8.Cisco ASA Hairpin Remote VPN Users
The Cisco ASA firewall doesn’t like traffic that enters and exits the same interface. This behavior is typically known as “hairpin” or “u-turn”. Sometimes however we need our ASA to permit this kind of traffic. Here’s an example:

Above we have an ASA firewall on the left side, there’s a remote VPN uses that connects to our firewall. This remote VPN user is not using split tunneling so all traffic is being tunneled to the ASA. Let’s say this user wants to reach some webserver (2.2.2.2) on the Internet behind R2.
Here’s what our traffic pattern will look like:

Our traffic will enter the ASA on its outside Gigabit 0/0 interface and exits the same interface. By default, the ASA will drop this traffic. The second issue with this setup is that the source IP address will be from the 192.168.10.0/24 subnet. Since this is a private range, R2 will drop the traffic when it has to be routed to the Internet.
Let’s see what we have to do to fix this issue…
- Startup Configurations
- R2
- ASA1
hostname R2
!
interface Loopback0
ip address 2.2.2.2 255.255.255.255
!
interface GigabitEthernet0/1
ip address 192.168.2.2 255.255.255.0
duplex auto
speed auto
media-type rj45
!
ip http server
!
endhostname ASA1
!
ip local pool VPN_POOL 192.168.10.100-192.168.10.200
!
interface GigabitEthernet0/0
nameif OUTSIDE
security-level 0
ip address 192.168.2.254 255.255.255.0
!
ftp mode passive
object network VPN_POOL
subnet 192.168.10.0 255.255.255.0
!
route OUTSIDE 0.0.0.0 0.0.0.0 192.168.2.2 1
!
crypto ipsec ikev1 transform-set MY_TRANSFORM_SET esp-aes esp-sha-hmac
crypto ipsec security-association pmtu-aging infinite
crypto dynamic-map MY_DYNA_MAP 10 set ikev1 transform-set MY_TRANSFORM_SET
crypto map MY_CRYPTO_MAP 10 ipsec-isakmp dynamic MY_DYNA_MAP
crypto map MY_CRYPTO_MAP interface OUTSIDE
crypto isakmp identity address
crypto ikev1 enable OUTSIDE
crypto ikev1 policy 10
authentication pre-share
encryption aes
hash sha
group 2
lifetime 86400
!
group-policy VPN_POLICY internal
group-policy VPN_POLICY attributes
vpn-idle-timeout 15
dynamic-access-policy-record DfltAccessPolicy
username VPN_USER password E5PbZWWQ.j3bJJHz encrypted
tunnel-group MY_TUNNEL type remote-access
tunnel-group MY_TUNNEL general-attributes
address-pool VPN_POOL
default-group-policy VPN_POLICY
tunnel-group MY_TUNNEL ipsec-attributes
ikev1 pre-shared-key *****
!
class-map inspection_default
match default-inspection-traffic
!
!
policy-map type inspect dns preset_dns_map
parameters
message-length maximum client auto
message-length maximum 512
policy-map global_policy
class inspection_default
inspect ip-options
inspect netbios
inspect rtsp
inspect sunrpc
inspect tftp
inspect xdmcp
inspect dns preset_dns_map
inspect ftp
inspect h323 h225
inspect h323 ras
inspect rsh
inspect esmtp
inspect sqlnet
inspect sip
inspect skinny
inspect icmp
policy-map type inspect dns migrated_dns_map_1
parameters
message-length maximum client auto
message-length maximum 512
!
service-policy global_policy global
!
: endLet’s take a look at the configuration…
1.Configuration
There are two things we have to fix here:
- We need to configure the ASA to permit traffic that enters and exits the same interface.
- Traffic from the 192.168.10.0/24 subnet has to be NAT translated.
Before we make any changes, let’s try a ping from our remote VPN user:
C:\Users\H1>ping 2.2.2.2
Pinging 2.2.2.2 with 32 bytes of data:
Request timed out.
Request timed out.
Request timed out.
Request timed out.
Ping statistics for 2.2.2.2:
Packets: Sent = 4, Received = 0, Lost = 4 (100% loss),As expected these pings are failing. Let’s configure the ASA to permit traffic that enters and exits the same interface:
ASA1(config)# same-security-traffic permit intra-interfaceThe command above will allow the traffic to be routed. The second thing to do is to configure a NAT rule:
ASA1(config)# nat (OUTSIDE,OUTSIDE) source dynamic VPN_POOL interfaceThe line above will translate traffic from our network object called VPN_POOL (which matches the 192.168.10.0/24 subnet) when it enters and exits the OUTSIDE interface. It will be translated to the IP address on the outside interface of our ASA.
