCP/IP Core Protocols ________________________________________________ 9
TCP ______________________________________________________________ 9
UDP______________________________________________________________ 9
IP__________________________________________________________________ 9
The Three-Way Handshake ___________________________________________ 10
ARP_____________________________________________________________ 10
ICMP____________________________________________________________ 11
IGMP____________________________________________________________ 11
TCP/IP Applications_________________________________________________ 11
TOPIC 4:
Windows
2000 TCP/IP Stack Enhancements _____________________ 13
NetBT and WINS ___________________________________________________ 13
DHCP ___________________________________________________________ 14
DNS_____________________________________________________________ 14
SNMP ___________________________________________________________ 14
TOPIC 5: Using TCP/IP Utilities _________________________________________ 15
ARP ______________________________________________________________ 15
Hostname __________________________________________________________ 15
Ipconfig ___________________________________________________________ 15
Nbtstat ____________________________________________________________ 16
Netstat ____________________________________________________________ 16
Nslookup __________________________________________________________ 17
Copyright 2003 by Syngress Publishing, All rights reserved
1
How to Cheat at Securing Windows 2000 TCP/IP
Ping_______________________________________________________________ 17
Route _____________________________________________________________ 18
Tracert ____________________________________________________________ 18
Pathping ___________________________________________________________ 19
Netdiag ____________________________________________________________ 20
SNMP _____________________________________________________________ 21
How Does SNMP Work? ____________________________________________ 21
Installing the Agent_________________________________________________ 22
TOPIC 6: Using Windows 2000 Monitoring Tools ___________________________ 24
Basic Monitoring Guidelines __________________________________________ 24
Performance Logs and Alerts _________________________________________ 24
Counters___________________________________________________________ 25
Log File Format_____________________________________________________ 25
Alerts _____________________________________________________________ 25
Network Monitor ___________________________________________________ 26
Filtering__________________________________________________________ 26
Security Issues ____________________________________________________ 26
Using Network Monitor _____________________________________________ 26
Capture Window Panes______________________________________________ 26
Buffer ___________________________________________________________ 27
Collecting Data ____________________________________________________ 27
Filtered Captures___________________________________________________ 28
Filtering by Address Pairs____________________________________________ 28
Display Filters_____________________________________________________ 29
TOPIC 7: Secure Sockets Layer __________________________________________ 30
How a Secure SSL Channel Is Established_______________________________ 30
Symmetric and Asymmetric Encryption ________________________________ 31
Symmetric Encryption ______________________________________________ 31
Asymmetric Encryption _____________________________________________ 32
Hash Algorithms ___________________________________________________ 33
Digital Certificates _________________________________________________ 33
Certificate Authorities_______________________________________________ 33
SSL Implementation ________________________________________________ 34
TOPIC 8: Secure Communications over Virtual Private Networks ______________ 35
Tunneling Basics ____________________________________________________ 35
VPN Definitions and Terminology _____________________________________ 35
How Tunneling Works _______________________________________________ 35
IP Addressing _____________________________________________________ 36
Copyright 2003 by Syngress Publishing, All rights reserved
2
How to Cheat at Securing Windows 2000 TCP/IP
Security Issues Pertaining to VPNs _____________________________________ 36
Encapsulation _____________________________________________________ 36
User Authentication ________________________________________________ 36
Data Security _______________________________________________________ 36
Windows 2000 Security Options _______________________________________ 37
Common VPN Implementations _______________________________________ 38
Remote User Access Over the Internet __________________________________ 38
Connecting Networks Over the Internet_________________________________ 38
Sharing a Remote Access VPN Connection ______________________________ 38
Using a Router-to-Router Connection __________________________________ 39
Tunneling Protocols and the Basic Tunneling
Requirements
____________ 39
Windows 2000 Tunneling Protocols ____________________________________ 39
Point to Point Tunneling Protocol (PPTP) _______________________________ 39
Layer 2 Tunneling Protocol (L2TP) ____________________________________ 39
Using PPTP with Windows 2000 ______________________________________ 39
How to Configure a PPTP Device _____________________________________ 40
Using L2TP with Windows 2000 ______________________________________ 40
How to Configure L2TP _____________________________________________ 40
