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IPSec In Depth
Encapsulated Security Payload
            (ESP)
• Must encrypt and/or authenticate in each
  packet
• Encryption occurs before authentication
• Authentication is applied to data in the
  IPSec header as well as the data contained
  as payload
IPSec Encapsulating Security Payload (ESP)
            in Transport Mode

                Orig IP Hdr TCP Hdr                 Data
                        Insert                               Append
Orig IP Hdr ESP Hdr TCP Hdr                  Data        ESP Trailer ESP Auth
                                     Usually encrypted

                                      integrity hash coverage



  SecParamIndex Seq# InitVector                                   Keyed Hash

  22-36 bytes total              Padding    PadLength NextHdr
ESP is IP protocol 50
                                                                © 2000 Microsoft Corporation
IPSec ESP Tunnel Mode

              Orig IP Hdr TCP Hdr         Data


IPHdr   ESP Hdr IP Hdr   TCP Hdr Data          ESP Trailer ESP Auth
                           Usually encrypted

                            integrity hash coverage

 New IP header with source &
 destination IP address



                                                      © 2000 Microsoft Corporation
Authentication Header (AH)
• Authentication is applied to the entire
  packet, with the mutable fields in the IP
  header zeroed out
• If both ESP and AH are applied to a packet,
  AH follows ESP
IPSec Authentication Header (AH)
            in Transport Mode

       Orig IP Hdr TCP Hdr              Data

                    Insert
  Orig IP Hdr AH Hdr           TCP Hdr          Data

        Integrity hash coverage (except for mutable fields in IP hdr)



Next Hdr Payload Len Rsrv SecParamIndex Seq# Keyed Hash
      AH is IP protocol 51               24 bytes total


                                                          © 2000 Microsoft Corporation
IPSec AH Tunnel Mode

         Orig IP Hdr TCP Hdr            Data




IP Hdr    AH Hdr Orig IP Hdr TCP Hdr                  Data

          Integrity hash coverage (except for mutable new IP hdr fields)



New IP header with source &
destination IP address

                                                          © 2000 Microsoft Corporation
Internet Key Exchange (IKE)
• Phase I
  – Establish a secure channel(ISAKMP SA)
  – Authenticate computer identity
• Phase II
  – Establishes a secure channel between
    computers intended for the transmission of data
    (IPSec SA)
Main Mode
• Main mode negotiates an ISAKMP SA
  which will be used to create IPSec Sas
• Three steps
  – SA negotiation
  – Diffie-Hellman and nonce exchange
  – Authentication
Main Mode (Kerberos)

                      Initiator        Responder


             Header, SA Proposals
                                      Header, Selected SA Proposal


Header, D-H Key Exchange, Noncei,
Kerberos Tokeni                       Header, D-H Key Exchange, Noncer,
                                      Kerberos Tokenr
 Encrypted
                Header, Idi, Hashi
                                      Header, Idr, Hashr
Main Mode (Certificate)

                          Initiator       Responder


               Header, SA Proposals
                                          Header, Selected SA Proposal


Header, D-H Key Exchange, Noncei
                                          Header, D-H Key Exchange,
                                          Noncer,Certificate Request
 Encrypted
 Header, Idi, Certificatei, Signaturei,
 Certificate Request                      Header, Idr, Certificater,
                                          Signaturer
Main Mode (Pre-shared Key)

                      Initiator       Responder


             Header, SA Proposals
                                     Header, Selected SA Proposal


Header, D-H Key Exchange, Noncei
                                     Header, D-H Key Exchange, Noncer

 Encrypted
                Header, Idi, Hashi
                                     Header, Idr, Hashr
Quick Mode
• All traffic is encrypted using the ISAKMP
  Security Association
• Each quick mode negotiation results in two
  IPSec Security Associations (one inbound,
  one outbound)
Quick Mode Negotiation

                    Initiator     Responder
Encrypted

      Header, IPSec Proposed SA

                                  Header, IPSec Selected SA



                  Header, Hash

                                  Header, Connected Notification

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Rooster ipsecindepth

  • 2. Encapsulated Security Payload (ESP) • Must encrypt and/or authenticate in each packet • Encryption occurs before authentication • Authentication is applied to data in the IPSec header as well as the data contained as payload
  • 3. IPSec Encapsulating Security Payload (ESP) in Transport Mode Orig IP Hdr TCP Hdr Data Insert Append Orig IP Hdr ESP Hdr TCP Hdr Data ESP Trailer ESP Auth Usually encrypted integrity hash coverage SecParamIndex Seq# InitVector Keyed Hash 22-36 bytes total Padding PadLength NextHdr ESP is IP protocol 50 © 2000 Microsoft Corporation
  • 4. IPSec ESP Tunnel Mode Orig IP Hdr TCP Hdr Data IPHdr ESP Hdr IP Hdr TCP Hdr Data ESP Trailer ESP Auth Usually encrypted integrity hash coverage New IP header with source & destination IP address © 2000 Microsoft Corporation
  • 5. Authentication Header (AH) • Authentication is applied to the entire packet, with the mutable fields in the IP header zeroed out • If both ESP and AH are applied to a packet, AH follows ESP
  • 6. IPSec Authentication Header (AH) in Transport Mode Orig IP Hdr TCP Hdr Data Insert Orig IP Hdr AH Hdr TCP Hdr Data Integrity hash coverage (except for mutable fields in IP hdr) Next Hdr Payload Len Rsrv SecParamIndex Seq# Keyed Hash AH is IP protocol 51 24 bytes total © 2000 Microsoft Corporation
  • 7. IPSec AH Tunnel Mode Orig IP Hdr TCP Hdr Data IP Hdr AH Hdr Orig IP Hdr TCP Hdr Data Integrity hash coverage (except for mutable new IP hdr fields) New IP header with source & destination IP address © 2000 Microsoft Corporation
  • 8. Internet Key Exchange (IKE) • Phase I – Establish a secure channel(ISAKMP SA) – Authenticate computer identity • Phase II – Establishes a secure channel between computers intended for the transmission of data (IPSec SA)
  • 9. Main Mode • Main mode negotiates an ISAKMP SA which will be used to create IPSec Sas • Three steps – SA negotiation – Diffie-Hellman and nonce exchange – Authentication
  • 10. Main Mode (Kerberos) Initiator Responder Header, SA Proposals Header, Selected SA Proposal Header, D-H Key Exchange, Noncei, Kerberos Tokeni Header, D-H Key Exchange, Noncer, Kerberos Tokenr Encrypted Header, Idi, Hashi Header, Idr, Hashr
  • 11. Main Mode (Certificate) Initiator Responder Header, SA Proposals Header, Selected SA Proposal Header, D-H Key Exchange, Noncei Header, D-H Key Exchange, Noncer,Certificate Request Encrypted Header, Idi, Certificatei, Signaturei, Certificate Request Header, Idr, Certificater, Signaturer
  • 12. Main Mode (Pre-shared Key) Initiator Responder Header, SA Proposals Header, Selected SA Proposal Header, D-H Key Exchange, Noncei Header, D-H Key Exchange, Noncer Encrypted Header, Idi, Hashi Header, Idr, Hashr
  • 13. Quick Mode • All traffic is encrypted using the ISAKMP Security Association • Each quick mode negotiation results in two IPSec Security Associations (one inbound, one outbound)
  • 14. Quick Mode Negotiation Initiator Responder Encrypted Header, IPSec Proposed SA Header, IPSec Selected SA Header, Hash Header, Connected Notification