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S2S VPN - ASA 5505 to ASA 5540 - Routing Problems

I'm a software developer (no doubt the issue) trying to setup my remote office (5505) to the main office (5540). No problem getting the S2S VPN up, but I definitely have problems with the routing. Using tracert, it shows it going into the remote network for a couple of hops, but then timing out. Packet tracer shows everything is fine. Using my client VPN credentials to the remote network, same on the return path...does a few hops, then gets lost. I've stripped down the config to the basics and ensured it isn't security settings on both ends, but still doesn't work. I've spent A LOT of hours trying to get this to work, so thanks for any assistance!

Current running config:

ASA Version 8.2(5)


hostname asa15

enable password XXXXX encrypted

passwd XXXXX encrypted


name remote-network


interface Ethernet0/0

switchport access vlan 2


interface Ethernet0/1


interface Ethernet0/2


interface Ethernet0/3


interface Ethernet0/4


interface Ethernet0/5


interface Ethernet0/6


interface Ethernet0/7


interface Vlan1

nameif inside

security-level 100

ip address


interface Vlan2

nameif outside

security-level 0

ip address dhcp setroute


ftp mode passive

access-list outside_1_cryptomap extended permit ip remote-network

access-list inside_nat0_outbound extended permit ip remote-network

access-list inside_access_in extended permit ip remote-network

access-list inside_nat0_outbound_1 extended permit ip remote-network

pager lines 24

logging enable

logging asdm informational

mtu outside 1500

mtu inside 1500

icmp unreachable rate-limit 1 burst-size 1

asdm location remote-network inside

no asdm history enable

arp timeout 14400

global (outside) 1 interface

nat (inside) 0 access-list inside_nat0_outbound_1

nat (inside) 1

access-group inside_access_in in interface inside

route outside 99.X.X.7 1

timeout xlate 3:00:00

timeout conn 1:00:00 half-closed 0:10:00 udp 0:02:00 icmp 0:00:02

timeout sunrpc 0:10:00 h323 0:05:00 h225 1:00:00 mgcp 0:05:00 mgcp-pat 0:05:00

timeout sip 0:30:00 sip_media 0:02:00 sip-invite 0:03:00 sip-disconnect 0:02:00

timeout sip-provisional-media 0:02:00 uauth 0:05:00 absolute

timeout tcp-proxy-reassembly 0:01:00

timeout floating-conn 0:00:00

dynamic-access-policy-record DfltAccessPolicy

http server enable

http inside

no snmp-server location

no snmp-server contact

snmp-server enable traps snmp authentication linkup linkdown coldstart

crypto ipsec transform-set ESP-AES-128-SHA esp-aes esp-sha-hmac

crypto ipsec transform-set ESP-AES-128-MD5 esp-aes esp-md5-hmac

crypto ipsec transform-set ESP-AES-192-SHA esp-aes-192 esp-sha-hmac

crypto ipsec transform-set ESP-AES-192-MD5 esp-aes-192 esp-md5-hmac

crypto ipsec transform-set ESP-AES-256-SHA esp-aes-256 esp-sha-hmac

crypto ipsec transform-set ESP-AES-256-MD5 esp-aes-256 esp-md5-hmac

crypto ipsec transform-set ESP-3DES-SHA esp-3des esp-sha-hmac

crypto ipsec transform-set ESP-3DES-MD5 esp-3des esp-md5-hmac

crypto ipsec transform-set ESP-DES-SHA esp-des esp-sha-hmac

crypto ipsec transform-set ESP-DES-MD5 esp-des esp-md5-hmac

crypto ipsec security-association lifetime seconds 3600

crypto ipsec security-association lifetime kilobytes 4608000

crypto map outside_map 1 match address outside_1_cryptomap

crypto map outside_map 1 set peer 99.X.X.7

crypto map outside_map 1 set transform-set ESP-AES-128-SHA

crypto map outside_map 1 set reverse-route

crypto map outside_map interface outside

crypto isakmp enable outside

crypto isakmp policy 10

authentication pre-share

encryption aes

hash sha

group 2

lifetime 28800

vpn-addr-assign local reuse-delay 5

telnet timeout 5

ssh timeout 5

console timeout 0

dhcpd auto_config outside


dhcpd address inside

dhcpd auto_config outside interface inside

dhcpd enable inside


threat-detection basic-threat

threat-detection statistics access-list

threat-detection statistics tcp-intercept rate-interval 30 burst-rate 400 average-rate 200


tunnel-group 99.X.X.7 type ipsec-l2l

tunnel-group 99.X.X.7 ipsec-attributes

pre-shared-key XXXXX


class-map inspection_default

match default-inspection-traffic



policy-map type inspect dns preset_dns_map


message-length maximum client auto

message-length maximum 512

policy-map global_policy

class inspection_default

inspect dns preset_dns_map

inspect ftp

inspect h323 h225

inspect h323 ras

inspect rsh

inspect rtsp

inspect esmtp

inspect sqlnet

inspect skinny

inspect sunrpc

inspect xdmcp

inspect sip

inspect netbios

inspect tftp

inspect ip-options


service-policy global_policy global

prompt hostname context

no call-home reporting anonymous

: end

Everyone's tags (3)

S2S VPN - ASA 5505 to ASA 5540 - Routing Problems

just out of curiosity, why do you have

route outside 99.X.X.7 1

You already set your default route through DHCP setroute under the interface. this could be the issue.

If your VPN config is ok and you are seeing encaps/decaps, it is likely a routing issue.

Does the remote device have the correct default gateway?

May be a Natting issue if you have a one-way tunnel (usually send but no receive)...