MCSE 05 Implementing of a Network Infrastructure 08 Theory

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    Implementing IPSec in aImplementing IPSec in a

    Windows 2003 NetworkWindows 2003 Network

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    Introduction to IPSecIntroduction to IPSec

    Uses and PlanningUses and Planning

    Windows 2003 IPSec componentsWindows 2003 IPSec components

    Implementation and best practices of IPSecImplementation and best practices of IPSec

    Troubleshooting and referencesTroubleshooting and references

    What will not be covered in this discussionWhat will not be covered in this discussion

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    Introduction to IPSecIntroduction to IPSec The history of IPSecThe history of IPSec

    Security properties of communicationsSecurity properties of communications

    The need for IPSecThe need for IPSec

    Benefits of IPSecBenefits of IPSec

    Windows 2003 IPSec design goalsWindows 2003 IPSec design goals

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    Introduction to IPSecIntroduction to IPSecHistoryHistory

    IPSec original work in 1992 by IEEEIPSec original work in 1992 by IEEE

    Originally a new feature for IP version 6Originally a new feature for IP version 6

    Adapted for IP version 4Adapted for IP version 4

    RFCRFC--based; currently in draft formbased; currently in draft form

    Windows 2003 IPSec jointly developed with CiscoWindows 2003 IPSec jointly developed with Cisco

    Systems, Inc. and MicrosoftSystems, Inc. and Microsoft

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    Introduction to IPSecIntroduction to IPSecSecurity PropertiesSecurity Properties

    NonNon--repudiationrepudiation AntiAnti--replayreplay

    IntegrityIntegrity

    ConfidentialityConfidentiality

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    Introduction to IPSecIntroduction to IPSecThe Need for IPSec (part 1)The Need for IPSec (part 1)

    EavesdroppingEavesdropping

    Data modificationData modification

    Identity spoofing (IP address spoofing)Identity spoofing (IP address spoofing)

    PasswordPassword--based attacksbased attacks

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    Introduction to IPSecIntroduction to IPSecThe Need for IPSec (part 2)The Need for IPSec (part 2)

    Compromised Key attackCompromised Key attack

    Sniffer attackSniffer attack

    Application layer attackApplication layer attack

    Denial of service attacksDenial of service attacks

    ManMan--inin--thethe--middle attacksmiddle attacks

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    Introduction to IPSecIntroduction to IPSecBenefits of IPSecBenefits of IPSec

    Provides endProvides end--toto--end protectionend protection

    Provides defense against attacks internal to the networkProvides defense against attacks internal to the network

    Transparent to applicationsTransparent to applications

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    Transparent to usersTransparent to users

    Can be configured to specific users and groupsCan be configured to specific users and groups

    Protects against attacks previously mentionedProtects against attacks previously mentioned

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    Introduction to IPSecIntroduction to IPSecWindows 2003 Design GoalsWindows 2003 Design Goals

    To protect IP packetsTo protect IP packets

    To provide a defense against network attacksTo provide a defense against network attacks

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    Uses of IPSecUses of IPSec

    IPSec as a protocolIPSec as a protocol

    Authentication Headers (AH)Authentication Headers (AH)

    Encapsulated Security Payload (ESP)Encapsulated Security Payload (ESP)

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    Internet Key Exchange (IKE)Internet Key Exchange (IKE)

    1.1. ISAKMPISAKMP

    2. Oakley2. Oakley

    Cryptographic algorithmsCryptographic algorithms

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    Uses of IPSecUses of IPSecIPSec as a ProtocolIPSec as a Protocol

    IPSec is a protocol not a serviceIPSec is a protocol not a service

    Two protocols with unique headers on each IP packetTwo protocols with unique headers on each IP packet

    1.1. Authentication Headers (AH)Authentication Headers (AH)

    2.2. Encapsulated Security Payload (ESP)Encapsulated Security Payload (ESP)

    RFC 2401RFC 2401

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    Uses of IPSecUses of IPSecAuthentication HeadersAuthentication Headers

