Hi,
Normally you would see ICMP "message too big" errors on the network. Sometimes those ICMP messages get blocked on a firewall and fail to reach their destination. Make sure that RELATED connections are allowed by any stateful firewalls in the network.
I know TCP MSS can be set per route, but I usually stick to TCP MSS clamping via netfilter.
https://tldp.org/HOWTO/Adv-Routing-HOWTO/lartc.cookbook.mtu-mss.html gives a good example, but use POSTROUTING instead of FORWARDING when using those rules on the endpoints. If all else fails, the --set-mss option can be used to test even lower values and stick a hard coded value on it to validate your assumptions.
Kind regards,
Erwin