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Help Setting Up DMZ

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Hey Spiceworks Community!

So, I am pretty new systems administrator and I have a pretty solid understanding of Windows Servers, Server Applications, VMware, etc etc. But I always find myself struggling on the network side of things, Cisco, Switches, Firewalls.

Currently, I am trying to Federate our on-site domain with Office 365, to do this I need to setup a proxy server in a DMZ on our network to communicate with Active Directory and authenticate users. I just can't for the life of me understand how to get this DMZ working correctly. Here's what I have setup so far:

We are working in a virtual environment, I setup one Ethernet Port on our ESXi server to be our DMZ network. I moved the proxy server other to that network in Vcenter. I then took that port from the ESXi server and plugged directly into our Firewall (cisco 5505). In the firewall I setup a new DMZ interface on switch port 2, which is the port I plugged the ESXi server into. I gave this Interface an IP of 192.168.50.3, which is the subnet I plan on using for the DMZ. I then setup a Dynamic NAT rule on the DMZ interface to access internet (I could be doing something totally wrong here)

2 Dynamic any TimeWarnerFiber class b_6 False Unlimited Unlimited Unlimited True

So at this point I wanted to test, I figured I should be able to at least access the internet. So on the proxy server I set the IP to 192.168.50.4 with a gateway of 192.168.50.3 and DNS 8.8.8.8

No dice, I can't even ping 192.168.50.3. I really don't know what I am missing, but any help to get me through this, would be greatly appreciated!!

Thanks so much spiceworks!


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