    Provides the following Security PropertiesProvides the following Security Properties

    1.1. AuthenticationAuthentication

    2.2. IntegrityIntegrity

    3.3. AntiAnti--replayreplay

    Does not encrypt the dataDoes not encrypt the data

    Data is readable but cannot be alteredData is readable but cannot be altered

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    Both the IP header and data are signedBoth the IP header and data are signed

    Uses the HMAC algorithmsUses the HMAC algorithms

    RFC 2402RFC 2402

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    Uses of IPSecUses of IPSecEncapsulated Security PayloadEncapsulated Security Payload

    Provides the following Security propertiesProvides the following Security properties

    1.1. AuthenticationAuthentication

    2.2. IntegrityIntegrity

    3.3. AntiAnti--replayreplay

    4. Confidentiality4. Confidentiality

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    Can be used with Authentication HeadersCan be used with Authentication Headers

    IP header is not signed unless it is tunneledIP header is not signed unless it is tunneled

    Data is signedData is signed

    Uses DES and 3DES algorithmsUses DES and 3DES algorithms

    RFC 2406RFC 2406

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    Uses of IPSecUses of IPSecIKEIKE

    Internet Key ExchangeInternet Key Exchange

    Made up of ISAKMP and OakleyMade up of ISAKMP and Oakley

    Standard method for building Security Associations andStandard method for building Security Associations and

    Key Exchange ResolutionKey Exchange Resolution

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    Uses of IPSecUses of IPSecISAKMPISAKMP

    Internet Security Association Key Management ProtocolInternet Security Association Key Management Protocol

    Used to build a Security Association (SA)Used to build a Security Association (SA)

    ISAKMP provides SA negotiationISAKMP provides SA negotiation

    RFC 2408RFC 2408

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    Uses of IPSecUses of IPSecOakleyOakley Oakley Key Determination ProtocolOakley Key Determination Protocol

    Oakley is second part to Build SAOakley is second part to Build SA

    Provides Key Exchange ServiceProvides Key Exchange Service

    RFC 2412RFC 2412

    Two modesTwo modes

    1.1. Main modeMain mode New key generation material and new encryptionNew key generation material and new encryption

    keykey

    2.2. Quick modeQuick mode Already have key generation material and needAlready have key generation material and need

    new encryption keynew encryption key

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    Uses of IPSecUses of IPSecCryptographic AlgorithmsCryptographic Algorithms

    IPSec as a protocolIPSec as a protocol

    AHAH -- HMACHMAC--MD5 or HMACMD5 or HMAC--SHASHA

    ESPESP -- DES (40 bit), DESDES (40 bit), DES--CBC,CBC, 3DES3DES

    DH DiffieDH Diffie--Hellman group for key materialHellman group for key material

    IPSec cryptographic related RFCs: 2085, 2104, 2403,IPSec cryptographic related RFCs: 2085, 2104, 2403,

    2404, 2405, 2407, 2410, 24512404, 2405, 2407, 2410, 2451

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    Planning for IPSecPlanning for IPSecIn This Section We Will CoverIn This Section We Will Cover

    When to use IPSecWhen to use IPSec

    When to use AHWhen to use AH

    When to use ESPWhen to use ESP

    When to use AH and ESPWhen to use AH and ESP

    When to not use IPSecWhen to not use IPSec

    Authentication methodsAuthentication methods

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    Planning for IPSecPlanning for IPSecWhen to Use AHWhen to Use AH

    When a secure connection is neededWhen a secure connection is needed

    Must establish authentication of sourceMust establish authentication of source

    Data itself is not sensitiveData itself is not sensitive

    Risk of packet capturing compromising data is lowRisk of packet capturing compromising data is low

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    Planning for IPSecPlanning for IPSecWhen to Use ESPWhen to Use ESP

    When the data itself must be protectedWhen the data itself must be protected

    1.1. Financial informationFinancial information

    2.2. Proprietary informationProprietary information

    3.3. Sensitive informationSensitive information

    Use only when data protection is justifiedUse only when data protection is justified

