So I though I should share a tip about an issue I had with setting up Apache reverse proxy in pfSense to serve internal HTTPS websites that are using self signed certificates.
I got a message similar to The proxy server could not handle the request. Error during SSL Handshake with remote server.
I solved it by going to the Virtual Hosts tab in the Web GUI, selecting the virtual host and then adding the below directives to the Custom Options field:
# Disable cert checks