I'm fairly new to pfSense, so bear with me please.
To summarize, I have:
- A network with split DNS enabled.
- A single IIS web server with a single IP, different sites running using different host header binding over port 80, all sites working fine for internal users.
- pfSense 2.3.4-RELEASE-p1 with Squid 0.4.40 installed on network edge.
- What I have looks like the image below:
What I'm trying to achieve:
- Publish the internal sites for external users using the same internal URLs.
- Transparent Proxy (for internal caching and CalmAV) and HTTPS are not needed.
I read that pfSense can do this trick using Reverse Proxy, I followed the steps mentioned here to enable it (with the exception of using the same 80 port for internal sites): https://www.reddit.com/r/homelab/comments/2vyiiy/til_reverse_proxy_via_squid_in_pfsense/
Problem:
- When external users type in the site URL and hit enter, the browser starts trying to connect, but after a few seconds it fails without loading the page, what is even weird is that the URL they typed is redirected from HTTP to HTTPS.
Troubleshooting:
- Disabled Transparent HTTP Proxy for internal communication.
- The Squid logs are not showing anything related to redirection of URL.
- The pfSense firewall logs shows that external users are able to connect once using HTTP, and then all the traffic is communicated using HTTPS
Questions:
- Is this scenario even valid with pfSense/Squid?
- If yes, what am I missing? if not, what is the alternative?
- Do I have to publish the sites by using different ports on IIS and enable port redirection on Pfsense? (which is the very thing that I'm trying to avoid)
Any additional steps or troubleshooting advice is very much appreciated.