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    Planning for IPSecPlanning for IPSecWhen to Use AH and ESPWhen to Use AH and ESP

    When a secure connection is neededWhen a secure connection is needed

    Must establish authentication of sourceMust establish authentication of source

    When the data itself must be protectedWhen the data itself must be protected

    When security of the network offsets the performance ofWhen security of the network offsets the performance ofthe additional processingthe additional processing

    Limit implementation to select hostsLimit implementation to select hosts

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    Planning for IPSecPlanning for IPSecWhen Not to Use IPSecWhen Not to Use IPSec Only use if there is a security needOnly use if there is a security need

    SNMPSNMP

    Security gatewaysSecurity gateways

    Input filtersInput filters

    Output filtersOutput filters

    DHCP, WINS, and DNS ServersDHCP, WINS, and DNS Servers

    Domain controllersDomain controllers

    DownDown--level clientslevel clients

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    Planning for IPSecPlanning for IPSecAuthentication MethodsAuthentication Methods

    Supported IPSec authentication methodsSupported IPSec authentication methods

    1.1. Kerberos version 5.0Kerberos version 5.0

    2.2. Public Key Certificate AuthoritiesPublic Key Certificate Authorities

    3.3. Microsoft Certificate ServerMicrosoft Certificate Server

    4.4. PrePre--shared Keyshared Key

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    Windows 2003 IPSec ComponentsWindows 2003 IPSec ComponentsIn This Section We Will CoverIn This Section We Will Cover

    IPSec Policy Agent serviceIPSec Policy Agent service

    Security AssociationsSecurity Associations

    Key protectionKey protection

    IPSec driverIPSec driver

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    Windows 2003 IPSec ComponentsWindows 2003 IPSec ComponentsIPSec Policy Agent Service (part 1)IPSec Policy Agent Service (part 1)

    Main TasksMain Tasks

    Retrieve the IP Security policyRetrieve the IP Security policy

    Deliver policy to IPSec driver and ISAKMPDeliver policy to IPSec driver and ISAKMP

    Periodically poll for new policiesPeriodically poll for new policies

    Update or replace IPSec/ISAKMP policiesUpdate or replace IPSec/ISAKMP policies

    Check for local IP address changes and update theCheck for local IP address changes and update the

    IP filtersIP filters

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    Local PolicyLocal Policy

    HKEY_LOCAL_MACHINEHKEY_LOCAL_MACHINE\\SYSTEMSYSTEM\\

    CurrentControlSetCurrentControlSet\\ServicesServices\\PolicyAgentPolicyAgent\\

    PolicyPolicy\\LocalLocal

    PollingPolling

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    Windows 2003 IPSec ComponentsWindows 2003 IPSec ComponentsSecurity Associations (part 1)Security Associations (part 1)

    Mutually agreed upon key, protocol, and securityMutually agreed upon key, protocol, and security

    parameter interface that define the Security levelparameter interface that define the Security levelbetween sender and receiverbetween sender and receiver

    Phase I SAPhase I SA ISAKMP SAISAKMP SA

    1.1. Policy negotiationPolicy negotiation

    2.2. DH exchangeDH exchange

    3.3. AuthenticationAuthentication

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    Windows 2003 IPSec ComponentsWindows 2003 IPSec ComponentsSecurity Associations (part 2)Security Associations (part 2)

    Phase II SAPhase II SA IPSec Driver SAIPSec Driver SA

    1.1. Policy negotiationPolicy negotiation

    2.2. Session key material refresh or exchangeSession key material refresh or exchange

    3.3. SAs and keys passed to IPSec driverSAs and keys passed to IPSec driver

    SA lifetimesSA lifetimes

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    Windows 2003 IPSec ComponentsWindows 2003 IPSec ComponentsKey ProtectionKey Protection

