ADFS not working on pfSense-managed Network

[KKIT]

Hi,

I have two networks:
Guest Network - Managed by pfSense
Internal Network - Managed by Windows Domain Controller / DHCP

When trying to access our company mails via Single Sign On (ADFS) on the internal network, everything works fine.

As soon as I try to log in via the guest network, I get a redirection followed by a "404 Not Found" Error.

The corresponding server has a NAT rule with its own WAN IP as well as a port forwarding.

Is there anything else I need to set on the pfSense?

I might try to enable the DNS Forwarder to forward all requests from Guest to the Internal network but I try to avoid that for security reasons.

UPDATE: I get redirected to the pfSense instead of the ADFS Server. So it might be a routing issue?

Any suggestions are appreciated, thanks much!

[crucialguy]

@kkit Not sure if you've figured this or not yet, but do you have any info on how your 'Guest' network is configured?

Is this a guest wireless network which is in captive portal mode? If so, that will initially intercept the traffic and fire you to the portal page you've setup in pfsense to authenticate your session, you won't have any access until you've authenticated your session.

Just missing the info on how the guest network is setup to know for sure what the problem is.