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DD-WRT, Netgear Nighthawk and reverse proxing problem

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So, I have hit a wall with a networking issue, typically I can sit and ponder and eventually figure things out, but not this one, I have an idea it is down to a simple something, but I am unable to pin-point it so looking for some help.

Components in the mix;

  • Netgear Nighthawk R7000 with DD-WRT firmware
  • McAfee Web gateway (licensed through work, used at home in a lab to gain knowledge)
  • Microsoft Exchange 2013 (TechNet)

although this part doesn't really matter as I believe my issue stops with the router.

Let me explain;

What I am trying to do here is setup a reverse proxy, that bit I can do and have done in work for several websites, however I wanted to mimic it at home so I can play with settings and figure things out, but it just does not work, however a colleague in work has this working, we both have residential broadband, same ISP, but he is not using DD-WRT so I can only guess there is an IP table, route or something I need to modify to solve this.

What works;

Ext > Router > internal client (HTTPS)

What doesn't;

Ext > Router >McAfee > Internal Client (HTTPS)

No matter what port or external name I use, it seems to stop at the McAfee system, but I think the router is blocking the connection since I do not get the proxy denied error I would expect

Both McAfee and the internal clients are on the same subnets (as is my colleagues).

Lets say it in IP form (made up details)

80.10.20.30 > 192.168.50.52 > 192.168.50.5 on port 443

This is all confusing I know, but when I try to use the reverse proxy it just simply fails, no error, no logs (that I can see), but a port scan does show the external ports open, the McAfee system is listening, but that's as far as I get.

Anyone have any other things I can try?


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