    Key lifetimesKey lifetimes

    Perfect Forward Secrecy (PFS)Perfect Forward Secrecy (PFS)

    1.1. Phase IPhase I -- master key PFSmaster key PFS

    2.2. Phase IIPhase II -- session key PFSsession key PFS

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    Windows 2003 IPSec ComponentsWindows 2003 IPSec ComponentsIPSec DriverIPSec Driver

    Responsible forResponsible for

    1.1. Stores existing filters and policy IdsStores existing filters and policy Ids

    2.2. Checks each IP packet for match to policy filterChecks each IP packet for match to policy filter

    3.3. Requests SA negotiations from ISAKMP for newRequests SA negotiations from ISAKMP for new

    connectionsconnections

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    4.4. Stores existing SasStores existing Sas

    5.5. Implementing IPSec policy as defined in SasImplementing IPSec policy as defined in Sas

    6.6. Tracks key time length and number of bytesTracks key time length and number of bytes

    transformed to request new keystransformed to request new keys

    7.7. Updates SA changes and deletes expired SAsUpdates SA changes and deletes expired SAs

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    Implementation of IPSecImplementation of IPSecIn This Section We Will CoverIn This Section We Will Cover

    Policies and Policy InheritancePolicies and Policy Inheritance

    RulesRules

    IP packet filteringIP packet filtering

    Filter actionsFilter actions

    Connection typesConnection types

    AuthenticationAuthentication

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    Implementation of IPSecImplementation of IPSecPoliciesPolicies

    IP Security Management snapIP Security Management snap--inin

    Predefined policiesPredefined policies

    Client (respond only)Client (respond only)

    Server (request security)Server (request security)

    Server (require security)Server (require security)

    Policy inheritancePolicy inheritance

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    Implementation of IPSecImplementation of IPSec Determine how and when a policy is usedDetermine how and when a policy is used

    Provide customization of policy based on source,Provide customization of policy based on source,

    destination, and specific IP trafficdestination, and specific IP traffic

    Rules are made up of five components:Rules are made up of five components:

    1.1. Connection typeConnection type

    2.2. Authentication methodsAuthentication methods

    3.3. IP filter listIP filter list

    4.4. Filter actionFilter action

    5.5. Tunnel settingsTunnel settings

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    Implementation of IPSecImplementation of IPSecIP Packet FilteringIP Packet Filtering

    Determines what packet types the security policy willDetermines what packet types the security policy will

    apply toapply to

    Set for both incoming and outgoing trafficSet for both incoming and outgoing traffic

    Contains the following parametersContains the following parameters

    1.1. The source and destination address of the IP packetThe source and destination address of the IP packet

    2.2. The protocol being uses to transport packetThe protocol being uses to transport packet

    3.3. Source and destination port of the protocolSource and destination port of the protocol

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    Implementation of IPSecImplementation of IPSecFilter ActionsFilter Actions DefaultsDefaults

    PermitPermit

    BlockBlock

    Negotiate securityNegotiate security

    CustomCustom

    Accept unsecuredAccept unsecured -- respond with IPSecrespond with IPSec

    Allow unsecured with nonAllow unsecured with non--IPSecIPSec--aware computeraware computer

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    Implementation of IPSecImplementation of IPSecConnection TypesConnection Types

    Rule propertiesRule properties -- Connection Type tabConnection Type tab

    All network connectionsAll network connections

    Local area networkLocal area network

    Remote accessRemote access

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    Implementation of IPSecImplementation of IPSecAuthentication MethodsAuthentication Methods

    KerberosKerberos

    CertificatesCertificates

    Trusted certificate authorityTrusted certificate authority

    Microsoft Certificate ServerMicrosoft Certificate Server

    Preshared keyPreshared key

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    Best Practices for IPSecBest Practices for IPSecIn This Section We Will CoverIn This Section We Will Cover Evaluate network dataEvaluate network data

    Determine network data flowDetermine network data flow

    Design a network security planDesign a network security plan

    Configure and test in lab before deployingConfigure and test in lab before deploying

