Could I hide my location if I connect to my own VPN before connecting to my work's VPN?

I’m starting my first remote job for a medium size company and I don’t want them to know where I am. They give us a company laptop and have us connect to a company VPN.

To hide my location from them, can I download my VPN provider on the company laptop or would they be aware of this? If not, could I just open the VPN and logon to a server in my supposed state before connecting to the company VPN?

Also - the server is in a specific city, would they therefore think I’m in that city? Or would they not know something as specific as that?

Let me guess, you want to work out of the country. Its not going to work. You can’t really stack VPN’s by starting them in any particular order.

Second, you probably won’t even be able to install your own software if its a company laptop. That would be a pretty weak security approach.

Third, there’s a range of ways your company can find out where you are even if you had a single VPN pointing you to a specific spot, not including a brief drop in the VPN.

Fourth, if the corporate VPN is split tunnel, then only portions of network traffic would pass through the VPN, leaving everything else open.

Search this sub for remote work. This is never a good idea and it never works out. In some cases it leads to terminations and even lawsuits. There’s tax implications and data security laws, etc.

No, because you are using your work VPN’s credentials.
No, because your work VPN might be logging on what IP address you used to connect to work VPN.

Hm, on the other hand I just got an email from my boss, where he quotes my email to him, and the quoted time stamp for my email is 10.5 hours ahead of when I actually sent it. The guy is literally working from India (or nearby) while claiming he’s in NY bahaha

No necessarily. But even if he was, it’s perfectly fine as long as the business approves it. The second you try to hide where you’re working is when it’s a problem.

You need to read up more on VPNs. One can safely work outside of their job’s country without being caught.