How L2TP Security Differs from PPTP _________________________________ 41
Interoperability with Non-Microsoft VPN Clients ________________________ 41
TOPIC 9: IPSec for Windows 2000 _______________________________________ 42
Overview of IPSec Cryptographic Services ______________________________ 42
Message Integrity __________________________________________________ 42
Hashing Messages__________________________________________________ 43
Message Authentication ______________________________________________ 43
Preshared Key Authentication ________________________________________ 43
Kerberos Authentication _____________________________________________ 44
Public Key Certificate-Based Digital Signatures __________________________ 44
Confidentiality______________________________________________________ 44
IPSec Security Services_______________________________________________ 44
Authentication Header (AH)__________________________________________ 44
Encapsulating Security Payload (ESP) __________________________________ 45
TOPIC 10: Security Associations and IPSec Key Management Procedures _______ 46
IPSec Key Management ______________________________________________ 46
Phase 1: Establishing the ISAKMP SA _________________________________ 46
Phase 2: Establishing the IPSec SA ____________________________________ 47
TOPIC 11: Deploying IPSec _____________________________________________ 48
Building Security Policies with Customized IPSec Consoles ________________ 48
Building an IPSec MMC Console _____________________________________ 48
Copyright 2003 by Syngress Publishing, All rights reserved
3
How to Cheat at Securing Windows 2000 TCP/IP
Flexible Security Policies _____________________________________________ 48
Rules ______________________________________________________________ 49
Filter Actions _____________________________________________________ 49
Flexible Negotiation Policies __________________________________________ 50
Filters _____________________________________________________________ 50
Creating a Security Policy ____________________________________________ 51
Making the Rule ____________________________________________________ 51
Copyright 2003 by Syngress Publishing, All rights reserved
4
How to Cheat at Securing Windows 2000 TCP/IP
TOPIC 1: A TCP/IP Primer
TCP/IP is a network protocol based on a 32-bit addressing scheme that enables networks to be
interconnected with routers. The bits in each address are separated into four sets of 8 bits, called
octets, which are separated by periods. With the binary number system, 8 bits can be used to
signify any number from 0 to 255, so the lowest theoretical IP address is 0.0.0.0, while the
highest is 255.255.255.255. Each device, or host, on the network must have a unique IP address
to communicate on the network. In order to communicate on the Internet, IP addresses must be
registered with the organizations that manage the Internet so that routing can be configured
correctly. Two specific network addresses and a range of network addresses are reserved for
private use and are not routed on the Internet. These two network addresses— 10.0.0.0,
192.168.0.0, 172.16.0.0–172.32.255.255—are used on networks that are not connected to the
Internet or connected by using network address translation (NAT) or proxy hosts. NAT and proxy
hosts have two IP addresses, one on the private network and one registered on the Internet, and
handle all communications between the private network and the Internet.
IP Address Classes and Subnets
As you can see in the following table, IP addresses are divided into classes, or blocks of
addresses, for administrative purposes. Each class is also assigned a default subnet mask. The
class structure is simply a way to manage address space. For example, the United States
government might have one or two Class A address spaces instead of thousands of Class C
addresses.
IP Addresses Are Divided into Three Usable Classes
Class Range
Default Mask
Addresses per
Network
A
0.0.0.0–126.255.255.255
255.0.0.0
16 million +
B
128.0.0.0–191.255.255.255 255.255.0.0
64,000 +
C
192.0.0.0–223.255.255.255 255.255.255.0
254
D
224.0.0.0–239.255.255.255 Reserved for multicast addressing
E
240.0.0.0–254.255.255.255 Reserved for experimental use
The subnet mask determines which bits in the IP address are the network address, and
which bits are the host address. If we assumed that the default subnet mask was 255.0.0.0 for a
Class A address, then from the above table it would imply that the first 8 bits (which equals 255)
are the network portion of the address, and the three remaining octets are available for host
addresses. It is not realistically possible to have 16 million hosts on a single network, or even
64,000, without segmenting the network with routers. Accordingly, networks with Class A and B
addresses do not typically use the default mask; often, their subnet masks end up similar to those
of Class C networks. When a mask other than the default is used, subnets are created that enable
the address space to be split up into several smaller networks and route traffic between them. A
Class B network address could be split into 255 networks by using a 255.255.255.0 subnet mask.
The actual number of usable networks, however, is a bit less than 255, due to network and
broadcast addresses.
Subnets and Routing
Routers are devices that connect networks together and relay traffic between networks according
to routing tables that are configured in their memory. IP networks that are not on the same logical
network must have a router to connect them in order for their hosts to communicate. TCP/IP
Copyright 2003 by Syngress Publishing, All rights reserved
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