    IP filter listsIP filter lists

    Things to consider (SNMP, DNS DHCP,WINS, DCs,Things to consider (SNMP, DNS DHCP,WINS, DCs,

    and performance)and performance)

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    Best Practices for IPSecBest Practices for IPSecEvaluating Network DataEvaluating Network Data

    What types of data travel the networkWhat types of data travel the network

    Financial dataFinancial data

    HR dataHR data

    Legal dataLegal data ProprietaryProprietary

    ClassifiedClassified

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    Risk of this information being compromisedRisk of this information being compromised

    Some data will require different protectionSome data will require different protection

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    Best Practices for IPSecBest Practices for IPSecDetermining Network Data FlowDetermining Network Data Flow

    Once the type of data is determinedOnce the type of data is determined

    Where is the data storedWhere is the data stored

    How does it route through the networkHow does it route through the network

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    What hosts access the dataWhat hosts access the data

    While gathering information, also look atWhile gathering information, also look at

    Network speedNetwork speed

    BandwidthBandwidth

    This will assist in optimization issues laterThis will assist in optimization issues later

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    Best Practices for IPSecBest Practices for IPSecDesigning a Network Security PlanDesigning a Network Security Plan

    Evaluate your risk of attacksEvaluate your risk of attacks

    Other security measures employedOther security measures employed

    Communications ScenarioCommunications Scenario

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    Level of security neededLevel of security needed

    Strive for a well balanced deployment of securityStrive for a well balanced deployment of security

    measuresmeasures

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    Best Practices for IPSecBest Practices for IPSecIP Filter ListsIP Filter Lists

    Filter ListsFilter Lists

    Try to use general filtersTry to use general filters

    Set up filters for logical network segmentsSet up filters for logical network segments

    Filter display order versus filter applied orderFilter display order versus filter applied order

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    Filter ActionsFilter Actions

    Rogue computersRogue computers

    ESP and custom security methodsESP and custom security methods

    RAS and knownRAS and known--key attackskey attacks

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    Best Practices for IPSecBest Practices for IPSecSpecial ServicesSpecial Services

    SNMPSNMP

    Security gatewaysSecurity gateways

    DHCP, DNS, WINSDHCP, DNS, WINS

    Domain controllersDomain controllers

    DownDown--level clientslevel clients

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    Best Practices for IPSecBest Practices for IPSec IPSec one part of a security foundationIPSec one part of a security foundation

    Designed for intranet not perimeterDesigned for intranet not perimeter

    Security is a balance ofSecurity is a balance of

    Perimeter securityPerimeter security

    User access controlUser access control

    Physical securityPhysical security

    IPSec is endpoint to endpointIPSec is endpoint to endpoint

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    Troubleshooting IPSecTroubleshooting IPSec

    System/Security logs and routesSystem/Security logs and routes

    Ping and IPSec monitorPing and IPSec monitor

    Network monitorNetwork monitor

    Policy AgentPolicy Agent

    Log filesLog files

    Knowledge BaseKnowledge Base

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    Troubleshooting IPSecTroubleshooting IPSecSystem/Security Logs and RoutesSystem/Security Logs and Routes Event ViewerEvent Viewer

    System Event logSystem Event log

    Security Event logSecurity Event log

    Default RoutesDefault Routes

    Multiple routes of 0.0.0.0 or lowest metricMultiple routes of 0.0.0.0 or lowest metric

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    Troubleshooting IPSecTroubleshooting IPSecPING and IPSec MonitorPING and IPSec Monitor CommandsCommands

    PingPing

    IPSec MonitorIPSec Monitor Ipsecmon.exeIpsecmon.exe

    Is IPSec enabled on hostIs IPSec enabled on host

    Displays current SAs on hostDisplays current SAs on host

    Displays whether the SAs are hard or softDisplays whether the SAs are hard or soft

