Great suggestions wallybybob. Thanks for the help.
@wallabybob:
Your laptop is using the wrong default gateway? (Perhaps you have another DHCP server on your network and the laptop got a lease from it.)
Negative. My laptop IP is manually set. I can ping both the VLAN102 and the VLAN101 interface from my laptop though. Synology is on VLAN101, laptop is on VLAN102.
macbook-pro-15$ ping 192.168.101.1
PING 192.168.101.1 (192.168.101.1): 56 data bytes
64 bytes from 192.168.101.1: icmp_seq=0 ttl=64 time=0.058 ms
64 bytes from 192.168.101.1: icmp_seq=1 ttl=64 time=0.092 ms
64 bytes from 192.168.101.1: icmp_seq=2 ttl=64 time=0.096 ms
@wallabybob:
Your packet capture specified the wrong parameter values?
Don't think so. I tried both synology IP of 192.168.101.2 and my IP of 192.168.102.6 with not specifying any ports. I can see 192.168.102.6 traffic, but nothing related 192.168.101.2
@wallabybob:
Your access attempt begins with a host name which gets translated to the wrong IP address?
Negative there also. I use https://192.168.101.2:5001 to access the synology device.
@wallabybob:
On the laptop try to tracert (Windows command prompt) or traceroute (Unix shell) the synology to verify path.
On the laptop set up a ping to corresponding pfSense IP address for a few hundred packets or so and tweak the packet capture until you can see the ping. Or use tcpdump on the pfSense console as the packet capture.
macbook-pro-15$ traceroute 192.168.101.2
traceroute to 192.168.101.2 (192.168.101.2), 64 hops max, 40 byte packets
1 * * *
2 * *traceroute: sendto: No route to host
traceroute: wrote 192.168.101.2 40 chars, ret=-1
*
Can't see ping traffic on packet capture or ping the Synology device, however, I can ping the interface the Synology is plugged into.