Website 301 Loop behind Cloudflare

Currently, I am experiencing a 301 redirect loop that is only affecting the pages of my wordpress website. All other subdomains and services work just fine with the configuration that is present. The weird thing is, is that I can access the login page and admin portal of the same wordpress site just fine.

I am currently hosting services with the following flow:

Cloudflare > Portzilla (8443) > ISP Edge (8443 forwarded) > Pfsense w/ Haproxy > Wordpress on IIS 10

Cloudflare is setup with the following:
A records
All others turned off/turned on in every combination while troubleshooting.

Portzilla is setup with 8443 being forwarded to the ISP public ip (all other portzilla entries with the same config work fine)

Haproxy config has been troubleshooted to the point that bringing it up gives me flashbacks, probably not the issue.

The following is a ss of the redirects:

Haproxy logs

Been really banging my head against the wall for a week now on this one, any help would be really appreciated.

The admin portal does show this error too:

Console network view of main url:

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