That’s all we have to configure, let’s verify our work!
2.Verification
Let’s start with a simple ping from the remote VPN user:
C:\Users\H1>ping 2.2.2.2
Pinging 2.2.2.2 with 32 bytes of data:
Reply from 2.2.2.2: bytes=32 time=498ms TTL=255
Reply from 2.2.2.2: bytes=32 time=14ms TTL=255
Reply from 2.2.2.2: bytes=32 time=14ms TTL=255
Reply from 2.2.2.2: bytes=32 time=268ms TTL=255
Ping statistics for 2.2.2.2:
Packets: Sent = 4, Received = 4, Lost = 0 (0% loss),
Approximate round trip times in milli-seconds:
Minimum = 14ms, Maximum = 498ms, Average = 198msThese pings are now successful. We can also verify our work on the ASA:
ASA1# show xlate
4 in use, 5 most used
Flags: D - DNS, e - extended, I - identity, i - dynamic, r - portmap,
s - static, T - twice, N - net-to-net
NAT from INSIDE:192.168.1.0/24 to OUTSIDE:192.168.1.0/24
flags sIT idle 0:10:21 timeout 0:00:00
NAT from OUTSIDE:192.168.10.0/24 to INSIDE:192.168.10.0/24
flags sIT idle 0:10:21 timeout 0:00:00
NAT from OUTSIDE:0.0.0.0/0 to OUTSIDE:0.0.0.0/0
flags sIT idle 0:04:54 timeout 0:00:00
ICMP PAT from OUTSIDE:192.168.10.100/1 to OUTSIDE:192.168.2.254/1 flags ri idle 0:00:00 timeout 0:00:30Above you can see the IP address of the remote VPN user (192.168.10.100) has been translated to the IP address on the outside interface of our ASA (192.168.2.254).
- Configurations
- R2
- ASA1
hostname R2
!
interface Loopback0
ip address 2.2.2.2 255.255.255.255
!
interface GigabitEthernet0/1
ip address 192.168.2.2 255.255.255.0
duplex auto
speed auto
media-type rj45
!
ip http server
!
endhostname ASA1
!
ip local pool VPN_POOL 192.168.10.100-192.168.10.200
!
interface GigabitEthernet0/0
nameif OUTSIDE
security-level 0
ip address 192.168.2.254 255.255.255.0
!
ftp mode passive
same-security-traffic permit intra-interface
object network VPN_POOL
subnet 192.168.10.0 255.255.255.0
!
nat (OUTSIDE,OUTSIDE) source dynamic VPN_POOL interface
!
route OUTSIDE 0.0.0.0 0.0.0.0 192.168.2.2 1
!
crypto ipsec ikev1 transform-set MY_TRANSFORM_SET esp-aes esp-sha-hmac
crypto ipsec security-association pmtu-aging infinite
crypto dynamic-map MY_DYNA_MAP 10 set ikev1 transform-set MY_TRANSFORM_SET
crypto map MY_CRYPTO_MAP 10 ipsec-isakmp dynamic MY_DYNA_MAP
crypto map MY_CRYPTO_MAP interface OUTSIDE
crypto isakmp identity address
crypto ikev1 enable OUTSIDE
crypto ikev1 policy 10
authentication pre-share
encryption aes
hash sha
group 2
lifetime 86400
!
group-policy VPN_POLICY internal
group-policy VPN_POLICY attributes
vpn-idle-timeout 15
dynamic-access-policy-record DfltAccessPolicy
username VPN_USER password E5PbZWWQ.j3bJJHz encrypted
tunnel-group MY_TUNNEL type remote-access
tunnel-group MY_TUNNEL general-attributes
address-pool VPN_POOL
default-group-policy VPN_POLICY
tunnel-group MY_TUNNEL ipsec-attributes
ikev1 pre-shared-key *****
!
class-map inspection_default
match default-inspection-traffic
!
!
policy-map type inspect dns preset_dns_map
parameters
message-length maximum client auto
message-length maximum 512
policy-map global_policy
class inspection_default
inspect ip-options
inspect netbios
inspect rtsp
inspect sunrpc
inspect tftp
inspect xdmcp
inspect dns preset_dns_map
inspect ftp
inspect h323 h225
inspect h323 ras
inspect rsh
inspect esmtp
inspect sqlnet
inspect sip
inspect skinny
inspect icmp
policy-map type inspect dns migrated_dns_map_1
parameters
message-length maximum client auto
message-length maximum 512
!
service-policy global_policy global
!
: end3.Conclusion
Hairpinning on the ASA isn’t very difficult. Once you understand why your firewall is dropping, it’s easily fixed with a few commands. If you have any questions, feel free to leave a comment.
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