Traffic Between VLAN's is being blocked PFSENSE

Couple of things:

The Allow all rules should be below the 2 Adam:ONE reject Rules.

Any reason you have allow all ‘TCP’ traffic only? I also see the rule has advanced settings, is that a traffic shaper?

The ping wouldn’t work, as there is no rule allowing ping out. I’m assuming the Alias ‘Server’ is on a seperate VLAN (192.168.5.100)? If so, create a rule to allow ICMP from LAN to Server