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Some Clarification on this issue would be nice. I have been having the same issue and came to the same result but no clear statement form DO on this matter. This would be quite good to be sure that we are not doing some mistake in our setups.
Kind regards Gradlon
I just landed here after some Googling around searching for anyone with the same issue. I have extensively documented my findings on this Reddit post: https://www.reddit.com/r/PFSENSE/comments/bs2lby/pfsense_sitetosite_openvpn_not_routing_properly/
DigitalOcean is definitely filtering something on their side given that packets routed to a different LAN via the internal interface are never reaching anywhere (confirmed by multiple tcpdump instances running not only the droplet but also my pfSense installation).
I have openend a support ticket asking them about this, but still didn’t get an answer.