Edison here it is

R5#traceroute 3.3.3.3

Type escape sequence to abort

Tracing the route to 3.3.3.3

1 192.168.4.1 892 msec 180

2 172.16.8.3 156 msec * *

R5#traceroute 3.3.3.3

Type escape sequence to abort

Tracing the route to 3.3.3.3

1 192.168.4.1 892 msec 180

2 172.16.8.3 156 msec * *

Gateway of last resort is not set

1.0.0.0/30 is subnetted, 1 subnets

R 1.1.1.0 [120/4] via 192.168.4.1, 00:00:21, FastEthernet0/0

2.0.0.0/32 is subnetted, 1 subnets

R 2.2.2.2 [120/4] via 192.168.4.1, 00:00:21, FastEthernet0/0

3.0.0.0/32 is subnetted, 1 subnets

R 3.3.3.3 [120/4] via 192.168.4.1, 00:00:21, FastEthernet0/0

5.0.0.0/24 is subnetted, 1 subnets

C 5.5.5.0 is directly connected, Loopback0

6.0.0.0/24 is subnetted, 1 subnets

C 6.6.6.0 is directly connected, Loopback1

172.16.0.0/16 is variably subnetted, 5 subnets, 3 masks

R 172.16.9.252/30 [120/4] via 192.168.4.1, 00:00:21, FastEthernet0/0

R 172.16.8.0/24 [120/4] via 192.168.4.1, 00:00:21, FastEthernet0/0

R 172.16.10.0/24 [120/4] via 192.168.4.1, 00:00:23, FastEthernet0/0

R 172.16.8.2/32 [120/4] via 192.168.4.1, 00:00:23, FastEthernet0/0

R 172.16.8.3/32 [120/4] via 192.168.4.1, 00:00:24, FastEthernet0/0

7.0.0.0/24 is subnetted, 1 subnets

C 7.7.7.0 is directly connected, Loopback2

192.168.4.0/30 is subnetted, 1 subnets

C 192.168.4.0 is directly connected, FastEthernet0/0

R5#

R3#traceroute 5.5.5.5

Type escape sequence to abort.

Tracing the route to 5.5.5.5

1 172.16.9.253 672 msec 1068 msec 80 msec

2 192.168.4.2 912 msec 2284 msec 2140 msec

R3#

R3#ping 5.5.5.5

Type escape sequence to abort.

Sending 5, 100-byte ICMP Echos to 5.5.5.5, timeout is 2 seconds:

.!...

Success rate is 20 percent (1/5), round-trip min/avg/max = 336/336/336 ms

R3#

Gateway of last resort is not set

1.0.0.0/32 is subnetted, 1 subnets

O 1.1.1.1 [110/1563] via 172.16.8.1, 00:41:22, Serial1/0

2.0.0.0/32 is subnetted, 1 subnets

O 2.2.2.2 [110/3125] via 172.16.8.1, 00:41:22, Serial1/0

3.0.0.0/24 is subnetted, 1 subnets

C 3.3.3.0 is directly connected, Loopback0

5.0.0.0/24 is subnetted, 1 subnets

O E2 5.5.5.0 [110/20] via 172.16.9.253, 00:40:52, Serial1/1

6.0.0.0/24 is subnetted, 1 subnets

O E2 6.6.6.0 [110/20] via 172.16.9.253, 00:40:52, Serial1/1

172.16.0.0/16 is variably subnetted, 5 subnets, 3 masks

C 172.16.9.252/30 is directly connected, Serial1/1

C 172.16.8.0/24 is directly connected, Serial1/0

O 172.16.8.1/32 [110/1562] via 172.16.8.1, 00:41:31, Serial1/0

C 172.16.10.0/24 is directly connected, FastEthernet0/0

O 172.16.8.2/32 [110/3124] via 172.16.8.1, 00:41:31, Serial1/0

7.0.0.0/24 is subnetted, 1 subnets

O E2 7.7.7.0 [110/20] via 172.16.9.253, 00:41:01, Serial1/1

192.168.4.0/30 is subnetted, 1 subnets

O E2 192.168.4.0 [110/20] via 172.16.9.253, 00:41:01, Serial1/1

R3#

The Ethernet segment between R5 and R1 seems to have a high latency.

From R5 to R1 the traceroute reports

192.168.4.1 892 msec 180

892ms is quite high for a LAN connection.

Then from R3 to R5, your first hop via the 128k Serial

172.16.9.253 672 msec 1068 msec 80 msec

a little in the high size, it seems you are facing bursty traffic

but when it reaches the LAN segment.

2 192.168.4.2 912 msec 2284 msec 2140 msec

That's over 2 seconds hence causing the request time out.

I suggest you monitor the traffic on those links for saturation. Do you have any network monitoring tool ?

Edit:

I also noticed you are experiencing assymetrical routing.

The path from R5 to R3 goes via the OSPF Area 0 backbone (Frame-Relay) while from R3 to R5 goes via the Serial 128kbps OSPF Area 1.

You need to troubleshoot the configuration there.

Edison thanks for the reply. On the assymetrical routing, what would be the best approach to troubleshoot that config?

You need to determine why a path is chosen over the other path. Plenty of things to list, that's how your troubleshooting skills come into play.

It seems this is a lab and not a production network, huh ?

yup it is a lab so although not mission critical, it would be nice to understand the reason behind it.