I'm in the process of enabling IPv6 on a working IPv4 3-LAN, 2-WAN setup using 
pfSense 2.2.6 (I'm also in the process of testing 3.0 and did a cursory test 
and got the same results with our 3.0 test setup).  We're getting IPv6 via a 
Hurricane Electric tunnel.

There are 3 LANs each with a /24 IPv4 and a /64 IPv6 subnet (the /64's being 
from the /48 allocated from HE).  Currently, incoming IPv6 WAN and WAN_IPv6 
access is blocked for all IPv6 except that ICMP types (other than redirect) are 
allowed.  Rules exist allowing unrestricted IPv6 access across all 3 LANs.

I have pfSense configured for DHCP6 on all 3 LANs and RA (on all 3 LANs) is set 
to "Assisted" and (maybe unnecessarily?) "RA Subnet(s)" is set to all 3 of the 
/64 subnets.

Each of the 3 LANs is also it's own VLAN.  There are 3x HP 1810 v2 switches 
across the network.

One of the hosts, the problematic one (and, of course, the only one for which 
we actually want IPv6), is a virtualized OS X 10.8.5 running under VMware 
Fusion 7.1.2 (also on OS X 10.8.5).  The VM host system has 2 VLANs and the VM 
guest has 2 NICs, one bridged to each of the VM host system's VLANs.

Multiple systems on the network, including the "problem" virtualized host, have 
multi-homed IPv4 and (of course) multi-homed IPv6 interfaces.  For simplicity, 
I've manually set the IPv6 addresses and am using only them for testing.

Everything works wonderfully, except that ...

I'm having a problem accessing the IPv6 IPs on the virtualized/guest system's 
interface that's bridged to VLAN3 of the VM host.  Accessing IPv6 and IPv4 
addresses on VLAN1 and VLAN2 works fine.  Accessing IPv4 addresses on VLAN3 
works fine.  "Sometimes" (see below) one of the 2 manually assigned IPv6 
addresses on VLAN3 can be accessed.

[Because of what (at least "sometimes") works, I conclude that neither pfSense 
setup nor a local host firewall is the problem.]

Here's the symptoms:

- boot the problem/virtualized host then, on another system (C) on VLAN1, run 
ping6 against both of the 2 IPv6 addresses on (the interface that's bridged to 
the virtualized host's) VLAN3 and I get "...from <VLAN1 router address> -> 
<target VLAN3 IPv6 address>: Destination Host Unreachable" (addresses are 
config'd and up, according to ifconfig but they're not listed in pfSense's NDP 
table, so this makes [pf]sense).

- on the virtualized/problem host, run ping6 against the other system C, and 
it's OK

- now, again run (the same) ping6 commands from the other system (C) on VLAN1 
against both of the 2 IPv6 addresses on the virtualized host's VLAN3 and it 
works against the first IPv6 listed via ifconfig, but not the second

[I'm assuming that the ping6 run from the virtualized/problem host caused 
pfSense to acquire the one IPv6 IP and that's why it's now accessible -- 
indeed, that 1 of the 2 VLAN3 IPv6 addresses is now in pfSense's NDP table.]

- run ping6 from the VM host system against both of the 2 IPv6 addresses on the 
(VM guest) virtualized host's VLAN3 and both work

[I'm assuming, due to the bridging, that local neighbor discovery works from 
the VM host to its VM guest.  pfSense does not acquire the additional IPv6 
address from VLAN3.]

Tests run from other hosts show results that are consistent with the above 
tests.  So, with 1 exception, everything works and is consistent with what's 
shown in pfSense's and various host's routing tables and via ifconfig.

The failure is that neither of the 2 IPv6 addresses (nor the auto-allocated 
private IPv6 address) from the interface (on the virtualized host) that's 
bridged to the VLAN3 interface are learned/acquired by pfSense unless a ping6 
is run from the virtualized host and then only the first ifconfig-listed 
manually assigned IPv6 address is acquired by pfSense.  As such, pfSense 
considers the IP(s) unreachable.

I'm guessing that there's an issue where OS X is either not reporting the 2nd 
interface (i.e., second in that the VLAN1-linked interface is ordered first in 
the network configuration) or that the bridging is interfering with that 
communication.

I'm assuming that pfSense is "asking" hosts to report via each RA-config'd 
subnet every "now 'n then" and, as such, VLAN3 is receiving such queries.  
(Hmmm, as I write this, maybe this is another thing to look at.)

QUESTIONS:

- has anyone experienced a problem anything like this and, if so, what were you 
able to do about it?

- what's the best way to go about confirming that the virtualized host is 
receiving whatever queries RA is sending out on VLAN3 (assuming that's what's 
happening)?  I do have packet-capture capability on the VM host and the 
virtualized/problematic host ... but is there anything simpler?

- does anyone have any ideas on how I might solve this issue and/or learn more 
about exactly what's happening?

My next attempt will be to configure rtadvd to run on the virtualized/problem 
host (with rltime 0) in an effort to get it to tell pfSense that the second 
interface is present ... but, from what I see in the man page, I don't have 
much faith that it will work and, after many hours worth of research and 
experimentation, I'm pretty much at the end of my (newbie IPv6) knowledge (and 
"rope") on this one.

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