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    Troubleshooting IPSecTroubleshooting IPSec Network MonitorNetwork Monitor Windows 2000 Network Monitor can view AH and ESPWindows 2000 Network Monitor can view AH and ESPpacketspackets

    AHAH IP packet 51IP packet 51

    ESPESP IP packet 50IP packet 50

    ESP packet data is not visibleESP packet data is not visible

    ISAKMP/OakleyISAKMP/Oakley UDP port 500UDP port 500

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    Troubleshooting IPSecTroubleshooting IPSecPolicy AgentPolicy Agent

    ServicesServices Policy Agent ServicePolicy Agent Service

    Start, stop, and restart Policy AgentStart, stop, and restart Policy Agent

    Clears out old SasClears out old Sas

    Refreshes policies from Active DirectoryRefreshes policies from Active Directory

    Allows the restarting of the IPSec driverAllows the restarting of the IPSec driver

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    Policy Agent log filePolicy Agent log file

    Ipsecpa.logIpsecpa.log

    Broken links in Policy AgentBroken links in Policy Agent

    Policy Agent checkPolicy Agent check

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    Troubleshooting IPSecTroubleshooting IPSecLog FilesLog Files Oakley logOakley log

    HKEY_LOCAL_MACHINEHKEY_LOCAL_MACHINE\\SYSTEMSYSTEM\\CCSCCS\\ServicesServices\\

    PolicyAgentPolicyAgent\\OakleyOakley

    Add REG_DWORD : DebugAdd REG_DWORD : Debug

    Value: 1Value: 1

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    Network Address Translation (NAT)Network Address Translation (NAT)

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    IntroductionIntroduction

    With network address translation (NAT) in WindowsWith network address translation (NAT) in Windows

    2003, you can configure your network to share a single2003, you can configure your network to share a single

    connection to the Internet.connection to the Internet.

    Fewer Internet valid IP addresses are needed.Fewer Internet valid IP addresses are needed.

    Improved security because clients are not directly on theImproved security because clients are not directly on the

    Internet.Internet.

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    IntroductionIntroduction (2)(2)

    Internet Connection Sharing (ICS) is included withInternet Connection Sharing (ICS) is included with

    Windows 2003 Professional and higher.Windows 2003 Professional and higher.

    Network address translation (NAT) is included withNetwork address translation (NAT) is included with

    Windows 2000 Server and higher.Windows 2000 Server and higher.

    This presentation focuses on network addressThis presentation focuses on network address

    translation.translation.

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    ComponentsComponents

    NAT consists of the following three components:NAT consists of the following three components:

    TranslationTranslation

    AddressingAddressing

    Name ResolutionName Resolution

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    Components: TranslationComponents: Translation

    NAT translates the IP addresses and TCP/UDP portNAT translates the IP addresses and TCP/UDP port

    numbers of packets that are forwarded between thenumbers of packets that are forwarded between the

    private network and the Internet.private network and the Internet.

    The packets sent out of NAT have a source IP address ofThe packets sent out of NAT have a source IP address of

    the NAT machine.the NAT machine.

    Therefore, external machines are never aware that NATTherefore, external machines are never aware that NAT

    is being used.is being used.

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    Components: AddressingComponents: Addressing

    The addressing component is a simplified DHCP serverThe addressing component is a simplified DHCP server

    called the DHCP allocator.called the DHCP allocator.

    Either the DHCP allocator or an existing DHCP serverEither the DHCP allocator or an existing DHCP server

    can be used.can be used.

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    Components: Name ResolutionComponents: Name Resolution

    The name resolution component of NAT is the DNSThe name resolution component of NAT is the DNS

    Proxy.Proxy.

    Either the DNS proxy or an existing DNS server can beEither the DNS proxy or an existing DNS server can be

    used.used.

