Wednesday, March 6, 2019

Cisco Meraki VPN working on Windows 10 laptops but not Windows 7 machines

Hi Guys, I work for a company which has two main domains (Essentially two companies merged and linked the AD's but did not merge them, they have two DC's and two seperate servers for the two seperate domains. Not every user on one can log into the other, this is being fixed in a few months but for now we've switched networks to Cisco Meraki, we've configured a VPN for both sites as we have a number of remote workers. Most of the remote workers are still on Windows 7.

The meraki VPN is built into windows so we install it as an L2TP with a preshared key and authenticate with the AD credentials, all seemed to be working fine but we've discovered a very weird issue and I'm hoping to get some insight from some more experienced system admins on where to look.

The set up we have is as follows. Domain 1 works fine, domain 1 has office workers and remote workers on Windows 7 and Windows 10, their VPN works fine when working remotely across both operating systems. Domain 2 works fine for the most part, domain 2 has office and remote workers on Windows 7 and Windows 10, the VPN only works for Windows 10 users though, Windows 7 just hangs on the first stage and doesn't seem to open the port for the VPN.

We've used a network sniffer and the laptops aren't even sending any sort of connection to us for the VPN so I thought it's something local thats not working on the machine itself, i've used multiple test machines with various settings and AD accounts and they all do the same and hang, I did a trace route to the VPN server and it seems to go through fine so nothing on the laptop itself is blocking the VPN. The same VPN configuration seems to work fine on Windows 10 too without any issues.

Can anyone point me in a direction of where to look for some more insight or what I can check? I believe it must be an issue with Domain 2 policy on Windows 7 machines as it works fine on Windows 10... I could be wrong though.



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