Hi all,

My first post to this list. 
A brief introduction, I am a sysadmin for a medium-sized company with a small 
dozen smaller and larger offices spread over the globe.
Some years back I worked for a company that put linux servers in place in 
offices with Windows workstations and back then I started using OpenVPN. I fell 
for its capability to do bridged networking and to run as a Windows service, 
completely transparent, so end users didn't have to do a lot of clicks to end 
up on the office network, log on to the domain, access internal systems, 
printers etc.

For my current employer I have deployed OpenVPN on Windows laptops for the same 
reasons. But as this is a larger scale operation, I run into some questions. I 
hope to find some ideas or answers here, as I can't find anything pointing me 
in the right direction in the manual or the FAQ.

1. I'd like to set up an OpenVPN server in each country office. All country 
offices have LAN-to-LAN connectivity with HQ and some also with their 
neigbouring countries office (through different means). We have a lot of 
travelers with laptops who visit different countries.
Is there a way to provide OpenVPN with a list of servers, then have it 
determine which one is responding fastest (by measuring ping time for example?) 
and then connect to that server - and all of this without the user having to do 
a manual selection like choosing between different OpenVPN config profiles?

2. Is there a way to have different OpenVPN servers share (or synchronize) the 
same certificates so we only have to create one certificate for each user to 
have access to all our OpenVPN servers worldwide? Or entirely validate through 
Active Directory only (probably combined with a single certificate)

3. I'd like to setup the laptops so that OpenVPN service always connects 
automatically. This would provide a transparent user experience from each 
internet connection. But is there a way to prevent OpenVPN from connecting when 
the users are at their home office or one of our other country offices? They 
have an IP address on the LAN then, in the same range that they would get as 
when their OpenVPN service connects to the bridge. This means that when 
connected to the LAN, the machines would get a double IP address in the same 
range, which is not necessary and may lead to IP address depletion on the DHCP 
server in the larger offices. How do I prevent OpenVPN from connecting when 
it's already 'home'/set it to connect only when the machine has a public IP 
address (or a private IP address on a different network)?

Alternatively, we could offer only an internet connection on our office LAN and 
make the entire LAN connection through an always-on OpenVPN, but I'm afraid 
that it would make things as slow as the internet connection is (which would 
not work well for things like rapid file server access) and make the OpenVPN 
server a single point of failure for the entire LAN. It would help to keep 
guest laptops that get plugged in off our LAN though...

Any ideas, experience, alternatives, scripts etc. are very welcome.

Best regards, 

Theo Fokkema
Digital Plumber


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