Openvpn connect not working with vmware (weird bug?)

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Settings:

Windows 10 vmware machine with openvpn connect. The vmware settings has network adapter set to bridged. Running Vmware workstation pro 14

Problem:

openvpn connect will not connect unless my pc is connected to my home wifi. Literally any other source of internet (hotspot, friends wifi, library, parents house, work wifi, etc) and openvpn connect will not. On my local machine (not vmware) ive ran openvpn connect without issue when connect to wifi besides my home wifi... this leads me to see vmware as the culprit.

Question:

Any ideas on how I can fix this? Ive exhausted openvpn support who agree vmware is the culprit. Ive ignored the problem for 8+ months but really need to find a solution to this now.

[RaSystemlord]

I don't know why there in an issue with OpenVPN.

However, I use Express VPN "all the time" without any issues. I use it in NAT. I don't think you need to use Bridged for VPN.

Have you tried NAT networking?

[louyo]

PMJI: Big difference connecting to an openvpn server in a router/firewall (used to connect to a site's LAN) versus using a vpn server somewhere for surfing the Internet anonymously. 

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Ive had an OPENVPN server set up for a good 4+ years now and using openvpn connect to connect to it. I like this setup I just need to find a solution to my problem as I cant work unless on my home wifi.

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I just tried NAT networking (see images). Still not working.

[louyo]

Went through similar, had nothing to do with VMware. Had to do with TLS/cypher encryption of my (rather old) router's openvpn server versus some devices "big brother" not allowing connection. Openvpn site has some workarounds but I decided to just replace the old router at my SOHO where I was connecting. Perhaps oranges to apples.

The first inclination I got was when a new smartphone refused to connect. 

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Connecting to my openvpn server with openvpn connect works on other wifi sources like using my phone as a hot spot or friends wifi, its just when using my vmware machine it breaks this process and refuses to connect. Personally im not dealing with any router openvpn cofigurations its simply just a openvpn server running on the oracle cloud and connecting via openvpn connect. 

[gbohn]

Just a few shots in the dark, but things that come to mind are

*) Router configuration/capabilities being used in each different spot

*) An MTU size issue of some sort.

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test

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1. Ive tried connecting the vmware machine via openvpn connect at 7 different internet locations besides my home wifi - none work. I dont suspect and weird configuration on my home wifi is what is allowing me to gain connection and other sources of internet (friends house, parents house, hotspot, library, etc) not to work.

2. Would connecting to a new internet source lower my MTU size breaking openvpn? Does openvpn naturally require a larger MTU size? Again here I dont think this would be the problem either. 

[gbohn]

If your home Router had some special setup (like a specific port forwarding, configuration/capability, or MTU size configuration on the working router) then that would also be consistent.

But it sounds like you don't believe that to be the case.

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Looks like I found a solution, I had DHCP disabled and reenabled it and openvpn connect works now on the vmware machine.

I had a bunch of strict routes and procedures made to ensure my IP would not leak on this vmware machine if I lost connection the the VPN (openvpn connect)