VPN Chaining using a Non-VM Solution

I am looking to setup VPN Chaining using a paid VPN service as the first VPN, followed by the company VPN I connect to for work.
Me >> Paid VPN Service >> Work VPN
My goal is to connect to the work VPN while already VPNed into the paid VPN service, so that from my work's VPN it shows me connecting from the paid VPN IP address, not my own.
By default, connecting to the company VPN using the Cisco Anyconnect Secure Mobility Client while already connected to IPVanish's VPN(my current paid VPN provider) will disconnect me from IPVanish's VPN.

I understand this can be done using VMware/VirtualBox, but I would like to avoid that if possible.

Because some faggot on Sup Forums needs all this shit for privacy when not even government leakers do. Get over yourself. Nobody gives that much of a shit what your useless ass is doing. Oh, no, you fap to porn and browse Sup Forums! What a rebel who needs to be safe from the powers that be.

Calm down hotshot. It has to do with me hiding my location from my employer. They expect me to be working in my own country but I plan being in another country for awhile (I work remotely).
The company has very stringent security policies due to the nature of their business, and I know that I will be found out eventually during their network audit if I don't find a way to hide the origin of my actual IP address.

You can avoid using a virtual machine by instead using a physical machine. Some higher-end routers let you set up an OpenVPN client on the router itself so that your entire LAN goes through it. If you then run the Cisco VPN on your PC, it should appear to be connecting from your paid VPN.

who is she

If i'm understanding correctly, this solution would require me to setup my own physical router wherever in the world I may be. The problem is that I will be spending time in hotels or other locations where I won't have control of their network. Also not sure if I want to lug around an enterprise router.

sounds like a retarded idea.

t. brainlet

Why not VNC or RDP into a machine in the location you're supposed to be in?

I'd probably recommend setting up your own VPN server at home if you can. It's possible they might notice that the connecting IP is owned by the paid VPN, or that the paid VPN may not be accessible from wherever you're traveling to (I know China tries hard to block access to VPNs, no idea what other countries might).

Hardly enterprise, I'm talking stuff like relatively newer Asus routers and such. But really all you need is a box with two ethernet ports that can run pfSense, it'd be small enough to fit in a carry-on. Plug the WAN side into the hotel jack, the other into your laptop, and you're encrypted. Look around, you'll find plenty of suggestions for specific models on Google.

(forgot to add) and then VPN from that machine to work.

use image search lazy fuck

Your home router should be running openvpn, you connect to your home router.

holy shit, she's PERFECT

Retarded idea to do what? Make my 6 figure american salary while I live like a king in thailand for 15k /year and retire by 30?

This may be viable, but I don't know what justification I would have to ask for a VDI to be spun up for me at work. I wouldn't be able to just RDP to any machine it wouldn't have access -- the whole network is segmented off. You only get access to things if you're supposed to have it.

I like the idea of setting it up from home. I do have a Cisco ASA and some cisco enterprise routers laying around. I'll see if those are capable. If not i'll bite the bullet for something newer.

rdp to your home machine that is vpn'd to work

I'm fairly certain the Cisco VPN software doesn't work if you're accessing the machine remotely. Understandably, that'd be a pretty obvious weak link in security. Plus, once the machine connects to the work VPN, OP will probably lose his remote desktop access if all traffic is being sent over the VPN.

This is a good solution. Though I see two possible issues -- should there be some power outage, issue with my PC, etc, I would need to have somebody go to my house to manually set it up again. Still, probably a small price to pay.
The second is latency.
Basically the path goes from:
My laptop > work >my laptop
Instead its:
my remote location > my house > work >my house > my remote location
Not sure what the actual performance will be, I guess there is just one way to find out.

It actually does, but you need to set the XML VPN profile file on the ASA to accept remote connections. You may also be able to do it from the client side but I haven't tried that.

Remote in a KVM switch connected to a computer at your house and then VPN to work, using the KVM device (could be a pc with hdmi input or something) to navigate since its a separate network device

Oops, this was a reply to

She's so pretty

The problem is most likely because the Cisco VPN shits on your routing table. Proprietary VPNs tend to do this with no way of preventing it.

A VM or separate machine is really your only option, or at least a container like LXC.

>thailand
enjoy your daily network slowdown from 8pm onwards and minimum 200ms latency. Links to US/EU in thailand can turn to shit pretty often, it’s ok for ssh but doing actual work in a gui session is going to be a pain in the ass.

or you could just stop watching cp you freak

if what you were saying was truly the case, wouldnt it be better to set up a home vpn? sounds like u just want cp bud

90% of my work is CLI based using SSH.
the other 10% will suck, but i'll manage.

A VPN tunnel from my laptop to my home? How would that work? From my understanding I would then need to either have to RDP to a host at my home to VPN into work on that host (which has been mentioned above and may be viable but is slow and would require physical intervention should the host go down), or setup a secondary ipsec tunnel from my home to the work VPN, which would be extremely visible from the engineers at work.

need name or nickname of that chick.