@pooperman there is some issue with SSL handshake:

@PiBa Good news, I got it to work! I did as you suggested and got a self signed certificate on the server using this guide. After that HAProxy is able to route traffic to the host. It even works with the Let's Encrypt wildcard cert I have through the ACME package, so there's no cert errors getting to the site. Thank you for the help again.

@phoadm Have you configured the haproxy webgui to 'monitor' a carp interface? If so it wont start on that node until that node becomes master.

@lido14 'Normally' IPFW is not running when only pfSense is used without captive-portal.. The quickest fix is probably to give pfSense a reboot.. Haproxy loads and configures IPFW if it 'needs' transparent-client-ip with its current config settings.. If none of the backends require this the IPFW related configuration code is likely completely skipped. It does not remember that it still needs to disable the old ipfw settings.... I guess i need to set a little 'flag' that transparent-client-ip was used and check that to remove the last rules if the current config doesn't use it anymore.. I'm not sure if unloading ipfw itself is possible.. i think there was a issue there...

and if you need more information to be able to assist. please let me know. i'm in a bit of a time crunch to fix this. :)

TLS 1.3 will require OpenSSL 1.1.x, which is only currently available on pfSense 2.5.0 development snapshots. Though it does look like net/haproxy-devel is at 2.0-dev2 on the branch used for pfSense 2.5.0 development, but the pfSense haproxy-devel package doesn't use it (yet). I'm not aware of any plans to switch that over yet, but it's probably just a matter of time.

Do it even easier: Run acme package on FW1 (I assume it's a CARP cluster with syncing?) and let it create a certificate for both names (fw1.xxx AND fw2.xxx). When it's done, select the cert for the webui. Then login to FW2 and select it, too, as certificates get synchronized automatically (if selected) to the secondary. There choose the same certificate as WebUI cert and be done :) Just check that you configure the acme service on fw1 to restart its own webserver after renewal AND via remote the service on fw2 (see the help for this)! Greets

Will be nice to learn how to do it both ways - using haproxy and just using the internal CAs as @johnpoz proposes. I went the haproxy route and couldnt get it to work. I have the certs issued and haproxy setup. Perhaps @Renat you can provide a guide how to do it and I will see if that can get me over the hump since I have already done most of the steps? ( some screenshots of haproxy setup). Also anything has to be done on the synology side?

@interloper Do you have a guide on how you setup your google domain settings for your subdomains? I am trying to figure it out but having a hard time. Here is my open topic on this forum (https://forum.netgate.com/post/830593). Thanks

The benefit is that you don't need to use port forwarding at all and you only need to have one port open. You can have HAproxy listen on the WAN on port 443 and send requests to the appropriate backend server based on the requested URL. You don't have to remember what port the services are running on externally just the FQDN. It isn't necessarily any more secure though. You only have one firewall rule on WAN so you can't apply different rules to each service at the firewall level. Connection limiting, traffic shaping etc. You still can have HAprxy listen on different ports though if you found you needed that. Steve

I moved the galaxy backend to the ssl offload fronted.

Added a custom ACL and used this https://stackoverflow.com/questions/23342036/haproxy-restrict-single-backend-by-ip-range

@jimp could you point me in the right direction how to setup so HAProxy on pfSense handels the certs ( not just getting them )

That was it, thank you for your help!

Probably not in this case.