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Please could someone assist me with an issue I am facing running a mail server and a webserver on the same network. Please excuse the long post, however, I would like to provide as much information as possible for the experts to analyze. My exact setup is as follows: 1: I have a Windows 10 PC with IIS installed, IP address 192.168.0.3 2: I have a Windows 10 PC with Kerio Connect Mail server installed, IP address 192.168.0.2 3: I have a D-Link DIR-825 router connecting me to the outside world. 4: I have a static external IP address. 4: DNS records are all setup correctly. Here is my question in a nutshell, with steps I have taken to try to resolve my issue: Question: How on earth do I run both the webserver and the Kerio Mail server on the same network using port 443 but on different IP addresses? Steps taken to resolve: 1: My D-Link will only allow one virtual server set up for port 443. At the moment it is pointing to 192.168.0.2 and my website is working 100% 2: The issue is that Kerio Mail Server also uses port 443 for the Web Mail Client and at the moment this is not working, it will not come up at all from the outside world. 3: If I change the virtual server from 192.168.0.3 port 443 to 192.168.0.2 port 443 and then try to access https://www.gmcomputers.co.za (my website) from outside the internal network I then get an error message saying that my certificate is invalid, and then the browser proceeds to bring up the Kerio Webmail Client on https://mail.gmcomputers.co.za So, is there ANY way I can somehow tell my D-Link router that when a request comes in for www.gmcomputers.co.za it must go to IP address 192.168.0.3 port 443 and for the Kerio Mail Server it must go to 192.168.0.2 port 443? Or is there something else I can do, please? I would prefer to NOT change any of the default ports as this would kind of defeat the object of having two servers. Thanking you.

  • No. The D-Link is not capable of that. This is typically the work of a reverse proxy. You can set that up on IIS. Forward all port 443 traffic to the IIS server and set up a reverse proxy to forward traffic matching the webmail URL to the Kerio server. https://medium.com/@gusterwoei/how-to-configure-reverse-proxy-on-windows-iis-52a48b90163a – Appleoddity Jun 08 '22 at 12:28
  • @Appleoddity thank you for your reply. I tried to set up the reverse proxy according to the link you provided, however, it does not seem to work and that is probably because this is most likely way out of my depth and I have NO idea exactly what details to actually input for my specific case. So thank you but I will just change the Kerio Mail Server port to 8843 and be done with it. This I know works. I appreciate the response – Mark de Wet Jun 08 '22 at 14:34
  • To get familiar with reverse proxy, you need to start with HTTP sites and tools like Wireshark. Then raw HTTP packets can be easily analyzed and you understand clearly how the reverse proxy rules modify incoming packets as outgoing ones. Without that piece of important knowledge, you cannot quickly move on to HTTPS sites which are more complicated. – Lex Li Jun 08 '22 at 14:43
  • @LexLi I do understand that, and appreciate the feedback. The main issue is I am 60 years old and while I appreciate that certain tools will assist, I was hoping for a simple solution to my issue, which there evidently is not. So thank you as well, however, I am not going to involve myself in something I obviously know very little about and have no real desire to get myself wrapped up in. – Mark de Wet Jun 08 '22 at 19:29

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