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Feb 20 10:33:41 racoon: ERROR: failed to pre-process packet. Feb 20 10:33:41 racoon: ERROR: failed to get sainfo.
This can result from mismatched subnet masks in the IPsec tunnel definitions. Check to be sure that the local and remote subnet masks match up on each side, typically they should be "/24" and not "/32".
racoon: ERROR: libipsec failed pfkey align (Invalid sadb message)
This should be fixed as of pfSense 1.2.1. If you still see this message after that, check to make sure that your Phase 2 timeouts match up on both ends of the tunnel. Some people still see this periodically with no ill effect. It shows up at intervals equal to the Phase 2 timeout, but nowhere near the actual expiration time.
ERROR: pfkey DELETE received
You might see this message repeatedly as Phase 2 is renegotiated between two endpoints (for multiple subnets). The tunnels still work, but traffic may be delayed while the tunnel is switched/reestablished. (more research needed for possible solutions)
racoon: INFO: unsupported PF_KEY message REGISTER
This is a normal log message. It is not indicative of any problem.
Client:
racoon: ERROR: none message must be encrypted
Server:
racoon: ERROR: can't start the quick mode, there is no ISAKMP-SA
Or also:
racoon: INFO: request for establishing IPsec-SA was queued due to no phase1 found.
Try to stop and restart racoon on the client/opposite side. This can turn up if one side still thinks Phase 1 is good/active, and the other side thinks it is gone.
If you have multiple/parallel IPsec tunnels and you have packet loss to one or more of the tunnels, it may be due to duplicate identifiers. Check your tunnel definitions, and be sure that for each tunnel you have defined between two given routers, there is a unique identifier.
Example:
Without unique identifiers for each tunnel between two given routers, the ipsec daemon cannot distinguish between the traffic for each tunnel, and will likely drop/lose packets.
You can run racoon in debug mode in the foreground to view details on negotiation. First kill racoon, then launch it from a SSH session by running:
racoon -d -v -F -f /var/etc/racoon.conf
Or leave out the -F to run it in the background but log details to the IPsec log.
Open the Trace app. Stop the IKE Service, and go to File, Options. Change the log output level to debug and click OK. Start the IKE Service and attempt to connect.
If you experience packet loss only when using specific protocols (SMB, RDP, etc), you may need to reduce your WAN MTU. IPsec does not handle fragmented packets very well, and a reduced MTU will ensure that the packets traversing the tunnel are all of a size which can be transmitted whole. A good starting point would be 1300, and if that works, slowly increase the MTU until you find the breaking point, then back off a little from there.
If some hosts can communicate across a VPN tunnel and others cannot, it typically means that for some reason the packets from that client system are not being routed to pfSense. This could happen for a number of reasons, but the two most common are:
If you experience dropped tunnels during periods of high IPsec throughput on an ALIX or other embedded hardware, you may need to disable DPD on the tunnel. When the CPU on an ALIX is tied up with sending IPsec traffic, it may not take the time to respond to a DPD request on the tunnel. As a consequence, the tunnel will fail a DPD check and be disconnected.