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    NAT ConfigurationNAT Configuration NAT is configured in the Routing and Remote Access service snapNAT is configured in the Routing and Remote Access service snap--

    inin

    The snapThe snap--inin

    IP routingIP routing

    RightRight--click General and click New Routing Protocolclick General and click New Routing Protocol

    Select Network Address Translation (NAT) and then click OKSelect Network Address Translation (NAT) and then click OK

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    NAT ConfigurationNAT Configuration (2)(2)

    After NAT is installed, it is necessary to specify a publicAfter NAT is installed, it is necessary to specify a public

    and a private interface.and a private interface.

    RightRight--click Network Address Translation (NAT)click Network Address Translation (NAT)

    Choose New InterfaceChoose New Interface

    Select the external interface and then click OKSelect the external interface and then click OK

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    Specify this interface as the public interface andSpecify this interface as the public interface and

    enable Translate TCP/UDP Headersenable Translate TCP/UDP Headers

    (recommended)(recommended)

    Repeat the process for the internal interface andRepeat the process for the internal interface and

    specify this as the private interfacespecify this as the private interface

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    Client ConfigurationClient Configuration

    Clients behind NAT:Clients behind NAT:

    Configured as DHCP client (discussion with DHCPConfigured as DHCP client (discussion with DHCP

    allocator)allocator)

    Configured as DHCP client (discussion with DHCPConfigured as DHCP client (discussion with DHCP

    server)server)

    Statically configured clientsStatically configured clients

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    Static Mapping: Address PoolStatic Mapping: Address Pool

    Address Pool:Address Pool:

    NAT also gives us the functionality to create a oneNAT also gives us the functionality to create a one--toto--oneone

    mapping between external IP address and internal IP addressmapping between external IP address and internal IP address

    Add external IP address to Address Pool listAdd external IP address to Address Pool list

    Click Reservations and specify the external and internal IPClick Reservations and specify the external and internal IP

    addressesaddresses

    Also enable Allow incoming sessions to this addressAlso enable Allow incoming sessions to this address

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    NAT EditorsNAT Editors NAT performs TCP port and UDP port translation, in addition to IPNAT performs TCP port and UDP port translation, in addition to IP

    address translationaddress translation

    If an application stores IP address or port information within its ownIf an application stores IP address or port information within its own

    header (like FTP PORT command), a NAT editor is neededheader (like FTP PORT command), a NAT editor is needed

    Two editors that Windows 2000 includes are FTP and PPTPTwo editors that Windows 2000 includes are FTP and PPTP

    Any service that encrypts these headers wont work (like IPSec)Any service that encrypts these headers wont work (like IPSec)

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    10.0.0.1

    10.0.0.4

    10.0.0.3

    10.0.0.2

    PPTP servera

    b

    c

    NAT

    204.x.1.10

    Internet

    Outgoing PPTP Client Through NATOutgoing PPTP Client Through NAT

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    Internet

    10.0.0.1

    10.0.0.4

    10.0.0.3

    10.0.0.2

    PPTP servera

    b

    c

    NAT

    204.x.1.10

    Connection request to port1723 from c to source 10.0.0.4, port1025.

    10.0.0.4, port 1025

    mapped to

    204..x.1.10, port 2000

    Connection request from c forwarded to source 204.x.1.10, port2000.

    Request received and accepted.

    During configuration, PPTP serverassigns 192.10.10.2 to cs VPN.

    Tunnel established

    Outgoing PPTP Client Through NATOutgoing PPTP Client Through NAT

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    Internet

    10.0.0.1

    10.0.0.4

    10.0.0.3

    10.0.0.2

    PPTP servera

    c

    NAT

    204.x.1.10

    Original packet has app data,TCP, UDP, etc., source192.10.10.2.

    PPP and GRE headers added.Encapsulated packet has

    source 10.0.0.4, destinationPPTP server.

    Original packet not touched,source 192.10.10.2.

    Encapsulated packets IP

    address translated. Source204.x.1.10, destination PPTPserver.

    Original packet not touched,source 192.10.10.2.

    Encapsulation removed by

    PPTP server.

    b

    Outgoing PPTP Client ThroughOutgoing PPTP Client Through

    NATNAT

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    ALL THE BESTALL THE BEST