More detail:
I connected to ovpn.
I then connected to a vmware vsphere application to use the console of one of the VM's in the office.
I compared pinging from the VM to pinging from my home laptop.
Format:
Internal IP / ping from home Y/N / ping from VM Y/N / description
ex:
1 Y/Y - office pfsense means the IP of the machine is 192.168.1.1 (note the "1"), and the Y/Y means I could ping it from both the internal VM and my home laptop.
To me, the anomalies are the .10 server attached to the same "server switch" that seems to provide the most reliable results. I assume this is a client firewall issue on the .10 machine itself.
Also the difference between the .60 and .68 - why would one machine on a random switch respond to ping, but the other would not? Again, do I assume a client firewall issue?
Finally, the .22 machine is the internal test machine we've been working with. Firewall on or off, no difference. Static route on the machine or not, no difference.
It still seems that most of the machines on the "server switch" want to act right, while most of the machines on other 8port workgroup switches in the office want to not work at all. I would chalk it up to "firewall" on all machines if it wasn't for the fact that I know we have 100% disabled the Windows firewall on the .22 Ip with the same (failed) results.
EDIT: I should note, notice that from an internal machine on the LAN, all pings to target machines worked as expected. (The "Y/Y? column has all Y in the 2nd part)
EDIT2: for IP's 57-84 I cannot comment on the OS or state of the firewall at this point - I assume some are on, some are off. I also assume that most (if not all) are Windows 7 workstations.
1 Y/Y - office pfsense
5 Y/Y - office 24port switch directly attached to pfsense
7 Y/Y - wifi access point daisy-chained to an 8port workgroup switch
9 N/Y - wifi access point daisy-chained to an 8port workgroup switch
10 N/Y - physical server (windows) attached to 8port "server switch"
11 Y/Y - physical server (linux) attached to 8port "server switch"
12 Y/Y - physical server (windows) attached to 8port "server switch"
13 Y/Y - physical server (imac running OSX) attached to 8port "server switch"
14 Y/Y - physical server (vmware esxi) attached to 8port "server switch"
15 Y/Y - 2nd physical server (vmware esxi) attached to 8port "server switch"
16 Y/Y - vm guest OS (linux) on vm1 (ip .14)
17 Y/Y - vm guest OS (linux) on vm1 (ip .14)
20 Y/Y - physical NAS server (synology) attached to 8port "server switch"
21 Y/Y - vm guest OS (windows 7) on vm2 (ip .15)
22 N/Y - physical workstation (windows) - my primary internal test machine
30 Y/Y - vm guest os (linux) on vm1 (ip .14)
33 N/Y - vm guest os (linux) on vm1 (ip .14)
35 Y/Y - vm guest os - linux - 2nd NIC of physical vm server - this is the mirror port of the 24 port switch attached to pfsense
37 Y/Y - vm guest os (linux) on vm1 (ip .14)
57 Y/Y - physical workstation attached to some misc 8port workgroup switch, attached to the 24 port switch that is attached directly to pfsense
60 Y/Y - physical workstation attached to some misc 8port workgroup switch, attached to the 24 port switch that is attached directly to pfsense
68 N/Y - physical workstation attached to some misc 8port workgroup switch, attached to the 24 port switch that is attached directly to pfsense
70 N/Y - physical workstation attached to some misc 8port workgroup switch, attached to the 24 port switch that is attached directly to pfsense
79 N/Y - physical workstation attached to some misc 8port workgroup switch, attached to the 24 port switch that is attached directly to pfsense
84 Y/Y - physical workstation attached to some misc 8port workgroup switch, attached to the 24 port switch that is attached directly to pfsense