pfsense: IPSec SSH connectivity issue

In this post I will setup an IPSec dynamic route-based vpn tunnel between two pfSense Appliances.

Main situation

I have two Pfsense firewalls for two sites. Sites are connected to each other with Pfsense IPsec tunnel. I experienced a strange issue, I can’t ssh from one site to a vm to the noter.

$ telnet  22
Connected to
Escape character is '^]'.

I can get SSH banner with telnet but does not work.

I’ve analyzed this a bit and with wireshark there are a lot of TCP - Retransmissions

TCP - Retransmissions

If I do a ping with Packet Size of 969 Byte everythin is okay, with 970 there is packetloss.

ping -f -l  969

The solution

So there is a Issue with fragmentation. I enabled Maximum MMS in VPN->IPSec->Advanced Settings and set value to 1350

MSS Config

With the upgrade of Pfsense 2.6 this menu is change. It is in System->Advanced->Firewall & NAT

MSS Config