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spovelec avatar Server

Unable to join domain from Site-to-Site VPN Server

cn flag
spovelec

I work for a small business that is looking to expand to the cloud so that our remote workers can access more of our systems. As a software dev and keen IT enthusiast, I jumped at the opportunity to get my hands dirty with this project. After spending the last 2 weeks attempting to get a test solution working on my PC with HyperV, I have a new found admiration for networking majors.

My Solution Since we still have most people working in the office on a daily basis, I thought that we should make use of a Site-to-Site VPN connection and treat our office as a branch and the cloud like head office. Simple, right?

To test all this out, I set up my environment in HyperV, with all firewalls turned off, just to make communication a bit easier. Please be aware that my selection of subnet came from a tutorial.

All servers are running Windows Server 2019 Standard

Cloud Servers - 10.1.1.0/24

  1. SRV01 (Domain Controller)
    • 10.1.1.4
  2. VPN01 (Remote Access)
    • 10.1.1.10
    • 192.168.15.20 External IP

Office - 10.1.2.0/24

  1. VPN02 (Remote Access)
    • 10.1.2.150
    • 192.168.15.21 External IP

The Issue Besides my limited knowledge, the issue that I am having is connecting VPN02 to the domain. I have the Site-to-Site VPN working, and I can ping SRV01 from VPN02, but I am unable to ping the other way. VPN01 can ping both servers, and vice versa. Running nslookup from VPN02 has seemingly good results as I can get the IP as well as the server name of both "cloud" servers.

I have setup 2 sites in AD Sites and Services, added the correct subnets to each site and linked them. I'm not really sure where to go from here. I know that I don't have the experience, but I also don't have the budget to get a professional in so I am all that I have. Plus, I like to add more things to my IT toolbelt.

Thanks in advanced.

EDIT: Adjusted IP ranges to not be on the same subnet. Still same issues though.

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djdomi avatar
za flag
djdomi
IMHO you setup the network wrongly, you should NOT using the same Subnets for using different locations, you will need to have different for been able to route them
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spovelec avatar
cn flag
spovelec
@djdomi What I am hearing is that I don't know how to read a subnet calculator. haha. I will adjust and come back with my results.
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